20@Microsoft: How Intentional Relationships Unlock Opportunity
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 first post is here: 20@Microsoft: How Unexpected Moments Shaped My Career
Today’s post is about something that’s often undervalued early on, but becomes obvious with time: the role of intentional relationships in your career path.
Relationships happen every day at work, but they don’t grow on their own. The ones that matter most are built with intention. That means making them a priority, investing in people, showing up consistently, and earning trust over time. These are the relationships that turn performance into opportunity and impact.
Looking back, nearly every pivotal shift in my career started with a relationship. Not a job posting or a formal plan. That first role at Microsoft? It happened, not because of a job application and interview, but because someone I knew, and who I invested in our relationship, put my name forward.
Since then, I’ve seen the same pattern repeat. Not because I was deliberately networking (although I do that too), but because I was showing up, contributing, and investing in people around me.
One of the clearest examples came during a stretch in Redmond, when I found myself helping prep executive keynotes for major conferences. I had this incredible opportunity to work directly with leaders like Scott Guthrie and Jason Zander to land the technical story behind what they were presenting on stage. It wasn’t just about code demos. It was about navigating perspectives, managing expectations, and building clarity under pressure. Although it came with some serious stress at times, I was proud that my leaders, as well as Jason and Scott, trusted me in that role.
That experience led to something I’ll never forget: the chance to work with Satya Nadella before he became CEO. At the time, he was leading the Server and Tools Business. I was invited to help shape the technical narrative for one of his upcoming events. I remember walking into his conference room, surrounded by senior leaders from engineering, and wondering what I was doing there.
At one point, I pulled a colleague aside and asked why I was even in the room. He said, “You’re here because you’re authentic. You don’t have an agenda. And Satya wants people around him who’ll give real authentic input.”
I realize that is some serious name-dropping, but those moments stuck with me. It taught me that people trust consistency, humility, and authenticity. I wasn’t the most senior person in the room—not even close. But I’d earned trust through quietly showing up, delivering, and supporting the work.
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That trust opened doors I couldn’t have scripted.
As a fun aside, the first time Satya visited Japan as CEO, I had a chance to brief him on a developer event. After the briefing, attended by our leaders in Japan, we talked about life and why I moved to Japan. The conversation started a rumor in the Japan subsidiary that I was “best friends” with Satya. Of course, that was far from the truth, but the relationship brought a bit of fun into my new job and life in Japan.
Even later in my career, when I moved from people management into an architect role, it was relationships that helped me build traction. There was no script for the work. I had to find it. We started to notice that customers were struggling to monitor GenAI solutions effectively. They couldn’t see how models were being used, what prompts were not working, or why performance was inconsistent.
I got curious. I dug into the problem. And because of the relationships I’d built across my organization, across Microsoft, and across the open-source community, I wasn’t alone. I connected with others who cared about the same challenges, and together we started shaping a vision for what better observability could look like for GenAI systems.
Those conversations turned into proposals, and those proposals turned into a new standard in the OpenTelemetry community focused on monitoring GenAI workloads. That work is now being adopted across the industry, and it’s already showing up in Microsoft products like Azure AI Foundry and Semantic Kernel.
One of the turning points came when a leader in the Developer Division, Joe Binder , who I worked with years ago, reached out to ask if I could help bring this standard into several of our product teams. We kicked off a weekly call, and around the table were people I reconnected with after working with them years ago. Because of that foundation, we moved fast. Teams were motivated, aligned, and already bought into the value. What started as an idea became a coordinated effort across product teams.
A pattern of customer pain points became an opportunity to influence how GenAI applications are built, monitored, and scaled. And none of it would have happened without the trust, collaboration, and shared momentum that comes from long-built relationships.
Intentional relationships don’t guarantee anything. But they unlock opportunities that you might not expect.
If the first article was about staying open to unexpected paths, this one is about what makes those paths appear in the first place. Relationships don’t show up overnight. They grow over time. Invest in them now to create opportunities later.
What’s one opportunity you got—not because of a title, but because someone trusted you?
Senior Software Engineer at Microsoft
1moWhat a great journey! Congratulations, Drew! You deserve the success in many ways. For me, you are like a 5 tools player. Technical skills, empathy, innovative thinking, thinking about others, and being lazy. I learned a lot from you.