🎂 Celebrating 17 years at Microsoft

Career, product, strategy, and leadership stories

Aug 28, 2022

August 2022 was an eventful month! We celebrated my 40th birthday & my 17th year of working for Microsoft. We also received news of my promotion to Vice President of Product. Combine this with our youngest entering kindergarten next month, necessitating a change in our childcare plans and overall family routines, and our first bout of COVID after our summer vacation, and overall, there is a sense of an inflection point in the air. Life is segmented a bit into “before now” and “onwards from here.”

I have a tradition of looking back when these types of moments occur and reflecting - the recent promotion only makes it more appropriate to think about learnings from my 17-year journey from fresh college hire to a VP of Product managing a team of 40+ product leaders and supporting hundreds of engineers.

For those not familiar with my journey, here’s a quick snapshot of my various roles and growth over the past 17 years:

It’s hard to capture the awesome privilege, luck, and support network that I’ve had in my time here that were the primary determinants of my success, and I’ll ask for grace as I do my best to synthesize my own lived experiences in the form of a note to my former self.

This is the 4th version of this note - every year on my anniversary I add a bit more to last year’s note to reflect my year’s learnings.

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

Congrats on your job with Microsoft! What an interesting time to start in tech - you just signed up for Facebook during your last week of final exams at UCLA, Google IPO'd one year ago, and the iPhone will launch in 2 years. You’ve seen cloud & mobile go from niche to indispensable worldwide utility and are beginning to realize the impact to your industry of all the unsolved negatives that powering the world economy brings.

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

The most controversial part of your career is that you stayed with the same company for 17 years, reinventing yourself as the company grew, extended, and transformed. This was not the plan and leaves you reflective on how to avoid states like good enough and comfortable. If “the unexamined life is not worth living,” how can one do enough self-examination without seeing what’s out there? Your own lived experience these past 17 years proves there are dividends in long term learnings of staking out a product and team as a home for a while.

Here are 17 things I’ve learned in 17 years.

Career

Let’s start with a few learnings on managing your career and the role of product manager.

1.👕 Early on: Prioritize fit over growth.

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

2. 🧼 Establish great fundamentals.

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

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

When you start your career, you were told it’s the start of a long upward journey that must build on itself. This “career ladder” metaphor does more harm than good. No, better, to think about your future as catching some waves. This gets you thinking about reptition and cycles, project (wave) selection, riding something with more momentum than you have yourself, and knowing when you are in the whitewash and need a change. And importantly, it helps you realize the need to take a break between sets and how much renewal and pauses and reflection are part of a strong career.

4. 🏓 Define the boredom & burnout boundaries.

If you are going to stay on the same team, you need to watch your own boredom. But what is boredom anyway? Frameworks help. You’ve seen many over the years and two stick out to you: Daniel Pink's Autonomy, Mastery, and Purpose is the best quick framing of what goes into staying motivated. And the Mihaly Csikszentmihalyi’s Flow Diagram is a high bandwidth way of ensuring you think about peak performance. And when you feel yourself burning out, don’t ignore the intuition; do something about it.

5. 🏖️ Great time off is a career enabler.

You’ll find that every couple of years, you’ll find a way to take an extended time away from work - more than just your typical PTO: at least 6 weeks, sometimes 10 weeks. The reasons vary - honeymoon, paternity leaves, sabbatical. There was no sense trying to time them to work milestones - one of them was timed two weeks after you got your dream gig running your first UX product team. You're fortunate to have a work culture that supports people through time off; it’s one of the reasons you’ll stay for so long. This is a privilege. These moments are not only important for your own life but for your career as well. They make you a more interesting person and unlock your understanding of what drives you. This inner purpose makes you a better teammate & leader as people gravitate towards those who are centered and calm. There is a lot to learn about how to maximize your recharge time - and it’s one of the most worthy skills to invest in.

6. ✌ Define what "Be Epic" means to you.

You’ll see a lot of laptop stickers with the word “epic” on them in your industry. Many will define it as founding a startup or doing something no one has done before. That won’t sit well with you – too much disruption worship and not enough human empathy. To you, epic means having extreme pride in the quality of the work, the results that delivers, and the brand it develops. You'll remember vividly that one of your first projects at the company was to write 50 error strings for various problem conditions. You took the time to understand each condition, establish a consistent error taxonomy, and just in general write the best damn error strings on the planet. It's not that it was hard; it was just that no one else had time to go deep like that. It felt good to see the positive response from your peers and management and it'll motivate you to keep looking for hidden opportunity you can be epic at. So ya, error strings can be epic too.

Software is about people, not bits

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

7.🧠 Wiring x-team neurons is big tech’s way of generating social proof for good ideas.

As you grow more to coaching aspiring PMs, the most impressive PMs are those who not only think they are right but are willing to put in the commitment to gain buyoff of that fact. Unabashedly, the job of a PM is to form a coalition around ideas and plans with stakeholders who have a different lens than you. In big tech, this is how social proof for ideas works – like how VCs funding certain startups and not others is a form of useful signaling too. There is no single playbook for x-team success, but when you find willing partners who can take the time to build a sense of shared safety and context than enables the intense exchange of different views, you’ll have the most fun and fastest progress.

8. 🥕 Thoughts, Wants, and Feelings.

You’ll be fortunate enough to be paired with a few different leadership coaches in your career and a common theme among them will be to take a holistic look at your relationships. Much focus is placed on influencing what people think – but coaches encourage us to examine what people want and how they feel as well. It turns out that our thoughts are impacted by wants and feelings, not the other way around. I think we all intrinsically know this when we react to a proposal from someone we dislike or when we judge our kid’s behavior more harshly after a tough day at the office. Our neural processing units are constantly impacted by our background feelings and wants. This frames the way that you’ll think about goal setting as you grow from product manager into product leadership roles. The most important goals are not influencing thoughts but developing hunger and drive and influencing feelings. You might be recalling the Maya Angelou quote right now, “I've learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

9. ☕ Over time, the most important conversations with peers transition from mastery (“How?”) to purpose (“Why?”).

You will wish someone had told you that finding your purpose happens over time. It’s common to focus on mastery in the first part of your career - society wants you to just get good at something in your 20s and early 30s. It’s much less clear on what to do with your now finely-honed skills in your late 30s and 40s. “What’s your purpose?” is a source of deep and meaningful connection with other leaders as you age. This is a conversation about how one’s contributions impact the well-being of others and enables you to mix together the passion for technology and its impact on the world at large and your team in particular.

10. 🤗 Find your “First Team.”

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

Strategy

Given your product’s large number of user jobs and businesses, you quickly grow into the role of portfolio owner and spend more time honing strategic framing skills. Your role can be best summarized as the counterweight such that a team focuses on outcomes they will achieve rather than the activities they perform – not how hard or cool something is, but why it is important and what we can measurably achieve.

11. ❓ Strategy is a hedgehog; execution is a fox (Reference).

For your journey, product strategy will be an exercise in crafting a simple, unifying theme mapped to team expertise (the so called single theory hedgehog), while execution will be a constant expansion of new tools and technologies and shared components (the multi-tooled fox). It will be important to concretely understand your team’s role and strategic influence – there are so many types of teams at Microsoft and it’s silly of us to deploy labor and capital in a non-specialized way (link). Be very suspicious when asked to do something not aligned with your team’s strengths. Answer the question: “Out of every team at Microsoft, is this the team we’d pick to deliver on this?” Yet once an idea is passed that sniff test, don’t be afraid to try new execution methods, technologies, and work in distant code bases.

12. 📈 In tech, it’s all a growth business.

The above point to stay in your strategic lane doesn’t imply growth isn’t important. Your job as a product leader is one of defining and manufacturing growth – in skills, headcount, usage, and charter. You career highlights are mostly tied to moment of org growth - from validating an investment with a key certification, spearheading x-product GTM with features that span products for the first time, and defining a UX and customer acquisition system to take advantage of time to value improvements of the cloud. You’ll learn to recruit and follow those who create growth.

13. 🥤 Middle managers make the New Coke mistake…CEO’s worry about the Innovators Dilemma.

The most interesting strategy tension you’ll see in your 17 years is one of reinvention vs. bringing customers along. Here’s the problem: You’ll find it’s naively easier to recreate from scratch. There is a worshipping to disruption and non-linear thinking in our industry. Startups need to counter position, so everyone else must as well. All of this leads very commonly to proposals for new architectures, products, IAs, and change for change’s sake. You’ll learn over time a healthy respect for the blood, sweat, and tears required to bring customers along for the journey. In short, you will commonly see proposals that make the New Coke mistake and you’ll find your strength in articulating stable ground truths and asking for a clear thesis for change.

And yet…while New Coke is the way more common mistake you’ll see on the day to day problems, you can’t help but reflect many of the existential problems your company will face will be more Innovator’s Dilemma inspired. The case study of Microsoft 365 will leave a mark on your thinking for the rest of your career. You’ll see your org embrace the cloud well before customers told us we needed to, ahead of much of the market, making incredibly tough tradeoffs to reuse existing code and brands for early mover advantage and customer familiarity with a clear thesis on business model and value chain placement.

It’s a fascinating balance – being a middle manager in a system designed to focus on the next incremental value to bring customers along, allowing leaders the bandwidth to choose the few existential Innovator’s Dilemmas to bet on. It will cause you to revere tension, balance, and context as core to your philosophy.

Leadership

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

14. 🧘‍♂️ The Power of Calm.

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

15. 🎁 Think about the gifts you want to give.

You’ll have moments of great vulnerability in your career as you take on new jobs you aren’t qualified for or have missteps. You’ll remember the grace people give you in those moments. You’ll remember managers and leaders being intentional about how they wanted to help you grow. While you’ll read a lot of different leadership books, nothing will stick with you more on how to be a good emerging leader than just asking yourself the simple question: “What gifts do I hope to give each member of my team?” It could be a desire to excel, it could be a place of psychological safety, it could be more recognition, or something else. Be curious and planful and unique in your generosity.

16.🪴Curiosity & learner’s mindset are an elixir.

When you are closest to burnout and giving up, prioritizing curiosity is your best go-to solution. It’s a reframe that forces you to seek out new perspectives when you were forgetting the need to. You are the son of a teacher, the love of learning was instilled in you at an early age and was foundational to your academic career. Your work career is also centered on a learner’s mindset, but you’ll need reminders periodically to get back into that headspace. Instilling curiosity and a love of learning into your culture and team will be a foundational part of who you are as a leader.

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

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

Summing It All Up

This newsletter is called Mind The Beet for a reason – it’s a quote from Tom Robbins' Jitterbug Perfume that speaks to the eternal struggle of defining your own reality in the face of processes and pressure and systems. The first 17 years of your career will be about influencing large systems, not letting them consume you. Mind the beet.

Mind the Beet

Discussion about this post