5 years launching AI at Google: 10 Lessons in Navigating Ambiguity

Let's be honest, my childhood obsession with spiders didn't exactly scream "future Google Product Manager." (Though, in retrospect, navigating a complex web is surprisingly relevant.) But after a whirlwind journey – coding since I could practically tie my shoes, mathlete glory, and a fateful talk on the very real risks of AI in hiring that got me recruited to Google – I found myself at 1600 Amphitheatre Parkway, feeling less like a conquering hero and more like a particularly confused tardigrade dropped into the Mariana Trench.

Before Google, I'd been slinging code and building AI products at startups. It was the Wild West, fueled by ramen and the sheer audacity of youth. Google? Google was a different beast entirely. It was a multi-generational workforce spanning, a tectonic shift in my definition of "success" (lines of code suddenly felt…quaint), and a product landscape so vast it made the Pacific Ocean look like a puddle. I missed the feeling of my fingers against a keyboard, creating something through python.

Five years of global AI launches, SVP and VP awards, and two promotions later, I've emerged from Google's Global Business Organization, blinking in the sunlight. The external validation was nice (who doesn't love a good VP award?), but the real prize was something far more valuable: the hard-won ability to not just tolerate ambiguity, but to thrive in it. To actually enjoy the art of wayfinding.

Now, I'm not claiming to be Tim Cook, calmly steering the Apple ship post-Jobs. (I'm still working on the "calm" part.) But I've learned a thing or two about leading teams through the fog of uncertainty, the kind that can paralyze even the most brilliant engineers with fear and doubt. My time at Google was a masterclass in global-scale problem-solving. I launched AI features into products like Google Play and Google Pay India, wrangled machine learning datasets into submission, and even helped customer service reps communicate across languages in real-time.

And through it all, one constant remained: change. Relentless, beautiful, terrifying change.

So, here's the thing. No amount of well-intentioned advice from a mid-career Googler (that's me, waving frantically) can truly prepare you for the rollercoaster. When I started, I couldn't even articulate my job description, let alone seek out relevant wisdom. It took a solid two years to confidently say, "I lead engineering and UX teams in commercializing AI research to solve real-world business problems for Google's top products impacting billions of users." And another year to actually believe it.

So, take these reflections with a grain of Himalayan pink salt (it's fancier). Times change, and what worked for me might be utterly useless tomorrow. But hey, maybe it'll spark something.

Navigating the Labyrinth: Hits, Misses, and Face-Plants

Here's a breakdown of what helped, what hindered, and what I probably should have done differently:

The Good Stuff (aka, What Kept Me Sane):

  • The Unshakable Mission: By the time I signed to the time I started full time, my organization had already undergone a reorg. Clinging to the core mission – using tech to solve real business problems – was my life raft. Find your why, and hold on tight.

  • Mentorship, Mentorship, Mentorship: PeopleDev's report on learning, how it's linear for reading, step-wise for conversations, resonated. I found three senior PM mentors outside my immediate org. They taught me how to frame my work, how to speak the language of Google, and how to navigate the political landscape (which, let's be honest, is a skill unto itself).

  • Sponsorship Finding 1 senior PM mentor and sponsor changed project opportunities. Thanks to Phil, a fellow Columbia alumni from the business school, I had a front row seat to the organization’s most important projects. Meanwhile, my starter project was the least of anyone’s concerns. All the early promotions and bonuses came from the high priority projects Phil and I worked on; all my early lessons on product management came from Phil’s mentorship.

  • The Morale Booster: During the COVID chaos, I felt this weird compulsion to step up and advocate for my team and project. Half of them were out on leave, and I figured, "If not me, who?" It was exhausting, but it kept the ship afloat. Sometimes, leadership is just showing up.

The Not-So-Good Stuff (aka, Lessons Learned the Hard Way):

  • HBR Case Study Overload: I devoured Harvard Business Review case studies like they were going out of style. Did it help me onboard faster? Absolutely not. Did it eventually help me speak the language of cost savings and revenue projections to leadership? Maybe. But mostly, it just made me feel like I needed an MBA.

  • The All-Nighter Trap: Spending 11+ hours a day at the office, plus nights and weekends? Rookie mistake. Burnout is real, people. And it doesn't make you a hero; it makes you a tired, slightly delirious mess.

  • The New Grad Echo Chamber: Befriending other recent grads was great for moral support…until I realized most of them were software engineers, and I was drowning in a sea of business strategy. It amplified the isolation. Find your tribe, but make sure it's a diverse tribe.

The Missed Opportunities (aka, Things I'd Do Differently):

  • The SVP That Got Away: I didn't cultivate a strong relationship with my first Senior VP. She was a Google veteran, a potential powerhouse sponsor. She left a few years later, so maybe it was a dodged bullet, but… what if?

  • The Silo Effect: Lean and agile are great for speed, but terrible for long-term organizational buy-in. I waited too long to engage key strategic teams. Big mistake. Build bridges early, even if you don't think you need them yet.

The Face-Plants (aka, Oops):

  • The Post-COVID Chain of Command Fiasco: During the pandemic, I got used to going straight to my director. Post-COVID, with a new reporting structure, I learned the hard way that hierarchy still mattered. Suddenly, I needed to navigate layers of middle management and build consensus before approaching the top. Awkward.

The Takeaway (aka, My Two Cents):

Google was a wild ride. It taught me more than I ever thought possible, not just about AI and product management, but about resilience, leadership, and the surprisingly complex art of navigating a giant, ever-shifting organization. It's a journey I wouldn't trade, even with the occasional face-plant. And who knows, maybe my spider obsession did come in handy after all. Because in the world of tech, it's all about navigating the web – one carefully placed step at a time.


And now I'm off to tackle more uncertainty, and more complex business problems.

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