Sometimes, a single question can change everything. For me, it wasn’t just a question—it was also a hallway run with Andrew Mason, Groupon’s CEO at the time, that shifted the trajectory of my career and taught me lessons I’m still unpacking to this day.
It started with a lunch that almost didn’t happen. Our engineering team had been scheduled to meet Andrew for months, but the meeting kept getting rebooked. By the time it finally happened, most of our team was at a conference, leaving just a few of us behind. We assumed the lunch would be postponed again, but it wasn’t. Nervously, a small group of us sat down in a meeting room, unsure what to expect.
As we waited, we saw Andrew approach through the glass walls of the office. He glanced in, did a double take, consulted with his assistant, and hesitated for a moment. I’ll never forget that moment of hesitation—it was as if he was deciding whether this meeting was worth his time. Then, he shrugged, walked in, and greeted us enthusiastically.
That decision—to step into a meeting with a smaller group than expected—would end up being pivotal for me, though I didn’t know it yet.
The Question That Changed Everything
The lunch was casual, filled with sushi and light conversation about engineering culture and corporate vision. Toward the end, Andrew asked if we had any questions. I hesitated, then decided to speak up:
"Are you aware of the current attrition rate?"
Andrew was surprised but thoughtful. His initial answer—that attrition was within industry norms—wasn’t unexpected. But I followed up:
"Does that account for who is leaving?"
I pointed out that many of our most skilled and experienced engineers—those who had been with Groupon from the earliest days—were leaving.
Andrew didn’t dismiss the question. He considered it and said he’d look into it. The lunch wrapped up shortly after, and I figured that was the end of it.
But it wasn’t.
The Hallway Run
As I walked back to my desk, I heard someone call out: "Hey, hey, what’s your name?" I turned to see Andrew running down the hallway toward me. He was out of breath by the time he reached me, but he didn’t care about the stares from passing employees. He motioned for me to follow him.
We ran through the office—me, completely bewildered, and Andrew, completely unfazed. Eventually, we arrived at an open-plan intersection where a group of people were deep in conversation with Brian, who was essentially head of engineering. Andrew, still catching his breath, didn’t hesitate to interrupt.
"Mike, this is Brian. Brian, this is Mike. Mike, tell Brian everything you just told me."
And then he ran off, leaving me standing there, completely stunned, in the middle of the intersection with Brian and half a dozen others who had clearly been in the middle of something important.
The Moment That Changed Everything
That moment was life-altering for me, though it likely wasn’t a big deal for Andrew. At the height of Groupon, with millions of things vying for his attention, he heard something I said and decided it mattered enough to act on immediately.
For me, it was overwhelming. At the time, I didn’t fully understand the weight of what had just happened. It was like being hit by a really cool car in an entirely unexpected circumstance—not something I planned for, but something I couldn’t ignore.
That conversation led to a new role as the "Talent Development Business Partner for Engineering," a role I could never have imagined for myself when I first began transitioning into software development.
More Than I Thought Possible
When I took my first timid steps into this new phase of my career, I struggled to believe I was worthy to work with the brilliant minds of Obtiva, let alone play any meaningful role in a company like Groupon. I thought being a Software Developer would be more than enough—that just reaching that point was my goal.
But this moment, this role, this responsibility—it was so much more than I could have imagined. And, honestly, it was more than I could bear at the time. I didn’t feel ready to be "more." It was intimidating to step into something so far beyond what I thought was possible for me.
The Leadership Lesson
That experience taught me a profound lesson about leadership: the further you are from the day-to-day realities of your employees, the harder it becomes to recover when you lose their trust or perspective.
Attrition isn’t just a metric; it’s a story. When you look at who is leaving, you begin to understand the unspoken dynamics shaping your organization.
Andrew didn’t just listen—he acted. That’s the part I reflect on most often. Listening is one thing, but acting before the moment passes you by is what makes the difference.
Why This Matters Now
Organizations often talk about transformation, innovation, and growth. But none of those are possible without the people who make them happen. If you’re in a leadership position, I encourage you to ask yourself: What am I missing? Who should I be listening to? What action can I take today to bridge the gap between strategy and experience?
Sometimes, listening means sitting down over sushi. Other times, it means running down a hallway. Either way, it means acting when the opportunity presents itself—even if it’s unexpected.