The Suit That Didn’t Fit

When I stepped into sales leadership, I felt like I did after losing a lot of weight a few years ago. At the time, I had a job where I wore suits every day. At some point, the old suits still technically fit, but they stopped fitting the right way. They hung wrong. They belonged to an earlier version of me.

That was what sales leadership felt like. Not leadership itself. I had been a leader for a long time. But this role carried a different template, and I could feel the mismatch immediately. Not because I thought I couldn’t do it. On paper, I could. In practice, I could. The mismatch was more subtle than that.

The identity of “sales leader,” at least as I had absorbed it, seemed shaped around someone who had finally moved on from building things. Someone smoother, more abstract, less inclined to tinker. Someone who had accepted that seniority meant distance from the tools. That was the part that didn’t fit.

This was not my first leadership role. I had been leading teams for more than twenty years. I built my first team in 2004. The tension was not about whether I knew how to lead. It was about what kind of leadership this role seemed to expect from me.

There’s a template for leadership that a lot of us absorb without examining it. The more senior you become, the more indirect your work is supposed to get. You increase your leverage and stop touching the work directly. You stop spending time in the weeds. You focus on strategy, relationships, coaching, and communication. Building becomes something you did earlier in your career, before you learned to lead.

I had already rejected that template in technical leadership roles. I had built a style that worked for technical teams because it let me stay close enough to the systems to understand what was real. But I did not believe my style would translate to sales leadership. I thought this was the point where I was supposed to grow out of it.

I thought I had finally reached big-boy leadership. The technical credibility I had leaned on before felt gone. The builder instincts that had always helped me suddenly felt like something I was supposed to apologize for or suppress. It didn’t make me better at the job. It just made me feel more like I was performing a role. That was the mistake. The problem was not that I was too builder-y for leadership. The problem was that I had accepted a version of sales leadership built for someone else.

I don’t think that was ever fundamentally true. I think it was a workaround for a constraint. Leadership has always been building. You are just building organizations instead of systems. None of that is less “builder” work than writing software or designing infrastructure. It is just more abstract, with far worse debugging tools.

For a long time it was the only kind of building most leaders had time left for. That was the real constraint.

As organizations get bigger and leadership scope expands, the practical ability to keep one hand on the tools falls away. Not because it stops being valuable, but because time and scale force a choice. You can build systems or you can build organizations, but not both. Over time, we started treating that forced tradeoff as if it were the natural shape of leadership itself. It wasn’t.

And now that constraint is lifting. That is the part I think AI is making obvious. Not because AI invented a new truth. It didn’t. It restored an old one.

For the first time in a long time, it is becoming practical again for a leader to build directly in ways that matter. Not just to have opinions about tools. Not just to sponsor experimentation. To actually touch the systems, work through the edge cases, and turn ideas into useful things without needing the kind of uninterrupted time that used to make it impossible.

That matters more than most people realize.

A lot of the current AI conversation still assumes the old template is intact. The “strategic” move is supposed to be delegating exploration, reading the memos, and letting other people figure out what is possible. The quiet fear underneath that posture is familiar: maybe if you are too hands-on, too interested in the tools, too willing to get into the weeds, it means you are doing leadership wrong.

I don’t buy that anymore. Some of the most credible leadership in this moment is coming from people who are willing to get close enough to the tools to understand what is real. That is part of how Shelley came into existence.

Shelley is one of the AI agents I built for my team. She did not come from a strategy offsite. She came from hands-on work: poking at the edges of the tools, seeing what was actually possible, and building something concrete enough to be useful. If I had stayed in the safe, abstract version of leadership, she never would have existed. And I would understand less about what AI can and cannot really do inside a working team.

That is the present-tense version of the same old tension.

The earlier version sounded like this: if you want to move into leadership, maybe you have to stop being the kind of person who builds things. The current version sounds like this: maybe you are too senior to still be this hands-on with AI. Maybe you should delegate the experimentation. Maybe staying strategic means staying out of the tools.

I think both versions are wrong for the same reason. They confuse distance with leadership.

The truth is that the instinct to build was never the problem. The discomfort was information. Feeling like I was a suit that didn’t fit didn’t mean I was in the wrong role. It was proof that I had inherited the wrong template.

There are two groups of people who need to hear that. The first is the technical seller or systems-minded operator moving toward leadership and quietly wondering whether they have to stop being who they are to earn the title. Whether the instincts that made them good — tinkering, building, wanting to understand how things actually work — are things they should mature past.

The second is the builder already in leadership who drifted into full abstraction because that was the only practical way to do the job for a long time. The person who still has a homelab, still wants to touch the tools, still feels a little apologetic about how much they care about the mechanics of things. Both of them are living with some version of the same insecurity.

Good. The insecurity is the proof. It means you are close to something real. It means you are rubbing up against a version of leadership that no longer makes sense. It means the old distinction between builder and leader is starting to break down in practice, not just in theory.

You do not have to grow out of building. That instinct is the thing. AI did not create it. AI just gave it room to matter again.