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🏄♂️ My Career Highlight Reel
The top learnings, big story arcs, and high moments, succinctly told
👋 Hi folks, Adam here. This week’s topic is career focused and specifically I discuss how I approach my career “highlight reel” - the brief, synthesized overview of my time in tech.
As I have been delivering various talks and podcasts at learning days and conferences this year, I’ve started including my career highlights reel in my opening remarks. This tour through big moments in my career gives context and satisfies audience curiosity about “how I got here.”
I’ve found the elevator pitch takes a lot of refinement to get tight. A career is hardly the single trendline that hindsight provides, and yet summarizing it well shows clarity of thought and a passion for good storytelling.
Everyone deserves an inspiring origin story.
A great career highlight reel is short - less than 3 minutes and 1,000 words. Every word either helps the narrative or frames a lesson. It also has these elements to it:
Organized: It breaks your career down into chapters, each with a chosen main learning and goal (while it’s tough to choose a single learning for years of work, it tightens the story).
Clean: It sacrifices humility for brevity. You should remove all the qualifiers and caveats that muddy the language - make it about what people can learn from your career, not what you want them to think about you.
Contextualized: It connects your career to what was going on in the industry at that time. The context makes the story more relatable and encourages people to connect their own career to something larger.
Romanticized: It removes all the people drama, short term setbacks, and daily struggles. You should focus on what still matters now, not what you thought mattered then.
Authentic: It includes just the right dose of vulnerability and uncertainty. While your highlight reel isn’t a time for wallowing on wrong turns and hesitations, incorporating a few times you questioned your path and experienced major headwinds encourages follow-ups and audience curiosity.
The rest of this post is my refined career highlight reel from all the practice this year, putting these five tips into action.
If you like the approach, consider doing Helen and me a favor and sharing out this post as a helpful best practice.
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My Career Highlight Reel
I like to think of a career as a set of waves to surf rather than a ladder to climb, so I broke down my past 18 years in tech into five waves I’ve caught, each representing major learning milestones and different coalitions I’ve been part of.
Wave 1: Years 1-2 - Fit Before Scale
Entry-level Program Manager
In 2005, I graduated from UCLA with degrees in Business Economics and Computer Science. I had a few technical and coding internships under my belt and more than average student leadership experiences.
In my final year, I earned an NSF fellowship that I could defer for up to two years to go back for a PhD. So when I got an offer from Microsoft to be a Program Manager (a job that seemed suited to my blend of business, tech, and human relationships), I leaped in and figured that if I didn’t like it, I’d go back to college.
I joined the Office organization in the last year of a three-year release cycle. I immediately fell in love with the job - working late into the evening after taking on stretch projects. The biggest difference for me was that I was working on systems and goals larger than myself - indeed, Office was one of the largest code bases in the world and the pride the organization had for organizing thousands of people’s efforts towards one final product was inspiring. The job of Program Manager was something that I took to instantly as well. My academic life had been split between classroom technical learning and student leadership: here was a profession that combined both into one.
I examined many potential paths, sitting in on MBA classes and considering whether to switch to a software engineer for instance, but the gravity well of PM working on global scale problems pulled me in.
Wave 2: Years 3-7 - Learning Customer Empathy
Program Manager Lead, Enterprise Security & Compliance Toolkits
After achieving confidence that I had found a profession that fit, it was time to be intentional about what coalition I wanted to join. At the time, Enron had collapsed and the new Sarbanes-Oxley regulations were increasing customers’ expectations for technology to help with compliance and security controls. It was clearly the start of a new wave and I had an opportunity to get in early.
Today, this is a business generating tens of billions of dollars of yearly revenue for Microsoft - but back then it was a brand-new business line and this was my first experience with the creation of a new economic engine. This was an intense crash course in analyst reports, market dynamics, sales blockers, and growth flywheels.
More importantly, this was a wave that allowed me to hone my customer empathy skills. Enterprise compliance and security requirements are esoteric - they require the creation of specialized software that I as a PM would never use myself since I’m not a lawyer or compliance office. As a result, my role as PM was to learn and then teach an entire model of customer behavior and needs to the team. I’m grateful I cut my teeth as a PM leader in an area that required such customer curiosity and one that put the role of PM front and center in defining a team’s worldview.
Wave 3: Years 8-9 - Building the Cloud
Group Program Manager, Cloud Backend
In 2013, my career was accelerated by a lucky opportunity. At the last minute, someone backed out of a GPM gig and the Director asked me to step in. I left my comfortable home building compliance solutions to lead a team laying some of the foundations for our cloud services - authentication, authorization, provisioning. It was at the very technical heart of a paradigm shift the entire industry was going through. Such paradigm shifts happen about a half a dozen times in one’s career. Mainframe → PCs → Mobile → Cloud → AI. They are a time to reexamine old assumptions, create massive new markets, and create bridges from old to new.
I still call this time my “tour of duty” deep in the technical stack. I knew it wasn’t going to be a long-term home for me since most of the problems were deeply technical and there were few user experience or business problems that would make best use of my skills. Yet it gave me respect, empathy, and awareness for global cloud scale tradeoffs that I still use today. And it was a great proving ground for me as a new group leader - focused on generating energy and reducing ambiguity during a time of momentous change.
Wave 4: Years 10-14 - Empowering a Design-Led Culture
Partner GPM, User Experiences Incubations and Refreshes
Zune and Windows Phone - while far from financial successes - served as a wakeup call at Microsoft during the mid 2010’s on the power of design-led product making. The bar was raised on user experiences and the company put more focus on high-craft, consumer-grade products.
This push was well timed for the need to overhaul the UX of my team’s product for the cloud era. I was plucked from my tour deep in the stack and asked to run a UX incubation team, which eventually turned into a full-fledged UX refresh of what is now a product used by hundreds of millions of people every month.
This was a time defined by needing to lead a team through significant role evolution. We doubled the size of our Design team and positioned User Research with mission critical responsibilities. We moved the Test function to Software Engineering. We hired a Data Science team as the cloud enabled UX experimentation. My role evolved from Program Manager to Product Manager. All this ambiguity was stressful - many colleagues left the organization and it was unclear for a while whether the organization was going to survive. It seemed like every day we were reforming expectations around who did what, tailoring our systems and processes to the cloud and the now higher expectations for craft and experience. It was a spicy time.
As a leader, this wave taught me grit, the power of focusing on customer outcomes during times of organizational upheaval, and how to use my privileged position in PM to help emerging disciplines thrive (in this case Design and UXR).
Wave 5: Years 15-18+ - The AI Era
VP of Product, Cloud Apps & Platforms
They say the seeds of the next paradigm shift show themselves on the tail end of the last one. So, while ChatGPT brought AI to the public consciousness in 2023, when I look back on my career, I’ll feel like the AI era started a few years earlier in ~2021 or so.
It was then that my job evolved with the changing needs of the business. With our tech infrastructure transformed for the cloud and our UX meeting the raised expectations, the next challenge was line extensions to our existing businesses - new tools & products sold to our existing customers.
This was a chance for me to combine the learnings from the previous waves of my career - customer empathy, technical leapfrogs, and high craft - into 0→1 product making. I helped launch and scale new product categories with multibillion dollar revenue potential.
This is a wave I, like the rest of the industry, am in the middle of surfing, but it’s coming into focus that I’ll combine these new product lines and the emerging AI revolution together to enable me to find just the right wave for me in the AI era.
Wrap Up: Bonus Content
If you are curious about my top lessons learned over this journey, check out my 17 top lessons from my career. I update this post once a year, adding one new lesson and refining the others, and later this month is my Microsoft work anniversary so you’ll see the refresh soon.