Over the last six months, Hannah and I sat down for three 10-minute conversations about the topics I care about most — and frankly, the ones that don’t get talked about enough: what it really feels like to travel for work as a mom, how to keep your head above water when you’re managing a big career and a full life, and how to return to work after parental leave without losing yourself in the process.

Whether you’re in the thick of it or just want to feel less alone in the juggle — these episodes are for you.

🎙️ Listen: My 3-episode series on De-Stress the Nest

Ep. 60 – How to Ditch the Travel Mom Guilt For anyone who has ever texted home from a hotel room at 9pm to check on bedtime. We talk about how to actually let go while you’re away — and why your family can thrive even when you’re not physically there.

Ep. 66 – Top 3 Tips for Working Parents My three most-used strategies for making working parenthood feel sustainable rather than like constant survival mode — including how to implement a weekly night off.

Ep. 73 – Returning to Work After Parental Leave This one is a marathon, not a sprint. I came back from leave twice, and both times it was hard and a relief all at once. If you’re in this season — or supporting someone who is — this episode is for you.

A Plug for Household Management

If you’re at a point where you’re thinking about outsourcing some of the household management mental load, do it. I’ve had both an in-person household manager and a virtual one, and the relief is real. It’s one of the best investments I’ve made in my own sanity as a working parent.

Which is also why I was so excited to be on Hannah’s podcast in the first place. She’s not just a great host — she’s a busy working mom of three who built Heron House Management because she lived this problem herself. If you’re curious about what virtual house management actually looks like, her company is worth a look.

📖 From the Mind the Beet archive — the posts that inspired these conversations

✈️ Work Travel and Mom Guilt

🏡 Building a Modern Village

7️⃣ Seven Pieces of Advice for Parents Returning to the “Office” After Parental Leave

Since I first published this, I’ve developed this post into a 45-min interactive learning session, and it is by far the most popular session that I do with teams at various learning days. (Reach out if you’d like to book me for yours!)

People intrinsically gravitate toward those who are comfortable with their own purpose. And I find discussing purpose helps me lead a team through tough decisions and it builds trust.

So whether you are just starting your journey or looking to refine your convictions, I hope this post inspires you to think about the big question of how you are contributing to the well-being of others. It’s worth it.

“Why are you here?”

With AI forcing us to re-examine our relationship to work, this question has been top of mind in our work life – both for employees seeking motivation and managers retaining and attracting teams.  

Long-time subscribers of Mind The Beet will know that the best framework I know for these questions of motivation is Daniel Pink’s Autonomy, Mastery, and Purpose.  It’s clear, it resonates, and it makes a complex problem easier:

Folks who are not yet long-time subscribers of Mind The Beet can correct that right here: 😊

This post today is focused on the aspect of Pink’s framing that was most disrupted by changing work patterns: Purpose. If Autonomy is about contracts among systems of people and Mastery looks inwards at improving yourself, Purpose asks how you want your toils to contribute to the wellbeing of others.  

The answer to “Why are you here?” involves all three drivers (along with providing economic security to yourself and loved ones), but today’s focus makes for some of the most interesting personal conversations about motivation.

Are You Ready to Discuss Your Purpose?

Purpose is easy to ignore for the sake of other drivers of motivation, especially when you are earlier in your career or younger in life.    

My own career focused first on chasing mastery and finding a place where “I can do my best work.”   The story I tell myself is that I chose computer science and business economics in college because they were the most difficult classes my freshman year and I thrived on the challenge of it.  

This motivation for mastery – the urge to get better and the worshipping of hard problems – drove the first 10 years or so of my career, which is natural.  I’m establishing myself and at that time being “good at something” is motivating enough.  

Transitioning a career to think more about purpose is a typical evolution many people undertake as they enter their mid-career (or at least it was for me).   You could define mid-life as the transition to deeper purpose – society is clear that you should establish your mastery of something in your 20’s and 30s; it’s less clear what to do with it in your 40’s and 50’s (hence the crisis!).

A Parable About Purpose

Let’s strip away the modern trappings of technology.   Imagine you live in a simple tribe of ancient times and are deciding what to do with your life (or that you are going on a Dungeon & Dragons quest if that’s your jam).    I’ve found in my study of life and literature that there are three things pulling us in different directions: The Explorer in you, asking to see what’s over that next hill.   The Villager, who is driven to stay in the town and contribute meaningfully to the community.  And the Healer, who wants to ensure the most disadvantaged of the tribe are thriving before we move forward.

Let me dig into each animating drive a bit more:

1. The Explorer, rooted in progress. This is the part of us that finds purpose in forward-looking opportunities.   This is the part of our soul rooted in capturing the unknown and is optimistic about applying human potential to unsolved problems.   In modern times, those that optimize here are researchers & astronauts & scientists.  

2. The Villager, rooted in the symbiosis of community. This is the part of us content to be part of the great cycles that define humanity as they repeat themselves.   This spirit is animated most by how our value serves the community.   In modern times, those that optimize here are the teachers, lawyers, politicians, chefs, and athletes.

3. The Healer, rooted in the lifting up of those in need. This is the part of us that finds the most solace in helping the downtrodden.   This area is rooted in a belief that society can’t move forward until the baseline for everyone improves.   In modern times, those that optimize here are doctors, community organizers, and social service workers.

Society needs a healthy balance between all three of these to function and you can argue whether an era needs more of one vs. the others given the challenges of the times.   As an individual, you optimize for your purpose as you tweak the harmony between these three pulls. 

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Applying To Tech Careers

Many jobs naturally gravitate towards one of the three animating drives at the expense of the other two (e.g. it is hard to be a doctor without optimizing for the Healer in you.  It is hard to take an Explorer-first mindset if you are a lawyer). 

Tech jobs, however, provide a lot of flexibility across all three dimensions.  Software is, after all, eating the world – it’s typical that the dominant economic force of our times provides a diversity of purpose.  

This is why I like Daniel Pink’s framing of your career as a “purpose maximizer.”  It implies a less stressful approach to finding your purpose, one rooted in continuous discovery and growth.  It rejects the philosophy that you find your purpose first and then go out hunting for career opportunities that align with it.  

Sometimes your current position that you stumbled into enables you to find a purpose that resonates; other times some burst of inspiration about what animates you enables you to take that next career step.

My Journey with Purpose

Let me share my own journey with these three aspects of purpose.  As I reflected while creating this framework, it became apparent to me that I’ve looked for a healthy balance between all three elements, finding different sources to draw purpose from - some intellectual and some emotional.

🔭 The Explorer: Information Technology at Global Scale

Aaron Sorkin’s West Wing has a great monologue that captures this spirit of the Explorer.  I remember it vividly from when I first watched it in my college days:

This is why I spend days consuming lots of information about where the world is going, reading science fiction, and in particular am fascinated by futurist thinking. 

I’m so thankful to have been lucky enough to be part of the first 0.5% of people connected to the internet, the biggest driver of productivity and economic progress in our generation. This was the launchpad for the Explorer in me and enabled me to be part of the infotech revolution of the past two decades and I’m committed that the next 30 years will be even more beneficial. 

The work I contribute to – helping organizations large and small have the tools to collaborate with one another and improve their written work product – helps the world at large move forward in two important ways:

• Productivity Gains.  “Productivity isn’t everything, but in the long run it is almost everything. A country’s ability to improve its standard of living over time depends almost entirely on its ability to raise its output per worker.” – Paul Krugman.   The information sector – especially enterprise productivity software – is absolutely essential to the productivity gains we are seeing today.  Continuing that trend will prevent war, decrease inequality, and expand the pie for everyone.

• Helping just a tiny bit with every single global problem.   The products and services I’ve worked on have been used by scientists to cure disease, government to mediate conflicts, and researchers to find green solutions to the world’s energy problem.  I go out of my way to share these customer stories with the team when I see them.  This shallow but wide impact on some of the most defining issues of our generation is one of the coolest aspects of working on enterprise tech.  

Much of tech is a cycle, but this Explorer purpose has me seek out the trends of progress and articulate their impact on global well-being.

🏠 The Villager: Building Tech Community

“You are not a platform unless your partners make more money than you do.” – Bill Gates

Creating economic opportunity and a community for others has been an extremely animating part of my work life.   It’s a unique aspect of the job I stumbled into that I’ve come to love.   One in ten developers in the world has written code on top of the platform I work on.  Our partners make 4 times the revenue per year than we do on the product we build.  This part of my job is about stewardship: being predictable so that others can bet on us, cultivating opportunities for an ecosystem, and feeding reinforcing cycles.

A few years ago, I prepared fresh material for a bootcamp for new hires in my organization.   It’s a great excuse to get back to base principles on what we do and why.   I chose to include a 4-minute podcast recording of someone who builds apps on top of our platform.  It told of his journey getting asked to learn this technology, driving hundreds of miles to a local conference to learn more about it, meeting like-minded individuals, and then getting into blogging, podcasting, and speaking.  His best friends are now members of the community built around the products my team delivers.  

I find so much solace and animation in ensuring the continuity of the ecosystem that hundreds of thousands of people depend on to feed their families and grow their careers and skillset.

💖 The Healer: My Role as A Team Leader

Back to West Wing clips (can you tell how seminal the show is for Millennials like me?): Here’s a poignant example of the role managers can play in caring deeply about employees as humans:

In my twenty-year career, I have been a manager for 15 of those years.  Early on in my career, I chose to be part of “management” and carry the burden of responsibility.  

Others might fill up their yearning in this area of purpose by working for an NGO or more directly ensuring their work helps specific forms of inequality.  For me, I’ve fueled this into my work as a manager and ally to others. I define my purpose as creating an environment not only centered on business success but on one where people of all types can thrive.

It’s been a journey over those 15 years as a team leader.  Moving from feeling like a judge of talent into always being a coach.   Honing in on my belief that the future of leadership is about vulnerability, allyship, and empathy.   These pivots were intuitions much before I was able to articulate that my purpose as a manager is to contribute to the wellbeing of the team and champion hidden figures.   

The Explorer in me impacts hundreds of millions.  The Villager, hundreds of thousands.  The Healer in me is focused more locally on deep relationships and empowerment of people I can name and know.

Wrapping up

I wear many hats - tech worker, husband, father, son, writer, and community member - so this is far from a complete picture of my purpose. Mastery and autonomy have also come much more naturally to me - I’ve struggled as I’ve found the need to become more of a purpose maximizer. I’m far from complete on the journey.

Over the last few months, I have had the privilege to witness and help clients, colleagues, and friends who have found themselves impacted by “reductions of force” — especially in tech.

I have seen the full range of emotions: anger, shame, frustration, relief, sadness, and grief to name a few. As someone whose job has defined me for many years, I have deep empathy for everyone who finds themselves without a “job” and the destabilizing effect that can have. It is well known that the loss of a job is a top-five stressor and anxiety inducer in the United States.

Here are the questions I have been asking my clients to help them clarify their next steps.

1️⃣ How much time do you have to find your next job?

When I talk to people who have been laid off, I often see them frantically networking and jumping into interviews for the next role. They’re surrounded by helpful friends and colleagues rushing to make introductions, offering advice on what role they’ll be great at next. If that feels great to you — awesome.

My advice: get the facts. How much time do you really have before you need to be in your next role, and how much of that time do you want to use for a break?

We live in a culture that incentivizes the hustle and the grind. With a layoff, whether you like it or not, you have a break. Most people I’ve spoken to end up realizing that they have more time than they think to take a breath and think about what’s next.

Things to consider:

• Understand your severance package.

• Do the math to understand how long you have (with some buffer) before you need to be working again.

• Factor in a realistic job search timeline — let data, not fear, be your guide. Remember: people who get jobs quickly rarely post about it on LinkedIn.

💡 Bonus reflection: If you knew you had six months before your next job, how would you spend it?

2️⃣ What do you want to remember you did during this time in your personal life?

Remember the pandemic? We experienced shared grief over the loss of in-person connection, and many of us processed it by finding a new hobby to focus on during that time. Some of us nurtured a sourdough starter, others baked cakes, and learned to knit, paint, etc.

The pandemic forced a pause that we were not ready for - and there are similarities with an unplanned layoff-induced pause. So how do you want to use this moment?

Is there a trip you’ve postponed, a book waiting to be read, or a hobby you’ve been curious about? Make this more than “the time you were job-hunting.”

Maybe you want to cook something new, try a sport, or relearn how to play with your kids without reaching for your phone.

Whatever it is, coping with grief will be part of your healing. You will also be a lot more appealing to an employer if you’ve processed the layoff by the time you get to the interview.

💡 Bonus reflection: What story do you want to tell about this chapter a year from now?

3️⃣ How do you want to show up to your kids and colleagues right now?

Real talk — this is a moment of deep vulnerability. Someone told you your role was no longer needed, and it’s jarring. No matter how much betrayal or hurt you feel, know that you will come out on the other side.

If you’re a parent, your kids are watching. You are their model for navigating something difficult.

What do you want them to learn from how you show up right now?

Is it resilience? The ability to ask for help? Finding joy in small things or savoring newly found time together?

Be intentional — for yourself and for those who look up to you.

💡 Bonus reflection: Who are you when you’re not your job title?

4️⃣ What do you want to learn professionally during this time?

Many people I talk to want to learn more about AI - usually entailing taking a course or getting a new certification. I would consider digging deeper on your why and what would be most interesting and impactful to learn for you right now.

If you are looking for a certification because you are hoping it will help you land a new job - remember to check your assumptions. Certifications and degrees matter, but oftentimes experience speaks louder.

If you are a product maker, think about what product play looks like at this time. Whether you are playing with Lovable or vibe coding - make it serve a purpose that you are passionate about.

Consider advising a start-up or getting involved in a non-profit so that you have stories and learnings to share during this time.

💡 Bonus reflection: If you had total creative freedom right now, what would you build, explore, or experiment with?

5️⃣ What’s important in your next phase?

Your next job will mark the beginning of a new chapter. Before you jump in, take a holistic view of what’s important to your whole self.

Ask yourself:

• What do you want to take with you from your previous setup? (e.g., in-person vs. remote, manager vs. IC, type of work, culture, pace, balance)

• What do you want to leave behind?

• What do you want to be true in your next chapter?

💡 Bonus reflection: What did your last job teach you about what energizes you — and what drains you?

Maybe it’s “the year I reclaimed my creativity,” “the year I learned to rest,” or “the year I became braver.” Naming it helps you live into it.

🌱 Closing Thought

A layoff is not the end of your story — it’s an unexpected intermission that will undoubtedly end. Fill it with intention rather than dread. It will help your next act be more fulfilling.

Give yourself permission to rest, rebuild, and reimagine what’s next.

So, I’ve made it a point to be more active on LinkedIn - last week, my LinkedIn follower count crossed 8,000 - and this post shares my journey so far.

If you’d like to follow along, you can find me at: https://www.linkedin.com/in/adam-harmetz/

But First, Why

In ranked order, here’s my purpose for spending time on LinkedIn:

1. Clarifying thoughts. Brevity is in vogue right now. The ritual of crafting 3-5 unique posts - be it product news, AI thought leadership, or product-making tips - has helped me practice being precise as a communicator and keep up with norms in tech.

2. Stewarding tech community. LinkedIn has become the leading home in the post-Twitter world for my product’s social tech community. Listening to feedback and sharing product news now happens on LI.

3. Selling my team. I get to practice how to talk about the virtues of my company & team - and role model the leader I want to be. Yes, I share open job recs when we have them, but more important is the way posting helps me clarify our “aspire to” culture.

4. Learning industry norms. Although there is certainly a vibrant AI community still on X, I find LI is a place where I can keep tabs on best practices for product making, learn what’s trendy, and connect with fellow product makers.

I feel like some people are still stuck in this stigma that LI is only for job hunting - and I’m here to say it’s quite the opposite: LinkedIn has become an essential tool to shape my thoughts.

Stats & Process

Here’s how I approach showing up on the network:

1. 3-5 scheduled posts/week. I prefer to find a quiet 30 minutes on Sunday night or Monday morning to schedule out the week’s post. After some research, I chose Buffer as my tool for doing this - it’s cheap but not free and has a depth of features specifically for LinkedIn.

2. Comment & listen. The key to showing up is not just broadcasting my thoughts, but engaging, commenting and capturing key feedback about my products. For product feedback, I share any interesting hot takes to internal Microsoft Teams channels we have that are dedicated to digesting feedback.

3. Keep up on social & LI trends. I stay curious and do research on content best practices and algorithm hacking - for example, whether hashtags help or hurt, how to get around the tax of having a link in a post, and trends on other networks that might transfer to LI. If nothing else, this makes me a smarter product designer and gives me empathy for more professional content creators.

For the sake of transparency, here are the views & user counts for my posts over the past 365 days. I am not anywhere close to being a Top Voice or hugely influential, and it’s a lot harder for a post to break through on LI now than it was just 1-2 years ago, as the network has matured and preference is given to the bigger influencers. But it is a start, and it’s only been a few months since I’ve gone into higher gear. I also don’t optimize my content for eyeballs; I try to prioritize authenticity and brand building more.

I think about my content in categories of post types - hopefully self-explanatory and I quickly did an analysis of any post with >2K impressions and what category they fell into:

It’s funny - a job posting used to be a guaranteed 20K impression post just 1 year ago, now they rarely break >2K impressions for me. The network has definitely transformed.

My Profile

Header

Lately, I’ve been on a kick to describe my job without using Microsoft’s product brands - which is reflected in my updated tagline on LinkedIn that is more industry-forward.

I decided to put my primary product logos in the banner and also decided to keep the explicit Call to Action (i.e. Follow me) with clear expectations on the type of content someone is opting in to.

About Me

I also recently rewrote the “About Me” section, focusing more on transformation and disruption and less on specific projects:

For 20 years, I’ve built & scaled apps, tools & technologies that help teams work better together and enable people in large organizations to gain expertise and find answers quickly. I’ve operated on the leading edge of every major change in collaboration & knowledge software, including web technologies, mobile, distributed computing, cloud, and AI. I excel at enabling product organizations to stay current with emerging technology, launch new products and line extensions, and grow a healthy tech ecosystem around a product.

Today, I manage a ~100 person team of product managers, data scientists, and customer success experts across the US, Europe, India, and China. We support a multi-thousand person engineering team and deliver a cloud service that serves over one billion users. I sit on Microsoft’s leadership team for collaborative apps & agents - which stewards the product strategy for some of the most iconic and resilient products in our industry, including Teams, SharePoint, OneDrive, and Viva.

I excel at building leadership teams of senior product executives, championing the career of group managers and senior product architects, and sponsoring cultural programs & product discovery processes that prioritize a fast-moving culture that drives growth outcomes using data.

I prioritize giving back to our industry, including as co-author of the Mind The Beet Substack, where we weekly share thoughts on product making & tech careers to 1k+ subscribers.

Follow for thoughts on enterprise adoption of AI, product making best practices, and maximizing tech careers.

Some Key Posts

Here are some key types of posts that have performed well for me.

Using AI

Posts about concrete use cases for AI always pop for me:

How I Work and the AI Transformation

I’ve used posts to uplevel my thinking about the way my team produces results. Here are a few examples:

Career Advice

With my career advice, it’s often a synthesis of the themes we discuss here on Mind the Beet. I try to ensure the career advice posts are novel, quick to digest, and get beyond surface level:

Product Framings

I use LinkedIn to try out tighter ways of describing the products I work on.

And I recently took an internal executive review on a product and upleveled into some industry framing:

A Bit of Lived Experience

A lot of people use LI to share milestones - and it’s always fun to celebrate and see people grow. I try to ensure my milestone posts “add to the conversation” with some insight or memorable take:

Wrapping Up

LinkedIn is far from perfect - it has a problem with bots & there is still a lot of performative and inauthentic content. And I have two big wish list items as a content creator:

• It’s a terrible product for historical knowledge - search is abhorrently subpar and most filters/roll ups are randomly lossy.

• It struggles with real-time events. Its hashtags are mostly meaningless, and it has no feature for onsite community gatherings or to monitor the zeitgeist of a moment like a tech keynote.

If LI invested in these two areas, they could completely corner the tech community market.

Follow me at https://www.linkedin.com/in/adam-harmetz/.

I have compiled a list of common themes that I wrestled with, shared with women who worked for me and whom I mentored and coached.

If you find this post helpful and you run or are a part of an Employee Resource Group for women or working parents, I would be honored to come speak to your group on this topic.

Building a Foundation at Work

Real talk - I have successfully navigated parenting and working because I have invested in building a high-trust relationship with my manager and team. To achieve this, over the years, I have learned how to communicate effectively and ask for what I need, while maintaining a strong track record of delivering results and demonstrating genuine care for my work, my team, and the company. Because I had this key ingredient, the rest of the journey of balancing pregnancy and returning to work was doable.

Family Planning

Here are the key themes that people ask about: timing of getting pregnant, sharing the news at work, navigating fertility treatment while working full time, and planning maternity leave.

Timing

My timing to start a family was not informed or dictated by my corporate job considerations (promotion timing for example). Because I expect my career to span decades, not years, it was easy to zoom out and understand that whatever short term bumps I’d experience by having kids at an “inconvenient time”, they would even out over the long term.

Instead, the factors that mattered to Adam and me as we contemplated timing were bucket list items that we wanted to accomplish before having kids. Mainly, we wanted to spend a few years being married without having additional responsibilities for other beings (hence we didn’t get a dog either), we wanted to do something epic that would be hard to do with kids, so we climbed Mt. Rainier.

When to share at work that you are pregnant

If you are working in the office, I would find a trusted colleague to share the news with on the earlier side in case you need coverage for meetings because of doctors appointments, etc. I had an office neighbor whom I told about because I needed her to cover an interview, and I was also seen running to the bathroom more often than usual due to morning sickness.

Timing to share with your manager is highly dependent on my original point of having a good relationship with your manager and how much you blend personal life and professional work. I shared early with both of my managers because of the trust and my personality of being open about what’s going on in my life. However, if you would not be comfortable sharing a pregnancy loss or have any concerns about this impacting you at work, then keep the news to yourself until it becomes awkward.

Navigating fertility treatment at work

I have never personally experienced this, but I have had direct reports who have been in this position. As a manager, I deeply appreciated the trust and faith that my direct report had when she shared this information with me and it allowed me to support her. I was able to offer additional resources, as well as step in to cover her work when she needed to be out. I never questioned her commitment—if anything, it gave me more empathy for her full life.

How to transition out to parental leave

Have a strong draft of your transition plan by week 34 and become optional in meetings/projects starting week 36. If your company policy/state laws support it, take the last two weeks before your due date off. Trust me, you do not want to be in the office at 38+ weeks pregnant. Adam also switched his phone ringer to “on” after I hit 36 weeks and assigned me a special ringtone in case I went into labor.

Make sure to inform your manager and team about the type of communication you prefer or don’t want while you are out. For example, I wanted to know if there was going to be a reorganization and I was going to get a new manager, I also wanted to know the results of my annual review.

Returning to work after maternity leave

Having a child is a seismic shift in your life akin to starting college or moving to a new city. When you return to work after something that big, expect things to be different. Also know that what you are going to need will be changing pretty frequently for the first 1-2 years of your life as a parent. But here are a few tips to get you started:

1. When you return, take a moment to assess what has changed and what has remained the same during your absence. Don’t rush to jump into the tactics on day 1. Give yourself a few days to get acclimated.

2. Figure out what your schedule needs to look like to support pumping, childcare pick up, etc. My kids went to sleep at 7:30pm for the first year of their life, so if I got home at 6pm, that meant I only saw them for 90 minutes, and that was not going to work for me. So I left work at 4pm but came back online at 8pm.

3. Make time for yourself - it may feel impossible to prioritize yourself when time at work and at home is going to feel scarce. But savor that cup of coffee alone on your way to work, make a plan to work out, or to periodically go out with a friend.

Here is a longer post I wrote about this - Seven pieces of advice for parents returning to the "office" after parental leave.

Working Mom Life

The key themes here are: what to do when kids get sick, how to manage daytime kid activities when you work 9-5, how to travel for work, and what do you do about morning/evening meetings that inevitably pop up.

Sick kids

Kids get sick. As you prepare for parenthood, take stock of your team culture around this - do people work from home, do many take the full day off, etc. If you are the first person on your team to have a child, discuss with your manager how you will approach and communicate with them when your kids are sick.

When my kids get sick, I go into “calendar crisis mode”: cancel non-urgent meetings, take a breath, and coordinate with my husband on coverage. My husband and I also apply the shift approach:

Also, I want to name that you will need to take time off when your kids get sick unless you have family in town that can cover for you. Day care and schools require 24 hours of being fever free before returning and even most nannies will not come in when your kids are vomiting or have a high fever. I mentally prepare myself for sickness entering the house at the beginning of the school year and during weeks when sickness is most inconvenient.

Daytime conflicts

What happens when your kid is going to be “graduating” from preschool at 1pm on a Tuesday, and it’s 30 minutes away from your workplace? The answer is it depends. If conflicts are planned far enough in advance (2+ weeks), I do my best to clear my calendar and attend. In addition, over the years, I have learned to block parts of certain days so that I can be a mom in moments that matter to me.

1. First day of school - I block the morning so I don’t rush after drop off. I love having extra connection time with fellow parents and reflecting on the years ahead.

2. Kids’ birthdays - frankly, that is as much of a celebration of me as it is of them, so if able, I always try to take half a day off for myself.

3. Halloween - Trick or treating energy is high and we head out around 5/530pm, which means I need to be home no later than 4:30pm. So I plan accordingly.

Work travel

I both love work travel and feel guilty for loving work travel. It’s ok to hold these two conflicting truths. To mitigate, I put in systems that enabled me to travel while knowing that home life was ok. This involved knowing when/how to connect with the kids when I was away, having a plan for when to come back early (if there was sickness), and most importantly, learning how to enjoy the time I had to myself.

Here is a post that gives 10 tips to help minimize “travel guilt.”

Morning/evening meetings

Whether you work across different time zones or deadlines/firedrills creep up, there will be a time when you will need to get on a call in the evening.

For predictable work, such as collaborating with teams in other time zones, I have found success by setting my availability for after-hours calls ahead of time and only having meetings on those evenings. I found doing that 1-2x a week for 1-2 hours was sufficient.

For urgent matters that periodically crept up, parenting taught me to better set boundaries (especially as a leader). I paused and asked questions like “Is this matter really urgent to discuss at 9pm or could it wait until the morning?” If the answer was yes, then I asked if I was critical or if I could send a delegate and catch up by listening to the recording or reading the notes. Sometimes I still have to get on an evening call but I learned to do due diligence and not just say yes.

Summing it up

I decided a long time ago that I wanted to be a working parent. I bring things I learn at work home and vice versa. I firmly believe that doing both helps me live a fulfilling life and brings me the most joy. I also know that this journey is better and easier when you are surrounded by those who are going through the same thing or are slightly ahead of where you are so they can share their path.

If you’re seeking support, I’m running two mentor circles this fall to help parents thrive at work and home and I offer individual coaching for working parents and leaders —drop me a line if you’d like to chat.

Congrats on your job with Microsoft!  What an interesting time to start in tech - you just signed up for Facebook during your last week of final exams at UCLA, Google went public one year ago, and the iPhone will launch in two years. 

You will be in the first 1% of humanity to use the internet, get a smartphone, sign up for a SaaS service, or chat with AI. You will see cloud & mobile go from niche ideas to indispensable worldwide utilities, and the AI era is just starting to usher in another paradigm shift as I write this. The most controversial part of your career is that you stayed with the same company for 20 years, so you rode all these waves while nurturing a resilient home for your work life.

Today, you are a VP of Product & Data Science - responsible for ensuring customers’ success with one of the largest online services in the world. As you constantly adapt to the times, here are 20 lessons you’ll learn in your first 20 years.

Starting Your Career

1. 🏄‍️ Ditch the career ladder. Learn to surf the right waves.

Find something bigger than yourself and attach to it. When it washes out, find a new wave to ride. Repeat. Intentionally choosing the right wave - team, technology, industry trend- will be way more important than any other career tactics.

2. 📈 Drive for 1% improvement every day.

The world’s information will double every 5-8 months, and workplace technology - from search to collaboration to AI - will keep improving to match. This means there are two skills that can and must constantly improve so you can keep up: synthesizing information & communicating your ideas. Practice, try new tech, and hone these a little bit every day.

3.🗞️Get paid to keep current.

Make learning an on-the-job habit - especially keeping up on the industry and a healthy information diet. This knowledge of the broader context of what’s going on around you will get you noticed.

4.🧱Be a finisher.

The tech industry glamorizes the start of new things. You’ll see, though, that it will be more important to find the resilience and grit to finish, to edit, to scale, and to bring customers along.

5. ⏱️ Learn the difference between urgent and important.

Getting the urgent done will foster your credibility on the team. But carving out time for the truly important work is how you will find creative success. Every year you’ll look back and realize that so little of your time - maybe 30% - was spent on that truly important, difference-making work. You’ll learn to trust your gut to identify it.

Sustaining Your Career

It’s not about “work/life balance” - it’s about managing your energy and exploring how what drives you will change over time.

6. ☕ Balance mastery and purpose as you age.

Society wants you to get good at something in your 20’s and early 30’s. It’s much less clear what to do with your now finely-honed skills in your late 30’s and 40’s. Uncovering your purpose - asking “Who am I helping?” - will ensure you avoid feeling trapped by being great at something that no longer gives you as much joy.

7. 🏓 Detect your boredom & burnout early.

“It’s easier to recover from being annoyed than pissed off.” You’ll get bored sometimes. You’ll burn out too. Detect it early - before it snowballs. Stay “in the flow” where job challenges and your skills match.

8. ⛓️‍💥 Fire yourself at the start of each new wave.

“What got you here won’t get you there.” Every time there is a paradigm shift in your industry - cloud, mobile, AI - the cycle restarts and everything gets reset - requiring you to show up differently. Andy Grove at Intel famously fired himself and rehired a new Andy to pivot from memory chips to CPUs - you will need to do the same to adapt to changing times.

9. 🏖️ Take your retirement along the way.

Every few years, you’ll find a way to take an extended time away from work - honeymoon, paternity leaves, sabbatical. The pauses will make you a more interesting person and unlock your understanding of what drives you.

Thriving in the Matrix

At Microsoft, the biggest multiplier to your impact is the scale of working on problems that require thousands of people to properly solve. You will learn to thrive in this matrix, not be a victim of it.

10. 🎁 Be generous.

Your job as a PM is not to own and explain the customer insights, but to teach engineering and design until they know the customer as well as you do. You’ll learn to think about this just like physics or economics - teach the team to run in their own heads a useful synthetic model of the world everyone can use to quicken decision making.

11. 🦝 Be curious.

Cross-team work will be some of the most rewarding projects in your career, but also the most tribal. Your biggest mistakes are when you are too critical too early - you’ll want feedback to be your love language to show you care, but it’ll be misinterpreted as unsupportive. Better instead to take the time to be curious - share context and understand the thoughts, wants, and feelings of the other tribes - before setting goals or evaluating plans.

12. 👟 Walk in your managers’ shoes.

Life is too short to have anything other than a deep, trusting two-way relationship with your boss. You will work to understand the unique ways in which each of your boss’s jobs is harder than yours. You will help them learn the lived experience of members of their teams.

13. 🤗 Find your “First Team.”   

The key to happiness will be to join a “first team” of peers that you can rely on for support.  Find the space where you can be yourself and broker the deep relationships among those who can relate to your struggles. Find people you can laugh with.   Your unhappiest times will be when your own pride makes you resist joining the tribe around you.

Making Great Products

Product Management will professionalize over the course of your career.  It’s part art, part science – and frequently calls for you to make decisions in the face of ambiguity. There will be a lot of noise and temporary trends, but three universal truths will become your grounding ethos on building products:

14. 📈 Champion results over activity.

Five years into your career, the cloud paradigm shift will begin.  This will fundamentally transform your profession – enabling data analysis, experiments, and more hypothesis-driven thinking.   You will learn to ask, “where do we need to be and how do we measure it,” and to help teams moved beyond an activity-focused mindset. Facts not adjectives.

15. 😍 Learn to have product taste.

Your job won’t only be about data and decision-making rubrics. You’ll also need to develop an innate sense of taste for high-craft products that generate user love. My biggest advice for developing this is product play - channeling that inner child as you make a habit of using the products around you. Yes, taste is learnable - not innate.

16. 🤝 Don’t just build products. Build customer trust.

The product itself is just a small part of the lived experience customers will have - you’ll develop a passion for the “around” product work of support, sales, adoption, customer success, and ecosystem stewardship.   As the pace of change accelerates, you will realize how much nurturing the industry around your product matters just as much as building the right product.

Leadership

Motivating and inspiring others and generating the legitimacy to do so will become an increasingly larger part of your job.

17. 🧘‍♂️ Harness the power of calm.

People are attracted to calm leaders. You will learn to tap into patience & optimism and create systems to help others do so as well. Your latest motto: Do hard things in a calm way with me.

18. 🎁 Give each person a unique gift.

Every person you manage will need you to push them to be their best - the trick will be to figure out what they need from you right now. Praise? A nudge to raise the bar? A reframe? Your attention to the gift each person uniquely needs defines how you give people autonomy, yet still show up meaningfully.

19. 🔍 Be intentional with your attention.

A retiring member of your leadership team will give you a big gift on his way out - he’ll say that you should use the phrases “I need” and “I expect” more. You will not need to solve most problems yourself - simply setting expectations on what you care about will let the team know what’s important and what needs to change.

20. 💖 Embrace empathy, vulnerability, and allyship.  

You’ll have friends who lose their jobs due to the disruption your product causes to the industry.  This will have a profound impact on their lives.   What a way to humanize abstract charts on cloud growth rate and disruption to the value chain.   Technology and society are more intertwined than ever.  Leading diverse teams will require showing vulnerability and speaking publicly about allyship.

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Summing It All Up

This newsletter is called Mind The Beet for a reason – it’s a quote from Tom Robbins' Jitterbug Perfume that speaks to the eternal struggle of defining your own reality in the face of processes, pressure, and systems. The first 20 years of your career will be about influencing large systems, not letting them consume you.   Mind the beet.

I expected to learn new tools—coaching frameworks, business development skills, new networks—and I did. But what surprised me was how much growth also came from unlearning habits and beliefs that no longer served me.

I’ve been mentoring and coaching for years, and my experience across tech, startups, and politics is part of what I bring to the table. But to truly support others, I had to let go of ways of working that were once helpful but no longer fit.

As I wrap up my time in the Hudson program, here are the top 3 things I’ve unlearned—and the top 3 I’ve learned.

🛑 Top 3 Unlearnings

Unlearning #1 - I don’t need to get an “A” because I already have it

For much of my life, success was measured by achievement—whether it was a promotion at work or earning top marks in school. It was how I knew I was on the right track.

And by those measures, I’ve earned my “A’s”—in education, in my corporate career, in titles and compensation. But stepping away from that world to take a “power pause” (a term coined by Neha Ruch in her newest book) was a conscious decision to pursue something more fulfilling.

In this new chapter, chasing an “A” isn’t the goal. What excites me more is the question: What would you do if you knew you couldn’t fail?

That shift has been incredibly freeing. I now treat my work as a series of experiments. I expect many of them to fall flat—but the ones that take hold will help me discover more of my own potential and, just as importantly, support others in discovering theirs.

Unlearning #2 - I am a great problem solver, but I can do way less of it and get better results

This week my two girls (8 and 11 years of age) got into a massive fight before we needed to leave for sailing camp. My oldest refused to carry a towel for her younger sister. The younger claimed that she could not possibly carry her own towel because her backpack was too small. They were at an impasse with a lot of screaming and crying. Instead of solving this for them, I told them to figure it out in the next 30 minutes. And I walked away. By the time I returned, they proudly told me that this was a silly argument and they had resolved it with a quick game of “rock, paper, scissors.”

They were beaming because they came to this understanding on their own. And there is no way any advice or troubleshooting that I was going to do, was going to be as effective as what they did on their own.

A core belief in coaching is that our clients are resourceful - it was cool to stop myself from solving a problem and see how the kids could do it themselves.

Unlearning #3 - I now try to lean into conversations instead of tuning out when I disagree, am bored or think that I have nothing to contribute.

This is one of the most challenging unlearnings I’ve been practicing. I consider myself to be a great listener, but the fact is, if I disagree (and don’t think it’s worth the discussion) or my job is to listen and not solve a problem, I find myself tuning out and not listening. For years, contributing by talking and doing has been what was most needed to be successful. But as a leader, a coach, and a mom, I need to do a lot more “being,” which means listening and asking questions vs. trying to prove something by talking or doing.

As a result, I am not only becoming a better listener, but am able to become more curious and less triggered about controversial topics (ie, politics). I am able to ask questions like “What really matters to you right now?” which has unlocked greater understanding.

💡 And here are my top 3 Learnings:

Learning #1 - I am exactly where I am supposed to be

I’m in the midst of a joyful and hectic summer and my kids have a different camp every week - so there is a new routine, hard transitions, and a new environment. And every week, I watch my kids go through a mini Odyssey journey. Right before the week starts, there is lots of excitement. The beginning has some lows, the middle is a bit of a slog and the end of camp usually ends on a high (after a last turn of events that keeps us all on our toes). My kids experience the full range of emotions through the arc of their journey. And I remind them that whether they are at the beginning, in the middle or the end, they are exactly where they are supposed to be.

It is the same for me in this chapter of my life - I am nearing the end of the “beginning.” I had the excitement nerves and now the “sunday scaries” of transitioning to the messy and exciting middle as a coach. But I remind myself that I have done transitions before and I am exactly where I need to be.

This is my favorite quote from Hope Floats that sums it up:

Learning #2 - Work less to achieve more

Many years ago, Adam and I went on a hiking and biking 10 person group tour in the Dingle Peninsula in Ireland. I was in my mid-20s and in great shape but the 70+ year olds in our group beat me every day on a bike. I learned that I wasn’t being efficient with my bike gears and was working too hard.

The same has been true in so often in my work life and is true again as I coach clients. When I am racking my head on which question to ask and how to phrase something, I remind myself that I am trying too hard. So much of beign a coach (and a leader) is about being present, listening and asking the simple questions. The hardest work for me has been getting comfortable with awkward pauses and not jumping in with my own experiences and advice but rather helping my clients arrive to the conclusion that is right for them.

Learning #3 - Every interaction does not have to be a coaching session

In the last 9 months, I have improved on so many skills - how to be a great listener, how to sit back and give less advice, how to ask better (and simpler) questions. And then I found myself feeling stuck in day to day conversations with my friends, family, and kids - where I felt like I had to show up as a “coach” and refrain from giving advice or having an opinion.

A few months into my coaching journey, I met with a coach who was farther along in her journey and I started with “I’m sure you won’t give me advice, but I could really use some.” And she reminded me that we did not set up our conversation as a coaching session and therefore we can just talk and share wisdom and advice as needed. It was a relief!

So I am learning that I can still offer advice when needed, I can still tune out of some conversations, and that not everyone wants or needs me to be endlessly curious about them (though many people do really like it). Being me, just as I am is great place to be.

Conclusion

I leave the program with a lot of gratitude, a new set of people who I know are in my corner, and with a feeling of lots of possibilities as I live my next chapter of life in support of the vision I created earlier this year:

As I look forward to the fall, I am taking new clients and if you know someone who could benefit from a partner in their leadership journey, please don’t hesitate to reach out here.

The first section of this post is the new content I wrote this week on the role of AI in the hiring process. And below that is a repost from 2022.

How to incorporate AI into your resume and interviews?

Whether you are interviewing for companies that are actively adopting AI, building AI or just thinking about AI, every hiring manager wants to know that you are aware that AI-powered technology is critical to consider in the context of every business and every job. So I highly recommend having your personal narrative on your relationship with AI.

More specifically, if you have been part of bringing AI into your organization, running experiments with various AI tools and in general embracing the new tech, you should bring a way to weave that into both your resume and your key stories. Many candidates that I talk to struggle to authentically claim business outcomes that have been powered by AI - that is totally fair. Try avoiding artificially creating outcomes where it is too early to tell. Instead, amplify your learner's mindset, the experimentation that you pioneered, and how you will bring lessons learned forward to your next job.

If you have no professional experience working with AI, then have a point of view of the role it should or should not play in the place you are applying to. To develop that point of view, do industry research, play with AI tech, and see how competitors are leveraging it.

How to use AI to prepare for your interviews?

It has never been easier to do mock interviews and get good feedback from ChatGPT (or tools like it) when getting ready for an interview. One thing to try is to run the job description through your AI tool of choice and ask for sample questions based on the job. I would also ask for sample classic product management questions (give me a product sense question, a product case study, etc.). Then record yourself answering the questions and give AI your recording or a transcript and ask it to give you feedback on how you did.

Don’t forget to ask AI to help you understand the company you are interviewing for - its culture, financial performance, summary of recent releases and press coverage.

Pitfalls to avoid

1. Be prepared to be thrown off - All hiring managers know that candidates are using AI to prepare their resumes and to practice answering questions. So do not be surprised if they try to get past your preparedness. Stay calm and curious. Take a deep breath and engage with your interviewer to get as much context on their questions/asks as it is reasonable.

2. Do not overstate your AI expertise - If you claim to be an AI expert in a product interview, be ready for deeply technical questions. So be clear if you have had experience building on top of AI with great user scenarios or you have experience with systems and models. Interviewers usually aren’t out to get you, so set yourself up for success by being clear on where your expertise lies.

3. Specialist PMs are more “in” than generatlist PMs right now - I am seeing more demand for PMs who have depth expertise vs. breadth. So if you have to choose a story of being a jack of all trades or going deep on your experience as a growth PM, I’d choose the latter. You can still talk about being adaptable and able to figure out any problem you have in front of you, but the depth (whether industry or type of PM) is in higher demand in this moment in time.

[Repost from November 2022]

By now with 10+ years in tech, I’ve been on both sides of the interview table (seeking as well as giving a job), so I’m going to share my lived experience as well as the tips and tricks I’ve gotten along the way that I have found to be most impactful. 

No one really likes interviewing for jobs (especially after a layoff when it’s hard to separate an economic situation from seeing this as a personal deficiency) - seeking a work opportunity requires you to open yourself up to scrutiny and potential rejection. In my professional career, I have been rejected at seven companies (these are ones I got past the recruiter screen with) and have succeeded at three (and every time I have landed in awesome places).  I have learned as much from the rejections as I have from the wins and have come to believe that an outcome of a job interview has very little to do with my worth and everything to do with preparation, circumstances and culture fit. However, since preparation is the only thing in our control, I will focus on that.

The first thing I recommend you do is read Cracking the PM Interview. The rest of this write-up is gravy, but really, if you are actively seeking a product role, stop what you are doing and go buy this book.

Also as you get into the interviews with all the ups and downs of the journey, here is a Ted Lasso reminder to be a goldfish:

Have a personal pitch – why you, why now, why this company

When I worked in politics, the first exercise I’d do with a candidate is to help them develop a 30-word and a 3- minute pitch on why they were running for office. I told them that success is if a constituent, donor, or endorser could name the top reasons why she was running for office. This same advice applies to interviewing. You should be able to tell a compelling and memorable story – why you, why now, and why this company. I recommend finding an opportunity at the beginning of the interview/conversation to get your pitch in. 

Why you. This question is always asked in some form. You may hear questions like “tell me about yourself” or “how did you get here.” This is your chance to be concise, humble, and preferably memorable. I’ve used lines like “my career has been more of a walk through a jungle with a machete rather than a career ladder” - which I have found people have remembered. Whatever your tagline is, I’d spend some time figuring it out and inserting it into your pitch.  

Why now. Even if you are in the job market because you have been part of layoffs, I recommend mentioning it quickly (if asked directly) but pivoting to excitement about the new opportunity that has come your way and its timeliness. Examples of things to say if you are in the market due to a reduction in force:  

“I’ve had your company on my radar and I have read an article about this cool new area of tech/investment/growth, so I’m excited to learn more.”  

“As I’ve had time to think about my career growth and what’s next, I’m excited to talk to you about this opportunity and my unique skills that can contribute.” 

Why this company. If you are changing jobs externally, be prepared to answer this question. The bigger the company – the harder the question. For example, when I was interviewing for Microsoft, the answer of “I’m really excited to work on problems that impact the whole world” is a B- answer – because you can easily substitute Amazon, Google, Meta, and the answer will not change.  Instead, focus on impact + something unique - like if you are interviewing for a role in Azure, being excited to overtake AWS because of the opportunity you see (insert some analysis you did).

If you are interviewing for a mission-based company, calling that out as a primary reason you want to work there falls into the same bucket – you can go work at a bunch of other mission-based companies, so why this specific one is the question. When I answered that question as I was going to Guild, I focused more on being excited to contribute to a company that was facing scaling challenges and why I was uniquely positioned to drive meaningful change.   

Behavioral questions – dig deep and make a table  

Almost certainly you are going to get questions that will ask you to reflect on your past experiences. These usually start with “tell me about your biggest professional accomplishment” or “tell me about a complex project you led and the challenges you overcame.”  

To prepare for these kinds of questions. I usually make a table with 1-3 rich examples from the past couple of years. I try to pick stories with many things that went well and didn’t go well and then I use that to draw upon when interviewing.  This approach helps me organize my thoughts and not be searching for new examples/experiences in the moment.   

As an interviewer, I really appreciate when interviewees have structured answers – in business school, I was taught to follow the STAR method by describing situation, task, action, and result – it’s easy to tell what the impact was of the outcome (moved key metric by x or impacted y customers). 

Embrace the case questions – showcase your curiosity, organized mind, and customer empathy 

As a hiring manager, I can teach new employees many things on the job – how to create a backlog, how to do a competitive analysis, how to present an idea, and so on. But there are “unteachable skills” that are almost impossible to teach. Examples include passion for the product, customer empathy, product judgment, and organized thinking. 

The best way for me as an interviewer to try to understand if you have the “unteachables” is to manufacture a scenario for you to reason through. Examples of case questions can be found here.

As an interviewee, the goal is not to come up with the perfect answer but to share your thinking process and showcase that you can organize your thoughts, clarify assumptions and lead with customer needs. There is no right answer to a case interview – so most importantly think out loud and bring your interviewer along on your journey.  

One more quick tip - if you get to pick the product to analyze, pick something that your interviewer is likely to be on equal footing with you, and do not pick a product the company you are interviewing for works on.  Only select the company’s product if you are explicitly asked to do so.

Things I’ve picked in the past for my “case” were Apple’s Fitness + program (and then I compared it to Peloton), Hydroflask and InstaPot. 

Ask good questions – People love to talk about themselves

 An interview is a two-way conversation. You are interviewing the company for culture and fit as much as they are interviewing you. As an interviewer, I look for whether or not the candidate has good questions because it tells me if they are thinking seriously about the role. But don’t stop there – the candidates I’ve been impressed by were those that could then carry on the conversation and balance letting me talk (who doesn’t like to talk about themselves) as well as engaging in the back and forth – following up and digging deeper to find that common ground.  

Here are some questions that helped me achieve a great conversation as an interviewee:  

“What does your day look like?” 

“What’s the biggest challenge you are facing at work today?” 

“What is your team’s culture?”  

Reality check: Practice is key – put on your “heels”, and record your “pitch” 

Interviewing is a muscle. If you haven't interviewed in a long time, don’t expect it to come back naturally. I have always hoped to do a practice interview with a company I didn’t care about, but really, every time I’ve gotten into the process, I got excited about the opportunity – realistically, a “practice” round never really worked for me.  

To that end, the best advice I’ve ever gotten is to actually practice. So I put on my heels, stand up tall and record my “why me” intro pitch on my phone. Then I listen to myself (cringing) and adjust my talk track.  

Second best advice I got is to do a mock case interview with a coworker or a friend. I have found this to be a very vulnerable practice but so helpful every time. If your friend doesn’t know what case to give you, Cracking the PM Interview has a section of them and they can follow along the guidelines. 

Pitfalls to avoid 

On average, I’ve interviewed every few years proactively or reactively. I always ask for feedback and while I don’t always get it, here are some of the patterns that I have collected and reflected on of where I have fallen short:  

Listen carefully. Jumping in too quickly without hearing the question has backfired on me multiple times. When I did that, I wasted precious interview time answering the wrong question. I chalk this up to nerves and lack of interview practice so to combat this, I paraphrase the question before I start answering it.  

Informationals ARE interviews, so prepare accordingly. While you don’t need to be prepared for a case, I have found that you need your personal pitch ready on why you, why now, and why this company (even if you are trying to get this latter question answered, to begin with). Be enthusiastic about the company by researching what it’s all about (product line, latest announcements) and ask thoughtful questions.  I once asked a late-stage start-up about their exit strategy. Unsurprisingly, I didn’t get a callback. While I don’t think that was a bad question to ask, that didn’t convey how excited I was about what the company was working on.  

Try instead “what is your competitive advantage” or “what do your customers love most about [specific product]”  

Cramming the night before an interview has never worked well for me. Good night’s sleep, exercise, and a meal have taken me farther than reviewing my pitch, or case questions in the 11th hour.  Also, remember to take breaks during the interview if you are scheduled to go back-to-back – most interviewers will offer you a chance to get a glass of water (if you are doing interviews remotely) or to take a break if you are in person. Take a breather and rest.    

Dwell less, follow up more – I often find myself spending time after interviews double-guessing and rehashing my conversations. As Ted Lasso says, be a goldfish (the happiest animal on earth because it’s got a 10-second memory) and move on. However, do send a compelling follow-up note (use AI to help you with your first draft and then edit) where you thank the interviewer for their time and share an insightful takeaway or an interesting resource.

Resources: 

Cracking the PM Interview has been the most effective resource to prepare for product management interviews. It will walk you through how to write your pitch, how to answer behavioral questions and prepare you for case questions.  If you are interviewing for a product job, this is a must read. No other book has come close for me.  

Guide to reading PM books by Nils Janse - This is a reading guide for you as a product manager. It is a curated list of the best book on product management. But it not just a numbered list of books to read. Instead, this guide is guided by your preferences, with visual guide to go with. Let's get into it. 

I hope you found this write up helpful. If you have other tips and tricks that have worked for you, please share. Good luck and remember it only takes one yes.

I’ve mentored dozens of people over the past twenty years. In larger companies with a hierarchy, the topic of “managing up” is one of the most frequent mentorship topics I see, especially from early-in-career employees.

While I hope you can spend most of your time focused on driving impact with the autonomy you want, this post is for those moments in your career where you find yourself needing to work within and leverage your management hierarchy.

The following is a “virtual mentoring session” – instead of solving your problem or telling you a playbook, I’ll give you the five questions I’d ask if you were a mentee of mine and wanted to unpack your relationship with your manager. Let’s Ted Lasso this thing together!

But first, why?

There is a saying: “People don’t quit their jobs; they quit their managers.” While this is mostly a plea to managers to deliver the right culture and support, it makes another point - your relationship with your manager is too important to be ignored.

When I think about my career, my investment to develop high-trust, two-way relationships with my managers over the years has been a force multiplier because it:

• Enabled me to feel safe enough to take risks and be more creative

• Gave me the context to work on something larger than I could do on my own

• Showed me what my next job might be like, if I chose to move up the hierarchy

This post isn’t for anyone in a truly toxic situation with their manager - that’s a whole other topic. Nor should anyone be spending most of their time on “managing up” - we all joined this profession to be builders, not talkers.

Yet a little bit of self-reflection and curiosity can go a long way here - so let’s get to the five questions designed to get you to complete just the right amount of pre-work before your next conversation with your manager.

1. Can you name 3-5 ways that your manager’s job is harder than yours?

This is my first go-to question. I find people can easily name the way their own job is harder, but it’s a “think and pause” moment to put yourself in your manager’s shoes. The goal is to name specific things your manager is struggling with, activities they are doing for the first time, or painful things they are handling for you that you don’t. If you don’t know, it’s completely normal to use a 1:1 to ask - I do it at least 2-3 times/year.

I’m not asking you to solve their problems and take on your manager’s stressors yourself - but the awareness is helpful not only for the acceleration towards a high-trust relationship but because there is often a high correlation with the top problems for your company and your customers.

2. What can you help your manager learn?

When I’m at my best over the course of my career, I’ve used office hours, skip levels, and roundtables to try to share my own lived experience on the team - what I love about the team, what’s getting in the way, and what’s changing. This can be specific things - “hey, did you know it takes over 10 hours to complete this process?” - to more generic - “I used AI in this way, and I think it could help others on our team.”

It’s the reverse of the previous question - I’m asking you to do your part to help your manager walk in your own shoes.

The best managers will be curious and ask proactively about this – some organizations even have “reverse mentoring” where a more senior employee shadows a newer employee.

The other benefit of investing here is that it organizes your own thoughts – you must self-reflect about what’s easy or hard or novel in your own work life before sharing with someone else.

3. Is your quality bar higher or lower than your manager’s?

Managers are hired to be editors – but they are at their best when they function as the newsroom editor on the big picture not a copy editor fixing details.

This is my “get beyond the basics” question – and it requires some honest self-reflection and awareness. In my career, one of the best “cheat codes” I’ve found is to have a quality bar that is higher than what your manager expects and the organizational average.

This is especially important in new employee/manager relationship - as norms are being set. So it’s worth spending the extra time being typo free, rewording for clarity, and delivering high quality and polished work.

If you are unsure, it’s a great idea to ask for examples - ask your manager and your teammates: “Can you share a few examples of the best work that you’ve seen in the past month?”

4. What part of your relationship with your manager is transactional? What part is creative?

I ask this when I’m trying to diagnose if something is off with the altitude that you approach conversations with your manager. Are you bringing half-baked work to your manager when you should have worked on it with a few peers first? Conversely, did you decide something yourself that needed creative alignment with a larger system?

Every 1:1 I go to with my manager, I try to have 2-3 transactional things I’m informing them on (e.g. budget I’m spending, customers I’m closing) and 1-2 creative topics I want their equity in (e.g. a major design tradeoff, an organizational problem I’m stuck on). Classifying my conversations into these two buckets is a helpful barometer of whether I’m living up to expectations of autonomy. I’ve often discovered things that I was going to bring to my manager only to realize “Hey, I can and should figure this one out myself.”

5. What do you want your manager to know about you, right now?

Most managers will develop a mini-model of their employees in their head – what kind of tasks they like to do, what their super strengths are, and if they are bored or challenged with their current assignment. There is no need for this to be a tacit conversation filled with assumptions – so I ask this question to drive intentionality in what you are sharing with your manager.

I add the phrase “right now” to the end of the question to reduce the stress of it - you don’t need to share your 5-year career plan with your boss. It’s a trust-building gift to appropriately share how you are feeling and what you need this month.

Of course, depending on the level of trust, there may be a host of personal issues or even professional fears that you aren’t comfortable sharing. This question isn’t designed to make you an open book – it’s to get you to be intentional and drive down assumption-making from you and your boss.

Wrapping Up

If you’ve found this post helpful and want more, I have an upcoming public talk that I wanted to make folks aware of. In under two weeks, I’ll be attending the Microsoft 365 Community Conference in Las Vegas (I’m actually the executive sponsor of the conference, too) and speaking about many of the themes you’ll find in Mind The Beet:

How To Thrive In Your Tech Career: Managing Burnout and Boredom

If you are attending the conference, I hope to see you there!

With age comes some amount of experience, which leads to reflection and perspective. I was in my mid-20s when the financial crisis of 2008 hit - I was fearless and indestructible. I had very little to lose financially at the time - no property, no responsibility to my family or children - the world’s events unfolding in front of me were a great adventure that I was able to have an intellectual conversation about with no real consequences.

Fast forward 15 years and the news of the Silicon Valley Bank collapsing (bread and butter for funding for many small and mid-size tech companies) - has a very different impact on me. Today, I work at a start-up, have a family, lead a team, and have a variety of responsibilities. Additionally, I am surrounded by people in various stages of their life - some of whom have little to lose and lots of excitement about the possibilities, and others are figuring out if they need to make a “plan B” because of all the worst-case scenarios running through their heads (real or imagined).

As the tech scene has been thrown into disarray over the last few months, I have been wrapping my head around what I can do to help my teams feel their ground shake a little less and what concrete steps I can take to be ready for the journey ahead.

Taking a step back - if you are new to Mind the Beet, I’m Helen and I am a Product Advisor and Executive/Leadership coach with 15+ years of mega-corp and start up experience as well as a mom of two kids under 11. I pride myself on having a strong bias for action, a sense of ownership, and deep care for the people I work with.

So the question I have been mulling over is how do I show up as a leader and what do I say to those who rely on me for clarity when moments of deep uncertainty come. While product managers deal with ambiguity every day, the game changes when there are macro events happen such as mass layoffs, banks collapsing, etc. In these moments, the people we lead need us (as their managers) to provide guidance and support

Here are the things I have done to support my team when I have had limited visibility or control over the situation at hand.

Keep calm and carry on

I remind myself that as a manager, I am in a fishbowl. People are watching me react and use that to inform their own actions and behaviors. So in difficult times, being intentional about how I show up to those who depend on me is critical.

Additionally, it’s important to weigh the context. Depending on the situation, it may be appropriate to give people time and space to step away and process their emotions in whatever way is needed (this is for example what my leadership team for on January 6, 2021, when the US Capitol was under attack). Or if the right message is to actually focus on the work and put one foot in front of the other.

What this means for me is that I need to watch my tone and body language when teammates bring me worrisome news and concerns.

So my goal is to do less of: “Oh my god, you are kidding me? Tell me more!”

And more of “I haven’t heard about this. Let me catch up, gather my thoughts and we can chat about this in a little bit. In the mean time, what worries you most?”

Connect using your past experience

As a manager, I often have the gift of past events that I can pattern-match and use to help with perspective. I use this tactic carefully to make sure this doesn’t become a conversation about me, but rather about finding relevant examples to showcase perseverance through a similar issue.

Awhile ago, I was in a situation when half of my team was laid off and I told my mentor at the time that I didn’t know how to stay and be productive. She told me that the choice was mine to own - I could see what’s happening as an opportunity and a reset or leave the organization. But staying and complaining was not a good outcome for my mental health or the business. I stayed and referamed my approach. It was hard, but worth it.

Focus on what you can control

While I hold space and listen to people and do my best to reassure them, I find a lot of comfort in falling back on processes and routines that I have established. Continuing to add value to the business and not getting distracted is always appreciated by leadership teams so my mantra is to “keep on swimming” and to not give up.

Whether it’s showing up to recurring meetings, sending a regular status meeting, or prepping for a strategy review with my leadership team, my goal is to keep moving the ball forward.

Eat, sleep, exercise - plan your week

Perspective for me comes with a good night’s sleep, healthy eating, and daily movement. So especially in stressful periods, I make an extra point to calendar my life so that I can fit in self-care. Recently, I have been following Daniel Rosenthal on Twitter/Instagram for daily motivation to stay healthy.

Tactically before the week starts, I’m finding at least one meeting a day to do as a “walk and talk” and planning my meals for the week.

Limit doom scrolling to 15 minutes a day

Adam and I are watching Shrinking with Harrison Ford and Jason Segel - where a therapist recommends giving yourself 15 minutes a day to feel all the feels. I apply this approach when I am compelled to do worst-case-scenario thinking in times of uncertainty.

This week, I’m giving myself 15 consecutive minutes once a day to worry and read the news on what’s going on with the banking industry and how it will impact the tech industry. After that, I plan to move on with my day.

Stay positive - limit gossip and cynicism

When all the information is not available or shared, it is easy to start making up stories and discussing all the possibilities, letting our imagination run wild. I have also seen the ease with which we all fall into criticizing the organization for not providing more updates and more information.

Especially in difficult moments, I try not to engage in rumor-mongering or cynical talk. Instead I remind myself (and others as appropriate) that everyone is doing the best they can with the information they have. A helpful tactic has been to talk to my stressed out teammates about indisbutable facts and together arrive to the conclusion that a lot of felt anxiety is based on assumptions and fear and not real information. I also pose the question to myself and to others - how is this action serving you right now and what is it getting in the way of?

If you’ve gotten this far in this post, you are likely in an organization that is going through a turbulent time. I hope you know that you are not alone and I hope you find a moment to catch your breath and be intentional about how you want to show up. And remember, you cannot take care of others if you have not taken care of yourself - so put your oxygen mask on yourself first.

If you are a manager, here are some other resources from our past writing:

• A day in the life of a frontline manager

• How does a product leader manage their time?

• Burnout & Boredom: A Manager’s Pandemic Retrospective on Mental Health

• 🔦 How You Can Find Learning Opportunities Everywhere

After having a much-needed sabbatical, I decided to launch my own executive coaching and product advising practice.

How did I get here?

As I live my life with intention and purpose, I reflected that at this point in my professional career, three things are most important to me right now:

1. Spending time on things I love and getting compensated for them - helping people be the best they can be (coaching), and supporting others to build great product teams by sharing my experience (advising)

2. Putting my expertise to work - I’m good at the people and the product stuff. Over the last twenty years, I’ve built products and teams, supported countless career transitioners (being one myself), led manager mentor circles, coached moms returning to work as well as aspiring and new managers, as well as leaders in organizations, looking to maximize their impact. I have been a manager at a mega-corp as well as a leader at a late-stage start-up and have written countless articles about my learnings over the years.

3. Continuing to learn - I need to stay challenged and engaged. Starting my own business and deepening my coaching practice are exciting new ways to grow.

I would also be remiss to say that being in tech is a weird time. I have no doubt that I could go out and get a full-time corporate job right now if I wanted to, but I am sure that I would need to compromise on the very things that are most important to me.

I am grateful for the tremendous support that I have received from Adam while pursuing this journey. Especially in today’s uncertain times, I do not take the space and ability to do that for granted.

Impact of coaching

I have been fortunate to work with various executive coaches who have supported me throughout my career. This experience has enhanced my self-awareness and helped me grow as a leader and as a person. While pursuing my coaching certification through the Hudson Institute of Coaching to expand my skills, I have reaffirmed my strong belief that effective coaching leads to long-term, sustainable change.

From an organizational standpoint, by taking a systems-based approach, coaching addresses both individual behavior and organizational dynamics, resulting in sustainable change, improved team performance, and stronger alignment across the business. Leaders become better equipped to handle complexity, hold tension, and influence outcomes with clarity and courage, ultimately enhancing overall organizational effectiveness.1

What will my focus be?

1. Executive and leadership coaching - navigating career transitions in matrixed organizations, elevating executive presence, and managing time effectively via 1:1 support.

   1. Reach out if you know someone who is: mid or advanced in career and is new to a large organization, is returning into the workforce after parental leave or a layoff, or is struggling to make the most impact during ambiguous times.

2. Product advising + coaching services - setting up repeatable and scalable product management processes, hiring the right team, building strategic roadmaps, and evolving your organization to thrive in the era of AI.

   1. Reach out if you or a leader you know is setting up your first product team in the era of AI and thinking about the skill sets you need to hire for and the repeatable and scalable systems you need to put into place.

3. Front-line manager coaching - workshops, mentor circles, and 1:1 coaching support

   1. Reach out if you know someone aspiring to be a manager or have recently become one and are seeking support in transitioning to this new role and setting up their first team for success.

How can you help?

The business I am entering is one based on referrals and relationships. If you or someone you know is looking for a thought partner, coach, or advisor - I’d be honored to support the next chapter of your journey. Check out all the details here.

Additionally, I am hosting a talk for first-time managers. This is a topic near and dear to my heart because I have seen firsthand that there is not enough support for emerging leaders in organizations, and I’d like to help.

If you are interested, I hope you’ll consider attending and sharing the opportunity with those in your network. The link to the event is here.

Register to attend

As always, thank you for being a part of Mind the Beet community, and I look forward to continuing to share my journey with you.

I have been lucky to have managers who made space for me to bring my whole self to work and since I’ve started coaching and advising, I’ve seen that not everyone has been so lucky. So whether you are a manager, a friend or a peer to those who find themselves shed tears in front of you, this post will help you navigate those moments. Please share this with anyone else who may find it useful.

Dear Manager,

I’m so excited that I have joined your organization. I am a servant leader and will move mountains for the business, for you as a leader and for the team you hired me to manage. I will deliver results and will do it with pride, energy and enthusiasm.

You need to know, though, as we work together, that there will come a time when I will cry in front of you or you’ll notice that I have been crying. As a redhead with very fair skin, it’s tough for me to physically conceal the redness in my face and the swollen eyes. Extra makeup just makes it worse. Believe me, I’ve tried.

I want you to know that I would give a lot to not cry at work and be able to contain it. I have been working on this for years and while it has definitely lessened with time, sometimes this will happen and here are some common reasons:

1. Work-related frustration: I care a lot about my work, and if it’s not going well, my frustration can evolve to tears. The kindest thing one of my previous managers has said to me is, “I know you cry because you care a lot. So please don’t stop caring.”

   1. What to do: Listen and ask if I’d like help troubleshooting or just need to vent. Be on my side and keep me accountable if it’s a deadline that I have slipped or not delivered on.

   2. Ask questions like “What help do you need?” and “What can I do to support you?”

2. Positive feedback - During reviews - when you give me praise, I may tear up. I am my own harshest critic and when you take the time to see me, I sometimes get moved to tears. Please don’t take that to mean you shouldn’t give me praise.

   1. What to do: Nothing in the moment. But if I am starved for positive feedback, reflect if you can dole it out more often in smaller moments.

3. I need to give you (my manager feedback) - You and I may have had an interaction that I have been noodling on and we need to talk through. It’s hard for me to give my manager feedback about something that impacted me (much easier if it’s about my team or someone else needing help) and despite my best preparations, tears may come.

   1. What to do: Get curious and stay calm. Agree where you can and share a different perspective as appropriate. Thank me for giving you feedback no matter how good or bad it was. This is an effective way to promote a culture of openness in the workplace.

   2. Ask questions like: “Tell me more.” and “Can you give me an example?”

4. Sometimes things at home are hard - sleepless night with a sick kid, a disagreement with my husband, etc.

   1. What to do: Get curious about what I need in this moment. I may be seeking work as a place to focus on work and not what’s going on at home. Or I may need to go home to take care of my child, parent, husband, friend. I once had a manager who saw that I was teetering on the verge of tears and when she learned that I had sick kids at home and haven’t slept for two nights. She sent me home for the day. I’ll never forget the grace that she gave me that day. Sometimes I forget that work can wait for a day.

   2. Ask questions like: What can I do to support you right now?

If you are new to being a manager or to people crying in front of you, here are some general tips:

1. Please stop yourself when you start saying “Oh my god, what’s wrong? Did I make you cry?” or “Please don’t cry, I don’t know how to deal with that.” - This moment is not about you. It is about a deeply vulnerable and personal opening that you are witnessing. Instead try: “What is behind your tears?” A head-on question with no judgment will move this situation forward or let the cryer say “I can’t talk about this right now.”

2. If you see that I am continuing to cry and can’t quite stop yet - insert a break. If in person, say you will go get a box of kleenex (even if you have one, keep it away in a drawer for this exact reason). If the meeting is online, excuse yourself to go get something in another room. The few minutes alone, help me take a few breaths and get re-centered.

3. After the moment has passed, come back to this situation - later that day or the next day and check in. Knowing that my manager cared enough to check in makes the workplace more human.

Thank you in advance for your understanding,

Helen

If you are interested in additional materials for managers, check out these articles from the archives:

1. Getting your first manager job

2. A Day in the Life of a Frontline Manager

3. Burnout and Boredom: A Manager’s Pandemic Retrospective on Mental Health

4. How I advocate for my people

5. What being a parent teaches me about work

6. How I lead when the world is uncertain

That was my coach’s advice when I asked about strategy in my tennis game. I remember staring back at him, slightly bewildered.

“But what about my opponent?” I asked. “When do we talk about how to respond to her shots?”

His response was surprising: “Focus on taking your best shot. Worry less about the other player.”

At first, this felt incomplete—wasn’t tennis about reading my opponent, anticipating their moves, and playing a strategic game? But over time, I realized how good this advice was for my tennis game, work, and parenting.

What’s in Your Control?

One of the most powerful questions I have learned to ask as a coach, manager and a parent is:

“What in this situation is in your control?” Or a variation on this “What are you doing to contribute to this situation?”

The question seems simple, but in today’s climate—especially in the fast-paced, high-pressure tech industry—a quick retort is often “not much.” Or as my 11 year old would immediately say - “Nothing! It’s not my fault that person X did this to me!” Amazing how even at 11, the reaction is to think about blame.

The current environment is undeniably challenging. Employees I talked to across the board, express exhaustion, stress, and the feeling that no amount of effort is enough. With AI touted as boosting productivity by 60% or more, expectations are sky-high, and workloads continue to pile up. There’s an undercurrent of fear—fear of falling behind, of not meeting impossible standards, of being perceived as a slacker.

And yet, when I ask a client and my daughter to pause and think about what is their part in the craziness, I observe a shift.

The Shift from Victimhood to Ownership

I’ve observed two consistent patterns when people reflect on this question:

1. A shift from feeling powerless to feeling in control.

When people see themselves as victims of external circumstances—market pressures, leadership decisions, unrelenting demands—it breeds frustration, resentment, and burnout. But when they focus on what they can control, they begin to reclaim a sense of agency. Even if the external situation remains unchanged, their mindset shifts from helplessness to empowerment.

I’ve been in this exact situation—facing a tight deadline where the team felt stuck with a bad, date-driven plan. They believed they had no control over the outcome. Instead of accepting that, I asked them to go back and bring me a proposal they were actually proud of. The change was immediate—there was energy, ownership, and a better plan.

This same principle applies to you: When things feel out of your control, look for where you can take agency, even in small ways.

2. Recognizing the inability to say “no.”

One of the most striking realizations is how many professionals tell me they struggle to set boundaries. They want to say no to unrealistic expectations but feel trapped by the fear of being perceived as not working hard enough. They recognize the pressure their managers are under and don’t want to disappoint. The result? They keep saying yes until they’re drowning.

I have felt this as a professional but more profoundly as a mom. Can I bend myself into a pretzel to get two kids to different after-school activities simultaneously, while coordinating carpool logistics and my busy work schedule? Sure, no problem. Or I could say no and counterpropose a less crazy solution like not doing an activity on one of the days? But then comes the guilt: Am I a bad mother?

When I unpack this with clients and myself, the reasons for not saying no vary:

• Some fear job insecurity.

• Some equate their self-worth with output.

• Some struggle with confrontation.

• Some have never seen healthy boundary-setting modeled in leadership.

But once we identify these internal barriers, the shift begins. You can start making intentional choices.

Reframing the Game

Just like in tennis, where focusing on my own shot made me a better player, focusing on what’s in our control makes us more effective and resilient. It’s not about ignoring external factors—it’s about shifting the priority to our own game.

So, what does that look like in practice?

• Clarifying priorities helps you say no more. Instead of trying to do everything, focus on the high-impact work that actually moves the needle. Some tools here are having a check in with your manager to go over your priorities and validate what’s most important. This is especially important when new things get added - you go back to your list and ask what can now be lowered or taken off. If nothing, then do two things (at least): (1) Agree to realistic timelines up front and (2) push to understand what success looks like so time is not wasted.

• Setting boundaries helps you be in control. Learning to say no isn’t about slacking—it’s about sustainability. Think about your tomorrow self and make sure you don’t set yourself for failure. As a product manager, my general rubric was for every 1 yes, I had at least 10 no’s. Set expectations upfront - when should people expect a response from you via Slack/Teams vs. email. If you are like me, and think that you need to respond to every message as it comes, stop yourself and breathe. Half of the time, the issue will be resolved by someone else if you give it 24 hours.

• Managing your energy is something that you can control. Recognizing what fuels or drains you can make all the difference in long-term performance. I am most productive in the mornings, so I save the work that requires most thinking for a fresh mind. I also really like working collaboratively on hard problems as opposed to by myself, so I get energized from group sessions and people’s energy. So I manage accordingly - save individual hard tasks for the morning and then find a way to collaborate where I can with peers.

• Finally, in your span of control is learning how to let go of perfection. Sometimes “good enough” is truly good enough. I have learned over the years that figuring out the right amount of work to do for the stage the project is in, is critical. For example, I often find myself putting together a very quick rough outline to share the direction I’m going in to get input before putting in more effort. I also think about how reversible the decision will be that we need to make and assess how much work needs to be put into accordingly. High-stakes decision = more work; lower-stakes decision = less work.

In the end, the lesson is the same—whether in tennis, work, parenting, or relationships. When I focus on executing my best shot rather than constantly reacting, I perform better and feel more in control. And the same goes for you: The more you focus on what’s in your control, the stronger and more sustainable your game becomes.

For the visual learners out there, here is a reminder wheel that illustrates control.

As always, thank you for reading. If you or someone you know is going through these hard moments right now, I’d love to talk and see if I can help. I am in the process of launching my own executive and leadership coaching practice and I am offering a variety of discounted packages for friends and family. You (or someone you recommend) can book a free introductory call with me here.

Congrats on your job with Microsoft!  What an interesting time to start in tech - you just signed up for Facebook during your last week of final exams at UCLA, Google went public one year ago, and the iPhone will launch in two years.  You will see cloud & mobile go from niche ideas to indispensable worldwide utilities, and the AI era is just starting to usher in another paradigm shift as I write this.

Your career will span the Golden Age of tech, with all the dividends that provides as well as all the unsolved risks that powering the world economy brings - security, privacy, and AI ethics to name a few.

Today, you are a VP of Product & Data Science. The most controversial part of your career is that you stayed with the same company for 19 years, reinventing yourself as the company grew and transformed.  This was not the plan and leaves you reflective on how to avoid states like good enough and comfortable.  Your own lived experience these past 19 years proves that you can thrive by staking out a home on a product and team if you maintain your curiosity about how to .

Here are 19 things you’ll learn in 19 years.

Starting Your Career

1. 🏄‍️ Ditch the career ladder. Learn to surf the right waves.

When you start your career, you’ll be told it’s the start of a stressful upward ladder climb that must build on itself in only one direction. No, better to think about your future as catching some waves. It’ll be more fun. It will get you thinking about repetition and cycles, project selection, riding something with more momentum than you have yourself, and knowing when you are in the whitewash and need a change.

2. 🧼 Learn the difference between urgent and important.

We live in a time when the information in the world is doubling every 5-8 months now – you’ll need to invest time to ensure your ability to consume information, tasks, and communications keep growing just as fast.  Smartly managing your time, your tasks, and your information diet has a way bigger impact on getting you to leadership roles than anything else.   

3.🪴Evolve your job until you get paid to learn.

You are the son of a teacher; the love of learning was instilled in you at an early age. This will help to remind you of the power of curiosity as a cure for burnout. Being around those who love to learn new things will help you anticipate trends. You’ll have a mantra for when you are at your best: You should spend 80% of your time on the job learning. That’s not a typo - it forces you to incorporate learning into what you do instead of just relegating learning to a couple of classes a few times a year.

4. ✌ Only ~33% of your work makes a difference. Make that part epic.

“No matter how good you are, you're going to lose one-third of your games. No matter how bad you are you're going to win one-third of your games. It's the other third that makes the difference.” - Tommy Lasorda

This maxim is just as true in the tech sector as it is in baseball. It’ll be clear in hindsight what projects and tasks moved the needle vs. which were busywork - the trick you will learn is to develop the intuition to puzzle that out at project selection time. And, sure, sometimes it’s the high visibility projects that are worth making epic but sometimes it’s the unsung efforts.  You'll remember vividly that one of your first projects at the company was to write fifty error strings for various problem conditions.  You will take the time to understand each condition, establish a consistent error taxonomy, and just in general write the best damn error strings on the planet.  It's not that it was hard; it was just that no one else had time to go deep like that.  Epic.

5. ⏳ Resilience and grit are underrated.

The tech industry will glamorize the start of new things. But you’ll get pulled to more important projects than that: being a great editor, transforming what exists, bringing customers along, and finding the grit to finish and not just start. Building resilient products and the organizations to match is where the real strength in tech lies.

Sustaining Your Career

It’s not about “work/life balance” - it’s about managing your energy and exploring how what drives you will change over time.

6. 🏓 Detect your boredom & burnout early. 

“It’s easier to recover from being annoyed than pissed off.”

You’ll get bored sometimes. You’ll burn out too. Detecting it early - before it snowballs - is the best advice you’ll get. Frameworks help.  Mihaly Csikszentmihalyi’s Flow Diagram is a high bandwidth way of ensuring you think about peak performance. You will learn to take stock and place your current job as a dot on this graph periodically:

7. ☕ That itch mid-career? It's probably your transition between being motivated by mastery ("Let me get good at something!") to purpose ("Who does it help?").

Society wants you to get good at something in your 20’s and early 30’s. It’s much less clear what to do with your now finely-honed skills in your late 30’s and 40’s. It’s amazingly universal that people stumble into a mid-career crisis, feeling indebted to a profession they spent thousands of hours getting good at but not feeling like it gives as much satisfaction as when it was new. For you, the solution will be to just talk about your purpose with colleagues and patiently explore what drives you over time.

8. 🏖️ Take your retirement along the way.

Every few years, you’ll find a way to take an extended time away from work - more than just your typical 4-5 weeks of scattered paid time off every year: at least six contiguous weeks, one time up to 12 weeks. The reasons vary - honeymoon, paternity leaves, sabbatical. The pauses will make you a more interesting person and unlock your understanding of what drives you. There is a lot to learn about how to maximize your recharge time.

Software is about people, not bits

At Microsoft, the biggest multiplier to your impact will be the scale of working on problems that require thousands of people to properly solve.  You’ll develop a core thesis of how you want to influence, connect, and bond.

9. ⛓️ Learn to thrive in the matrix.

“Matrix is the worst form of organizations, except for every other.” - From a recent leadership training I took

Your job as a PM will be to form coalitions around ideas and plans with stakeholders who have a different lens than you.  You’ll work on problems that span across disciplines and org structures - so you’ll need to learn to thrive in this matrix, not be a victim of it. Some of the best work you’ll do is when you establish a sense of trust and safety across disciplines and orgs so that you have fun with cross-team work.

10. 🚦 Don’t start solving a problem when you should be signaling support.

“I've learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”  - Maya Angelou

There is power in plainly sharing support for an idea or a colleague’s mission, especially by praising their work. Behind this is the need to not only focus on what people think, but what they want and feel as well. Your biggest mistakes will be when you started solving someone’s problem instead of being clear first that you recognize their agency and strengths.

11. 🤗 Find your “First Team.”   

The key to happiness is to ensure you can join a “first team” of peers in PM and other disciplines that you can rely on for support.  Find the space where you can be yourself and broker the deep relationships among those who can relate to your struggles. Find people you can laugh with.   Your unhappiest times are when your own pride made you resist joining the tribe around you.

Making Great Products

Your chosen profession of product management will professionalize over the course of your career.  It’s part art, part science – and a lot of time making decisions in the face of ambiguity. As you deliver and scale more products, four major themes will emerge that define your craft: empathy, impact, love, and trust.

12. 🌌 Empathy: Build a model of customer needs. Enable your team to run the simulation.

You will grow up early in your career as a product manager in a specialized area of software with complex customer requirements. This will be a gift - it will force you to be an expert at synthesizing customer intent. Like physics or economics, PM empathy is about building a useful synthetic model of the world around us that quickens decision making and group understanding. Importantly, you won’t build this by sitting around thinking - you will build these models by deep interaction with customers, solving their problems, hearing them complain, and trial & error.

13. 📈 Impact: Champion results over activity.

Five years into your career, the cloud paradigm shift will begin.  This will fundamentally transform your profession – enabling data analysis, experiments, and more hypothesis-driven thinking.   You will be responsible for transforming a slower and less dynamic product culture into one that embraces these now standard practices. You will learn to replace adjectives with facts in your performance evaluations and to always be ready with the “why” behind an activity.

14. 😍 Love: Product intuition is a learnable skill. Practice with lots of hands-on time with product.

Your job won’t only be about data and decision-making rubrics. You’ll also need to develop an innate sense of taste for high-craft products that generate user love. My biggest advice for developing this is product play - channeling that inner child as you make a habit of using the products around you.

15. 🤝 Trust: Honor the faith customers are placing in you.

There are only two jobs in tech: you build product, or you build trust.   The latter refers to the “around” product work of support, sales, adoption, and customer success.   As the pace of change accelerates in your industry, you will realize how much building customer trust matters just as much as building the right product. This is why you will gravitate towards nurturing the community around your products – it will be an honor to support the people who bet their careers on the ecosystem your product creates.

Leadership

Motivating and inspiring others and generating the legitimacy to do so will become an increasingly larger part of your job.

16. 🧘‍♂️ The Power of Calm.

People are attracted to calm leaders. You will learn to tap into patience & optimism and create systems to help others do so as well. Your latest motto: Do hard things in a calm way with me.

Do = Act, not think or talk.

Hard Things = We do what’s difficult so our customers don’t have to.

In A Calm Way = Patience, attention, focus, and optimism.

With Me = We are in this together.

17. 🔍 Where you put your attention matters.

A retiring member of your leadership team will give you a big gift on his way out - he’ll say that you should use the phrases “I need” and “I expect” more. Plainly & simply setting expectations is an essential part of being a bar raiser. Of course, there are more problems than time and resources - so leadership is about great judgment on where you focus and what you ask for.

18. 🌪️ Transitions are hard. They are when the team needs you the most.

Cloud. AI. Reorgs. New strategies. Pivot moments are when your team is most vulnerable. You’ll learn that’s when your job as a leader is to ensure the org does things that wouldn’t have happened anyway. It’s a careful balance of generating energy for the new and creating clarity out of the unknown.

19. 💖 Modern leadership is about empathy, vulnerability, and allyship.  

You’ll have friends who lose their jobs due to the disruption your product causes to the industry, as moving to the cloud requires less racking and stacking servers by IT staff.  This has a profound impact on their lives.   What a way to humanize abstract charts on cloud growth rate and disruption to the value chain.   Technology and society are more intertwined than ever.  Leading diverse teams requires showing vulnerability and speaking publicly about allyship.   You can read from Jack or Eric if you want, I suppose, but modern leaders need to spend more time reading Ijeoma and Brene.   Less table thumping, more humanity.

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Summing It All Up

This newsletter is called Mind The Beet for a reason – it’s a quote from Tom Robbins' Jitterbug Perfume that speaks to the eternal struggle of defining your own reality in the face of processes, pressure, and systems. The first 19 years of your career will be about influencing large systems, not letting them consume you.   Mind the beet.

Further Reading

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Starting a Career:

• 🏄‍♀️ Why New Grads Should Surf, Not Climb: The #1 piece of advice for new grads.

• ⌛ How does a product leader manage their time? Thoughts on time & task management and what’s worked for Adam

• 📚 Information Diet: Recommendations for news outlets, analysis, podcasts, and newsletter subscriptions from an information junkie

• 🪴How You Can Find Learning Opportunities Everywhere: A philosophy on incorporating learning into your product management routines.

• 💎 From Product Manager to Product Leader: A career guide with a focus on the most important inflection point.

Sustaining a Career:

• 💭 Finding Purpose in Tech Careers: My journey to becoming a purpose maximizer.

• 🥱 Burnout & Boredom: A Manager’s Pandemic Retrospective on Mental Health: Learn about Flow and other tips for managing burnout

• 🏖️​ Adam's Field Guide to Happiness: The Secret to Amazing Paid Time Off

• 🐟 Adapting to mega-corp culture: Context for people moving into Big Tech jobs.

• 🎞️ My Career Highlight Reel: How to synthesize your career journey.

Sofware is about People, not Bits:

• 🔗​ The People Angle: How to build x-team products

• 🤝 Thriving in the Matrix: An informal podcast interview on x-team work.

Making Great Products:

• ⚒️ Thriving as a GPM at Microsoft: 4 key roles that product leaders need to play.

• 🧱 Building AI Brick by Brick: What product making is like in the AI era.

• 👓 Developing an eye from high-craft product making: How to be a UX PM

• 📣​ My 10 Favorite Productisms: Pithy sayings with pearls of product wisdom behind them

• 🎶 Taylor Swift & Product Management: Tips for PMs from her latest album

• 👓 Interpreting Blurry Situations: Making decisions in the face of ambiguity.

• 🪀 Product Play: Where my best product ideas will come from

• 🧳 Sharing the Point of Tech Conferences: How to be inspired by your community.

• 🔍 Community, Resiliency, Purpose: Themes from my product making career

• 🔮4 Futures & Product Management: How to think about the future as a PM

Leadership:

• ✈️ How to rock your onsite & team bonding moments: A playbook for getting your team together

• 🎁 The Gifts We Hope to Give: Learn a bit about how we approach parenting and leadership

• 🐝Survival Tips for Team Leaders: Reorg Edition. How to plan, decide, and announce an organizational change.

• 💼 VP of PM: What’s the job really like?

• 😶‍🌫️ My Mood Board: A visual way to show how I lead

This summer, Adam and I sent both our kids to a week-long sleepaway camp (second year in a row but a new camp this time). Less than 24 hours into it, I got a call from the Assistant Director to pick up my oldest child because she was having a hard time and the camp “wasn’t staffed” to support this level of neediness. On my drive over, I agonized over what this means - is my child really not equipped to be at this camp, did I do something wrong to not prepare her or is there something else going on that’s not clear to camp but will be to me if I can get everyone to take a breath and have a discussion. I made a commitment to myself on the drive to show up calmly, actively listen and also advocate for another path forward.

When I showed up, and we talked it through, it was clear that no extraction was needed and instead a bit of context and compromise went a long way. When I came back on the designated day for pick up, my 10-year-old told me that this was the best camp ever, and she couldn’t wait to go back. TL;DR - This was a misunderstanding and an over-escalation by the camp.

In my lived experience, I have seen that people are at their best at work, at home and in their community when they know that they have people in their corner who will stand up for them in hard moments. Personally, it is when I know that my leader, my partner and my team have my back, then I can bring my best, most daring and thoughtful self to hard problems that need to be solved.

So as a manager, I offer you a few examples of how I’ve shown up as an advocate for my team using stories from home and work.

Stay curious to get context

Whether you are giving advice, coaching, or intervening to drive a better outcome, it is key to start by understanding where the person is coming from.

In this situation with my daughter, the counselor did not have context that she is a strong rule follower and gets anxious when she perceives rules are being broken. She needs reassurance and then space to process her emotions.

If you are in the position of authority - parent, manager, leader - it is your job to ensure that whoever is giving feedback or course correcting your people has the relevant context and information so that they are able to do the right thing. As a leader, I have found that I must create the space so that everyone can take a deep breath and be in the right headspace to get curious about the context.

Here are a few tips:

1. Often, emotions are running high, and stories about what has happened have been established. Ask for the facts from both sides. Use words like:

   1. “Tell me what happened” - and have each party take turns; be neutral as much as possible while collecting data

   2. “What happened next/what else happened” - keep probing and you’ll be amazed at how much emerges with a little bit more time and questions

   3. “Why did this upset you/was not acceptable” - ask for context on why whatever happened was triggering

2. Context is also having a shared understanding of expectations

   1. When my daughter had an outburst in camp, she didn’t know that she wasn’t allowed to exit the hall without telling her counselor that she was going outside to cool down. They assumed she was running off. They also didn’t know that my daughter would never run off. So once she understood that she needed to say where she was going, that paved the path for better expectation setting.

   2. I remember when I got overwhelmed with work in the early days of my professional life, I was too embarrassed to share that I would miss a (self-etablished) deadline. My boss then clarified that he would be happy to help if he knew I was flooded, but he needed me to tell him.

   

   You can be respectful and be an advocate at the same time

   The story I’ve told myself that advocating (especially for your kids) makes you a high-maintenance parent. I’ve prided myself on “going with the flow” and making the system work since, at the end of the day, I don’t have an exceptional reason to seek extra support or help. I think this applies at work as well - I’ve never really wanted to be a “squeaky wheel” as a manager on my people's behalf unless something warranted a different approach.

   Over the years, I’ve grown past this mentality and think it’s much better to respectfully push past the “standard” if it doesn’t work for you and make your own reality.

   Here are two concrete things you can do:

   1. Respectfully ask for what you need - I had an employee seeking coaching, but the company I worked at only supported that for managers and not individual contributors. I found the program's owner and asked if it would be possible to put my direct report in if one of the managers backed out/extra seat became available. The answer was yes! My employee got in, was grateful, and became better for it as a team member.

   2. Challenge things that don’t look right even if they are small (but important) - Our school district does highly capable testing, and my daughter tested high for Math but not as high for English. She was not invited into a highly capable program for both, but I asked if there was a path for just Math. As it turns out, there was and it was a mistake that she didn’t get invited to it originally. Fixing it has meaningfully provided a higher rigor of education for her, and I could have missed out on this if I had feared rejection or conflict.

   

   Model being an ally

   I’d like my daughter to remember from this incident that I showed up to advocate for her and did not take camp’s assessment at face value until digging in further. She was in the room when we walked through the details and the misunderstanding. She also saw that I did not lash out or get upset with the camp folks and listened to them as carefully as I listened to her. I also found opportunities to insert context and color throughout her storytelling and theirs to help bridge the gaps between the two parties.

   Here is what I have seen work:

   1. Advocate in the open and fight the urge to get to a resolution behind closed doors (unless there is a really good reason to do that). Your people need to see how you show up for them during conflict. In my very early marketing days, a product manager dismissed my argument of why we can’t change product a certain way since we positioned it differently - he said “well, marketing lies anyway, so it doesn’t matter.” I shared this incident with my manager, and she called a meeting where she educated and clarified what marketing does and why insinuating that positioning is dishonest or irrelevant is unacceptable. This was now 13 years ago for me, and I still vividly remember her showing up for me.

   2. Lift people up - another meaningful memory for me is when a senior leader looked to my boss in a meeting to answer a question I was the expert in answering. While my boss could answer the question for me, he paused and redirected to me to answer, reminded the leader of my name and shared that I have been thinking about this problem for a long time and have a thoughtful perspective to share. Not only did he give me the opportunity, but he also gave me credibility in the room.

   3. Speak up when it’s inconvenient, especially when you are in a position of power - five years ago, I observed a mentor (“big buddy”) to an intern frequently talking over her in presentations. When I saw it happening again, I paused the speakers and asked the mentor to stop interrupting and let the intern finish her presentation. Later, she later reflected to me how impactful that was for her to see.

Parting Thoughts

Earlier in my career, I was not always able to be an advocate and did not understand how to necessarily even be one. So, watching others model it for me was both a gift and a lesson that I am now trying to pass on. Parenting also taught me that you can (and should) fight for your people at every opportunity, big and small, regardless of how ready you feel, because there is always someone near you that could benefit from you lifting them up. You never know what life you are impacting in a meaningful way.

We build more impactful organizations, create stronger leaders, and create better communities when our people are supported.

If you are new to this newsletter, subscribe and follow for more candor and real-life talk on what it’s like to be a leader in tech while balancing parenting and life.

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I remember when I was deciding to join Guild, I had an open mind that I had no idea of what the tech world or product management outside of a giant megacorp looked like. I knew I wouldn’t be at Guild forever (any late-stage growth company seems to be 2 years from an exit), but I did not know for how long or all that would learn. It was a scary leap to make, and I have loved every minute of it and would wholeheartedly recommend to my friends in big tech to find a way to expand your horizons and see what else is out there.

Three years ago, I came to Guild as a front-line manager from Microsoft, but I leave as a more confident leader with experience leading multiple teams (product and operations), as well as a more evolved leadership and product coach. I also leave with a much better understanding of the differences between a megacorp and a growth start-up (mega-corp to growth stage company transition), how to onboard to an organization as a leader and be intentional about listening first/acting fast next, as well as how to lead teams through ambiguous times (both because of the macro tech environment and the fluidity of start-up world).

So, if you are considering making a jump like this or are finding yourself at the beginning of a similar adventure, here are the three pieces of advice I’d give you based on my lived experience.

Unapologetically keep raising the bar

Joining Guild was the first time I came in as a leader (vs. earlier in my career when I’d join teams in more junior positions). While I took the time to listen and learn about what has been done and the decisions that have been made to date, I did not shy away from asking for high-quality work off the bat.

I led with curiosity and questions rather than an opinion of whether something was good enough or not. As a leader, I learned how easy it was to miss the context of assumptions being made and what the team was solving for at any given moment. Getting to that truth quickly and then sharing a point of view on whether or not the assumptions are logical helped me keep the team focused on ultimate success.

Key questions I practiced asking: Are you proud of your work? What are you optimizing for? Is this the winning plan or the most feasible plan?

I learned that expecting excellence early and consistently set me apart and made people want to follow me and work with me. I loved that I had a reputation that I expected people to bring 100% of their effort to work.

Build trust with sales and customer success teams

In a business without a large commercial install base, I was building a product that needed to meet the needs of future customers as well as set the company up for renewal of contracts with existing customers. Balancing the roadmap to strike this balance required a deep understanding of both what the sales teams were seeing and what customer success teams were dealing with on a daily basis.

It’s easy coming in as a product leader to focus on operational inefficiencies, internal stakeholders, and cleaning up processes and backlogs, but the focus I wish I had more of from day 1 was spending more time with go-to-market teams and really understanding their needs and worldview.

Marketplace businesses, especially, make it easy to unintentionally focus on just one persona instead of seeing the broader picture (e.g., the end user vs. the buyer). However, I learned that I could not be successful without that end-to-end view, empathy, and deep understanding.

While it is natural in a new role to focus on building relationships with dev and design counterparts, my learning is to actually focus more on customer-facing teams in the first 90-120 days.

Key questions I practiced asking: Is what we are building market viable? What will adoption barriers be? Why are we struggling to close deals/retain customers? What competetive plays are you most worried about?

Resilience and optimism will win the day

While every job I’ve ever had demands grit and perseverence, the ride of a growth stage start up requires it at a different level than I knew. On my best days, I was able to see every twist and turn as a new opportunity and a new thing to learn.

The burnout from this kind of churn is very real, and learning how to thrive in this environment is a skill to be mastered. Those who succeed are able to not just embrace the change but be a part of it, help define it, and ride the wave. As a leader, it’s also important to realize that this is the phase that the organization is going through and hire accordingly - ie not just PMs/Devs who know how to be product managers or coders, but those who have the patience to go through a lot of growing pains, change, two steps forward/one step back types of days.

Key question to ask: Will this candidate be able to lean into change? How much tolerance will this candidate have for strategic shifts? What are the things that will trigger a burnout?

What’s Next

As I close this chapter of my career, I’m ready to take a pause. I have been in the workforce for 20 years with no breaks, and I expect that I will have another 20 years to go before retirement. So, to avoid burnout, I’m bringing my retirement along and taking a breather to recharge and get ready for the next thing.

To that end, I’m going to learn how to live life at a different speed for the summer and take a page out of Adam’s playbook and build myself an amazing sabbatical. I plan to focus on health (physical and mental), connection with my kids, friends and family, and joy through giving.

My goal is to keep myself open to the possibilities for the future as I refill my tank and get ready for whatever comes next.

Check out and subscribe to her newsletter, Working Mom - especially if you are looking for insights and resources. For example, I learned that there is a Working Mom’s support group that you can sign up for!

[Bhavika] What do you do for work?

[Helen] I work at a late-stage startup that serves adult learners to help them upskill and reskill in service of economic mobility. I drive the student product experience from onboarding through conversion and engagement on our platform. I have a couple of teams under me and engineering and design counterparts. I love getting to solve interesting problems with smart people. My other passion is coaching so getting to do product work and coaching people I work with on a daily basis is very satisfying. 

[Bhavika] What does a best case work day look like? 

[Helen] My best day is one that I was able to plan. It would mean that I got to do deep thinking/strategy/customer insights work in the morning and then have a mix of product reviews and brainstorms and coaching 1:1s in the afternoon with people on my team. 

[Bhavika] How has parenting changed as your kids went from toddlers to their current age? 

[Helen] When the kids were younger, my life felt transactional. Winning meant getting through the day - changing diapers, feeding, bathing, reading a book, getting the kids to bed, etc. And because sleep was unpredictable, a day could get derailed at any time, so I had to be very pointed with my time at work. Parenting taught me to ruthlessly prioritize. Tactically during that period, it was hard to have hobbies or extra time with co-workers or friends. When I had extra time, I would sleep or workout. It was all about survival and meeting basic needs. 

Now there’s a little more time. Kids are in school longer and they have a lot of activities (I can see why Uber for kids like start-ups are trying to figure out this market). In some ways, it’s busier and more hectic, but it also feels physically easier. For example, two years ago, my husband and I decided to start a blog on parenting, leadership, and product management - Mind the Beet, the kids were four and seven. Things were more tenable and we were both able to commit to writing a weekly post. 

One other big shift that happened to us as kids moved from the toddler phase to elementary school is the establishment of family norms as they align with our values. Some examples include using TV as a tool to help us manage, daily reading rituals and the mentality of self-sufficiency and 100% responsibility. 

[Bhavika] You mention your use of screen time as a tool - I love that and we follow a similar philosophy for our son. Can you expand on that and talk about the other family practices have you found helpful?

[Helen] TV - it’s a tool that is in service of parenting sanity. We opt to use TV when it helps us get life and work done. So kids watch TV in the mornings when we try to sleep, on travel days or if we have late meetings and kids need to be occupied. But to that end, we don’t utilize screens during dinner time. This means that as we go places where dinners take longer (family gatherings or Paris this summer) - we plan for what that will look like and how to get kids fed and either excused or occupied. To that end, I carry age-appropriate activities to restaurants and we also have a list of conversational topics and games to help dinners go smoothly. 

Reading and learning - daily routine. My husband and I have strong conviction that fostering a love of learning and specifically reading is a gift we should give to our children. So even as kids are getting older, we continue to read to them every night and reach for books in our spare time.  

Morning efficiencies - As they got older and I didn’t have childcare in the mornings anymore (when my youngest started kindergarten), we switched to a checklist. The checklist has both pictures and words for morning tasks like wash your face, make the bed, pack a snack and they just check things off as they go each morning. 

[Bhavika] Insert amazement here from me, a toddler mom. I asked Helen how she gets them to follow it and she was like what do you mean?

[Helen] We tell them to, and they do. Amazing 🤩

And sometimes they don’t - they might get distracted and we just bring them back to the checklist. It’s an activity to do and there are fun items, too, like doing a dance or the word of the day. 

[Bhavika] Are there parts of work you bring into parenting or vice versa? 

[Helen] Curiosity is the big thing. I’m big into letting kids try and solve their own problems and not prescribing a solution for them unless it’s safety related - like crossing the street. Being curious about what they’re going through, what their ideas are, asking a lot of what/how questions, not a lot of yes/no questions. All the things we do at work, too, right? I try to create spaciousness for feelings, and conversations in daily life at home and at work as much as possible. 

[Bhavika] How do you balance the parenting load with your husband?

[Helen] My husband and I try to be interchangeable, while still sometimes specializing in certain things - a good parallel to being a T-shaped product manager. 

To make this real, I travel once a month so I’m gone for 3 or 4 days. While we have systems set up in place to manage our day-to-day - shared calendars, and WhatsApp carpool groups, when I travel for work, I don’t do anything special to prep the household like pre-make meals or do carpool communication ahead of time. We seamlessly pass the ball of day-to-day responsibility between us and add our own twist to it and embrace it as opposed to trying to micromanage it. For example, when I am out of town, the family goes out to eat more than they do when we are all home. They have rituals and special restaurants that they go to together. This gives everyone something to look forward to and to break up the hard work of single parenting.

This works in reverse as well. Last week my husband was out of town and our patio flooded so I needed to figure it out. I called a friend and learned how to stop the leak. When my husband and I were able to check in, we made a plan for the next steps. But no trip was cut short or plans canceled because of a problem at home. Having said that, we still have our specializations - he’s responsible for taxes and I manage the babysitter rolodex. But we try to be as interchangeable as possible because we want to be able to substitute for each other in a pinch. 

[Bhavika] Since you and your husband are both in leadership positions, does that ever come into conflict? How do you decide whose job is more important on any given day? 

[Helen] We actually have talked about this a lot - we have not found a lot of role models in our lives where both spouses had active careers. So to accommodate this, we communicate and try to be intentional about whose important or urgent thing we are prioritizing at any given time. 

A specific example where this comes up is around work travel. I travel monthly but for shorter periods of time. My husband travels quarterly but for a week at a time. Tactically, he supports me monthly but when he has a big trip coming up, I work my monthly travel around his quarterly one. For short term priorities (someone has an early or a late meeting and we need to juggle kid pick up/drop off) - we look at the week ahead every Sunday and write down who is doing drop off, who is in charge of dinner and who is on point for carpool. We also reduce decision making as much as possible. Meal planning happens on Sundays which includes regularly planned takeout on Fridays. We alternate reading to the girls - so each of us is in charge of bedtime for one of the kids and we switch the day after.   

I think the thing I’ve learned - and this seems like a woman thing - is not to overcompensate and just volunteer to figure everything out. For example, when someone gets sick and the plan goes out the window - my natural instinct is to absorb the load and be a hero. I’ve learned to stop doing that and instead we sit down, look at our calendars, and make a plan together. 

[Bhavika] What do you find most challenging right now? 

[Helen] Quieting the voice of not being enough continues to be a challenge. When the kids were younger, I was operating at the lower level of Maslow’s heirarchy of needs. But now, I’m back to asking myself - am I being a good parent? Being a good spouse? Am I connecting with people who matter most? As my mental space opened up, the question is - am I living the life I want with the intentionality that I aspire to. 

Reflections on spontaneity

[Helen] I redefined spontaneity in this phase of my life. My life is not very spontaneous right now, in fact, it’s pretty scheduled. And that’s okay because that’s what it has to be for my life to work right now. I also know that this period will pass and I will be able to make plans on a whim. I can already picture the day when my girls won’t want to hang out with us on Friday nights – it’s not that far away, so I am savoring this period for everything that it is. 

[Bhavika] I joked about how it takes me 3 times to schedule anything with a friend these days - someone gets sick, something comes up, and usually by the third attempt we’re making it happen. It’s kind of funny but also seriously exhausting at times. 

[Bhavika] How have you thought about career growth and parenting together? 

[Helen] I love working - I think it makes me a better parent. What I’ve been thinking about recently now that my kids are in fourth and first grade is the next 10 years. It’s really not that long and I want to spend time with them before they leave the house. So I think about what are the career paths that can support me in that goal and how much of it can I achieve working full time vs. adjustments or tweaks that I will want to make to achieve increased flexibility. 

Rapid fire questions (answered by Helen)

1. Go to recipe: Roasted broccoli - it takes 5 minutes to prep and if it’s crispy and salty enough, my kids will eat it as a pre-dinner snack. It makes me feel like I’m winning in parenting. 

2. Must have for your office: Standing desk - my husband set this up for me when we switched to working from home and it has been a game changer. 

3. Favorite kids toy: We are in Friends lego phase 

4. Best parenting hack: Pick 10 - when we need to clean up, we declare a “pick 10” and everyone needs to pick up 10 things off the floor or put them in the right place. It’s an outcome-based activity and gets the house tidy pretty fast. 

5. What are you reading/watching/listening to right now?

   1. Reading: Tomorrow, Tomorrow and Tomorrow by Gabrielle Zevin

   2. Watching: Succession with my husband in the evenings and Virgin River by myself 

   3. Listening: A lot of podcasts - the Daily, Lenny’s Podcast, Acquired, Happier by Gretchen Rubin, and Lex Friedman 

What’s one question you have for other working moms?

What do you do for self-care? 

Further Reading on Mind the Beet  

• How I lead when the world is uncertain

• Mega-corp to growth stage company transition

• Three careers by mid-30s

• Why Mentorship Matters

• A day in the life of a frontline manager

• How You Can Find Learning Opportunities Everywhere

• Interview guide for PM jobs

• Learning from failures and setbacks

• Hidden Gems for PM's Inside Taylor Swift's New Album

And while parenting and leadership may seem like two entirely different realms, beneath the surface, they share a wealth of commonalities. Both require a delicate balance of guidance, support, and the ability to inspire growth. As a parent and a leader, I've come to realize that these roles aren't as distinct as they might first appear. One of the things one of my female co-workers once said to me was:

I love that you are a mom and a working ambitious professional. You talk about it what it takes to do both and how lessons apply both ways.

I became a manager after I became a mother, and over the years being a leader at work has shaped me as a parent and vice versa. I wouldn’t have it any other way and this week I’m reflecting on how intertwined my identity is. My parenting approach is the ying to the yang of my leadership at work.

Before I get into the parallels, I want to call out an important distinction - I do not subscribe to the philosophy that my co-workers are my family. Instead, I do think of my colleagues akin to how I’d think about sports teammates. And to the extent that sometimes as a family, we are also competing or showing up as a team, there is some overlap.

So I hope to continue normalizing how being a mom helps me be a better leader and vice versa and not pretend that these parts are disconnected. So let’s dig into some of my learnings over the years.

I lead with authentic empathy

In the professional world, I am constantly reminded that I don’t know the shoes someone else is walking in. Whether it is an ailing parent or a complicated relationship with authority - through lots of curiosity, I pride myself on understanding and seeing people as a whole.

The line I often come back to at work and at home is

“I can’t imagine how hard that' person’s life is right now.”

This fundamental assumption shapes how I approach problems and people relationships and is a core tool in establishing my brand of leading with inclusion and empathy.

At home, Adam and I spend a lot of time figuring out which open-ended questions will get our kids to actually tell us what is happening in school and with their friends. I have learned about poppet trading drama at school as well as the latest trials in gaga ball games.

In both parenting and leadership, deep empathy is a fundamental trait that enables me to connect with my kids and team members, helps me understand their needs, and creates a positive and productive environment. It not only improves communication and our dynamics but also contributes to higher levels of happiness, productivity and success at work and at home.

I set clear expectations and make clean agreements

In the first few days of school, my daughter left her sweatshirt at school. I asked her to please check with her teacher and then lost and found to see where this was. She non-commitally said that she’ll try. I clarified with her that I expect her to do this and she adjusted her phrase that she will take these steps and find her missing item.

In both parenting and leadership, setting clear expectations is key. Just as my child benefits from knowing what success looks like from their commitment, a team thrives when they have a clear understanding of their goals and responsibilities. It lays the foundation for a harmonious and productive environment. At work, I am known as someone who is very clear about what I will and will not do; what we agreed to, and where there is still work to be done.

I am a problem solver and lead by example

When I think about what kind of leader I am known for, it is one who makes positive progress and produces results. I live that value at home as well.

An exercise we do at home when we need to clean up is a “pick 10” rule. We all pick up/put away 10 things around the house (or can be a specific room). I love this because it is an outcome focused activity vs. an activiity one (clean your room for 5 minutes).

My children learn more from what we do than what we say, and the same holds true for teams.Exemplifying outcome-based behaviors values and work ethic sets a powerful precedent. It fosters a culture of integrity and accountability. At home, it also creates an environment of solving problems as a team - which I also bring to work.

I am resilient and adaptive

What do re-orgs and parenting have in common? Everytime summer hits in our household, we have a mini re-org - when you have a different schedule every week with camps and travel, it brings on scheduling changes, calendars adjustments and an update to our rhythm of business. For that intense 10 week period, every week is hard and slightly unpredictable. Once fall hits, we restructure again and there is a steep curve to adapt to the new order but every week gets easier.

At work, my goal is to show up as unflappable and calm through the storms. Whether it is a change in strategy or resourcing, I strive to adapt to solve the latest and the biggest problem the organization needs help with. As a PM, that is the core job to be done - solve the right problems at the right time.

Both parenting and leadership require the ability to adapt to changing circumstances. Flexibility in approach, especially in the face of unexpected challenges, allows for more effective problem-solving and the ability to navigate through uncertainties.

In my hardest moments at work, I remember that I survived two newborn phases and two labor and deliveries. The resiliency that parenting demands serves me well in the workplace (and no, shipping features is not the same as birthing babies).

I am an empowering leader

As kids are getting olrder, they own certain things that they need to do in our house. For example, our 9 year old packs her own swim bag. This means that I don’t touch her bag or help her with it because this is her job. She also packs it in a very different way than I would (in stages and not all the once). However, the important thing is that it gets done and she is in charge it.

Empowering my children to make decisions and learn from their experiences is akin to entrusting my team members with responsibilities. It fosters a sense of ownership, boosts confidence, and ultimately leads to greater autonomy and growth. My team solves problems very differently than I would - so as long as I paint clear success, I then step back and let the team figure out how to get there. As it turns out, there is more than one way to solve any problem and it doesn’t have to be my way.

I celebrate success - big and small

Cheering people on is a work in progress for me. At home what it looks like is celebrating hard work to earn a personal best swim time or an improvement on a spelling test. Adam and I reward paying attention and learning fun facts at the zoo or a museum with other fun experiences or small treats.

At work, I give praise privately as soon as possible and publicly as often as I can. I also pass on praise to teams and people who have earned it so that people feel seen. I remind myself that I most likely do not say thank you or send enough appreciation into the world - so booking time at the end of the week to send a couple of notes to people is a hack I try to use.

Acknowledging achievements, no matter how small, is vital in both parenting and leadership. Celebrating milestones, progress, and contributions boosts morale, fosters a positive environment, and reinforces a sense of accomplishment.

So what?

What I love about working at Guild, is that it does a great job supporting people to be their whole selves. I don’t feel like I have to check my “mom” persona at the door, which is great because as a human, I can’t compartmentalize being a parent and a leader. I think deeply about how lessons in one part of my life, apply to another. In fact, I plan to do a post soon on how managing a family is not too different than managing a product (basically my take on Emily Oster’s Family Firm).

If you are just joining us, here are the topics Adam and I write about:

• Career - We are both leaders in the tech industry, so these are articles that reflect on the growth and intentionality with which we approach our careers

• Product - Adam and I are also both product makers, so we write about important lessons for product managers from Taylor Swift’s lyrics as well as more serious topics of skill building, possible product manager futures, etc.

• Parenting - We are both very active with our family life and our two girls. So if you are looking for the latest books and TV shows for kids, travel and back-to-school survival guides, or musings on mom guilt while traveling, check out this section

As is tradition on my work anniversary, here is a note to my 2005-era self, just starting a career in tech. It’s the fifth version of this note; I add one more thing every year and refine the rest to reflect the biggest concepts on Mind The Beet.

It’s hard to capture the awesome privilege, luck, and support network that I’ve had in my time here that were major determinants of my success, and I’ll ask for grace as I do my best to synthesize my own lived experiences with these eighteen biggest lessons.

Dear fresh-out-of-college Adam from 2005:

Congrats on your job with Microsoft!  What an interesting time to start in tech - you just signed up for Facebook during your last week of final exams at UCLA, Google IPO'd one year ago, and the iPhone will launch in 2 years.  You will see cloud & mobile go from niche to indispensable worldwide utility and the AI era is just beginning as I write this.

Your career will span the Golden Age of tech, with all the dividends that provides as well as all the unsolved risks that powering the world economy brings - security, privacy, AI ethics to name a few.

In your own corner of the industry, you will live through a generational shift in computing from on-premises to the cloud.  A paradigm shift will be fascinating to experience as you’ll try to stay customer focused under a cycle of unbundling and re-bundling.   You’ll read about DEC and IBM and Intel and be shocked at the historical similarities.   This will also teach you that large organizations are not as set in stone as intuition implies.  Satya’s leadership as CEO will allow you to experience a transformation when culture, business model, and strategy align to the right market conditions.

The most controversial part of your career is that you stayed with the same company for 18 years, reinventing yourself as the company grew, extended, and transformed.  This was not the plan and leaves you reflective on how to avoid states like good enough and comfortable.  If “the unexamined life is not worth living,” how can one do enough self-examination without seeing what’s out there?   Your own lived experience these past 18 years proves that one can thrive by staking out a product and team as a home for a while.  

Here are eighteen things you’ll learn in eighteen years.

Starting Your Career

Let’s start with a few lessons on how to start and evolve your career.

1. 👕 Early on: Prioritize fit over growth.   

For the first 5 years out of college, you’ll ask yourself more what you love to do rather than how to have a great career.   You will treat this just like a product backlog and ensure you have a flow of good options to sort your current job against.  You’ll have a fellowship that gives you an option to go back for a PhD in 2 years. You’ll consider switching to being a dev. You’ll sit in on MBA classes. All of these will rank poorly against the notion of going deep on product at a large company, but you’ll gain confidence about the Tech-x-Business career path by asking yourself the questions.  Doors will indeed start to shut 5 years into the career, where the consequences of a non-linear career shift increase, but the unhappiest folks you work with are those who never pressure tested their role or job.  They optimized for growth over fit.

2. 🧼 Establish great fundamentals: Time, tasks, info diet.

We live in a time when the information in the world is doubling every 5-8 months now – you’ll need to invest time to ensure your ability to consume information, tasks, and communication keep growing just as fast.  Early in career, you’ll focus on the basics of being a curious, informed, and hungry member of the knowledge economy.  Smartly managing your time, your tasks, and your information diet has a way bigger impact on getting you to leadership roles than anything else.   You’ll learn the difference between urgent and important.

3.🪴Evolve your job until you get paid to learn.

You are the son of a teacher; the love of learning was instilled in you at an early age. This will be your best secret weapon. It will help to remind you of the power of curiosity as a cure for burnout. Being around those who love to learn new things will help you anticipate contemporary trends and paradigm shifts. You’ll have a mantra for when you are at your best: You should spend 80% of your time on the job learning. That’s not a typo - it forces you to incorporate learning into what you do instead of just relegating learning to a couple of classes a few times a year.

4. 🏄‍️ Think about your career as finding, catching, and riding the right waves.

When you start your career, you’ll be told it’s the start of a long upward journey that must build on itself. This “career ladder” metaphor does more harm than good. No, better to think about your future as catching some waves. This will get you thinking about repetition and cycles, project selection, riding something with more momentum than you have yourself, and knowing when you are in the whitewash and need a change.

5. ✌ Find the epic difference makers in your work.  

“No matter how good you are, you're going to lose one-third of your games. No matter how bad you are you're going to win one-third of your games. It's the other third that makes the difference.” - Tommy Lasorda

This quote speaks to how you think about the quality bar for your work. There is only a part of your work that will be a difference maker - and puzzling out where to stretch yourself every season will be the key to remarkable results. You’ll gravitate to the word “epic” to represent this. Epic means finding the problems where extreme pride in the quality of the work will make a difference. This will sometimes be high visibility projects but sometimes it’s the unsung efforts that are just as epic.  You'll remember vividly that one of your first projects at the company was to write fifty error strings for various problem conditions.  You will take the time to understand each condition, establish a consistent error taxonomy, and just in general write the best damn error strings on the planet.  It's not that it was hard; it was just that no one else had time to go deep like that.  For you, that season as a junior employee focused on high craft, stellar error strings will be the highest impact way to be epic.

Sustaining Your Career

It’s not really about “work/life balance” - it’s about managing your energy and exploring how what drives you will change over time.

6. 🏓 Define the boredom & burnout boundaries. 

If you are going to stay on the same team, you need to watch your own boredom.  But what is boredom anyway?   Frameworks help.  You’ve seen many over the years and two stick out to you: Daniel Pink's Autonomy, Mastery, and Purpose is the best quick framing of what goes into staying motivated.   And Mihaly Csikszentmihalyi’s Flow Diagram is a high bandwidth way of ensuring you think about peak performance.

7. ☕ Over time, it becomes less about mastery (“How?”) and more about purpose (“Why?”).

You will wish someone had told you that finding your purpose happens over time and the desire for deeper meaning crescendos mid-career. It’s common to focus on mastery in the first part of your career - society wants you to just get good at something in your 20s and early 30s. It’s much less clear on what to do with your now finely-honed skills in your late 30s and 40s. It’s amazingly universal that people stumble into a mid-career crisis trying to figure out how their work has meaning - and the solution is just to talk about it with colleagues and explore what drives you over time. “What’s your purpose?” will be a source of deep and meaningful connection with other leaders as you age.

8. 🏖️ Take your retirement along the way.

Careers need to be like the old magnetic hard drives - they need serious pauses in them for maintenance defrags. Every few years, you’ll find a way to take an extended time away from work - more than just your typical 4-5 weeks of scattered paid time off every year: at least six contiguous weeks, one time up to 12 weeks. The reasons vary - honeymoon, paternity leaves, sabbatical. You will intersperse your retirement time into your career while you are young enough to enjoy it. You'll be fortunate to have a work culture that supports people through time off; it’s one of the reasons you’ll stay for so long. This is a privilege. The pauses will make you a more interesting person and unlock your understanding of what drives you. This inner purpose will make you a better teammate & leader as people gravitate towards those who are centered and calm. There is a lot to learn about how to maximize your recharge time.

Software is about people, not bits

At Microsoft, the biggest multiplier to your impact will be the scale of working on problems that require hundreds or thousands of people to properly solve.  It will be the biggest reason you don’t go back for the solitary pursuit of a PhD.  You’ll develop a core thesis of how you want to influence, connect, and bond.

9. 🧠 Learn to thrive in the matrix.  

As you grow to coaching aspiring PMs, the most impressive PMs will be those who not only think they are right but are willing to put in the commitment to gain buyoff of that fact.  Unabashedly, the job of a PM is to form a coalition around ideas and plans with stakeholders who have a different lens than you.  When you find willing partners who take the time to build a sense of shared safety and context with you that enables the intense exchange of different views, you’ll have the most fun and fastest progress.

10. 🚦 Don’t start solving a problem when you should be signaling support.

“I've learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”  - Maya Angelou

“Give praise” will be one of the top pieces of advice from one of your favorite managers. It’s obvious on the surface, but all too often in this fast-paced tech world we move to solutioning or sharing advice too quickly. There is power in plainly sharing support for an idea or a colleague’s mission, especially by praising their work. Behind this is the need to not only focus on what people think, but what they want and feel as well. Our thoughts are impacted by wants and feelings, not the other way around.  I think we all intrinsically know this when we react to a proposal from someone we dislike or when we judge our kid’s behavior more harshly after a tough day at the office.   Our neural processing units are constantly impacted by our background feelings and wants - nurture them with praise.

11. 🤗 Find your “First Team.”   

Microsoft is highly matrixed, even more so as a middle manager: your team, vTeams, partner teams, other disciplines, peer PMs.   And it’s important to create a great environment for the people who report through you – but the key to happiness is to ensure you can define a “first team” of peers in PM and other disciplines that you can rely on for support.  Find the space where you can be yourself and broker the deep relationships among those who can relate to your struggles. Find people you can laugh with.   Your unhappiest times are when you tried to create your own team tribe vs. joining the one around you.

Making Great Products

Your chosen profession of product management evolves and professionalizes over the course of your career.  Part art, part science – and a lot of time making decisions in the face of ambiguity. As you deliver and scale more and more products, four major themes will emerge that define your craft: empathy, impact, love, and trust. These are the four elements of product management.

12. 🌌 Empathy: Build a model of customer needs. Enable your team to run the simulation.

You will grow up early in your career as a product manager in a specialized area of software with complex customer requirements. This will be a gift - it will teach you the power of building a model of customer behavior and teaching it to the rest of your team.   For you, this will be a familiar part of a PM’s job – like physics or economics, it’s building a useful synthetic model of the world around us that quickens decision making and group understanding. Importantly, you won’t build this by sitting around thinking - you will build these models by deep interaction with customers, solving their problems, hearing them complain, and trial and error. Translating your stress and daily struggles into actionable insights is the essence of PM.

13. 📈 Impact: Champion results over activity.

Five years into your career, the cloud paradigm shift will begin.  This will fundamentally transform your profession – enabling data analysis, experiments, and more hypothesis-driven thinking.   You will be responsible for transforming a slower and less dynamic product culture into one that embraced these now standard practices.   It will teach you how much discipline it takes to prioritize outcomes and impact over activity.  You will learn to replace adjectives with facts in your performance evaluations and to always be ready with the “why” behind an activity. You’ll learn to drive for results.

14. 😍 Love: Nurture your product intuition about what pulls people in.

There will be a debate in your profession about whether product intuition exists - Can one develop an innate gut feel for high craft products that generate love from users?  Or can it all be distilled down to data and decision-making rubrics?   You will conclude that there absolutely is product intuition. Indeed, product intuition is what gives legitimacy to a great PM - many people can look at an experiment results and translate it into how it helps move internal metrics, but great PMs can do that and stay grounded in what will make people love the product. My biggest advice for developing this is product play - channeling that inner child as you use the products around you.

15. 🤝 Trust: Honor the faith customers are placing in you.

I heard a quote recently that at a tech company, there are only two jobs: you build product or you build trust.   The latter refers to all the “around” product work of support, sales, adoption, and customer success.   As the pace of change accelerates in your industry, you will realize how much building customer trust matters just as much as building the right product.   Building bridges to help customers migrate from old to new is one of the most overlooked parts of product management.   This is also why you will gravitate towards nurturing the community around your products – it will be an honor to support the people who bet their careers and livelihoods around the ecosystem your product creates.

Leadership

Motivating and inspiring others and generating the legitimacy to do so will become an increasingly larger part of your job.

16. 🧘‍♂️ The Power of Calm.

As a leader, you’ll pride yourself on not tapping into the stereotypical table-thumping tech dude persona - anger is not your vice. It will take you time to realize there are a wide variety of negative emotions to watch out for - cynicism and frustration are yours. They can be good bellwethers that detect intractable situations where you need help, but often they are the cause of your biggest stumbles. Indeed, people are attracted to calm. Learning to tap into patience & optimism and creating systems to help others do so too will become a focus area. Your latest motto: Do hard things in a calm way with me.

Do = Act, not think or talk.

Hard Things = We do what’s difficult so our customers don’t have to.

In A Calm Way = Patience, attention, focus, and optimism.

With Me = We are in this together.

17. 🔍 Where you put your attention matters.

A retiring member of your LT will give you a big gift on his way out - he’ll tell you that you should use the phase “I need” and “I expect” way more. Plainly & simply setting expectations - not digging in to solve problems - is an essential part of being a bar raiser. Indeed, senior leaders on your team don’t want you to solve their problems, they want to show you how they can do great work. Of course, the problem with this is that there are more problems than time and resources - so leadership is about great judgment on where you focus and what you ask for.

18. 💖 Modern leadership is about empathy, vulnerability, and allyship.  

You’ll have friends who lose their jobs due to the disruption your product causes to the industry, as moving to the cloud requires less racking and stacking servers by customers.  This has a profound impact on their lives.   What a way to drive home abstract charts on cloud growth rate and disruption and value chain.   What we work on matters.  I can’t for sure know what would have happened if Microsoft had invested more in training and job evolution when we launched our cloud, but I can say having more people at our company from historically economically and socially marginalized communities will help us see blind spots like this earlier.   Technology and society are more intertwined than ever.  Modern product is so iterative that it requires deeper empathy for our customers.   Leading diverse teams requires showing vulnerability and speaking publicly about allyship.   You can read from Jack or Eric if you want, I suppose, but modern leaders need to spend more time reading Ijeoma and Brene.   It’s where the hope of tech’s future lies.

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Summing It All Up

This newsletter is called Mind The Beet for a reason – it’s a quote from Tom Robbins' Jitterbug Perfume that speaks to the eternal struggle of defining your own reality in the face of processes and pressure and systems. The first 18 years of your career will be about influencing large systems, not letting them consume you.   Mind the beet.

Further Reading

Subscribe now

Starting a Career:

• 🏄‍♀️ Why New Grads Should Surf, Not Climb: The #1 piece of advice for new grads.

• ⌛ How does a product leader manage their time? Thoughts on time & task management and what’s worked for Adam

• 📚 Information Diet: Recommendations for news outlets, analysis, podcasts, and newsletter subscriptions from an information junkie

• 🪴How You Can Find Learning Opportunities Everywhere: A philosophy on incorporating learning into your product management routines.

• 💎 From Product Manager to Product Leader: A career guide with a focus on the most important inflection point.

Sustaining a Career:

• 💭 Finding Purpose in Tech Careers: My journey to becoming a purpose maximizer.

• 🥱 Burnout & Boredom: A Manager’s Pandemic Retrospective on Mental Health: Learn about Flow and other tips for managing burnout

• 🏖️​ Adam's Field Guide to Happiness: The Secret to Amazing Paid Time Off

• 🐟 Adapting to mega-corp culture: Context for people moving into Big Tech jobs.

• 🎞️ My Career Highlight Reel: How to synthesize your career journey.

Sofware is about People, not Bits:

• 🔗​ The People Angle: How to build x-team products

• 🤝 Thriving in the Matrix: An informal podcast interview on x-team work.

Making Great Products:

• 📣​ My 10 Favorite Productisms: Pithy sayings with pearls of product wisdom behind them

• 🎶 Taylor Swift & Product Management: Tips for PMs from her latest album

• 👓 Interpreting Blurry Situations: Making decisions in the face of ambiguity.

• 🪀 Product Play: Where my best product ideas will come from

• 🧳 Sharing the Point of Tech Conferences: How to be inspired by your community.

Leadership:

• 🎁 The Gifts We Hope to Give: Learn a bit about how we approach parenting and leadership

• 🐝Survival Tips for Team Leaders: Reorg Edition. How to plan, decide, and announce an organizational change.

• 💼 VP of PM: What’s the job really like?

• 😶‍🌫️ My Mood Board: A visual way to show how I lead

As I have been delivering various talks and podcasts at learning days and conferences this year, I’ve started including my career highlights reel in my opening remarks. This tour through big moments in my career gives context and satisfies audience curiosity about “how I got here.”

I’ve found the elevator pitch takes a lot of refinement to get tight. A career is hardly the single trendline that hindsight provides, and yet summarizing it well shows clarity of thought and a passion for good storytelling.

Everyone deserves an inspiring origin story.

A great career highlight reel is short - less than 3 minutes and 1,000 words. Every word either helps the narrative or frames a lesson. It also has these elements to it:

1. Organized: It breaks your career down into chapters, each with a chosen main learning and goal (while it’s tough to choose a single learning for years of work, it tightens the story).

2. Clean: It sacrifices humility for brevity. You should remove all the qualifiers and caveats that muddy the language - make it about what people can learn from your career, not what you want them to think about you.

3. Contextualized: It connects your career to what was going on in the industry at that time. The context makes the story more relatable and encourages people to connect their own career to something larger.

4. Romanticized: It removes all the people drama, short term setbacks, and daily struggles. You should focus on what still matters now, not what you thought mattered then.

5. Authentic: It includes just the right dose of vulnerability and uncertainty. While your highlight reel isn’t a time for wallowing on wrong turns and hesitations, incorporating a few times you questioned your path and experienced major headwinds encourages follow-ups and audience curiosity.

The rest of this post is my refined career highlight reel from all the practice this year, putting these five tips into action.

If you like the approach, consider doing Helen and me a favor and sharing out this post as a helpful best practice.

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My Career Highlight Reel

I like to think of a career as a set of waves to surf rather than a ladder to climb, so I broke down my past 18 years in tech into five waves I’ve caught, each representing major learning milestones and different coalitions I’ve been part of.

Wave 1: Years 1-2 - Fit Before Scale

Entry-level Program Manager

In 2005, I graduated from UCLA with degrees in Business Economics and Computer Science. I had a few technical and coding internships under my belt and more than average student leadership experiences.

In my final year, I earned an NSF fellowship that I could defer for up to two years to go back for a PhD. So when I got an offer from Microsoft to be a Program Manager (a job that seemed suited to my blend of business, tech, and human relationships), I leaped in and figured that if I didn’t like it, I’d go back to college.

I joined the Office organization in the last year of a three-year release cycle. I immediately fell in love with the job - working late into the evening after taking on stretch projects. The biggest difference for me was that I was working on systems and goals larger than myself - indeed, Office was one of the largest code bases in the world and the pride the organization had for organizing thousands of people’s efforts towards one final product was inspiring. The job of Program Manager was something that I took to instantly as well. My academic life had been split between classroom technical learning and student leadership: here was a profession that combined both into one.

I examined many potential paths, sitting in on MBA classes and considering whether to switch to a software engineer for instance, but the gravity well of PM working on global scale problems pulled me in.

Wave 2: Years 3-7 - Learning Customer Empathy

Program Manager Lead, Enterprise Security & Compliance Toolkits

After achieving confidence that I had found a profession that fit, it was time to be intentional about what coalition I wanted to join. At the time, Enron had collapsed and the new Sarbanes-Oxley regulations were increasing customers’ expectations for technology to help with compliance and security controls. It was clearly the start of a new wave and I had an opportunity to get in early.

Today, this is a business generating tens of billions of dollars of yearly revenue for Microsoft - but back then it was a brand-new business line and this was my first experience with the creation of a new economic engine. This was an intense crash course in analyst reports, market dynamics, sales blockers, and growth flywheels.

More importantly, this was a wave that allowed me to hone my customer empathy skills. Enterprise compliance and security requirements are esoteric - they require the creation of specialized software that I as a PM would never use myself since I’m not a lawyer or compliance office. As a result, my role as PM was to learn and then teach an entire model of customer behavior and needs to the team. I’m grateful I cut my teeth as a PM leader in an area that required such customer curiosity and one that put the role of PM front and center in defining a team’s worldview.

Wave 3: Years 8-9 - Building the Cloud

Group Program Manager, Cloud Backend

In 2013, my career was accelerated by a lucky opportunity. At the last minute, someone backed out of a GPM gig and the Director asked me to step in. I left my comfortable home building compliance solutions to lead a team laying some of the foundations for our cloud services - authentication, authorization, provisioning. It was at the very technical heart of a paradigm shift the entire industry was going through. Such paradigm shifts happen about a half a dozen times in one’s career. Mainframe → PCs → Mobile → Cloud → AI. They are a time to reexamine old assumptions, create massive new markets, and create bridges from old to new.

I still call this time my “tour of duty” deep in the technical stack. I knew it wasn’t going to be a long-term home for me since most of the problems were deeply technical and there were few user experience or business problems that would make best use of my skills. Yet it gave me respect, empathy, and awareness for global cloud scale tradeoffs that I still use today. And it was a great proving ground for me as a new group leader - focused on generating energy and reducing ambiguity during a time of momentous change.

Wave 4: Years 10-14 - Empowering a Design-Led Culture

Partner GPM, User Experiences Incubations and Refreshes

Zune and Windows Phone - while far from financial successes - served as a wakeup call at Microsoft during the mid 2010’s on the power of design-led product making. The bar was raised on user experiences and the company put more focus on high-craft, consumer-grade products.

This push was well timed for the need to overhaul the UX of my team’s product for the cloud era. I was plucked from my tour deep in the stack and asked to run a UX incubation team, which eventually turned into a full-fledged UX refresh of what is now a product used by hundreds of millions of people every month.

This was a time defined by needing to lead a team through significant role evolution. We doubled the size of our Design team and positioned User Research with mission critical responsibilities. We moved the Test function to Software Engineering. We hired a Data Science team as the cloud enabled UX experimentation. My role evolved from Program Manager to Product Manager. All this ambiguity was stressful - many colleagues left the organization and it was unclear for a while whether the organization was going to survive. It seemed like every day we were reforming expectations around who did what, tailoring our systems and processes to the cloud and the now higher expectations for craft and experience. It was a spicy time.

As a leader, this wave taught me grit, the power of focusing on customer outcomes during times of organizational upheaval, and how to use my privileged position in PM to help emerging disciplines thrive (in this case Design and UXR).

Wave 5: Years 15-18+ - The AI Era

VP of Product, Cloud Apps & Platforms

They say the seeds of the next paradigm shift show themselves on the tail end of the last one. So, while ChatGPT brought AI to the public consciousness in 2023, when I look back on my career, I’ll feel like the AI era started a few years earlier in ~2021 or so.

It was then that my job evolved with the changing needs of the business. With our tech infrastructure transformed for the cloud and our UX meeting the raised expectations, the next challenge was line extensions to our existing businesses - new tools & products sold to our existing customers.

This was a chance for me to combine the learnings from the previous waves of my career - customer empathy, technical leapfrogs, and high craft - into 0→1 product making. I helped launch and scale new product categories with multibillion dollar revenue potential.

This is a wave I, like the rest of the industry, am in the middle of surfing, but it’s coming into focus that I’ll combine these new product lines and the emerging AI revolution together to enable me to find just the right wave for me in the AI era.

Wrap Up: Bonus Content

If you are curious about my top lessons learned over this journey, check out my 17 top lessons from my career. I update this post once a year, adding one new lesson and refining the others, and later this month is my Microsoft work anniversary so you’ll see the refresh soon.