I Don’t Know Shit

I spent fifteen years leading sales teams. Then I joined Braze and took an IC seat instead of another leadership title. First time in a long time my job didn’t come with a headcount. Nobody throws you a parade for that one, for the record.

The polite version of why is “I wanted a change.” The truer version is I wanted to find out if the things I’d been teaching other leaders actually held up, or if I’d just gotten good at saying them with conviction.

Turns out the fastest way to test that is to sit in the room as the person being led instead of the person doing the leading.

One week in, I watched an all-hands that reorganized what I thought I knew about running one. Someone talked a rep through an objection in a way I would have fumbled at that stage of my own career. A deal closed that 30 minutes before EoQ, and the energy in the room had nothing to do with the size of it. It was about how hard the team had fought for each other to get there. I kept waiting to spot the gap, the obvious thing my experience would fix. It took longer than I expected. Longer than my ego wanted.

I’m noticing things right now I never used to notice, mostly because I was too busy being the one who was supposed to already know. How someone carries themselves in a review when the number is bad. Whether they get quieter or louder when a rep pushes back on them in front of the team. Whether the praise they hand out is specific and earned or just a warm noise they make to keep morale up. You can watch someone run a meeting for twenty minutes and learn more about their character than their resume would tell you in twenty pages. Resumes lie. Meetings, eventually, don’t.

What surprised me is that not one of the leaders here has been self-reverent. Not the ones closing the biggest deals, not the ones with the longest tenure, not the ones who could coast on reputation alone and nobody would blink. I’ve worked in rooms before where confidence curdled into something that never touched the ground, that never questioned itself out loud. I walked in, half-expecting to find that here too, because I’d built a career around organizations where it was the norm, and some days I was the one doing it. I haven’t found it. Not once, not in the least. Either the hiring process here is unusually good at screening it out, or I just haven’t been in enough rooms yet. I’ll report back.

What I’ve found instead is a room full of people who ask a question and then actually wait for the answer. Who give credit in the meeting, not in a Slack message after the fact, once it’s safe to be generous. Who will say “I don’t know, let’s figure it out” in front of a VP without flinching, which is a smaller thing than it sounds and also a much bigger one. I used to think admitting that out loud in front of my own team would read as weakness. Watching it from here, it reads as the opposite. It reads as someone secure enough not to need the room’s approval every ten minutes.

Competence has a failure mode nobody talks about much: it becomes a costume. You stop walking into rooms curious and start walking in ready to perform the role of person-who-already-knows. Efficient, most days. Also how you stop learning anything new, because pattern recognition tells you what you’re looking at before you’ve actually looked at it. You match the new thing to an old one and move on. Usually you’re right. When you’re wrong, it rarely announces itself, because being wrong quietly doesn’t feel like anything. Running teams that long taught me a lot of real, useful things. It also taught me to be convincing, which is not the same skill as being right, and somewhere along the way I let the two blur together more than I’d like to admit. I was very convincing. Ask anyone who bought what I was selling. Including me.

I’ve spent a chunk of the last several years at retreats, sitting with strangers, trying to quiet the part of me that always wants an answer ready before I’ve actually listened. The same decentering keeps happening there. You show up thinking you’ve finally gotten a handle on who you are, and something reorganizes that a week later. Not gently, either. Carlos Warter, who I’m co-writing a book with, has handed me a lot of lines over the years, but three have outlasted the rest.

That third one, from a physician who’s spent fifty years studying consciousness, delivered with the same energy as a trucker slapping a Yosemite Sam mudflap on his rig. It’s some of the best advice I’ve ever gotten. I used to file both under spiritual work and assume neither had anything to do with how you run a sales floor. I’m less sure about that split than I used to be. Watching leadership from an IC seat, the first one is doing most of the work: paying attention to what’s actually happening in a room without needing to worship it or write it off. The second one is just true on the days when the real answer to how it’s going is still figuring it out, still here. Taking a step down in title turned out to be its own version of the same lesson, just with a badge and a Slack handle attached.

I don’t know yet whether this seat is temporary or the new normal. What I do know is that watching leadership from underneath it, instead of from inside it, is teaching me things all that time in the job never did. Mostly it’s teaching me how much of what I called leadership was actually just certainty, performed well enough that nobody, including me, checked underneath it. And it’s teaching me that the absence of that performance, the plain “I don’t know” said out loud in a room that could punish it, might be the actual skill I spent a career mistaking for something else.

Keep on truckin’, like the man says.