🎂 Celebrating 20 Years at Microsoft with 20 Lessons for PMs
A note to my younger self about my product building journey
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 went public one year ago, and the iPhone will launch in two years.
You will be in the first 1% of humanity to use the internet, get a smartphone, sign up for a SaaS service, or chat with AI. You will see cloud & mobile go from niche ideas to indispensable worldwide utilities, and the AI era is just starting to usher in another paradigm shift as I write this. The most controversial part of your career is that you stayed with the same company for 20 years, so you rode all these waves while nurturing a resilient home for your work life.
Today, you are a VP of Product & Data Science - responsible for ensuring customers’ success with one of the largest online services in the world. As you constantly adapt to the times, here are 20 lessons you’ll learn in your first 20 years.
Starting Your Career
1. 🏄️ Ditch the career ladder. Learn to surf the right waves.
Find something bigger than yourself and attach to it. When it washes out, find a new wave to ride. Repeat. Intentionally choosing the right wave - team, technology, industry trend- will be way more important than any other career tactics.
2. 📈 Drive for 1% improvement every day.
The world’s information will double every 5-8 months, and workplace technology - from search to collaboration to AI - will keep improving to match. This means there are two skills that can and must constantly improve so you can keep up: synthesizing information & communicating your ideas. Practice, try new tech, and hone these a little bit every day.
3.🗞️Get paid to keep current.
Make learning an on-the-job habit - especially keeping up on the industry and a healthy information diet. This knowledge of the broader context of what’s going on around you will get you noticed.
4.🧱Be a finisher.
The tech industry glamorizes the start of new things. You’ll see, though, that it will be more important to find the resilience and grit to finish, to edit, to scale, and to bring customers along.
5. ⏱️ Learn the difference between urgent and important.
Getting the urgent done will foster your credibility on the team. But carving out time for the truly important work is how you will find creative success. Every year you’ll look back and realize that so little of your time - maybe 30% - was spent on that truly important, difference-making work. You’ll learn to trust your gut to identify it.
Sustaining Your Career
It’s not about “work/life balance” - it’s about managing your energy and exploring how what drives you will change over time.
6. ☕ Balance mastery and purpose as you age.
Society wants you to get good at something in your 20’s and early 30’s. It’s much less clear what to do with your now finely-honed skills in your late 30’s and 40’s. Uncovering your purpose - asking “Who am I helping?” - will ensure you avoid feeling trapped by being great at something that no longer gives you as much joy.
7. 🏓 Detect your boredom & burnout early.
“It’s easier to recover from being annoyed than pissed off.” You’ll get bored sometimes. You’ll burn out too. Detect it early - before it snowballs. Stay “in the flow” where job challenges and your skills match.
8. ⛓️💥 Fire yourself at the start of each new wave.
“What got you here won’t get you there.” Every time there is a paradigm shift in your industry - cloud, mobile, AI - the cycle restarts and everything gets reset - requiring you to show up differently. Andy Grove at Intel famously fired himself and rehired a new Andy to pivot from memory chips to CPUs - you will need to do the same to adapt to changing times.
9. 🏖️ Take your retirement along the way.
Every few years, you’ll find a way to take an extended time away from work - honeymoon, paternity leaves, sabbatical. The pauses will make you a more interesting person and unlock your understanding of what drives you.
Thriving in the Matrix
At Microsoft, the biggest multiplier to your impact is the scale of working on problems that require thousands of people to properly solve. You will learn to thrive in this matrix, not be a victim of it.
10. 🎁 Be generous.
Your job as a PM is not to own and explain the customer insights, but to teach engineering and design until they know the customer as well as you do. You’ll learn to think about this just like physics or economics - teach the team to run in their own heads a useful synthetic model of the world everyone can use to quicken decision making.
11. 🦝 Be curious.
Cross-team work will be some of the most rewarding projects in your career, but also the most tribal. Your biggest mistakes are when you are too critical too early - you’ll want feedback to be your love language to show you care, but it’ll be misinterpreted as unsupportive. Better instead to take the time to be curious - share context and understand the thoughts, wants, and feelings of the other tribes - before setting goals or evaluating plans.
12. 👟 Walk in your managers’ shoes.
Life is too short to have anything other than a deep, trusting two-way relationship with your boss. You will work to understand the unique ways in which each of your boss’s jobs is harder than yours. You will help them learn the lived experience of members of their teams.
13. 🤗 Find your “First Team.”
The key to happiness will be to join a “first team” of peers that you can rely on for support. Find the space where you can be yourself and broker the deep relationships among those who can relate to your struggles. Find people you can laugh with. Your unhappiest times will be when your own pride makes you resist joining the tribe around you.
Making Great Products
Product Management will professionalize over the course of your career. It’s part art, part science – and frequently calls for you to make decisions in the face of ambiguity. There will be a lot of noise and temporary trends, but three universal truths will become your grounding ethos on building products:
14. 📈 Champion results over activity.
Five years into your career, the cloud paradigm shift will begin. This will fundamentally transform your profession – enabling data analysis, experiments, and more hypothesis-driven thinking. You will learn to ask, “where do we need to be and how do we measure it,” and to help teams moved beyond an activity-focused mindset. Facts not adjectives.
15. 😍 Learn to have product taste.
Your job won’t only be about data and decision-making rubrics. You’ll also need to develop an innate sense of taste for high-craft products that generate user love. My biggest advice for developing this is product play - channeling that inner child as you make a habit of using the products around you. Yes, taste is learnable - not innate.
16. 🤝 Don’t just build products. Build customer trust.
The product itself is just a small part of the lived experience customers will have - you’ll develop a passion for the “around” product work of support, sales, adoption, customer success, and ecosystem stewardship. As the pace of change accelerates, you will realize how much nurturing the industry around your product matters just as much as building the right product.
Leadership
Motivating and inspiring others and generating the legitimacy to do so will become an increasingly larger part of your job.
17. 🧘♂️ Harness the power of calm.
People are attracted to calm leaders. You will learn to tap into patience & optimism and create systems to help others do so as well. Your latest motto: Do hard things in a calm way with me.
18. 🎁 Give each person a unique gift.
Every person you manage will need you to push them to be their best - the trick will be to figure out what they need from you right now. Praise? A nudge to raise the bar? A reframe? Your attention to the gift each person uniquely needs defines how you give people autonomy, yet still show up meaningfully.
19. 🔍 Be intentional with your attention.
A retiring member of your leadership team will give you a big gift on his way out - he’ll say that you should use the phrases “I need” and “I expect” more. You will not need to solve most problems yourself - simply setting expectations on what you care about will let the team know what’s important and what needs to change.
20. 💖 Embrace empathy, vulnerability, and allyship.
You’ll have friends who lose their jobs due to the disruption your product causes to the industry. This will have a profound impact on their lives. What a way to humanize abstract charts on cloud growth rate and disruption to the value chain. Technology and society are more intertwined than ever. Leading diverse teams will require showing vulnerability and speaking publicly about allyship.
Summing It All Up
This newsletter is called Mind The Beet for a reason – it’s a quote from Tom Robbins' Jitterbug Perfume that speaks to the eternal struggle of defining your own reality in the face of processes, pressure, and systems. The first 20 years of your career will be about influencing large systems, not letting them consume you. Mind the beet.