20@Microsoft: How to Bring It All Together
Drew Robbins
Engineering Leader | Driving Innovation and Observability in Generative AI Applications
This month marks 20 years since I joined Microsoft.
To reflect on that milestone, I’m sharing a short series about the moments that shaped how I think about growth, leadership, and building a meaningful career.
The previous posts are here:
Today, in this final post of the series, I want to reflect on what actually matters when building a long, meaningful career in tech, what’s worth chasing, what isn’t, and what I’m still figuring out. Because I’m not done learning.
When we talk about career growth, we often picture something linear, where each step brings more responsibility, bigger teams, and clearer scope. But that’s not how it works for most of us. The decisions that define our path don’t come with big neon signs. They show up as a one-on-one where a mentor makes you rethink what you want. A role that looks like a step sideways but teaches you something you didn’t know you needed. A moment where the work gets hard, even scary, and no one’s telling you what to do next. I’ve had all of those. Some turned into major milestones. Others just shaped how I show up.
Over time, certain lessons become part of you. They stop being things you heard in a hallway conversation or a manager training and start becoming the way you operate. Not all of them show up as advice. Some come from uncomfortable feedback. Some come from watching other people succeed or struggle. And some only made sense after learning them the hard way. Over time, those lessons turn into thoughts, those thoughts shape actions, and those actions become habits you don’t even realize you’re relying on anymore.
Growth doesn’t always feel like growth while it’s happening. It often feels like friction. Taking on something you’re not fully ready for. Sitting in a room where you’re not the expert. Getting feedback that’s hard to hear. It took me a while to recognize that those uncomfortable moments weren’t signs I was in over my head. They were signals I was learning something I hadn’t needed to know before. This type of growth isn’t handed out easily. It’s messy, and it feels uncertain when you’re in the middle of it.
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The roles that shaped me most weren’t always the most visible. Sometimes they were the ones where the path was least defined. The expectations were vague, the outcomes uncertain, and no one was telling me what to do next. I had to learn how to be effective in that kind of ambiguity, when the metrics weren’t clear and the payoff wasn’t guaranteed.
In those moments, I learned how to create clarity for myself and for others. I didn’t pretend to have all the answers. Instead, I focused on asking better questions or at least asking more questions. I wanted to understand what the real challenge was and what context I might be missing. From there, I could narrow in on a concrete next step. That approach of asking questions and creating clarity became one of my strengths. But it also came with a tradeoff. I sometimes slowed things down when others were ready to move fast. I still wrestle with when to push forward and when to pause.
And through it all, the thing that’s made the biggest difference is relationships. Not in a soft, nice-to-have way. But in the very real sense that people are more likely to share context, take risks, or build something new when there’s trust. Some of the best work I’ve been part of started as a simple conversation with someone I’d invested in years earlier. Being intentional in those relationships, long before I needed anything from them, has been one of the most consistent accelerators in my career. One of the first relationships I invested in at Microsoft 20 years ago was with Josh Holmes . That connection has paid dividends for two decades, shaping both my professional path and personal life in ways I never could’ve predicted.
What matters most to me now is pretty simple. First, investing in people. There’s nothing more rewarding than helping others grow in their own careers and knowing that the impact doesn’t stop with me. When you help someone else level up, that momentum carries forward in ways you can’t always predict.
Second, making sure the work we do connects to real value for our customers. It’s easy in tech to get caught up in the solution and forget why it matters. I want to keep focusing on the gaps that get in the way of our customers realizing that value and making sure we’re solving the right problems.
And finally, staying curious. Curiosity is what first drew me to this industry in the first place. It’s what made me dream about a job at Microsoft when I was a kid. Every time I’ve grown in my career, it’s been because I stayed curious and leaned into what I didn’t know yet. I want to keep that spark alive.
The truth is, careers aren’t built in milestones. They’re built in moments. The moments when you choose to lean into discomfort instead of pulling away. The moments when you decide to invest in someone else’s growth, even when no one’s watching. The moments when you stay curious enough to keep learning, even when you could coast.
If there’s one thing I hope you take from this series, it’s that building a meaningful career isn’t about following a clear path. It’s about how you show up when the path isn’t clear at all. It’s about how you treat people when you don’t need anything from them. It’s about whether you keep asking questions when everyone else is ready to move on.
The impact you leave won’t come only from the roles you held or the projects you delivered. It will come from how you made others better and how you grew along the way.
You don’t need permission to lead, learn, or make an impact. You just need to start where you are, with what you have today. The career that matters most isn’t defined by titles or milestones. It’s built in the small, consistent choices you make when no one’s keeping score.