21 years – 10 life lessons – 3 chapters

Learning to thrive at Microsoft

October 9, 2021, marked my 21st anniversary with Microsoft. My career was finally old enough to pull up a barstool and have a drink! In all seriousness, it was a great milestone, and caused me to reflect on the lessons learned over those 21 years. Turning 50 in March put me in an even more reflective mood. What have I learned? What have I accomplished? Who have I helped? What is my legacy?

Reflecting on those 21 years, I identified 10 lessons that have helped me to thrive professionally. I was able to share these virtually with some of my colleagues at Microsoft last month. Here they are, organized in three chapters that represent three significant eras in my career, for my friends on LinkedIn.

Chapter 1: Growth, Opportunity & Wonder

I arrived at Microsoft as a contractor in the Spring of 2000 at the age of 28. While the job itself wasn’t a dream, it was absolutely a dream to be on Microsoft’s campus. As a local kid who grew up in Ballard (a neighborhood in northwest Seattle), I’d observed with amazement at the company that Bill & Paul had built. To be a part of it was a dream come true. It was a time of professional growth, remarkable opportunities, and wonderment.

Lesson 1: Attitude controls altitude

While the phrase seems pithy and cliché, it is perhaps the most important thing to remember throughout your career. While I had a lot to learn when I arrived as an entry-level Software Test Engineer, I had a great attitude, a “learn it all” mentality, and a strong desire to make others around me great. It put me on a pathway to accelerated growth & opportunity that's still paying dividends 21 years later.

Lesson 2: Adaptability is the key to success

Well, “duh,” you might say. But the truth is, throughout my career I’ve seen more people fight change than embrace it, preferring the way things are to the way things could be. That attitude was the foundation that enabled me to grow rapidly in the company and to become a team lead after only 18 months. The only constant is change – and if you can’t adapt to the change around you, you will eventually become obsolete.

Lesson 3: With persistence you can learn anything

I arrived at Microsoft as a self-taught computer scientist (and I use the term "scientist" very loosely). One of the benefits of coming in a low-level position is that expectations were commensurately low. I used that time to study and to practice, and by 2003 I was writing code in three different languages and supporting developers all over the world across a breadth of technologies. I encourage people in any role at Microsoft to avoid the phrase “I’m not technical, but…”. Instead, just think to yourself, “I may not know this technology yet, but I’m confident I can learn anything.” The same applies to other environments too!

Lesson 4: The only constant is change

In 2009, I was unexpectedly asked to take over management of the Windows Driver Kit User Assistance team. Drivers! The things that make your PC blue screen when they’re not created correctly. I had never written a driver in my life (and still haven’t). Rather than pushing back or declining the opportunity, I embraced the change. While it was a difficult assignment, it was also one of the most gratifying of my career, and I still have many friends from that era who appreciated my willingness to step up and provide direction and vision for a team that needed it.

Lesson 5: If you’re not growing, it’s time to move on

It can be incredibly difficult to leave a team that you love. But sometimes it’s exactly the right thing to do. In my own experience, after 13 years in the Windows division, it became clear that I was no longer growing in my role, so I made the decision to make a change. That decision had interesting consequences, but it was still the right decision. Be honest with yourself – if you’re not growing in your role, you’re probably in the wrong place. It’s likely time for a change.

Chapter 2: Ambition, Disappointment & Reinvention

After 13 years in Windows, I made a move to the Cloud & Enterprise division (now Cloud & AI). It was a dream come true at the start that two years later seemed like a nightmare. In hindsight, it was an important period in my career where I learned a lot, made some great new friends, and realized that I needed a mid-career reinvention.

Lesson 6: Business is never personal

In 2015 my manager and mentor retired from Microsoft, leading to a new GM joining the team. Three months later, I was in his office being informed of his intent to replace me. “You seem great, but I need my own person in your role.” It felt like a dramatic setback, and I’ll admit that I took it personally. But I shouldn’t have. Business is never personal – it’s just business. And if you let petty grudges and professional slights eat you up, you’ll never be happy. Honestly, in retrospect, leaving the team was one of the best things that could have happened to me – it was just hard to see that at the time. ?

Lesson 7: Passive pushback == tacit approval

I landed in our Learning Experiences team in a bit of dream job, responsible for our portfolio of online learning assets and GTM strategy, which came with responsibility for a $60 million P&L (a fact that convinced me it was time to go back to school to get my MBA). I inherited a strategy that saw us pivoting away from certifications and moving everything to freely available MOOCs. I was skeptical of the approach, as it was severely impacting revenue and wasn't leading to the kinds of transformational change we'd hoped for. Despite my reservations, I was unable to change the course of the team. By 2017 I could see the writing on the wall – we were failing financially. While I had stated my disagreement, by not stating my disagreement loudly or clearly enough, it became my strategy. And when it failed to yield the results expected by finance, I had failed by extension. I was complicit because I let it happen on my watch.

Lesson 8: Think Global, Act Local

In late 2017, I became the leader of the Field Apps & Data Services (FADS) team. One of the most appealing aspects of the role was the chance to manage a global team. FADS had people in 14+ countries, and I can honestly say it was the most joyous part of that job. I continue to be inspired by that incredibly talented group of people and even wrote about that life changing experience on LinkedIn . Make no mistake – global teams can be challenging, but they make life so much richer, and the creativity they inevitably foster makes your solutions so much better.

Lesson 9: Culture matters

After 2.5 years with FADS, I was tempted to try something new. Fueled by feedback by classmates, peers, and mentors, I took a chance by moving to the Solutions team as the Director of Communications for the Data & AI Azure Solution Business. While the job was interesting, and I learned a lot, it became clear to me quickly that the team culture wasn’t a great fit for me. The pace was frantic, goals weren’t clear, and too often, trust seemed to be lacking. I did my best to fit in, but I wasn't thriving. Never underestimate the importance of a strong culture, based on a foundation of trust. You might not realize how good you have it until it’s gone.

Chapter 3: Peace, Clarity, Home

After spending a year away, I was fortunate enough to be able to return to my former team. Why did I come back? A few obvious reasons – culture, vision, friendships. But most importantly, I realized that this team had become home.

Lesson 10: Love what you do. And importantly, who you’re doing it with

All it took for me to realize how good I had it was a trip to a team with a challenging culture. While no culture is perfect, the team I'm part of now tries harder to get it right than any team I've been part of previously. The way I was welcomed back by my former team was a reminder of just how important a high functioning culture built on a foundation of trust can be to your happiness, productivity, and career satisfaction.

And thankfully, I’m still growing – so I know that I’m right where I belong. And I hope that will be the case for many years to come. I’m home.