There's something uniquely humbling about being the quietest person in a room full of people. Recently, I had the opportunity to sit in on an executive level IT strategic initiative meeting for the City of Virginia Beach. Not as a presenter. Not as someone with a deliverable on the agenda. Just as an observer. I had good sense to keep my mouth shut. I want to be careful about what I share here, because the specifics aren't mine to share. What I can talk about is what it felt like to watch, and what I took away from it.
Different Seat, Different View
Walking in, I knew the titles: CISO, CTO, CIO and so on. I wasn't a stranger to those acronyms. What I wasn't ready for was watching those roles actually show up with something to say. The CISO was thinking about risk. The CTO was focused on what was actually buildable. The CIO was looking at the organization as a whole. Same room, same agenda, different priorities, and everyone got to put theirs on the table.
What struck me was how much that mattered. Each perspective covered something the others didn't naturally see. By the time the conversation landed somewhere, it had been looked at from enough angles that you could trust where it ended up. I've heard "collaborative decision-making" enough times to be skeptical of it. Watching it actually work gave the phrase its meaning back.
Nobody Was Playing Defense
One of the things I half expected was some version of turf protection. The CISO drawing a hard line. The CTO pushing back on constraints. The CIO trying to hold it all together like a referee. That's not what I saw.
What I saw instead was a group of people who seemed genuinely invested in getting to the right answer, even when that meant yielding ground. Ideas got challenged, but the people behind them didn't seem to take it personally. Someone would push back, the room would sit with it for a second, and then the conversation would move, not sideways, but forward.
I don't want to make it sound frictionless, because it wasn't. There were moments of tension but it was productive. It was the kind that sharpens something rather than the kind that just makes everyone uncomfortable and tired.
I Learned More by Listening Than I Usually Do by Talking
I'll be honest...I'm not always the best at just listening. My default mode in technical conversations is to start problem-solving pretty quickly, sometimes before I've fully heard the problem. It's a habit that I'm increasingly aware will need to change as I grow.
Sitting in that room with no pressure to contribute was a breath of fresh air. It gave me space to absorb, the way questions were framed, the way priorities were weighed, the way one executive would restate someone else's point slightly differently to move the conversation forward without it feeling like a correction.
That last thing in particular I've been thinking about a lot since. There's a skill in that. A real one.
What This Looked Like From the Outside
Here's what I came away with, stripped of any specifics:
Strategic conversations at the executive level aren't just higher stakes versions of team meetings. They have a different architecture. The agenda is almost secondary to the process, how you work through ambiguity, how you surface the right disagreements, how you make sure the person who hasn't spoken yet still gets to shape the outcome.
The executives in that room weren't just smart about their individual domains. They were smart about each others. They knew when to press and when to let something breathe. They knew whose input was missing and found ways to draw it out.
That's not a technical skill. It's something else, something I'm not sure I have a clean word for yet. Leadership feels too generic. Facilitation feels too small. Maybe it's just knowing how to be useful in a room where everyone else is also trying to be useful.
One Thing I'll Carry Forward
I was in that room because someone thought it would be good for me to see it. I'm grateful for that, more than I expected to be.
That's the thing about a mentorship like this. You sign up thinking you'll get advice and maybe some career perspective. What you don't fully anticipate is someone handing you a front row seat to something you couldn't have gotten yourself. Peter didn't just share his experience with me. He let me sit inside it for a couple hours.
I'm at a point in my career where I'm trying to be intentional about growth, not just getting better at the technical enterprise architecture work, but understanding the bigger picture of how organizations move and how decisions actually get made. That room was a window into something I've been working toward without always being able to name it.
I left with more questions than answers. That's fine. I'll take that over leaving with nothing new to think about.