Celebrating 16 Years at Microsoft

Career, people, strategy, and leadership stories

It’s time to celebrate my Sweet 16 at Microsoft.  It’s been an incredible 16-year journey from fresh college hire to a Partner Director of Product managing a team of 30+ product leaders and supporting hundreds of engineers.  

Most controversially and uniquely, I’ve stayed on the same product that entire time, riding it’s growth and expansion and transformations, and I think it’s given me a unique perspective on career, leadership, and our role as technology’s stewards that I reflect on below in the form of a note to my former self.  This is not the first edition of this note – I have a bit of a tradition of adding one thing to it every year and otherwise editing to reflect my latest thoughts.

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.

The best way to wish me congratulations on the anniversary is to support my new writing passion by subscribing to Mind The Beet if you haven’t already or share with a friend if you have. 😊  Weekly Sunday morning notes on career, parenting and life from my wife and me exploring many of the themes you’ll read in this post.

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 worldwide indispensable 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.  

The most controversial part of your career is that you stayed with the same product and team for 16 years, reinventing yourself as the product 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 owned lived experience these past 16 years proves there are dividends in long term learnings of staking out a product and team as a home for a while.   Here’s 16 things I’ve learned in 16 years, most of which I wouldn’t have learned had I jumped around teams and products frequently.


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 consumer 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.   

3. 🏓 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.

4. ✌ 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.

5. 📝 Write about it.   You chose a job that is more about pattern matching than most other professions.  What is this product problem most like?  Have conditions changed or is the right answer the same as before?   You’ll quicken your pattern matching skills by taking the time to synthesize and reflect.   You’ll get a reputation for blogging about topics like career and time management and strategic takeaways from major events and you hope some folks find it useful, but the truth is you use these to organize your own thoughts and speed up your own decision making.   You are an essayist at heart.

6. 🏄‍️ Your profession is a wave to surf not a ladder to climb.   Over 16 years, the job of PM at Microsoft has totally transformed.   Well over half of the skills that mattered when you started are not useful 16 years later.  When you started, new PMs read Design of Everyday Things, dreamed up ideas with only qualitative data, and owned most of the UX flows of the product.   16 years later, PMs read Inspired and we partner deeply with a strong design and data science team to set outcomes and test directions.   Every 2-3 years new trends will develop or be recycled – data, design, jobs-to-be-done frameworks, scenario focus, OKRs - you’ll spend the time to stay on top of them for yourself and your team.  Don’t get lazy or complacent here – your job requires constant reinvention.  Context + Experience == Intuition so it’s especially important you listen to industry influencers and research trends.

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.  Satya’s leadership principles are some of the best framing around this that you’ll see – in particular the explicit bifurcation between generating energy around new ideas vs. creating clarity on committed plans.  Those are different activities with different tools and needed awareness of mode.

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 I think about goal setting as a leader.   The most important goals are not influencing thoughts but developing hunger and drive and influencing feelings.  Many of 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. 🤗 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.


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.   The context here is that your product matures from a new entrant for Microsoft into an established business and a usage well for the company that needs to be modernized.

10.  👊 Outcome over activity.  Product Management can be best summarized as the counterweight such that a team focuses on outcomes they will achieve rather than the activities they perform.  As our industry races to put ever more complex pieces of technology together, there is increasing momentum to take execution-mindset thinking.   Great product managers reframe to the impact – 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.  Finally, one of your more important growth moves will be to help establish Project Cortex – showing innovation and growth within an established business, with clarity on emerging tech enabling a differentiated line extension.

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 16 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.


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

14. ⌛ Have respect for history and trends.  Speaking of the paradigm shift to the cloud, you’ll be shocked to see how many people frame it as a forward progress.  That’s a naïve view of the history of our industry.  It’s a cycle of client to server to client and bundle to unbundle to bundle that repeats itself in tech.   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.

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. 💖 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 16 years of your career will be about influencing large systems, not letting them consume you.   Mind the beet.

One More Thing

My organization is hiring awesome product people! If you think you might thrive in a culture that thinks deeply about career, people, strategy, and leadership like the themes above, you should apply!