For about four months, the team has been planning an event that marks the moment, including:

• Public previews of new user experiences and AI enhancements to the product.

• A digital event that recognizes the community & announces these new product enhancements.

• Blogs, demo videos, and website updates to reframe the product for the new era.

• An employee event to celebrate as a team & a smaller founders’ dinner to bring together the original builders with the current leadership.

You can view a recording of the digital event here:

Marking these milestones is an important part of building a resilient product and ecosystem. And launching product and managing digital events is a skill we’ve been building capabilities around for years within my organization, in tight partnership with design and marketing.

Here are 10 tips for any product leader sculpting a product announcement event.

Tip #1: Respect the fans

When we started planning for the event, our first principle was that we didn’t want to turn the event into an ad for our product. There were 25 years of history – careers built, events attended, projects launched on top of our platform – to recognize. And a vibrant community that is embracing new ways of working.

To recognize this, we started our digital event with a huge thank you to the community and showed a preview of a movie we are producing called “Beyond the Code” that gives voice to the community and puts people at the center of the storytelling.

Tip #2: Balance the past and future with intention

We also had a principle that we wanted the moment to look forward – to the next 25 years. After some debate, we landed on a goal of 80% looking forward, 20% recognizing where we’ve been. We baked this into how we thought about the event, for instance with its primary graphic: A tagline all about the future, with some graphics that nod to history and the moment:

We also turned the birthday into an engineering delivery milestone – ensuring new innovations were ready to be announced on the day. This allowed us to lay down a clear vision framework, back it up with new product releases, and generate buzz about what’s new. I was happy to see that attendees anchored on the future in their social recaps:

Tip #3: Show, not tell

People love stories and they love seeing things in action. They don’t love having things described to them. So, another principle we lived by for this event is to “show not tell.” This came out in two flavors.

First, where possible, customers shared their scenarios - in their own words. It was intentional that we closed our live broadcast with customer testimonials.

Second, when we had a choice, we let the product speak for itself vs. telling people about the product. For instance, our design and video production team produced an “Anthem” video, a 2-min tour that shows the product at its best:

Tip #4: Explain your product in basic terms

One thing missing from v1 of our event script that we caught during the review process was a simple restatement of what people hire our product to do. We were so focused on the new product announcements that we didn’t put ourselves in the shoes of the audience enough.

This reminds me of this graphic by John Cutler (who runs a great product Substack called The Beautiful Mess):

Our fix was simple - before getting into the product news on the live broadcast, my design counterpart and I spent the time synthesizing the top 3 major use cases for the product, told through customer examples.

Tip #5: Deliver different content, tuned to various audiences

It was a relatively last-minute decision for us to split our blog strategy into two: My boss would have the byline on a short post on a primary Microsoft blog that was designed to garner some press attention. I would be the assigned author for a long and detailed post designed for our community and current customers. (Fun fact: Those blog posts are written by a team of a dozen of us across marketing, product & design, despite a single byline on the post itself).

This type of audience bifurcation is important to maximize reach – and it also inspires the best content ideas because you aren’t trying to make everything appeal to everyone.

For instance, an engineering leader on the team wrote a technical deep dive on our new AI architecture. The post isn’t for everyone - it’s by a dev for devs to read - but that type of “long tail” content can connect with a reader in a stronger way than the high-level content.

The extended content should relate back to the main points you are trying to get across. In this case, this technical deep dive enabled us to explain that the AI functionality we delivered was only possible because of the latest frontier AI model advancements of the past few months, reinforcing that customers can draft behind the latest advancements by using the product.

Tip #6: Simplify momentum & customer stories

One truth I’ve learned is that the toughest paragraph of the blog post is almost always the first one. There are three goals when deciding how to start a product announcement blog:

• Establish credibility and momentum for the product

• Speak in the language of customers & reference their successes

• Cement the narrative of how the product and the announcements are part of a larger story.

Here’s where we ended up with our most recent launch:

Tip #7: Have clear calls to action (CTAs)

Early on when you are planning an event, write down exactly what you want audience members to do after they attend the show. For instance, our CTAs were:

• Turn on the public previews of the new feature announcements in your Microsoft 365 tenant

• Participate in a hackathon to see what you can build on the platform

• Share your story and history of the product, to recognize the moment

• Join us at the upcoming Microsoft 365 Community Conference in April.

Oftentimes, teams get so caught up in describing the new feature or announcements that they leave CTAs as an afterthought. If you bake it in up front, you can tailor your content strategy. For instance, I mentioned our hackathon is the very first sentence of our detailed blog post. And we held the final version of our community video to premiere at the upcoming conference, allowing us to reinforce the conference during our broadcast.

Tip #8: Establish a quality bar

These product launch events are just like weddings - they can be planned in a day, or they can be planned in a year. They will fill whatever time you give it.

Ensure the workback time is well spent - especially by setting a quality bar, giving clear guidance on how far from the finish line something is, and in general setting a culture of going the extra mile. It’s an important tone to set “from the top” early on in the workback.

I talk about this in my recent essay on how to edit work:

The editing to be done here can be both big & small.

Example of big: I decided a week before the event that our customer testimonials weren’t strong enough, and I asked the team to go hunt for more.

Example of small: I sweated every detail of the blog post, for instance ensuring we never take possessive ownership over the product or customers (i.e. it’s never “our customers” or “our product”). And I ask for a “de-jargon” pass - removing insider terms or non-humanistic language.

Tip #9: Make each member of the cross-functional team feel seen

One of the best things about these events is that it brings every discipline in the product making process together in a way that let’s everyone see others doing their best work - and stresses that so much of enterprise software is more than just the code written. For instance:

• Product: Putting customer scenarios at the center of demos, landing schedules, evangelizing the news

• Marketing: Simplifying the complex, aligning to bigger narratives and missions, attaching to larger funnels.

• Design: Leading how the product is showcased, co-delivering the messages, graphics & swag elevation

• Engineering: Delivering on time, describing the architecture and tech bets.

• Community organizers: Collecting fan feedback, nurturing watch parties, attaching to community events.

• Customer experience PMs: Finding customer case studies, synthesizing statistics from previews

• Data science: Synthesizing evidence to support the message, assessing readiness to launch

• Chief of staff and executive assistants: In person event execution, decorations, logistics, and keeping everything running smoothly

• Event producers: Setting a bar for production quality, owning the workback, preparing on screen talent

• Video producers: Visual narrative, polish, production quality

There is a member of my LT who drove this event as the primary event producer - she’s been in tech for decades but has a degree in film. It was so fun to see her in her element - fully activated by what she loves to do and what she does well.

It’s a great reminder that certain work activities - especially those with a “big day” to lead up to - are fantastic for helping a team bond and celebrate a shared success.

Tip #10: Have fun

It can be so easy to get caught up in the workback, deadlines, unexpected hiccups, and urgent review cycles. It’s important for you as the product leader to navigate through this with a sense of levity, celebration, and gratitude. Breath. Recognize the work. Remind people what a privilege it is to have people who are interested in the product you create. Have fun.

In that vein, I’ll leave you with our blooper reel:

Giving feedback with situational awareness and consistency is a complex skill - it’s helpful to have a name for it. I call it embracing an Editor’s Mindset. In a newsroom, journalist writes articles - it’s their name on the byline. Yet the newsroom editor plays a critical role - establishing standards, connecting the big picture, and owning the tiebreaker when necessary.

As 2026 is now at full speed, I’ve found myself needing to be an editor of key work - product strategies, exec presentations, budgets, marketing pillars, conference logistics. It’s got me reflective on what I’m like when I’m at my editorial best. Here’s a few things I try to keep in mind.

Nudge towards a team outcome

Your job as an editor is not to share the right answer - it’s to drive the right behavior so that the team self-owns the path forward. First, decide on the outcome you want - how you want the team to act, the final product success, the alignment among disciplines in the organization. Then, with that outcome in mind, figure out the right feedback that will nudge the team in the right direction.

Example: If I know a cross-team dependency will be tricky, I will ask “Is the other team onboard yet?” and offer to make intros to cross-team leaders. I do this instead of listing all the gotchas I think might exist. The outcome is to build the x-team bonds and let the team discover, own, and work the issues.

Tailor to the receiver

The best feedback is tailored to the people receiving it. How do they like to receive feedback? How blunt do you believe you can be? Does a certain discipline respond better to certain language? This often requires a “stop and pause” moment in yourself - to not only think about the outcome and your insights, but how to phrase them in a way that’ll be best received.

Example: I’ve got colleagues who I know need validation before feedback. I’ve got others who prefer blunt 1:1’s to hash things out, as they believe conflict breeds conviction. Some of my team prefers to be told what I want them to do; others prefer loose operational guidelines. And for new people to the organization, I try to provide more context than normal to frame the rationale behind a suggestion. Rather than one specific example, the point is to go through the editorial process with recognition on how to speak to each person in a way that’ll have the most impact.

Less is more

There is a “Schrodinger’s cat” element to feedback: If you give a second piece of feedback, it impacts and often dilutes the first piece of feedback that you give. Lots of feedback can muddy the water - or leave the most important feedback hidden. Sometimes your role is to leave line-level comments on a document, but don’t let that be the only altitude you work at.

Example: One tactic I use in some situations is to limit myself to two or three top nuggets of feedback. It forces me to prioritize and home in on what I hope will be the biggest unlock.

Uplevel the storytelling

The role of an editor involves giving advice on how to frame and deliver the story. Beyond just the ideas themselves, an editor gives feedback on the way it’s communicated to stakeholders. It’s good to have intentionality on when you are giving feedback about the ideas/plans/goals and when you are giving advice on how to communicate it.

Example: One phase I use often is, “I think we are aligned on the goal - now let me give you some thoughts on how we can best communicate it to stakeholders.” I’ve established a contract on my team that I often rely on them for the best ideas, and they can rely on me to know the dynamics of the company well enough to know the best way to sell it.

Force the team to use first principles

Most meetings jump ahead to focus on the “problem being discussed today” or “to recap last time, now we only have to dig into these remaining issues.” This approach is often efficient and useful.

However, there is another tactic I see used frequently, especially by very senior and busy execs. They intentionally broadcast ignorance about a topic - even if they’ve met on it before - to force the subject matter expert to explain it from first principles. A cousin to the ELI5 communication style (Explain It Like I’m Five Years Old), this forces a presenter to think about the assumptions they are making and do the prep work to be able to communicate the end-to-end picture to someone smart and on their side, but not deep.

Example: We have quarterly strategy reviews with higher management and often I show run them on behalf of the team. Explaining our product and strategy to busy people who have not been in the weeds with us is a gift. Every time, we use it as an opportunity to hone the craft of explaining what our product is hired to do & de-jargonify our presentation style.

Give a grade

Part of the job of the editor is to give clarity on how far away from the finish line the work is. Great editors learn to give a grade that is not about judgment but is rather an empathetic signal to the team about expectations. Many people struggle with this because friends don’t give friends grades. But an editor is not a friend. So, it’s a recognition that you have to use your authority to drive clarity in a way only you can.

Example: I have two methods for this. First, if appropriate, I give letter grades - especially if it’s not about an individual document but rather collective effort (e.g. “Collectively, we’ve done a B+ job of embracing industry standards here.”). If it’s about a particular work product, I use a % complete assessment - “What I saw today feels about 60% complete, you’ll get there once you address X and Y.”).

Use rituals to give feedback early

The most stressful type of feedback is the feedback that comes too late - the type of feedback that is right but costly because it requires the team to unwind things that have already been put in motion.

A “culture of safe, early feedback” is a norm you can set as an editor using rituals and operating rhythms. Official pre-reviews. Core Design Sessions. Repeatable Budget Reviews. Well-run teams don’t hide behind “needing to move fast” to skimp on the feedback forums that set norms.

Example: Our org sets an expectation that important work will need multiple forums to hone the idea. We codify “pre-reviews” and “hot issues” to work something urgent and set expectations that ideas are not final in those forums. Likewise, we have official forums for reviewing final plans, to give that sense of completion and sign off.

Wrapping up

Embracing an editor’s mindset is different than mentorship, as it is fundamentally about being “in the arena” with the team and co-developing strong plans and work product. But it shares a lot of characteristics - often it’s about teaching, not telling, and it involves removing the ego from your communications. It’s one of the most powerful ways you can signal that you care about a culture of high performance.

Give it a try - especially if you catch yourself seagulling.

Today, a couple years into the AI Era, I feel ready to talk about how I’m leading through what has been an even bigger change to my team and our industry.

For many of us, the current operating environment is a crucible i.e. a severe test. In the past year, we’ve mix shifted resources on the team from 20% on AI to 50%. That’s half the team producing a new type of software that we have never built before! It’s forced us to relearn, rethink, and retool our production function at the same time as we deliver immediate results to compete with high velocity, AI-born competitors. And stay excellent at the traditional web app development that we’ve been world class at! Throw in layoffs and a return to office mandate that is upending the contract between company and employee across the industry - and we have a full cocktail of operating environment changes.

I know many product leaders feel this exact same angst - maybe you do too! What defined mastery in our profession has changed. I don’t feel like an expert yet, but we have missions and mandates that requires us to perform as experts immediately.

If your job as a product leader this year feels extra stressful, tricky, and prone to imposter syndrome, you are not alone. Read on for my approach on how to rethink leadership during times of change.

Fire & Rehire: An Andy Grove-ism.

One of my favorite stories in the history of tech is how Andy Grove at Intel responded to a changing business environment. Intel’s original product was memory chips and Japanese memory companies were dumping cheap chips on the US market. It was clear that Intel’s entire business needed to change, which lead them to pivot to making CPUs.

Andy Grove realized it wasn’t just the business that needed to change - how he showed up as a leader and the entire culture of the company needed to shift in order to transform from low-cost commodity to high performance computing. As this came into focus, he famously fired himself, physically walked out of his office door, and walked back in with intentionally on how he was going to lead differently.

Navigating the Crucible: Eight Behavior Changes

So what’s my version of walking out and walking back in? I’ve had some time to think about and test a few strategies for what this moment calls for - and I’ve landed on eight behavior changes that I’m holding myself accountable to.

I am naming it to tame it.

One of the biggest tensions of this era is that existing systems weren’t designed for the new environment. It’s important to name that - it provides the motivation for non-linear work. For example, at a recent extended leadership team meeting, I spelled out my worry list, the problems requiring my personal energy, and a list of things that need to change. I got more unsolicited praise for that format of XLT meeting than any other I’ve done in 2025 - people are hungry to see leadership name what’s broken.

I am prioritizing mission clarity.

People are scared - they see promises of AI redefining the different categories of software that exist and they are questioning the longevity of their teams and job. So, I’ve leaned in even more than normal into mission clarity - at the macro level, this means writing down our products’ role in a new world and our core thesis for differentiation. At the micro level, this means creating space for more single-threaded “squads” with a clear single mission and mandate.

I’m wading in the river of online news & learnings.

Social media is the “town hall” of product making & AI news right now - engaging online is table stakes for me as a product leader. Contributing to the conversation is a way to practice brevity and synthesis, and consuming enables me to guide the team towards the latest trends. This is one reason why I upped my LinkedIn presence recently - but X, Substack, and tech podcasts are all critical right now.

I am setting expectations that are always slightly out of reach for the old way of doing things.

This one is critical to the transformation of an existing team - either we set the new bar for excellence, or it gets sets by others (execs above us, competitors, other stakeholders). I know my personal trainer at the gym uses the same philosophy because it creates growth. For example, earlier this year, I created a very busy September for a particular part of the team - a series of aggressive strategy and product reviews that in normal times I would have let spans 2-3 months. But I felt it was important to set a new anchor point, inspiring the team to find creative ways to meet the new bar.

I am staying paranoid about what’s not working.

As leaders, we all decide how much time to spend on problem identification vs. problem solving. During times of change, it’s important for senior leaders to shift the spotlight more to problem identification - asking the team to “bring me problems,” injecting the right amount of entropy to see if plans hold up to questioning, and finding comparisons that expose underthinking. Momentum and consistency are much less important now - that’ll come in the growth stage. This works best when you have an LT (like I do!) who can run the team, leaving me to focus on what might be missing vs. reviewing plans. (Think XO and Captain vibes). Another Andy Grove-ism: “Only the paranoid survive.”

I am assembling the new system, piece by piece.

At Microsoft, we are calling the new way of building product the new “production function.” AI-born startups get the luxury of starting from the latest first principles; we have to retool an already at scale system. This has increasingly become more of my job - weekly x-company meetings on AI accelerators, incorporating Applied Science into the mix, ensuring new aspects of product making like vibe coding prototypes and rigorous AI evals are deployed. Systems thinking about the production function here creates a sense of order in the chaos.

I am empowering the next generation.

I distinctly remember in the early days of the cloud transformation a decade ago, my org leader asked me - an up-and-coming frontline manager at the time - to take point on the strategy for continuous delivery of our cloud software (vs. our 3 year on prem release cycles). Crucibles are a great time to reach out to every level of the organization to solicit ideas and empower solution building. It’s not like the top of the hierarchy has it all figured out anyway!

I am managing burnout - in myself and the team.

My pandemic post on leadership framed this balance between boredom and burnout - the COVID crisis saw people on both sides of the spectrum. The AI transformation is overweighted to burnout - look at my list above: naming what’s broken, relentlessly higher expectations, and paranoia around unknown unknowns. So, I’m watching myself and my team - ensuring we get good breaks to recharge, practicing self-care, and doing what I need to ensure I bring my best self to work.

A New Hope: It’s All A Repeating Cycle

The good news about 2025 - we’ve been here before. The industry is a repeating cycle of technical shock, category recreation, product/market fit, and scale. And while the early stages are more stressful than average for existing products, it’s a well-worn path. And it gives me deep purpose to build resilient software that customers can trust, and an operating environment that adapts so people can do career defining work.

Onwards to the new era!

1. Your team won’t all mirror your pace, ambition, or work style. High-performing teams thrive on diversity of strengths, not uniform intensity. Find a way for everyone on your team to be in their optimal state, and embrace that their state will look different from yours.

2. Have the courage to hire people who are better than you - if you can hire for strengths beyond your own, everyone will benefit. To do that, ensure you have awareness of where you excel and where you have room to grow.

3. Your job is to be an editor of your team’s work - when your team comes to you with a problem that they need help with, they don’t actually need you to solve it for them. Ask what they have thought of and have tried already. Offer input and guidance first.

4. Keep your 1:1s sacred and have your direct reports drive the agenda. It is their time - sometimes they may need you to coach them, sometimes to support them, and listen. If you need to work on something on your list, try to schedule a separate meeting for it.

5. Don’t underthink task assignment - as a manager, you have a lot of work to assign - special projects, fire drills, areas of focus. Your job is to be thoughtful in who gets to work on what. Don’t go on autopilot - stay intentional.

6. Remember to give more praise than you think you need to for work well done - genuine and authentic appreciation is the cheapest way to motivate a team.

7. At the same time, don’t reward people for doing the basics - your praise needs to be meaningful, so don’t insult people’s intelligence by thanking them for doing things that are basic expectations of the job and the team

8. One size does not fit all in management - consider what different people on your team need and adjust your management approach. One model I use (invented by Paul Hersey and Ken Blanchard in the 1970s) is the Will Skill matrix, as a starting point.

   

9. Be mindful of the team members with whom you spend your time. It’s easy to get bogged down managing low performance, but your high achievers are the ones driving impact for your team. Where you spend your time sends a message to the team on what is most important to you.

10. Avoid being a “helicopter” manager when you’re on vacation or out of the office. Jumping in from afar signals that you don’t trust your team and that disconnecting isn’t truly acceptable. Plus, your input will often be mediocre because you’re weighing in without full context.

If you are looking for more content as a manager, here are some previous Mind the Beet articles:

1. Part 1: Onboarding a Product Manager

2. Part 2: Recognition

3. Part 3: How to Engage and Motivate Product Managers Stuck in a Rut

4. 🎪The Perfect Team Onsite: A Guide

5. 🧐 Product leader’s role in building trust

6. 💎 Advancing from Product Manager to Product Leader

7. How I Lead When The World Is Uncertain

Without further ado, here are some tips on product that all you Swifties out there can relate to.

🎵It’s me. Hi. I’m the problem. It’s me. 🎵

Enough said. If you are PM, Step 1: Show up. Step 2: Take accountability. Many times, being present & helpful is more useful than being absolutely right.

🎵If you fail to plan, you plan to fail. Strategy sets the scene for the tale.🎵

Great PM’s know how to generate energy and drive consensus to quicken decision-making. A product strategy doesn’t answer every product question you’ll have, but it’ll provide the right bounding box for the sandbox you play in.

🎵I had a bad habit of missing lovers past. My brother used to call it “Eating out of the trash.”🎵

AI is creating new categories and disrupting norms. Don’t fall into the bad habit of loving old ideas or failing to question previous assumptions. Lean into the latest trends.

🎵 At least you know exactly who your friends are. They’re the ones with matching scars🎵

Great x-discipline partnerships stem from shared accountability. Ensure your designers and engineers feel responsible for the same outcomes as you do. Celebrate wins together and learn from failure jointly.

🎵I keep my side of the street clean.🎵

Set a quality bar for your own work higher than what’s expected of you. Sweat the details.

🎵 And it’s fine to fake it til you make it. Til you do. Til it’s true. 🎵

Everyone has Imposter Syndrome. Product making is part art, part science, part intuition. Developing that intuition takes time and practice.

🎵 I polish up real nice. 🎵

One of the most magical parts of product management is the art of great synthesis. PM’s transform raw and messy customer input, data and market trends into a coherent product idea that will drive impact.

🎵Get out your map, pick somewhere, and just run.🎵

In product making, if you are standing still, you are falling behind. Analysis paralysis is a real thing. You learn by doing & collecting data.

🎵She needed cold hard proof, so I gave her some. 🎵

Clearly, Taylor goes out of her way to have a great relationship with her Data Science team. Definitely a top tip for any new product manager.

🎵 He wanted it comfortable. I wanted that pain. He stayed the same. All of me changed. 🎵

You can’t develop product intuition without failure, pain, and trying new things. Find a team where it’s ok to fail and learn. View boredom and comfort as signs of needing change.

🎵 Bend when you can. Snap when you have to.🎵

Iterate or pivot? Change is costly, so as Taylor is saying here, always iterate and grind it out when you can, but don’t be afraid to pivot when the data is clear that what you are doing is not working.

🎵Familiarity breeds contempt. 🎵

If you work in software long enough, you know that user experiences age. People worship disruption and sometimes a “new way of doing the same thing” is a feature in itself. Startups by definition need to counterposition against incumbents, so there is a natural tendency to look down upon the current solutions.

🎵 Did you ever have someone kiss you in a crowded room, and every single one of your friends was making fun of you, but fifteen seconds later, they were clapping too? 🎵

Figuring out how to manage a non-consensus bet is an important part of product making. Persistent, differentiated product success often comes from seeing something other people didn’t and capturing it. It takes careful management of your stakeholders to survive through the crucible of judgment before the bet clearly plays off.

🎵 I gave my blood, sweat, and tears for this.🎵

You’ll work on many features that end up shipping, but there will be a time when you’ve poured everything in, but the feature needs to get cut. Sometimes not shipping is a feature and that’s ok. You earn your stripes as a PM upon your first failed experiment or cut feature.

🎵If it feels like a trap, you're already in one.🎵

Taylor, were you talking to Clay? If you work in Big Tech, you think about the Innovator’s Dilemma - your current customers will encourage you to iterate on what is perceived as the highest value, only to be disrupted by new entrants who focused on lower-value customers and then iterate to the next big thing. The tough part of this strategic quagmire is that incumbents don’t know they are in this situation until it’s too late.

🎵So what if I told you none of it was accidental. Cause I’m a mastermind.🎵

Yes, you are, Taylor, yes you are.

With a diverse and remote team (49% are outside Puget Sound), we’ve created rhythms for bringing the team all together once or twice a year to fill up our cups together. It’s become a bit of a team ritual.

This week’s post is dedicated to explaining how I approach these team onsites and how we’ve made them a touchstone of our culture and rhythm.

Create Separation Between Urgent Business & Team Development

When we fly in the team for the week, we create space both for both “getting stuff done” and “context & team.” We’ve had success when we create explicit space for both. A day for team-level planning. A day for ad hoc 1:1’s and synchronizing on whatever is urgent. And a day dedicated to developing employees and the team.

It’s this last day that the rest of this post is dedicated to. And it really is a mind shift: We plan a day around improving skills, driving alignment, and setting context for every team member. The goal is to wire up neurons and drive mutual understanding and shared norms. We pretend it’s Day 1 of a new team when bond building has traditionally been most critical. We ask, “What can give us enough context and connection that we can all thrive as a distributed team for the next chapter?”

Let’s dig into some of our most important rituals as we create a day focused on connection and context.

Choose a Theme

I am intentional in setting the frame of mind that I want team members to walk into the onsite feeling. It’s a signal to people on how to show up and it creates an extra sense of safety as folks walk in.

One way I do this is by picking a theme for the onsite. A theme is a one-word summary that runs through all the agenda topics for the day. For instance, as we were leaving the pandemic, we chose the theme of Sunrise to spark a sense of renewal. One time, we had a theme of Prism that enabled a fresh look at our work. Later, with the paradigm shift of AI and the macroeconomic climate requiring us to respond to a lot of change, we chose the theme of Transcend to capture the spirit of rising above the typical tradeoffs we find in our product and team.

You get the picture: the point is to pick a theme that reminds folks that onsites are about stepping back from the daily grind and give a name to the most important context for the team’s situation.

The theme is introduced in the invite to the onsite (like a wedding invitation). Here are some banners & framing text in the invite to previous onsites we’ve done:

Individual agenda owners are asked to find a clever way to reference the theme. I also find it fun to create a PowerPoint deck template aligned to it (e.g. the section header slides for Sunrise were all around the sun during different seasons of the year) and we’ve even created Spotify playlists aligned to the theme to play during breaks.

Measure How You Made People Feel

The post-event survey is where the mental shift to employee development as the goal takes shape. This drives intentionality around how I want the team to feel when the day is done.

Here are the top questions I use on the post-event survey:

1-5 Star Rating
Agree/Disagree: “The offsite was worth my time”
Agree/Disagree: “I feel more in the know about what's going on around the team”
Agree/Disagree: “I feel more energized about my job"
Agree/Disagree: “I feel like I can now prepare for what's coming”
Agree/Disagree: “I feel like I got to know people on the team better”
Agree/Disagree: “After today, I'm more convinced that my workplace is a safe & inclusive place where I can do my best work”
“What was your favorite part of the onsite and why?”
“If you have a shout out to a particular speaker, leave that here”
“Next time we have an onsite, I suggest that we…”

Brutal Agenda Simplicity: Why, What, How

The frothy mix of connection, mission, context, culture, and strategy can be tough to create a crisp agenda around. I don’t want people to feel like the day lacks cohesion. We use a simple frame for the agenda that focused the day on three parts:

• Why: Focused on our mission, customers, and how we as humans are motivated to do great work.

  • Example agenda topics: Motivating customer stories, leadership AMAs, geeking out on the latest workplace research on what motivates humans

• What: Focused on celebrating successes, learning what the rest of the team is doing, and what our next objectives should be.

  • Example agenda topics: Celebrating past successes, stories around big learning moments, a look ahead to upcoming events and milestones

• How: Focused on our culture, process, and diversity & inclusion.

  • Example agenda topics: Brainstorming on how to improve product craft, retro on why we aren’t moving fast enough, D&I programming

This ordering is intentional: “Leaders start with Why,” after all. And brainstorming around How is richer when everyone has a greater understanding of our objectives.

1-2 agenda topics per question is appropriate for a 1 day onsite.

Tell Stories and Retros

One of the problems with onsites is that often speakers feel the need to get into hardcore information dissemination mode. Nothing sucks the energy from an onsite more than a 20-minute recap of the latest Objectives and Key Results.

I create a counterweight to that inform-first mindset and it’s one steeped in my experience as the sponsor for years of Lunch & Learns within our team: stories are more powerful than charts & tables & bullets. I ask speakers to think about specific events with a cast of heroes, problems to overcome, surprising setbacks, and an exciting climax.

In short, onsites should go for a sitting-around-the-campfire feel:

Here are a few ways we’ve done this over the years:

• Have each team tell a story of their biggest learning

• Share stories of transformation and renewal from the past six months.

• Choose agenda topics focused around sharing personal stories and learning moments

• Tell the origin story of a particular business line or product

Icebreakers-With-Meaning

I believe in icebreakers at onsites just like I believe a coffee shop needs background music. It’s our job to get people into the right headspace. However, I want my team to be a special place to work so I like icebreakers to go beyond the surface level. I take inspiration from D&I activities that help icebreakers have a deeper meaning:

• Sort your values. The mechanic has people choose their top five values that are important to them by sifting through a 50-card deck of values (Autonomy, Purpose, Justice are example values).

• Glad It Didn’t Happen. The mechanic is that each person shares something they are glad didn’t work out in their life. It’s a meaningful way of learning about the tradeoffs coworkers have made in their lives and the path each of us takes to find a sense of belonging.

• Life in Thirds: The mechanics asks each participant to divide their life into three parts and write short bullets about important moments in each of the three chapters. As you share out, spend equal amount of time on each chapter.

• Value Snapshot: Everyone creates one slide with pictures of things that have meaning and value to them. Photos, meaningful books, graphics of important hobbies - anything is fair game.

• Privilege survey. The mechanic asks folks to examine and discuss the privileges they’ve had in their life. It starts with a private ranking of privilege using for instance this Better Allies 50 forms of privilege. It’s a creative way of getting people to discuss where they’ve come from as larger D&I concepts are explored.

The crucial point here is to engage the team to share meaningful lived experiences and connect it to a sense of belonging to the team.

Don’t Skimp: Celebrate milestones. Frame the Future.

Over the years, we always get close to overprogramming the day and need to cut back on the agenda items. I've found that the popular things to cut are celebrating our recent milestones (excuse: didn’t we already send the victory mail on that? or what if I miss something?) and the look ahead of what’s coming soon (excuse: oh, didn’t we cover that in planning report outs?).

Both are critical and it’s a mistake not to fit them into the agenda - people will feel like the day is too fluffy unless you really give them these left-to-right views.

There are mechanics we’ve tried that can enable you to fit these in even when the day seems full already:

• Celebrate milestones as rotating banners during breaks and on the slides between agenda topics.

• Team members can recognize great work in async chats or in a Cheers for Peers board on the wall.

• Present a single slide that lists out the major events and milestones for the next 3-6 months. Even if you don’t have time to cover it in detail, it’ll be a resource to enable people to plan their lives around the rhythms of the team.

Here’s one PowerPoint template I’ve used over the years to frame a season for a team:

Vary the Interaction Format

Now we get into the mechanics more so than the content. The biggest challenge of an onsite is keeping people engaged for a 7 to 8 hour stretch. The key to doing this is to vary the format of each agenda topic - the variety breaks up the day. Options:

• TED-like presentation: Single speaker with an engaging topic.

• Small group break outs: An owner frames a problem and asks for discussion among table groups.

• Big group discussions: A facilitator frames a problem and asks for a large group discussion.

• Structured activities with report backs: A facilitator frames a problem, asks smaller groups to work it, and then facilitates a large group report back.

• Leadership AMAs & outside in perspectives: A guest is invited to share top of mind thoughts and answer questions.

• Round robin stories from across the team: A facilitator frames a problem and asks a leader from each team within the org to share a story or lesson about it.

• Private activities: Each person spends time privately creating a slide or sticky notes on a topic. Where appropriate, people can share in small or large groups.

Each of these formats has pros and cons - but the key is to choose many of them throughout the day.

Be Intentional About Hybrid Participation

Sometimes team members can’t fly in or sometimes we invite partner teams and disciplines that didn’t prioritize the travel budget.

It’s been hard for us to balance the energy and connection inspired by in person face time with a duty to still ensure remote participants feel included.

While there is no perfect solution for this, a few things can help:

• We state our hybrid intentions at the start of the day. We recognize the goal of including remote participants as we kick off the day.

• We create an opening for people to give real-time feedback on the remote experience. I use the phrase “See something, say something” at the beginning of the onsite to ask for the interruptions in real time if a camera fails or microphones stop working.

• We project a shared chat. We always project a shared onsite chat in the room and encourage in person attendees to use it as well as remote folks.

• We nominate a remote champion. We choose someone who feels accountable for validating the remote experience is working well and who we can lean on to suggest improvements during the day.

• We try to have a least one remote presenter. This ensures someone remote is on the planning committee for the onsite, which is a useful voice to have.

• We check in with remote folks several times an hour. We ask presenters to validate microphones are working and screens are shared in the right way. This serves to remind in person attendees about remote participants as well.

End Early

Onsite days can be long, especially for remote participants. We try to create the time and space to make connections ad hoc - a morning and afternoon break and an extended lunch if we can. What’s more, I plan to end earlier than the time I publish - so if I tell people the onsite will end at 4PM, I secretly plan the day to end at 3:30PM. Yes, it’s a bit of a hack, but the anchor point is a way of managing the energy level.

Wrapping up

I’ve always felt a deep responsibility and accountability for these onsites on two dimensions.

First, I want to show respect for people’s time - that’s why I go the extra mile to choose a theme, define goals, and think about the little things that make people feel special and taken care of for the day.

Second, and even more important, these onsites are a mirror to reflect how clear my vision is for what it’s like to excel on the team. It’s a chance to crystallize what’s important and what we stand for. I care deeply about a customer-driven culture, a sense of belonging, a strong mission and purpose, and a culture that celebrates the past but sets ever-higher expectations for the future. Too many of my days I barely get to make one of these points to the team - but onsite days are a chance to make all of them in one pre-programmed way. I try not to waste the chance.

Organizing my life and being a conduit for information has always been something I have gravitated towards intuitively. I’m not sure it helps at cocktail parties, but it did earn me the award of “Most likely to name his clipboard” in high school.

And here I am, a quarter century later, still living an organized life. I 💖📋.

In previous posts, I’ve discussed what tools I use to manage my time and my information diet of podcasts, Substacks, and AI digests. This post will look at how I spend my time at work - and how you, too, can easily do a calendar audit.

Strategy, Product, Team and Customers

For over a decade, this is how I’ve broken down how I spend my time. I organized my top level calendar audit around it, structure my extended leadership staff meetings around it, and often frame written notes to the team around these buckets. Here’s how my time breaks down into these for May 2025:

From most to least:

• Customers: This bucket represents the time I spent hearing feedback from customers or advising them on their progress. I also include User Research & Data Science user analysis wallows. In May, I attended the Microsoft 365 Community Conference, so my time here was a bit higher than average as I spent a week off the typical routines and surrounded by our community.

• Team: This bucket represents time focused on team culture, career advice and mentoring, all hands, and the systems and operations of the team. In May, it was performance management/commitment check-in time at Microsoft, so that meant more quality time preparing and delivering what we call Connects with my team.

• Strategy: This bucket represents time spent on aligning and communicating the What and Why, allocation of resources, executives rhythms, and cross-org syncing. In May, I spent less time in this area than normal due to some big planning deliverables finishing up in April - but I still had an important review with a technical analyst firm to share my product’s multi-year vision.

• Product: This bucket represents time spent in the depth of product tradeoffs, backlog reviews, and product play - using products and capturing things like friction logs. In May, I had less product reviews than average due to the conference and talent management processes taking up oxygen - yet I still found time to try out some emerging AI tools & give some detailed feedback to the team about some of our freshest live code.

Three Takeaways:

1. I’m happy that my number one bucket was time spent with customers. I have a friend who has a personal metric to “spend more time with customers than other company executives.” Check.

2. I’m surprised that my time on strategy was so little, especially the executive rhythms. While the cross-company executive rhythms take up a lot of energy, they take up less calendar time in the month than I thought.

3. I’m eager to increase my time on product. While a VP will often have less in this bucket than a GPM or individual contributor Product Manager, I especially want to spend more time in product play and bar setting.

How My Time Has Evolved Over My Career

It’s worth pointing out that how I’ve spent my time over the years has evolved. Here’s an idealized breakdown:

Here’s my advice for each stage:

• Early Career PM: Go deepest in crafting product & learning from customers.

• Senior PM: Start to incorporate some strategy, but with a deep focus still on core product making.

• Principal PM: Strategy and core product tend to be more equally balanced (lots of x-team work!), and the time you invest in team culture starts to increase.

• Frontline manager: You are pulled in many directions as you incorporate more of the team bucket yet still need to balance it all.

• Group Manager: A bit more time for strategy, but still pulled in all four directions.

• VP: Team and customers are the top drivers of time (30% each), yet when you look at strategy + product together, that combined bucket is still the dominant part of your time (40%). This gives the right space to senior leaders on the team yet keeps you close to what’s going on.

Collaboration vs. Focus Time

My job requires both dedicated focus (drafting whitepapers, using product, creating customer messaging) and a high amount of time aligning with others (editing work, bar setting, x-team syncing) - and I was curious about the breakdown on two dimensions. First, what is the raw breakdown between focus and meetings for me:

This feels about right to me. If I worked at a start up, the job is to grind out the sole product that the company was founded for - spending more time in focus mode. But that’s not my job - coordinating and syncing with others is a larger component of what I’m hired for.

On the other hand, I have a job where 100% of my time could be taken up by meetings, so starting at 0% focus is my anchor point and 33% focus time represents a lot of calendar protection.

We all know that focus is more than just brief periods of no meetings - it takes dedicated longer time to get into the flow. So I was curious to analyze meeting load:

Here is where I realized that there were only three days during the month where I had less than three hours of meetings/day (mostly No Meeting Fridays). Indeed, my most common format for a workday is over six hours of meetings/day. #thestruggleisreal

Diversity of Meeting Type

One last analysis I did for May was to look at the types of meetings I’m in, to see if it fit to my preconceived notions.

Here I found my month to be pretty balanced - a healthy amount of outside input and a good balance between working within the team and with others at the company. This analysis motivated me to take another look at my cadence of 1:1 meetings, as at 25% and no meeting Fridays, that means I spent one day/week in total on 1:1 meetings - it’s a place that can easily balloon.

And Now You Can Too….

I share this post not only because it’s an insightful look into how someone with my job spends their time, but also to motivate you to do your own calendar audit. My process is pretty informal:

• I keep my calendar up to date so it’s easy to look back on the month.

• Sometimes, I will add a dummy calendar item at the end of the day with notes on where I’ve spent focus time.

• I create an Excel spreadsheet with one table per chart above - the rows are the days of the month and the columns are the buckets. It takes less than thirty minutes to tabulate my time into numbers on these tables.

It’s a super lightweight process yet it can drive a lot of intentionality and clarity. Even the act of knowing I’ll audit myself drives better decision making.

If you don’t have time for the full audit, try asking Copilot to analyze your month. It’ll provide a pretty good start, too.

If you try it out, let me know what you learn about yourself!

Do you know someone graduating soon and entering the workforce?  Consider a forward and share with a few of your own recs thrown in!

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When I graduated college 20 years ago, I got many pieces of advice from elders.  A memorable one was from Dr. Rick Tuttle, a student leadership advisor to both Helen and me and it was this: Subscribe to The Economist magazine.

The Economist’s approach to journalism has stayed with me throughout my career: a global perspective catering to world leaders that incorporates history, long-form analysis, and data journalism.

So, it was a gift that Dr. Tuttle gave Helen and me, although I suppose it wasn’t the greatest one – as he did end up officiating our wedding several years later:

Consuming news, analysis, and information has been both a habit and a hobby.   It’s been one of the most important career enablers in my job because it’s provided me with the broader context I’ve needed to make career decisions.   Consuming information – about the world, my industry, and my profession – is how I develop intuition, something my organization prioritizes as I get more senior in my career.

So, whether you are a new grad looking to develop habits or just looking for a few content recs, here’s my own blueprint of the information I consume on a weekly basis.  Call it my Information Diet and I included tips on staying info-nutritious in an increasingly info-junk world.

Newest Part of My Info Diet: ChatGPT

Conversing with ChatGPT has replaced some of my podcast listening during morning and afternoon commutes. I queue up a list of things I want to learn more about and run through it in a natural back and forth conversation during my drive. Here’s a few things I asked it for in the past couple weeks:

• “Tell me what happened in Andor Season 1 - I want to start watching the new Season 2, so what do I need to remember?”

• “I saw that Spain had a power outage, and people were concerned about ‘inertia’ in the electrical grid. What is that? What is it harder for renewable resources to have inertia?”

• “What exactly are the rules around how old and tall kids need to be to ride without a car seat?”

• “I’ll be home in five minutes. Can you give me a few dad jokes to have on hand during dinner time?”

I’ve started to keep a side note of things I want to converse with ChatGPT about - from the curious to just the mundane research I need to fit into my day.

Industry News & Analysis

It’s part of my job to stay updated with what’s going on in my industry.  If you are a new graduate, making this a part of your weekly habits can accelerate your early career and differentiate you.

TechMeme.  This is the one news aggregator I’ve let into my Information Diet.  It’s curated by humans but with little original content of its own – it features breaking news updates on the latest in my industry.   It’s widely recognized in the industry and my company’s PR teams cite how high a media push was on the site in their recaps.

Acquired.fm. “Every company has a story.”  Ben Gilbert and David Rosenthal run a fantastic podcast that recounts the founders’ stories and strategy for major firms in our industry.  The histories of Airbnb, Sequoia, TSMC and Pinduoduo have been my favorites. David was recently interviewed by the Wall Street Journal where he made the point that corporations’ origin stories are the best nonfiction stories of our day - it our generation’s hero tales.

Benedict Evans.   Benedict is a fantastic author with a succinct and sardonic writing style and content that is a mix of news summary + analysis.  He has a weekly free newsletter with hundreds of thousands of subscribers with the stated topic of “what happened in tech that actually mattered, and what it means” and his paid newsletter is one of my favorite weekly reads.

Stratechery by Ben Thompson.   A taste maker for our industry, Ben is one of the first sovereign authors before that was a term of art.  He’s managed to democratize (and monetize) what would ordinarily be a tech company’s in house strategy department’s work, and he’s used his influence to score great interviews and insider news.

My Professional Skills: Product Management

This was the biggest hole in my early-in-career information strategy.  I just didn’t appreciate how much wealth of insights there was by reading up on the skills of my profession, separate from my industry.   And wow has this area matured and consolidated in the past few years!

Lenny’s Newsletter & Podcast: Lenny’s work is now known as one of the most popular product management newsletters.   His content is targeted to those who like to skim vs. read in depth, and the content is so high level that it’s geared towards those new to the industry. His podcast series has interviewed the biggest names in our industry, and it is a source of great wisdom.

Peter Yang’s Creator Economy Newsletter: Peter’s my second favorite PM influencer after Lenny. Good practical advice on product and career.

I sometimes follow John Cutler’s Beautiful Mess, Shreyas Doshi, and Will Lawrence’s Product Life but I find they have fallen behind Lenny & Peter.

Great book recommendations are outside the scope of this post, but this section feels incomplete if I didn’t mention the work of Marty Cagan from Silicon Valley Product Group.  His book Inspired is the #1 book I recommend to new product managers.

Leadership

I framed that an outcome of my Information Diet was to develop intuition, and intuition on influencing people, building coalition, and storytelling is a large part of most knowledge worker jobs. Here’s a few recs in that area:

Finding Mastery Podcast by Michael Gervais.   A sports psychologist interviews leaders, mostly sports coaches but not always, about high performance and being in the flow.   Gervais is a fantastic interviewer who gets people to open up about their personal struggles yet synthesizes how to apply it to the life of his listeners. 

Brené Brown’s Dare to Lead Podcast.  If you’ve subscribed to Mind the Beet for a while, you know our philosophy on leadership is rooted in allyship and vulnerability.   Brené is the public face of vulnerability. 

The Moth Storytelling Podcast.  The Moth is an organization dedicated to the craft of storytelling and their podcast features the best of their “story slams” – true stories told live without notes to an audience.  Not only are the stories fantastic, but it inspires clarity in communication in my own work life.

Journalism

So far, I’ve talked about how to be a knowledgeable information worker, using examples of my profession and industry (tech and product management).   In addition, my information diet hobby involves consuming news and staying up to date as a citizen of the world.  

There is an intentional philosophy in my approach to new, namely that I a) avoid infotainment, TV, social media and AI-based aggregators as sources of news b) prioritize the highest quality journalism c) find a counterbalance to whatever is my primary source and d) support local news. 

The New York Times.  It’s clear to me that the NYT is one of the few journalism organizations to cross the chasm to a new economic model and is pouring the profit into redefining quality journalism.   This fantastic analyst report delves just into how the organization has transformed itself and how they prioritize paying journalists. 

Wall Street Journal.  The NYT has a bias for David over Goliath and stories that prioritize those marginalized by the system.   WSJ is a great complement to the NYT in this respect. Both are pretty centrist overall and that is my goal; I want to support quality journalism vs. extremes.

Seattle Times.   I make it a point to prioritize news of my local community.  Like many, I’ve noticed the steep decline in quality for local news compared to just a decade ago – but keeping up with local news makes me a more interesting conversationalist with fellow parents and neighbors.

TikTok. My TikTok feed includes late night TV show snippets, SNL recaps, dad jokes, sports highlights, and breaking news from the major organizations. I find TikTok is often where I will hear about a breaking event first, before then diving into it with mainstream media.

ChinaTalk & Sinocism. These are two Substacks that cover in depth analysis of China, which was a goal of mine to increase my info diet on.

World Context

Dwarkesh Podcast. Dwarkesh Patel is a fantastic interviewer who in the past year has really broken out - especially with his interviews of tech CEOs like Satya Nadella and Mark Zuckerberg. He gets into great details with experts on a range of topics.

Lex Friedman’s Podcast. “Conversations about the nature of intelligence, consciousness, love, and power.” From world leaders to tech CEOs, almost every major figure in the world has done a long form interview with Lex. He’s known as a friendly interviewer with softball questions - almost never challenging the people he interviews. Yet the soft style often brings out some unique insights.

Search Engine. “Search engine is a podcast that tries to answer the questions that keep you up at night.” Each episode is a 45 min - 1.5 hr deep dive into an interesting yet random topic - ranging from the curious (“Is there a swimming pool in Buckingham Palace?”) to the important (“Does the national debt matter?”).

The Economist, including their podcast spinoffs. I opened with The Economist, so you know it’s a primary source of data journalism, world context, and news analysis for me. Their podcast spinoffs - from Boss Class which dives into management theory to The Prince which covers the history of President Xi of China - are good deeper insights.

Long Now Foundation Podcast. The Long Now foundation seeks to counterbalance traditional thinking with interesting talks and projects focused on the 10,000 year time horizon. I find it a fantastic way of broadening my thinking on culture, product, and government.

Life Hacks & Parenthood

Part of my info diet is ensuring a steady stream of “new things” into my life - here’s a few ways I do that:

Omar Knows. Omar’s recs on products he loves are aligned to my lifestyle - Helen and I buy nearly one of everything he recommends.

Recommendo. Cool stuff, once a week. Eclectic mix across nearly everything across digital and physical products. I often pick up something random to try.

New Fatherhood. Building community around fatherhood with a frank and vulnerable discussion of being a father.

In Closing

The trick is not to get overwhelmed.  I have busy weeks where I get to little of the above content – and I always have a queue I feel slightly guilty about. Regardless of whether you plan to make this a small or large part of your time, I encourage new grads entering the workforce to plan their Information Diet.  Not only is it a career accelerator, but most jobs require you to get great at quickly consuming the right information and this is a way to build the muscle.

At Microsoft, we have a Product Leader job called GPM (Group Product Manager). While much of the industry uses the GPM title to denote frontline manager for 2-4 people, at Microsoft for historical reasons it’s a larger role and typically a “manager of managers” job. The standard team size is 12-20 PMs coordinating the work of 50-90 engineers and the job has direct accountability for one or more end-to-end product areas or services.

It’s the sweet spot for someone who wants to stay close to product yet wants to drive impact on something massively bigger than they could accomplish on their own.

My first GPM job was in 2013. Just as the cloud wave was gaining momentum, I ran a team that delivered a set of key infrastructure services (e.g. authentication, provisioning) to what would become Microsoft 365. Since then, I’ve had other classic types of GPM gigs: a) incubating new product lines b) refreshing the UX of an existing product c) building x-company partnerships to transform our product portfolio for a paradigm shift.

Today, as a VP of Product, I manage a leadership team of GPMs and other discipline leaders across a diverse portfolio and much of my job involves growing, empowering, and securing the resources for GPMs to succeed. (You can read my career highlight reel).

This post is speaking to new GPMs. First off, congratulations on the opportunity. Undoubtably you were put in this job because you are a fantastic manager and capable of empowering the careers and supporting the work of your team.

Yet I bet you feel like this new GPM gig requires manager excellence and more. You are asking, "What is the 'and more' part exactly?" This post attempts to answer that question, breaking the job down into the distinct characters you need to grow into to thrive in the role.

I like this idea of approaching new roles like this - writing down “who you need to become” as you adapt and grow.

🗞️ Step 1: Become an editor

“Become an editor.” These three words were at the top of my first performance review as a GPM. The GPM job is a force multiplier role because you raise the bar for your entire team using your accumulated product sense. However, being an editor is more than giving notes on work. Talk to any professional author or news reporter, and their editor also provides context, alignment, encouragement, and is there to navigate tough tradeoffs. This is the first and most important set of skills to invest in as a new GPM.

I asked some of my colleagues in other disciplines what makes a great GPM - one response that stood out to me is that they rely on GPMs to drive “tasteful production decisions.” Judgement, product sense, and a taste for highly crafted products - this is all part of the editor role.

Practical Tips & TODO’s:

• Establish great product discovery fundamentals. Your team’s ability to deliver written clarity should be as rigorous as any engineering manager’s code review process. Be transparent with the throughput of specs, whitepapers, or notes on product definitions (tables of status and dates are your friends). Own and run a synchronous (virtual or in person) review process of both core design/big decisions and the details of investments. Utilize a central doc repository and ensure the doc templates exemplify your philosophy on product discovery (e.g. Why before What, success definition).

• Give great notes. Yes, I said that giving good notes isn’t the only aspect of being an editor, but it is an important one. Practice bar raising, using good judgement on what to hold the line on, and how to be clear & concise & actionable in your feedback. You should set norms with your team that your notes are an expected part of the operational model of the team.

• Share the burden of your biggest problems with your most senior people. The GPM job can be lonely and burdensome at first, until you tap into the support network you have, starting with your own team. Ensure the 2-4 most senior people on your team are fully thriving and working on your most important problems. I like using the Flow model for assessing this.

• Be the most frequent user of the product. I’m a huge fan of product play - using your product and others in the industry where the goal is to be both idea generative and feedback-oriented. Great GPMs get hands on with product and know how to use the time spent in product as a form of editing.

🌍Step 2: Become an ambassador

A great ambassador in the U.S. Foreign Service requires a mix of storytelling & relationship building - all while managing a complex set of stakeholders, including their own boss.

For GPM’s, after you’ve looked internally and made yourself a great editor, look outward and learn to represent your team and bring back key insights to them.

Practical Tips & TODO’s:

• Repeatedly sell your strategy. As Andy Grove used to say, “repetition never spoiled the prayer.” You should be finding opportunities to practice & refine the pitch of your product to customers, partners, and internal stakeholders at least 2-3 times a week. Sweat the details on your written pitch deck and supporting docs - keep it evergreen as you learn what’s hunting. Be persuasive, not informative.

• Build shared values and mutual understanding in your cross-team relationships. Your team requires your help to feed the internal alliances with partner product teams. Don’t fully delegate relationship building, even the healthy ones. Keep a hit list of sticking points to work. Treat inclusion and shared values as equally important to strategy and priority alignment.

• Be systematic about bringing customer signals back to your design and engineering team. In the US Foreign Service, “cables” are an important process where ambassadors share insights about the world with the organization in real time. Find your own way of ensuring you are providing new signals - about customers, industry, or partner relationships - at least 2-3 times a month.

• Understand the thoughts, wants, and feelings of your design and engineering counterparts. GPMs have positional authority at Microsoft and they should use their privilege to help other disciplines thrive. Deeply understand the needs and priorities of your x-discipline peers and practice allyship.

• Using status reporting to drive impact. Your team should be sending weekly, monthly, or quarterly status reports on every major facet of your product. The frequency depends on urgency and investment level - and you yourself should own a roll up of the e2e product health & growth at least monthly. All of this reporting is NOT project management, it’s a chance to refine your storytelling, emphasis the important, and manage stakeholders. Hold your team accountable.

🔮 Step 3: Become a futurist

The best GPMs are two steps ahead of the rest of the organization. Not twenty steps - we don’t need GPMs to have their heads in the clouds - but the GPM gig requires you to figure out “what’s next.” Yes, this requires studying industry trends and paradigm shifts but equally important is anticipating the smaller details - the workback to key internal reviews, upcoming initiatives, and likely emergencies.

Practical Tips & TODO’s:

• Drive awareness of how much vision runway is left. I find that most products can define durable 18-month visions, 6-month roadmaps, and 1-month backlogs. It’s the GPMs job to drive consensus on when these need to be updated - before they run out. Establish a rhythm and in particular catch the vision runway expiring before anyone else does.

• Own the Six-Month Calendar. A gift that a GPM can give a team is their brain dump of all the important milestones coming up in the next six months. Key deliverables, reviews, conferences and more. It helps the team feel in control and positions the GPM to be the one charting what’s coming.

• Always have 1-3 low percentage shots in motion. It’s easy for backlogs to get filled up with only high confidence, urgent ideas. GPMs are in the unique position to ensure 10% of the team’s resources are taking some high risk/high return bets. This is how you manifest your futurist thinking into concrete actions.

• Speak in the language of impact. Establish finish lines. Practice saying "Here's where I think the goal state is..." not "Look at how far we can go." Adjust your language to speak with intentionality. This impact vs. execution mindset thinking is critical to being taken seriously when talking vision.

🛩️ Step 4: Become a maverick

In the Era of AI, things are changing fast and new patterns are yet to be established. We need GPMs who are mavericks, trend setters, and people who can successfully interrupt “what would have happened anyway.” This is a significant difference from a couple of years ago when we needed consensus builders and planful, careful thinkers. It’s important for GPMs to embrace the times.

If steps 1-3 are about becoming comfortable in your job, this step is about using your authority to help Microsoft break out of the status quo.

Practical Tips & TODO’s:

• Be OK with conflict. This can be hard for new GPM’s, but being a maverick means upsetting the consensus and other leaders’ concepts of what success is. Often the unlock is to be OK with conflict vs. jumping to consensus building too early. Be OK with being the “bad cop” sometimes.

• Look for patterns to break. Be curious about whether old patterns still apply and don’t be afraid to ask if we should still be doing something the “way we’ve always done it.” It starts with just asking.

• Find places where your team is stuck in a local maximum. This is a mindset shift - spend the right time auditing your own team’s work, looking for “good but not great” thinking.

• Pick smart places to push. A maverick GPM will have 3-4 instances every month of “things that wouldn’t have happened anyway because of their effort.” Develop good sense for these “course changing” moments to push on - a stuck partner relationship, a team setting the bar too low, a product strategy that was too incremental - these are all good examples.

• Use praise to reinforce new behaviors. Learning to give authentic praise frequently is an overlooked skill but it’s a force multiplier for GPMs who are changing the status quo.

The Five Biggest Traps for New GPM’s

Posts like these need anti-patterns as well as the best practices. Here is my top five “Don’t do This” list that I’d advise new GPMs to avoid.

1. Stressing over problems everyone else also has. Matrixing and resourcing are often the top two stressors for GPMs. Everyone would love to work single threaded with more resources than they have. And everyone thinks their situation is worse than their peers. It’s all a distraction to thriving as a GPM. Fit to plan and plan to fit.

2. Focusing on the urgent at the expense of building the system. GPMs who struggle often involve someone who couldn’t rise above the day to day and invest in the systems and processes for long term sustainability. Yes, create urgency but don’t create a sense of persistent emergency.

3. Letting others define the job for you. All GPMs need to deal with strong willed stakeholders - be that other GPMs or activist engineering leaders or design leaders with a POV on product. While a GPM needs to listen and be responsive, they must own their own job definition. If others are defining your job for you, it could be a sign that you don’t have a deep enough product sense for the role yet.

4. Doing your previous job. Don’t forget to punch at your new weight class. The GPM title requires you to build senior-level partnerships across teams and disciplines and operate at the portfolio/product vs. feature area level. Often new GPMs stumble when they don’t adapt to the new altitude of relationships and scope.

5. Not balancing vision and execution. GPMs need to invest in both ends of this spectrum - generating energy with a compelling product story and creating a x-discipline environment that executes faster on that vision than if they weren’t around. Ask for smaller scope if you are having trouble finding time to drive excellence in both.

Wrapping Up

One theme throughout this post is this notion of ownership within the matrix. A great GPM defines their job, defines their product, defines the outcomes for their team, and defines the path to deliver on the vision - yet is grounded in the fact that they operate within a larger system and actively builds the partnerships required to succeed. Finding this balance between ownership and partnership is key to thriving in the role. Good luck!

Using existence proofs and pattern matching can quicken understanding - both bringing new people along quickly, reminding a close knit-crew of people about successes (or failures) they’ve had before, and acting as shorthand for explaining a project’s goals.

Let’s dig in and learn how any designer, product manager, or product leader can use these tactics to generate energy and drive clarity.

But Wait - This is the Era of AI - Everything is New!

Some of you are thinking, “But Adam, our industry is in a paradigm shift moment - the winning plans will be upending status quo, creating new categories, and defining novel UX metaphors - why anchor in the past?”

And it’s a great point (indeed, I’ve done a post about AI’s ambiguity before!) - there is a role and separate set of tactics for total revolution instead of reinvention. But the question, “What is this most like?” is still useful - in fact, it can help you hone exactly what is changing and what is staying the same. It drives intentionality with where you want to point the innovation machine on your team.

Indeed, whenever I use this question, I try to clarify which aspect of product design I’m talking about:

1. Is it about the job to be done? (e.g. “This is solving the same type of problem as Windows Control Panel does.”)

2. Is it about the go-to-market and business model? (e.g. “This is Uber for X”)

3. Is it about the UX model? (e.g. “This is just like Search in ChatGPT!”)

4. Is it about a simplicity/complexity bar? (e.g. “This should be as easy as iPhone’s Clean Up feature”)

This allows me to say things like “We are going to reinvent the user experience for this area, but the job it accomplishes is just like X.” This can focus a group on the right part of the problem.

Storytime: Three Examples from the Past Month

We use this often on our team, so as I was writing this post, I only had to look back a month or so to produce three examples of using this in practice.

“Agents are people, too.”

My first example comes from the world of AI. A lot of us in the industry are talking about AI agents - what skills they have, how they appear in a product’s UX, and how to explain them to users. In this case, agents are likely to cut across existing product and market categories to be hired for an entire process or job.

Here the pattern match has been less to existing pieces of software and more to the jobs that will be augmented by an agent. This agent is “most like” a project manager, or a software engineering or a marketing intern. Anchoring something new to an existing job quickens decision making and helps conceptual understanding.

“Let’s inventory what exists…”

We are looking at making some changes to the navigation and wayfinding of one of our products, and the homework that my design partner assigned us all was to suggest products in the industry that have a similar level of needs to combine multiple tools and apps into one framework.

This was effective in taking an abstract and ambiguous problem and enabled us to rapidly align on where the bar is for our new project based upon our shared use of apps and UX. We can say things like “We need a plan that is simpler that Adobe” or “We felt good about how WeChat approached tool aggregation.” It’s not about copying the ideas, it’s about aligning on the bar and then doing the hard work to contextualize them to our products.

“As simple as…”

Bar setting through example and metaphors can also be used for product storytelling as well.

As someone who owns an existing product (indeed, one that is 24 years old!), I’ve been trying to coach my team to simplify our product storytelling. It’s too easy to feel the need to explain every gotcha (we’ve had a lot of time to discover all of them!) instead of keeping our pitch simple and focused on a primary insight or truth.

That’s easy to say - but “make this simpler” is also feedback that is easy to dismiss. So what did I want our storytelling to be “most like?” I decided to take it to the extreme to really make my point.

The metaphor I chose was to be more like a traffic light, less like an airplane cockpit. Universally understood, simple, designed for even distracted drivers to understand. That’s what I wanted to set as the anchor point for the team in our pitch decks.

Wrapping up

As you can tell from these three examples, you can use the question “What is this most like?” in unique ways - it’s not just about “This product is Uber for X” but it can be used to set a simplicity bar, improve storytelling, or clarify what stays the same vs. changes across a paradigm shift.

I’ll close with one more tip: You can also use the opposite of this question, asking “What should this feature be NOT like?” This can help people name what needs to change or traps to avoid, like a pre-postmortem. Name the anti-pattern to avoid and you can often identify the whitespace a new product should tackle.

Even the most successful products have a meandering path to success and too often the backtracks and failed side quests get glossed over. Some amount of failure is a fact of the product making environment, and planning for and learning from failure is how excellent product teams create durable products that customers can trust.

In the Era of AI, with a lot of viral flash-in-the-pan ideas cropping up, I’ve been spending time thinking about how to create products that will evolve with the times and are “built to last” - and the role failure still plays in getting there.

But first, let’s talk about the Savannah Bananas. Have you heard of them? If not, you are in for a treat. They are an exhibition baseball team for the TikTok era - combining trick catches, dance routines, and a fast-paced play for a fresh take on a day at the ballpark. Go check them out - I’ll wait:

And just in case viral moments aren’t your thing - you can view their journey on product counterpositioning as written up in The Economist.

Learning From Failure

I’ve been looking for material to talk to my team about experimentation, cycle time, and trying new things and this 1-minute gem from one of the founders of the Savannah Bananas is product management gold:

I love when tech truths show up outside tech products - it puts them into stark relief - here’s some excerpts from the video above:

Everything we’ve done for the first time we’ve failed at. We had no idea what we were doing. Most people, when that happens, they give up. We do so much that we aren’t afraid of “so called failure.” If we are not failing, we are not trying big enough things. We have a willingness to get through the messy to get to the great.

Pete Rose has more hits than anyone who has played baseball. He also has 2,000 more at bats than anyone who has played baseball.

Our mindset is to keep coming to bat every single day. Failure doesn’t scare us - it’s part of what we do.

Follow @yellowuxjesse on TikTok. And they are making their way to Seattle in September 2025 - check out their ticket lottery!

Product Making in an Uncertain World

Here are four things I’m incubating to put more of a focus on the uncertain nature of product making:

1. I’m being intentional with my language around failure.

As I talk about this more with my team and stakeholders, I want to choose language that is focused on positive outcomes and strengths that are authentic to our situation. I’ve settled on two phrases: Build resilience and practice curiosity.

Resiliency in product making turns a potential tension into a strength and gives a name to the duality of both transforming ourselves while still executing on the urgent. It can be dialed up in times of momentous change to mean a lot of reinvention or dialed down to focus on sustainable systems. It encourages intentional conversation about context.

Curiosity establishes a mindset of experimentation, calmness, and openness. It reminds the team that product cultures need to collect signal and embrace the unknown.

2. I’m normalizing talking about failure.

As a product leader, I spend most of my time thinking about how to market the most successful parts of the product. I do keynotes on the features and scenarios that survived the Darwinian product fit & scale process. But internally I’m trying to be more circumspect - I know the team needs to hear from me that it’s safe to fail. I will self-admit that like most leaders I am imperfect at this, but I have three tools that I’ve seen that I like:

1. “Share Your Fail.” Twice a year our team has Hack/Hack/Learn weeks and one of the scheduled sessions is a space for people to share stories of failure. 5–10 minute lightning rounds where people sign up to talk about things that didn’t go as they planned.

2. I’m not sweeping history under the rug. Recently, I presented at a leadership onsite a list of projects we’ve cancelled, products we’ve deprecated, and systems we’ve had to replace in the product over the past ten years. It was a busy PowerPoint slide - 3 columns and over 30 items on it! This reinforces that projects and products failing is a fact of life that must be planned for.

3. I spend pre-coding time naming our risks. My biggest takeaway from Marty Cagan’s Inspired: Instead of a pre-code specing process focused on only driving alignment, instead I use pre-code time in a product discovery process focused on identifying and reducing risks of failure. Our PM doc templates embed this in - requiring people to identify and rank the types of product risk (e.g. design, business, value, et cetera) and create a plan to minimize. The risk is there - I’m trying to get the team to remember to name it.

3. I’m institutionalizing learning on the job.

Over the years, the leadership sponsorship role I’ve had the most fun with is sponsoring our Learning & Development programs. I’ve thought deeply about how to embed learning while on the job. This is why to me habits, mindsets, and bets around learning-while-doing are more important than structured coursework. I talk about this in detail here:

4. I’m stepping in to make sure the team takes some low percentage shots.

Tell me if you’ve been here: I’ve got a backlog that is so overflowing that I must make tough tradeoffs around extremely urgent and important items. Every item I’ve prioritized for the next sprint - and the first ten I can’t yet prioritize - has a high percentage chance of delivering value that customers have explicitly asked for.

I hear this story from busy GPMs all the time. It’s impossible for backlog owners on their own to make room for anything except the urgent. But what about the unarticulated need? That’s much more risky - and I’ve found that it requires an interruption from senior leadership - an explicit requirement to focus and fund some high risk/high return speculative investments - to break the logjam. Examples from my work life over the years are often tied to emerging tech - mixed reality, AI, new social media trends. I’m sponsoring tools like Design Sprints - focused on non-urgent ideas with lots of upside - to give product teams a chance to dream.

Wrapping Up

If this post were about startup culture, it would have been easier to write - worship disruption, experiment without emotional attachment, and embrace long-shot odds. And hey, if it fails, someone else in the VC’s portfolio will succeed.

But my needs are to talk about failure and pushing the envelope as part of an existing product in a large company. It’s much more nuanced with a lot more riding on the outcome: existing customers are betting on my product to evolve with them. But at the end of the day, it gives me deep purpose to be part of that journey with them.

Oh, and here’s one more Savannah Banana video to brighten your day:

The fact that the umpire dances too is 💯.

Recently, I shared on LinkedIn a historical recap of this past decade long journey of UX transformation and new product creation:

Modern SharePoint: A Brief History of Product Making (LinkedIn)

Writing that piece made me reflect about what’s most important to me as a product maker. It made me realize there are three key themes that I continually come back to that give me energy as a product leader:

1. Community. As Bill Gates once said, “You are only a platform if your partners make more money than you do.” The best part of my job is working with the community around our product, many of whom have bet their careers and livelihood building on top of the work of my team. Managing and nurturing an economic ecosystem is both a privilege and responsibility, and it creates a unique set of stakeholders and superfans that are influential to my thinking as a product leader.

2. Resiliency. Most products fail. Those that don’t still tend to fade away over time. Longevity is rare in our industry. Yet SharePoint’s been around for 23 years, and these past ten years are just its latest pivot to thrive across a paradigm shift. This requires a product culture that champions resilency, which to me means two things. First, it means building trust with customers and being a partner with them through change. Second, from a business perspective, it means learning to love the grind and respect the power of compounding growth. The Office business (which we are part of) consistently finds a way to grow revenue by 10-15% every year. For a business in the tens of billions of dollars, that’s like growing several new S&P500-sized companies every single year!

3. Purpose. SharePoint helps people collaborate remotely. It gives me deep purpose to know how much this technology helps bring ever more diverse teams and ever larger organizations together in a more productive way. We wouldn’t have had a COVID vaccine as fast as we did if people couldn’t collaborate remotely. Our technology helps teams working on global warming exchange information on novel solutions. It helps democratic institutions find consensus faster. Yes, my personal impact is a mile wide and an inch deep on these problems - but no other area of technology is as transformative at helping groups of humans collaborate on the world’s toughest problems.

As a tech leader, I often look to the future more than the past. But this week’s post takes a moment to breathe and looks at what I’ve learned to value based upon where I’ve been.

READ MORE: Modern SharePoint: A Brief History of Product Making

Sad but true: This is the experience I will most remember from my truck. Not the carrying capacity of its bed, its horsepower, how it drives over rough roads, or any intended delighter. It’s often these rough edges that define a customer’s primary emotion towards a product.

Peeling Back the Curtain

For me, I always view my interactions with a product as the manifestation of the tradeoffs of its product teams. Call it the curse or the blessing of seeing a bit of product management wherever I look.

I can just imagine what happened here in my Toyota example: The audio team was proud of having just navigated the complex handoff between phone and car. The touchscreen team assumed no one really needed to interact with it immediately upon car start. And anyone who was thinking about the design was more concerned about achieving the outcomes (“Yay! We support the iPhone resume functionality”) vs. watching for unintended pitfalls (“How easy would it to be recover if that’s not what the user wanted?”)

My post this week is about how you can develop “product sense” - an intuition about how to avoid these rough edges - and combine it with the people skills needed to drive impact within your organization. It’s the most important development goal you can invest in if you are a PM on a UX team.

The Role of PM on a UX Team

These little flaws and inconsistencies in product are an unavoidable evil of modern product making. We spend a lot of time worrying about how to systemically build a product culture that rids us of them: talks of “shifting left” to catch things earlier, scenario health dashboards, quality pushes - things that promise that if the culture & processes are exactly right, quality & craft happen naturally.

These all help – but the individual mindset and tenacity for quality from PMs on a UX team can make a huge difference as well.  It takes discipline, skill, and grit to constantly improve the customer experience.

All PMs drive growth of some kind – but this is a specific type focused on growing customer love.   As such, this post isn’t for all types of PM’s or all business contexts.  If you just own a button or onboarding flow in a UX, you are probably a growth PM driving revenue.  If you are working in stealth mode on a brand-new product, you are primarily spending your days being curious to quickly discover product-market fit.  However, if you are responsible for the management of a large UX surface area, delivering competitive gaps in an at-scale product, or increasing the retention of a product in scaleup mode, these “UX PM” skills are essential to your role.

Yes, This Can Be Your Super Skill

How to show up as a high-craft PM is not talked about enough in the product management community. Maybe because it’s a shared ownership with design and engineering. Maybe it’s more “grinding final mile” than “exciting new big bang.” Maybe “product sense” is controversially fuzzy in an increasingly data driven world.

Regardless of the reason for the white space from the PM-advice-mill, driving product craft is an in-demand skill and well worth practicing and honing if you are a new PM.

Here’s a few tips to get started.

1. Make Product Play your most important ritual. With meetings and reviews and data synthesis needs, a PM’s life can get busy. That focus is OK if you are a Growth PM or TPM - but if you are a PM on a UX team, you must prioritize hands on time with the product. I have a method I call Product Play that makes this more fun and inspirational.  There are time-on-task improvements that come from putting in the hours of using products introspectively - it’s how you develop product sense.

2. Practice structure and broadcast rigor. Since the goal is to impact the craft and catch the rough edges, a structured framework for rigorously walking through product helps. I’ve blogged about Friction Logging before, which I’ve heard that Stripe uses.   This enables you to turn your product sense into something concrete.

3. Respectfully hold a mirror to design. On many product teams, design is more of a hidden figure than they should be - needing support and allyship from PM to have as strong a voice as they should have. Even the best UX PM’s are B+ designers and threaded across many things; you need A+ designers who are single threaded on the problem of user interaction to achieve the highest-craft product.  The more you view your job as one of intentional allyship of design’s ideas, the more your bar raising and friction hunting will be viewed as a helpful mirror to catch gaps. 

4. Help the team recognize that the bar is always being raised. In a well-run product organization, it’s always a race to the top. What would have been “good enough” 12 months ago is now below the bar. Trends change, compute gets cheaper and faster so UX interactions speed up, and new possibilities open up.  This is why the job of high craft UX is never done – it’s a grind. Invest in learning new industry trends and incorporate product making material into your information diet.

5. Seek out and support those thinking about the entire UX system.  Let’s go back to my Toyota examples, which ultimately was a failure to see end to end between multiple groups within the product.  This is a common pitfall and in the best product culture, there is someone ultimately responsible for the entire system.   Sometimes this is a design director, sometimes it is a product leader, and sometimes it is an engineering leader. It can be a consulship of all three. Have empathy for this role and ask how you can best help them carry this burden. Even just asking “Who is ultimately responsible for deciding the bar that the product needs to reach?” is an unlock question.

Product Sense + People Skills = Impact

There is a falsehood out there that product sense is some innate and unteachable skill. Nothing could be further from the truth - this five-step plan is a mix of improving your own skills and intuition mostly through rigorous time-on-task, and then applying them to the human-systems around you. It takes commitment - but anyone willing to invest the cycles can develop it.

Hit me up in the comments if you enjoyed this look at the UX PM aspects of product making. There’s a lot more to share in this vein, including topics like a) measuring user love b) balancing backlogs across product growth and craft c) creating fluid systems of work across design, specing, and coding and d) incorporating user research into the product discovery process.

Do you know someone graduating and entering the workforce?  Consider a forward and share with a few of your own recs thrown in!

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P.S. If this got forwarded to you and you want to subscribe for free to see our weekly posts on career & product making, I’ll make it easy for you:

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When I graduated college over a decade and a half ago, I got many pieces of advice from elders.  A memorable one was from Dr. Rick Tuttle, a student leadership advisor to both Helen and me and it was this: Subscribe to The Economist magazine.

The Economist’s approach to journalism has stayed with me throughout my career: a global perspective catering to world leaders that incorporates history, long-form analysis, and data journalism.

So, it was a gift that Dr. Tuttle gave Helen and me, although I suppose it wasn’t the greatest one – as he did end up officiating our wedding several years later:

Consuming news, analysis, and information has been both a habit and a hobby.   It’s been one of the most important career enablers in my job because it’s provided me with the broader context I’ve needed to make career decisions.   Consuming information – about the world, my industry, and my profession – is how I develop intuition, something my organization prioritizes as I get more senior in my career.

So, whether you are a new grad looking to develop habits or just looking for a few content recs, here’s my own blueprint of the information I consume on a weekly basis.  Call it my Information Diet and I included tips on staying info-nutritious in an increasingly info-junk world.

Industry News & Analysis

It’s part of my job to stay updated with what’s going on in my industry.  If you are a new graduate, making this a part of your weekly habits can accelerate your early career and differentiate you.

I’ve tried industry periodicals over the years but found them too surface level.  My steady state here has been a useful content aggregator that can find the best piece on any given news event + key sovereign analysts:  

TechMeme.  This is the one news aggregator I’ve let into my Information Diet.  It’s curated by humans but with little original content of its own – it features breaking news updates on the latest in my industry.   It’s widely recognized in the industry and my company’s PR teams cite how high a media push was on the site in their recaps.

Acquired.fm. “Every company has a story.”  Ben Gilbert and David Rosenthal run a fantastic podcast that recounts the founders’ stories and strategy for major firms in our industry.  The histories of Airbnb, Sequoia, TSMC and Pinduoduo have been my favorites. David was recently interviewed by the Wall Street Journal where he made the point that corporations’ origin stories are the best nonfiction stories of our day - it our generation’s hero tales.

Benedict Evans.   Benedict is a fantastic author with a succinct and sardonic writing style and content that is a mix of news summary + analysis.  He has a weekly free newsletter with hundreds of thousands of subscribers with the stated topic of “what happened in tech that actually mattered, and what it means” and his paid newsletter is one of my favorite weekly reads.

Stratechery by Ben Thompson.   A taste maker for our industry, Ben is one of the first sovereign authors before that was a term of art.  He’s managed to democratize (and monetize) what would ordinarily be a tech company’s in house strategy department’s work, and he’s used his influence to score great interviews and insider news.

Last Week in AI. While I mainly get my AI news from sources internal to my company, I have found this newsletter a great skim to ensure I’m not missing anything in the AI arena.

My Professional Skills: Product Management

This was the biggest hole in my early-in-career information strategy.  I just didn’t appreciate how much wealth of insights there was by reading up on the skills of my profession, separate from my industry.   And wow has this area matured and consolidated in the past few years!

Lenny’s Newsletter & Podcast: Lenny’s work is now known as one of the most popular product management newsletters.   His content is targeted to those who like to skim vs. read in depth, and the content is so high level that it’s geared towards those new to the industry. His podcast series has interviewed the biggest names in our industry, and it is a source of great wisdom.

Peter Yang’s Creator Economy Newsletter: Peter’s my second favorite PM influencer after Lenny. Good practical advice on product and career.

Deb Liu’s Perspectives: Former Facebook Product Executive and now a CEO, she often covers the more human elements of being a tech professional. Her post on what a Growth team should focus on is my favorite.

Sam Shillace’s Sundays Newsletter: A founder of Google Docs now at Microsoft, I find Sam’s informal ruminations on product making inspirational.

I sometimes follow John Cutler’s Beautiful Mess, Shreyas Doshi, and Will Lawrence’s Product Life but I find they have fallen behind Lenny. John and Shreyas also seem to do more click bait now a days by shaming anti-patterns; I miss the honest advice that fueled their early rise.

Great book recommendations are outside the scope of this post, but this section feels incomplete if I didn’t mention the work of Marty Cagan from Silicon Valley Product Group.  His book Inspired is the #1 book I recommend to new product managers.

Leadership

I framed that an outcome of my Information Diet was to develop intuition, and intuition on influencing people, building coalition, and storytelling is a large part of most knowledge worker jobs. Here’s a few recs in that area:

Finding Mastery Podcast by Michael Gervais.   A sports psychologist interviews leaders, mostly sports coaches but not always, about high performance and being in the flow.   Gervais is a fantastic interviewer who gets people to open up about their personal struggles yet synthesizes how to apply it to the life of his listeners. 

Brené Brown’s Dare to Lead Podcast.  If you’ve subscribed to Mind the Beet for a while, you know our philosophy on leadership is rooted in allyship and vulnerability.   Brené is the public face of vulnerability. 

The Moth Storytelling Podcast.  The Moth is an organization dedicated to the craft of storytelling and their podcast features the best of their “story slams” – true stories told live without notes to an audience.  Not only are the stories fantastic, but it inspires clarity in communication in my own work life.

Journalism

So far, I’ve talked about how to be a knowledgeable information worker, using examples of my profession and industry (tech and product management).   In addition, my information diet hobby involves consuming news and staying up to date as a citizen of the world.  

My approach to journalism may seem obvious (I essentially recommend the most well known and commercially successful journalistic entities in the world) - but that’s the point and there is an intentional philosophy around this, namely that I a) avoid infotainment, TV, social media and AI-based aggregators as sources of news b) prioritize the highest quality journalism c) find a counterbalance to whatever is my primary source and d) support local news.  I don’t have a problem with quality organizations being gatekeepers – in fact, I pay a premium for that synthesis.   Here are some details:

The New York Times.  It’s clear to me that the NYT is one of the few journalism organizations to cross the chasm to a new economic model and is pouring the profit into redefining quality journalism.   This fantastic analyst report delves just into how the organization has transformed itself and how they prioritize paying journalists. 

Wall Street Journal.  The NYT has a bias for David over Goliath and stories that prioritize those marginalized by the system.   WSJ is a great complement to the NYT in this respect. Both are pretty centrist overall and that is my goal; I want to support quality journalism vs. extremes.

Seattle Times.   I make it a point to prioritize news of my local community.  Like many, I’ve noticed the steep decline in quality for local news compared to just a decade ago – but keeping up with local news makes me a more interesting conversationalist with fellow parents and neighbors.

TikTok. My TikTok feed includes late night TV show snippets, SNL recaps, dad jokes, sports highlights, and breaking news from the major organizations. I find TikTok is often where I will hear about a breaking event first, before then diving into it with mainstream media.

ChinaTalk & Sinocism. These are two Substacks that cover in depth analysis of China, which was a 2023 goal of mine to increase my info diet on.

World Context

Long Now Foundation Podcast.   The Long Now foundation seeks to counterbalance traditional thinking with interesting talks and projects focused on the 10,000 year time horizon.  I find it a fantastic way of broadening my thinking on culture, product, and government.  

Lex Friedman’s Podcast. “Conversations about the nature of intelligence, consciousness, love, and power.” From world leaders to tech CEOs, almost every major figure in the world has done a long form interview with Lex. He’s known as a friendly interviewer with softball questions - almost never challenging the people he interviews. Yet the soft style often brings out some unique insights.

The Economist, including their podcast spinoffs. I opened with The Economist, so you know it’s a primary source of data journalism, world context, and news analysis for me. Their podcast spinoffs - from Boss Class which dives into management theory to The Prince which covers the history of President Xi of China - are good deeper insights.

Life Hacks & Parenthood

Part of my info diet is ensuring a steady stream of “new things” into my life - here’s a few ways I do that:

Omar Knows. Omar’s recs on products he loves are aligned to my lifestyle - Helen and I buy nearly one of everything he recommends.

Recommendo. Cool stuff, once a week. Eclectic mix across nearly everything across digital and physical products. I often pick up something random to try.

New Fatherhood. Building community around fatherhood with a frank and vulnerable discussion of being a father.

In Closing

The trick is not to get overwhelmed.  I have busy weeks where I get to little of the above content – and I always have a queue I feel slightly guilty about. Regardless of whether you plan to make this a small or large part of your time, I do encourage new grads entering the workforce to plan their Information Diet.  Not only is it a career accelerator, but most jobs require you to get great at quickly consuming the right information and this is a way to build the muscle.

There is a variety of reasons why teams lose motivation - both macro and micro reasons are often times at play. When that happens, I have seen product managers gripped with fear and disengagement, which creates a vicious psychological cycle of negativity. As managers, it’s our job to figure out what to do to get our folks back on track. While any unhappy team member will have ripple effects on the team, an unhappy PM’s influence is particularly extensive due to the glue that the PM often times provides across the organization.

In this post, I will discuss what I’ve done as a manager to get teams out of a rut - specifically when PMs feel demoralized.  This post lists resources and tools that have helped me navigate as a leader in the context of a late-stage growth start-up.

△ Name it - Victim, Villain, Hero triangle  

No one gets disengaged and unmotivated overnight. What I have learned to watch for in 1:1s and other team engagements is how my team and I are showing up on “the drama triangle.” 

I first learned about the Drama Triangle in the 15 Commitments of Conscious Leadership from Kaley Klemp. And one of the tools it offers helped me identify if I am inside the drama triangle (which is common for all of us, myself included) and then shift my mindset to be more intentional and aware.

Especially when my team struggles, I first and foremost reflect on where and how I am contributing to the drama going on and how do I model an owner’s mindset.

During coaching conversations, I ask in 1:1s to name where a team member is on the drama triangle and acknowledge it—usually, the demoralized and unmotivated folks are hanging out in the victim corner, villainizing the circumstances around them.  To break the ice, I ask my team to name where someone else appears to be and then move to self-reflection.

I know I need to engage in this exercise when I hear statements like this (or similar):

“I have no control over this situation,”

 “Leadership just doesn’t get it” 

“This decision has been made and now I’m stuck with it” 

“I’m excluded from x” 

Here are questions I use to get folks to name where they are and reframe it: 

“Where on the triangle are you right now?” - I have seen that just stopping to name it goes a long way.

“What is in your control?” 

“What can I do to help you get unstuck from your anchor” 

This technique is a starting point of the conversation, and where I go next from here is reminding my team of what success looks like.

🏆 Clarify success  

Many times success criteria gets lost in the shuffle of the day to day and I see my team getting stuck in activities over outcomes. To be clear, activities are necessary to achieve the outcome but when the big picture gets lost, morale and impactful productivity suffer. 

As a leader, my job is to be my team’s compass so I try to step in and remind them on where we are going so they can reflect and make a plan on how to get there.

Here are some specifics to support this:

1. First, I work with each PM to make sure they know how their success aligns to business goals and remind them why this is so. Sometimes the big picture gets lost and as a manager, it’s easy to take for granted that my team knows why their work matters. If through a conversation, together we uncover that there is a lot of time being spent outside of business-aligned goals, then we talk through why that is and how to minimize these efforts.

   “Leaders must get across the why as well as the what. Their people need more than milestones for motivation. They are thirsting for meaning, to understand how their goals relate to the mission.” ~ Measure What Matters, by John Doerr

2. I ask PMs to reframe investments in value that they are driving - so they can tell a story like “By delivering x and y investment, [this thing] will increase/decrease x% and therefore the business will make [x% more next quarter] or [see y% less customer churn].

3. When possible, I assign a PM to a specific and focused business metric and ask them to throw everything they can at moving it. I’ve seen that PMs sometimes struggle with attribution of their work to a business metric, so breaking things into key results or KPIs to clarify how investments latter up is helpful.

👥 Increase customer connection

When I am in a rut at work, I go back to the basics - get more sleep, work out more and talk to customers to remind me why I love my job.

As a manager, when I observe that my team is also in a rut, the best way to help them get back to customer connection is to model it.  Here are two specific tactics I do:

1. Ensure that every week I have time with a customer - it can be a customer conversation, watching FullStory of users going through the product, listening to a support call, or reading a competitive analysis.

2. I use customer learnings and insights in day to day language around my team. Sometimes I drop an observation in a conversation or a stand up, or send out a recap of what I learned and what it means to me.

⛹️‍♀️ Product play 

Additionally, I’ve seen product play help PMs get re-centered and re-energized. So whether it’s doing a product tear down or playing with an adjacent product is both inspiring and invigorating. Others get a boost in energy by switching context and hacking away at something as a team - encouraging your team members to participate in a Hackathon is also envigorating.

Adam has written about the way he thinks about Product Play in the past and here are 3 of my favorite tactics that he recommends to make this be a habit:

Have a project or goal. This isn’t tire-kicking - relate Product Play to a real need to use the product, for instance using a website creation tool to create a place to share information about a learning program for my team.

Asking “What if?” and “5 Whys?”. This is about generating energy. Ask yourself “What if?” and also ask yourself “Why?” and then “Why?” again at you answer at least 5 times.

Go far afield. I love the quote about how it is better to be pretty good in 3 areas and put them together in new ways rather than be an expert at 1 thing. It’s the essence of being multi-disciplinary. To that end, some of my Product Play will be with things far afield of anything I work on. Connecting gaming to enterprise software, for instance.

💪🏻 Boost morale - onsites, team building and recognition

Lastly, I turn to boosting morale- especially in a hybrid remote world. My key go to tools in my toolbox include quarterly onsites, team building activities and focused and intentional recognition. As a leader,  this stuff takes time and intentionality and while ideally this is always on, when times are tough, I’ve found extra attention here especially important. 

Here is an excerpt from Adam’s “How to Rock Your Onsite” on structuring a simple agenda focusing on Why, What, How:

Why: Focused on our mission, customers, and how we as humans are motivated to do great work.

Example agenda topics: Motivating customer stories, leadership AMAs, geeking out on the latest workplace research on what motivates humans

What: Focused on celebrating successes, learning what the rest of the team is doing, and what our next objectives should be.

Example agenda topics: Celebrating past successes, stories around big learning moments, a look ahead to upcoming events and milestones

How: Focused on our culture, process, and diversity & inclusion.

Example agenda topics: Brainstorming on how to improve product craft, retro on why we aren’t moving fast enough, D&I programming

Additional resources: 

1. Transformed by Marty Cagan - I have mixed feelings about Inspired and Empowered, but this book has helped me with practical tactics of empowering PMs, especially in a non-product-led environment

2. 15 Commitments of Conscious Leadership by Kaley Klemp - This is the book where I was first introduced to the Drama Triangle

3. Daniel Pink’s Autonomy, Mastery Purpose - What really motivates employees

4. Measure What Matters by John Doerr

This week’s post is a reprint of a write-up I did last Fall on the topic. Enjoy!

As a team leader, I want to foster deep bonds within my team. I feel a responsibility for rallying the team around a mission and constantly improving team culture.

With an ever more diverse and remote team (over 40% of my team is outside Seattle and well over 50% don’t come in daily), creating these bonds in a post-pandemic world is challenging. I’ve needed to learn new tools to help the team thrive in a distributed manner - and one way I’ve done that is to have rhythms for bringing the team all together twice a year to fill up our cups together.

Let’s dig in to how I approach these team onsites and how we’ve made them a touchstone of our culture and rhythm.

Create Separation Between Urgent Business & Team Development

Pre-pandemic, when most of us saw each other every day, onsites were primarily focused on urgent business objectives - planning summits & pivot executions for example.

Now the concept of connection & community building among team members and across disciplines is just as important.

We’ve had success when we create explicit space for both. A day for team-level planning. A day for ad hoc 1:1’s and synchronizing on whatever is urgent. And a day dedicated to developing employees and the team.

It’s this last day that the rest of this post is dedicated to. And it really is a mind shift: We plan a day around improving skills, driving alignment, and setting context for every team member. The goal is to wire up neurons and drive mutual understanding and shared norms. We pretend it’s Day 1 of a new team when bond building has traditionally been most critical. We ask, “What can give us enough context and connection that we can all thrive as a distributed team for the next chapter?”

Let’s dig into some of our most important rituals as we create a day focused on connection and context.

Choose a Theme

I am intentional in setting the frame of mind that I want team members to walk into the onsite feeling. It’s a signal to people on how to show up and it creates an extra sense of safety as folks walk in.

One way I do this is by picking a theme for the onsite. A theme is a one-word summary that runs through all the agenda topics for the day. For instance, as we were leaving the pandemic, we chose the theme of Sunrise to spark a sense of renewal. Last year, we had a theme of Prism that enabled a fresh look at our work. And this year, with the paradigm shift of AI and the macroeconomic climate requiring us to respond to a lot of change, we chose the theme of Transcend to capture the spirit of rising above the typical tradeoffs we find in our product and team.

You get the picture: the point is to pick a theme that reminds folks that onsites are about stepping back from the daily grind and give a name to the most important context for the team’s situation.

The theme is introduced in the invite to the onsite (like a wedding invitation). Here are some banners & framing text in the invite to previous onsites we’ve done:

Individual agenda owners are asked to find a clever way to reference the theme. I also find it fun to create a PowerPoint deck template aligned to it (e.g. the section header slides for Sunrise were all around the sun during different seasons of the year) and we’ve even created Spotify playlists aligned to the theme to play during breaks.

Measure How You Made People Feel

The post-event survey is where the mental shift to employee development as the goal takes shape. This drives intentionality around how I want the team to feel when the day is done.

Here are the top questions I use on the post-event survey and of course I take this impending grade into account as we plan out topics:

1-5 Star Rating
Agree/Disagree: “The offsite was worth my time”
Agree/Disagree: “I feel more in the know about what's going on around the team”
Agree/Disagree: “I feel more energized about my job"
Agree/Disagree: “I feel like I can now prepare for what's coming”
Agree/Disagree: “I feel like I got to know people on the team better”
Agree/Disagree: “After today, I'm more convinced that my workplace is a safe & inclusive place where I can do my best work”
“What was your favorite part of the onsite and why?”
“If you have a shout out to a particular speaker, leave that here”
“Next time we have an onsite, I suggest that we…”

Brutal Agenda Simplicity: Why, What, How

The frothy mix of connection, mission, context, culture, and strategy can be tough to create a crisp agenda around. I don’t want people to feel like the day lacks cohesion. We’ve homed in over the years on a simple frame for the agenda that focused the day on three parts:

• Why: Focused on our mission, customers, and how we as humans are motivated to do great work.

  • Example agenda topics: Motivating customer stories, leadership AMAs, geeking out on the latest workplace research on what motivates humans

• What: Focused on celebrating successes, learning what the rest of the team is doing, and what our next objectives should be.

  • Example agenda topics: Celebrating past successes, stories around big learning moments, a look ahead to upcoming events and milestones

• How: Focused on our culture, process, and diversity & inclusion.

  • Example agenda topics: Brainstorming on how to improve product craft, retro on why we aren’t moving fast enough, D&I programming

This ordering is intentional: “Leaders start with Why,” after all. And brainstorming around How is richer when everyone has a greater understanding of our objectives.

1-2 agenda topics per question is appropriate for a 1 day onsite.

Tell Stories and Retros

One of the problems with onsites is that often speakers feel the need to get into hardcore information dissemination mode. Nothing sucks the energy from an onsite more than a 20-minute recap of the latest Objectives and Key Results.

I create a counterweight to that inform-first mindset and it’s one steeped in my experience as the sponsor for years of Lunch & Learns within our team: stories are more powerful than charts & tables & bullets. I ask speakers to think about specific events with a cast of heroes, problems to overcome, surprising setbacks, and an exciting climax.

In short, onsites should go for a sitting-around-the-campfire feel:

Here are a few ways we’ve done this over the years:

• Have each team tell a story of their biggest learning

• Share stories of transformation and renewal from the past six months.

• Choose agenda topics focused around sharing personal stories and learning moments

• Tell the origin story of a particular business line or product

Move Beyond Icebreakers with D&I Activities

There are many reasons to focus on Diversity, Equity, and Inclusion at onsites - it’s a great reminder to ensure all voices are heard and DEI-fluency is an important skill to teach the team. In addition, they can be powerful ways of fostering team connections and ensuring a deeper sense of belonging on the team.

Many D&I activities are actually icebreakers-with-meaning. Here are a few of my favorite:

• Privilege survey. The mechanic asks folks to examine and discuss the privileges they’ve had in their life. It starts with a private ranking of privilege using for instance this Better Allies 50 forms of privilege. It’s a creative way of getting people to discuss where they’ve come from as larger D&I concepts are explored.

• Sort your values. The mechanic has people choose their top five values that are important to them by sifting through a 50-card deck of values (Autonomy, Purpose, Justice are example values).

• Glad It Didn’t Happen. The mechanic is that each person shares something they are glad didn’t work out in their life. It’s a meaningful way of learning about the tradeoffs coworkers have made in their lives and the path each of us takes to find a sense of belonging.

• Life in Thirds: The mechanics asks each participant to divide their life into three parts and write short bullets about important moments in each of the three chapters. As you share out, spend equal amount of time on each chapter.

• Value Snapshot: Everyone creates one slide with pictures of things that have meaning and value to them. Photos, meaningful books, graphics of important hobbies - anything is fair game.

The crucial point here is to engage the team to share meaningful lived experiences and then layer in key diversity, inclusion, equity, and belonging concepts while steeped in learning about each other’s lives.

It’s more powerful than any typical icebreaker and more memorable than context-less explanation of a D&I concept.

Don’t Skimp: Celebrate milestones. Frame the Future.

Over the years, we always get close to overprogramming the day and need to cut back on the agenda items. I've found that the popular things to cut are celebrating our recent milestones (excuse: didn’t we already send the victory mail on that? or what if I miss something?) and the look ahead of what’s coming soon (excuse: oh, didn’t we cover that in planning report outs?).

Both are critical and it’s a mistake not to fit them into the agenda - people will feel like the day is too fluffy unless you really give them these left-to-right views.

There are mechanics we’ve tried that can enable you to fit these in even when the day seems full already:

• Consider celebrating milestones as rotating banners during breaks and on the slides between agenda topics.

• Consider mechanics where team members can recognize great work in async chats or in a Cheers for Peers board on the wall.

• Consider a single slide that lists out the major events and milestones for the next 3-6 months. Even if you don’t have time to cover it in detail, it’ll be a resource to enable people to plan their lives around the rhythms of the team.

Here’s one PowerPoint template I’ve used over the years to frame a season for a team:

Vary the Interaction Format

Now we get into the mechanics more so than the content. The biggest challenge of an onsite is keeping people engaged for a 7 to 8 hour stretch. The key to doing this is to vary the format of each agenda topic - the variety breaks up the day. While the search space initially seems large, the fact is there are only a few typical mechanics for onsite agenda topics - and I try to have one of each:

• TED-like presentation: Single speaker with an engaging topic.

• Small group break outs: A owner frames a problem and asks for discussion among table groups.

• Big group discussions: A facilitator frames a problem and asks for a large group discussion.

• Structured activities with report backs: A facilitator frames a problem, asks smaller groups to work it, and then facilitates a large group report back.

• Leadership AMAs & outside in perspectives: A guest is invited to share top of mind thoughts and answer questions.

• Round robin stories from across the team: A facilitator frames a problem and asks a leader from each team within the org to share a story or lesson about it.

• Private activities: Each person spends time privately creating a slide or sticky notes on a topic. Where appropriate, people can share in small or large groups.

Each of these formats has pros and cons - but the key is to choose many of them throughout the day.

Be Intentional About Hybrid Participation

Sometimes team members can’t fly in or sometimes we invite partner teams and disciplines that didn’t prioritize the travel budget.

It’s been hard for us to balance the energy and connection inspired by in person face time with a duty to still ensure remote participants feel included.

While there is no perfect solution for this, a few things can help:

• We state our hybrid intentions at the start of the day. We recognize the goal of including remote participants as we kick off the day.

• We create an opening for people to give real-time feedback on the remote experience. I use the phrase “See something, say something” at the beginning of the onsite to ask for the interruptions in real time if a camera fails or microphones stop working.

• We project a shared chat. We always project a shared onsite chat in the room and encourage in person attendees to use it as well as remote folks.

• We nominate a remote champion. We choose someone who feels accountable for validating the remote experience is working well and who we can lean on to suggest improvements during the day.

• We try to have a least one remote presenter. This ensures someone remote is on the planning committee for the onsite, which is a useful voice to have.

• We check in with remote folks several times an hour. We ask presenters to validate microphones are working and screens are shared in the right way. This serves to remind in person attendees about remote participants as well.

End Early

Onsite days can be long, especially for remote participants. We try to create the time and space to make connections ad hoc - a morning and afternoon break and an extended lunch if we can. What’s more, I plan to end earlier than the time I publish - so if I tell people the onsite will end at 4PM, I secretly plan the day to end at 3:30PM. Yes, it’s a bit of a hack, but the anchor point is a way of managing the energy level.

In the worst case, we have buffer for agenda topics that run long but in the best case, you give people the gift of extra time for ad hoc connection at the end of the day.

Wrapping up

I’ve always felt a deep responsibility and accountability for these onsites on two dimensions.

First, I want to show respect for people’s time - that’s why I go the extra mile to choose a theme, define goals, and think about the little things that make people feel special and taken care of for the day.

Second, and even more important, these onsites are a mirror to reflect how clear my vision is for what it’s like to excel on the team. It’s a chance to crystallize what’s important and what we stand for. I care deeply about a customer-driven culture, a sense of belonging, a strong mission and purpose, and a culture that celebrates the past but sets ever-higher expectations for the future. Too many of my days I barely get to make one of these points to the team - but onsite days are a chance to make all of them in one pre-programmed way. I try not to waste the chance.

My key insight over the years is that it’s almost impossible to recognize and say thank you enough to people around you. Every person I have managed and worked with has gone further and worked harder when they felt seen and appreciated for their contributions. However, doing it authentically and in a meaningful way is the art that requires thoughtfulness.

As a manager, I view ways to recognize people as a set of tools in my toolbox. Depending on circumstances, some are more available to me than others. Before discussing the different types of rewards, I want to share three things I believe to be true in a high-functioning organization.

1. Context matters—It is important to know how people who work for you like to be rewarded. If you are building a relationship and haven’t worked with this individual, a simple question of “What motivates you?” will open the door to this understanding. Remember that the first answer is often not complete, so keep digging.

2. No gold stars for doing your job—Thank people for a job well done but not for doing their job. For example, I don’t thank people for meeting deadlines we agree upon, but I do thank people for meeting deadlines despite x number of things that randomized them in the process, making it hard to achieve the initially defined goal. The difference is subtle but important.

3. A reward for good work is getting to work on bigger, harder things. The opportunity to be trusted with the business’s most impactful challenges is a reward for a job well done. I won’t cover this as a type of reward in this write-up, but it's important to put this into perspective with people on your team.

I categorize recognition into the following 4 buckets: financial, experiential, symbolic, and social signal. In this post, I will discuss which tool I pull out for what situations and pitfalls to avoid.

💰 Financial Rewards

This is the most obvious and clear type of recognition that sends signals and also one that is most “regulated” and organized in companies around review cycles, bureaucracies, and hierarchies.

Examples: promotions, merit increases for high performance, variable compensation, and spot bonuses

Great managers understand how the system works and how to maximize it to reward their team. If you are not aware of how your organization thinks about recognition from beginning to end, you may be missing an opportunity to secure additional resources for your team.

Here are some questions you should be able to get answers to from your people/HR team:

1. What are the inputs into how the rewards budget is allocated?

2. What budget is at your disposal vs. your managers’ disposal?

3. Do promotions vs. merit increases vs. spot bonuses come from the same budget?

4. If you have a budget at your disposal, are you expected to use all of the budget you have during the rewards season?

5. Is there an opportunity to do off-cycle promotions if there is merit?

6. What’s the path for spot bonuses?

Pitfalls to avoid: It’s easy to not fight for more money for people who are not constantly asking for it. So make sure that you are watching to not overlook people who aren’t asking for more money and/or promotions. It is natural to listen to the squeaky wheels, but don’t accidentally ignore your quiet employees who trust that you will do the right things for them based on their work.

🏖️ Experiential Rewards

When you look at your tool kit and what’s available, understand what experience-based things are available. Some will be centrally managed and locally approved (sabbaticals), and some will likely be completely in your control as a manager.

Examples: Bonus day off, lunch and a movie as a team, a reward trip, sabbaticals, volunteering as a team, tickets to a sporting event, etc. Here is what I have seen be used as experience awards:

1. Vacations - Top sellers get to go on a tropical vacation for a week after a good year. I know some companies do a week-long annual vacation as an entire company and invite families to join, too.

2. Sabbaticals—Many companies offer an extended period of time off as a reward for years of service. Usually, these require manager approval, so as one who approves them, congratulate and encourage your employees to take advantage of this recognition.

3. Day off - if your team had to be on call and give up their weekends and/or evenings, giving them a day off to make up for it is meaningful

4. Milestone rewards - on one of my teams, we used to take a half day off after hitting a milestone. We would go get lunch and see a movie as a team

5. Box tickets - often companies have access to sporting event boxes and these can be used as rewards

6. Participating in a conference - whether getting to work at a booth and talk to customers, giving a talk and a demo on your work, or going to a conference to learn - these can and should be considered as rewards and an opportunity to be an ambassador for your company and team

Pitfalls to avoid:

1. Not everyone likes more team time as a reward. So if you have people on your team who’d prefer not to have “team fun,” normalize opting out.

2. Be clear if you are sending someone to a conference, whether this is a reward experience or a work requirement, and approach it accordingly.

🏆 Symbolic Rewards

Examples: trophies/ribbons, certificates, handwritten thank you notes, superlative awards

I like these rewards because so many are at the manager’s discretion, they are fun to do, and they can be meaningful mementos to people who receive them. Nothing is preventing you from writing a handwritten note and mailing it to express gratitude or from creating homegrown certificates on your team to celebrate people’s accomplishments.

Pitfalls to avoid: The most meaningful part is the few bullets explaining why the person receiving it is worthy. As a manager, when asked to provide that input, take the time to share your insight!

👏🏻 Social signal

This is the simplest and easiest to forget - the daily recognition for small victories.

Examples: public praise in meetings, 1:1s, Slack messages, emails, ambassador of the work

Here is how I approach it:

1. End every meeting with a positive sentiment. There is always something positive to reflect on, and I try to remember to do it at the end

2. When someone does a good job with driving to a decision, synthesizing insights, etc., I forward it to others both for awareness but also highlighting what I liked about the work

3. 1:1 positive feedback - just as I send constructive feedback pretty immediately, I try to send kudos after interactions with people on my team. Something as simple as “I learned a lot from your presentation” or “I thought you did a good job driving us to clarity.”

Pitfalls to avoid: The biggest one here is not doing it or worrying about perfecting it. Try to say thank you quickly and earnestly. If you get caught up and know that you need reminders, put time on your calendar to do it once a week for 15 minutes.

Thanks for reading, and please drop in comments anything you have done to recognize your teams or you have been on the receiving end of that has left an impression.

Leave a comment

Other Mind the Beet Articles in support of managers:

1. Part 1: Onboarding a Product Manager by Helen

2. 🦃 Product Team Rituals by Helen

3. Burnout & Boredom: A Manager’s Pandemic Retrospective on Mental Health by Adam

4. A day in the life of a frontline manager by Helen

5. How I Lead When The World Is Uncertain by Helen

6. The Gifts You Give: A New Year's Resolution Framing 🗓️ by Adam

Imagine I am pitching you on my new business idea. I’m trying to get people to visit my mountain property.

It requires me to build towers that stretch thirty feet into the air to carry people in chairs where it is easy for people to fall off.

Once they get to the top, they travel under their own control at rapid speed - so much so that over the course of the day, enough people will sustain injuries that I’ll have to have a team available to go collect immobile people throughout my property.

The natural landscape isn’t suitable for me, so every night I’ll have to use giant machines to get it ready for the next day.

I’m subject to the whims of the weather and even in the best case, I’m only open five months of the year.

Oh, and I require my customers to wear the most uncomfortable footwear of their lives.

Pretty crazy, right? No one in their right mind would think this is a sane business idea - and yet there are almost twenty million people in the United States that went skiing last year.

The only reason you believe me that this is a viable idea is because of the existence proof. The industry couldn’t be exactly foreseen ahead of time, but instead it was built up over the years, with creative solutions to each of the unique risks and challenges that cropped up.

Why Am I Telling You This?

As our industry embraces the paradigm shift of AI, I’ve been looking for the right non-tech examples to explain to my team how to operate differently in the early stage of a new era.

Like many of us, for the past few years, I’ve led a team that was capturing value from a pretty well-defined flywheel born out of the transition to the cloud. Ambiguity was (relatively) low, a product culture of stability and predictability was an advantage, and there was high alignment between customer feedback and the right backlogs.

Now we find ourselves in a new situation:

1. There is no existence proof for the endgame. While we have strong intuition about the scenarios that AI will evolve to help with, we have no straightforward way of describing the end state. What will it all look like after we’ve gone through the dozens of incremental steps to get there? We are staring at a snowy hill with no idea of all the problems we will have to tackle to invent a modern ski resort. We need both vision and humility to tackle this.

2. It’s easy to focus on downsides. My description of skiing above focused on pitfalls and negatives - I didn’t talk about the thrill of the epic powder days, the kids who learn grit and agility on ski teams, or even the quotidian opportunity of ski lodge food service profits. Ambiguity breeds a focus on risks - it’s natural (and essential to understanding externalities and unintended consequences) yet an overfocus on it can be harmful to ideation and product making.

3. There are many more failure paths than success paths. We have flipped from “most incremental investments will pay off quickly” to “all plans inherently have more risk and the hit rate goes down.” Tech risk, design risk, business risk - all the classic forms of product discovery risks are on the rise.

Time To Act Different

So if the endgame isn’t clear, many roads lead the failure, and we naturally gravitate towards articulating risk - what’s the right way to lead?

Resilience in a business context like this is what it means to have a “tech” culture. Being in tech is less about whether a company writes software or not and more about their ability to pivot to embrace new ambiguous paradigms.

Like many, I believe that the future must be built brick by brick from smaller bets that cut through the ambiguity. It’s intentional that just last month, I reviewed The Geek Way, a book that frames leveraging science, openness, and speed. Here’s a few other ways I’m leading through the change:

1. Drive with more intensity. I’m spending more of my time with my LT setting ambitious expectations on outcomes and driving to a culture of ever higher performance. The beginning of something new naturally leads to a sense of needing “this team to capture this moment,” and it establishes a norm of problem solving instead of problem admiring.

2. Extreme awareness of context. I’ve upped the amount of “state of play” communications I’m sending to my leadership team. Staying informed is even more important when things are changing rapidly and it’s an easy way to create more safety among the team. I’ve always prided myself on being the glue.

3. Focus on opportunity cost. The sunk cost fallacy is top of mind for me as a leader. In particular, I’m asking more “What’s the opportunity cost of things we could be doing instead?” I’m framing how in hindsight it’ll look like a bigger mistake to leave folks working on an OK opportunity at the expense of rapidly tackling a great opportunity.

4. Resolve disputes with real code. I’ve found that one of the best way to reduce ambiguity is more hands-on time with product. Code wins. Using tech to solve real problems in your own life is clarifying. It’s been especially useful to clarity new conceptual models and UX patterns.

Resist the Urge to Promise Stability

As a leader, I often ask myself, “What would have happened anyway if I wasn’t around? What unique value do I provide over the team self-organizing?”

A couple years ago, I might have answered that question with a focus on providing stability, consistency, and nurturing a safe and stable place for people to learn and thrive at making product.

Today that’s evolving. I’m here to help the team embrace change and thrive in an environment where we are not afraid of evolving to meet new expectations. We’re proud that we are on the vanguard of the unknown. One leader on my team had shirts made for her team that say, “Sunny with a chance of chaos.” Love it.

This week, I’m kicking off a series of posts about supporting product managers through the employee lifecycle. While the cycle is the same in many information worker realms, I will share what has worked to support product folks specifically.

This topic is near and dear to my heart because what has emerged clearly for me in my career is that I get the most joy out of leading and supporting teams. The biggest gift any of my co-workers can give me is to say that they’d want to work with me or for me in the future and I strive to earn that right every day.

Over the years, I have actively participated in every part of the wheel - from attracting great people all the way through to them leaving my team. So, as in the true spirit of Mind the Beet, I want to share what I have done that worked well in each phase of the lifecycle.

Part 1: Onboarding a Product Manager (aka Get Me Started)

I find the onboarding phase to be critical to the success of a Product Manager and I take it very seriously given the time and effort it takes to hire. If the new hire is wildly successful, it will be in big part because I was able to set them up for initial success but if they don’t onboard and thrive, it will be in big part because I didn’t do my job well as a manager.

In this post, I will cover how I approach the first 90 days of a new hire on my team. However, before I dive in, here are the three things I remind myself every time a new person joins:

1. Do not use a one-size-fits-all approach - I think differently about onboarding a Senior/Staff PM, a Junior PM, a Career Transitioner, or a Manager. Specifically, I think about the onboarding projects, people to meet, and context needed differently and personalize the playbook for best results.

2. Be intentional - There are two main differences in how I think about the immersion of the new hire into my team. Sink or swim approach or gradual onboarding. I opt for a gradual approach for new hires and more junior folks, while throwing more senior folks into the fray quicker.

3. Be patient - I have a strong conviction that it takes 90 days for someone to find their feet, 6 months to start adding value, and a year to run at full speed in their role. I have tried to beat this pace and I keep coming back to this being the truth. Therefore, I have to remind myself to not jump to quick conclusions on the quality of the work or the new person on the team until at least 90 days.

Let’s now dive into what I do for the first 90 days and how I support a new hire in 30-day increments which I refer to as the sponge, the analysis, and initial action periods. After 90 days, I expect the new hire to function as a fully ramped member of the team - fully ramped, delivering and always learning.

30 Days - The Sponge Period 🧽

As an employee, I love the first 30 days in a new role. It is this magical period of everything being fresh and exciting, the calendar is not yet filled up with meetings and I am not yet committed to deliverables (or if I am, but I don’t quite understand what they mean yet).

During this period, I expect a new hire to spend 80% of their time in meeting people, understanding the organization, listenening, and learning - like a sponge soaking in water.

Here is what I do to help my employees during this time:

1. Provide the list of people to meet with and write out how that person can be helpful to them - including their role, what they work on, how their role is relevant to the new hire’s role, and some primer questions to start with

2. Share context on the organization and the product team - I have a packet ready with an org chart, links to previous All Hands decks, strategy documents, examples of briefs/one-pagers/PRDs, and directions on how to access the product so that the new hire can touch it as soon as possible

3. Build in support - before a new hire starts, I identify an onboarding buddy that this person can turn to with basic questions as well as a team buddy/peer mentor. I meet with these team members and ask them to support the new hire and also share about the new person’s role and what their onboarding project is all about

4. Be available - For the first 30 days, I try to meet with my new hires 2x a week for 15-30 minutes and then pair down to once a week (or every 2 weeks depending on the size of my team). Tactically, I schedule those times because the new employee doesn’t know what they will need and they often don’t want to impose

60 days - Analysis Period 📈

One thing that I have seen taken for granted is just how quickly the fresh perspective passes and the organization’s culture (and baggage) permeate one’s thinking. While it is a necessary evolution because that means that you are onboarding to the context of the team, there is a lot of value in getting these reflections written down.

To capture the early insights, during this period, I expect to get a read out from the new hire of what they have learned and an analysis of the “so what.” This is also a first chance I get to see how an employee thinks and synthesizes lots of signals into a coherent story to give back to the team.

Here is what I do to help my employees during this time:

1. Make your expectations clear and that this is an onboarding deliverable. Provide examples and templates (past onboarding projects are helpful as a reference point).

2. Make it safe to share learnings. As a new person, it can feel scary to make observations that may be too basic, not well-informed, or offensive for some other unknown reason. My job as a manager is to put all that aside and create space

Examples:

Here are some examples of insights that I have created as part of my onboarding or received from team members who joined my team:

Leader onboarding: When I came to Guild (as a Sr. Director), I did a 30 day listening tour and then sent around my insights to everyone I talked to as well as to the leaders of the organization. The benefit of this approach was that it forced me to stay curious and synthesize what I learned before jumping into action. This helped me build credibility and trust with my team as well as with the broader organization.

Senior PM onboarding: One of the people on my team went through the product experience end to end and used it to question historical decisions, identify and document bugs, and use his “new guy” card to improve the product experience. He instantly got credibility because he understood our product, showed curiosity, and got context.

Career Transitioner onboarding A project that I love giving to transitioning PMs is to do a functional diagram of the product they work on and present it back to the PM, Design, and Dev leadership. It gives the new hire a forcing function to get comfortable with technology that they need to understand at a functional level and helps stakeholders understand how the product actually works from a customer-first lens.

90 days - Take Action 💪🏻

I expect by the end of three months, a new hire will be fully ramped up and is delivering value to the business. I have extra bonus points if the value is customer-facing, but internal process improvements can also be really helpful especially if this is a culmination of a manager ramping up.

During this period, the new hire may be exiting their “honeymoon period” and they realize that it is hard to get stuff done and move the needle. However, this is the time to start showing value to the team and the organization and to push through real or perceived obstacles.

Here is what I do to help my employees during this time:

1. Just as the 60-day readout, hold the 90-day “value delivery” as a core deliverable for the new hire. By this time, it is easy to lose focus and get caught up in the day-to-day urgent matters, but I have found that if I make my expectations clear that this work is important, it will come to fruition.

2. Provide hands-on support and coaching to drive a project to a conclusion at the 90-day mark. This is the time when the reality of how hard it can be to get stuff done shows up. For me, this often means doing more dot-connecting and blocking and tackling to help my teammate get to an impactful outcome.

3. Celebrate the win - No matter how big or small the value that was delivered, as long as it happened, I celebrate this moment by acknowledging it as a graduation from initial onboarding. For me, this has been an official milestone at work via a performance review, public kudos or private recognition of the path traveled in a 1:1.

Examples of what delivering values in 90 days could look like:

1. Collect customer insights and share out learnings and action plan around them

2. Stand up an experiment based on learnings from onboarding, get it into the hands of users and share out learnings

3. Fix a problem that has been painful for a team - a broken planning process, consolidate relevant customer insights into one place that’s easy to find and use, create a sizzle video explaining the roadmap in a novel way to stakeholders - pick a pain point and address it.

Additional resources:

1. The First 90 Days by Michael Watkins

2. Deb Liu’s Perspectives: A Guide for Onboarding to a New Role

Thanks for reading! Drop me a comment with any feedback or thoughts on your experiences and I look forward to covering the rest of the employee lifecycle wheel in future posts.

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Summary: Adam reviews the 🔥 new business book that is all the rage in the hallways of tech right now. The final verdict: A great read for those new to the industry & it inspires good questions about where our culture should go next.

Am I a geek? At 15, the Doom-playing, PC-building, 12-sided-dice-using, varsity-academic-team-member that was me would have said yes. I was part of the first 0.1% of the people on the planet to use the Internet - my tinkering was 1990’s geek-fueled counterculture and part of my identity.

Now in my 40’s, well, a lot of what made me a geek back then has gone mainstream. We are in the Golden Age of geek-built tech, I am in a profession that is as close to tinkering with Legos as you can get, and I play Legends of Zelda: Tears of the Kingdom with my two daughters. But it’s all so aligned with what many think is the default success pattern in life now.

Andrew McAfee’s new book - The Geek Way - would say that it’s not me that has changed; I’m just as much of a geek as ever. It’s just the rest of the world that has caught up - and the definition of “geek” has expanded to be a much bigger tent, with a long tail of things in the world that anyone can geek out about, including how to build a business.

McAfee dives into the success patterns of the geek-built company, its culture, and its operating model. From Netflix’s famous Culture Deck to the story of how Microsoft Hit Refresh, The Geek Way is a tour through some of the most famous cultural principles of tech-driven companies.

Let’s take a deeper look at one of the Books of the Year by both The Economist and Forbes.

The Four Norms of Geekdom

Like any good business book, The Geek Way has a list to help frame the thesis. McAfee proposes four norms to a geek-built company: Science, openness, speed, and ownership. Let me describe each and share my own lived experience with them.

Science

What it is: Geek-driven cultures prioritize metrics, data & output-driven thinking paired with rigorous scientific inquiry and debate. Tinkering, experimentation, and curiosity are all prized above edicts and command/control.

Where it comes from: Early geek culture prioritized learning, curiosity, and the fun of sharing facts and debating. It’s about turning that childlike need to explore into a coherent system of decision making.

My experience with this: Clearly anyone in tech is familiar with metrics-driven product making, especially in the SaaS era. What I love about McAfee’s framing here, though, is the core frame of “science” instead of just “data.” I like that reframe because it captures the biggest nuance that I see in my life: metrics can tell whatever story you want them to. So you must pair metrics with a culture of inquiry, curiosity, and healthy candor. Being metrics-driven is a social activity that still requires driving consensus, just like the scientific method.

Openness

What it is: Openness is about embracing failure, avoiding fake success narratives, rejecting conformity and group-think, driving transparency, and making everyone invested in the success of an organization by inviting everyone to perform their own analysis. It often involves the radical sharing of data.

Where it comes from: Geek culture was counter-culture - it was about being different, not conforming to societal norms, and accepting people for how l33t they are more than anything else. Openness translates those roots into a culture where hierarchy matters less and there is a constant hunt for the best idea and decision.

My experience with this: I’ve always worked in transparent cultures and prided myself on the grind and rigor required to develop that transparency. McAfee’s reminder to ask for dissent (with cool stories about companies who require a process of written pre-mortems on any idea) was inspirational. I’ve also found transparency to underdeliver results as an organization and project scales as people get too overwhelmed by so much data. It requires a commitment from busy people to look outside their swim lanes.

Speed

What it is: “Observe, orient, decide, act” and then repeat. Geek-driven companies prioritize learning, iteration, and fast cycle-time. They were born from the ashes of waterfall software projects that are constantly late and especially susceptible to the last 10% of a project taking longer than the first 90%.

Where it comes from: I actually thought the relationship to geek culture here to be weak. It just comes from empirical analysis of how to build great software vs. anything inherently “geeky.”

My experience with this: Speed is highly relative to the business problem and tech stack I’ve worked in. The fastest projects in my career were the ones starting with a fresh code base; not every project has that luxury. So I’ve always seen this less as some finish line (“Yay, we are fast enough now!”) and more about prioritizing a constant improvement in decision and execution velocity. I especially try to prioritize quick decisions on so called “49%/51%” problems where the difference between two paths is small. I also try to ask “Is this a one way door?” as a way of crystalizing how much time to spend on a decision which could be reversed easily.

Ownership

What it is: Ownership is about a culture of autonomy and avoiding “proxies” that are distanced from the real results (e.g. the activity of a status report is a proxy for actually completing the project which is a proxy for sales lift).

Where it comes from: Geek culture was rooted in a being on the outside of the social and hierarchical power structure. Once on the inside, it’s rooted in avoiding the bureaucracy that is seen as toxic to individuality and autonomy.

My experience with this: I apply McAfee’s lessons here to my x-team work, as my job is mostly to build software sold as part of a larger suite, with the high coordination cost that entails. My strongest x-team relationships are rooted in this ownership mentality and in particular creating bonds between “a network of do’ers” instead of a hub/spoke model where a central hub feeds out work to spoke teams.

I Was Left Wanting More

In some ways, McAfee’s book left some of the most important questions unsolved, especially on where the future of geek culture needs to evolve and whether it gate keeps too much. If geek culture created the Golden Age of tech, how does it need to be augmented and changed for stewardship of what’s been created? Here’s questions I was left asking:

• How well does geek-culture build software that reflects and improves humanity? It clearly captures economic results, but does it drive the empathy & inclusion that is required now that it’s on the world stage? What can geek-driven culture learn from other operating models?

• Who thrives in this culture? What are the cultural weaknesses? McAfee focused on business results, but not employee wellness and development. How do the cultural norms need to be augmented to ensure more people can succeed inside the culture? Despite a couple pages on psychological safety, McAfee didn’t fully explore how wells those who “didn’t grow up a geek” can survive and thrive in these cultures.

• What role do the humanities play in product making? Given how critical my Design relationships are in my work life - and how terrible the business outcomes have been for companies who don’t prioritize superior design - it feels like a real miss to not frame how the best run tech companies have incorporated humanities into their product making processes.

Final Analysis

The Geek Way is most useful to folks new to tech or outside the tech bubble. Folks who already subscribe to Ben Thompson and Benedict Evans will find it surface level and the famous stories familiar. Yet regardless, it’s an important crystallization of key trends that matter deeply to product making in the 2020’s and forces us to ask important questions about what’s next for geek driven companies, how we adapt to a changing role in the world, and how to ensure the cultural norms work for all, not just geeks.