Leading From the Front When Nobody Knows Where the Front Is

It's the first day of spring. Friday night. 10 PM. The kind of quiet where you actually hear yourself think. I've been sitting with something lately — this idea of being handed a leadership role for something nobody has fully figured out yet. AI Initiative Team Leader sounds impressive on paper. In practice, it means being the person in the room who's supposed to know where this is all going, when the honest answer most days is: nobody does. That's not a complaint. It's actually the interesting part. There's a specific kind of pressure that comes with being on the frontier of something. Not the pressure of doing a job wrong — that's ordinary, there are standards for that. This is the pressure of doing a job where the standards are still being written. Where the best practices of six months ago are already outdated. Where you're not following a playbook, you're writing one. I think about the people who had to figure out what the internet meant for their organizations back in the mid-90s. Most of them got it wrong. Not because they were incompetent — because it was genuinely unknowable at the time. The ones who did alright weren't necessarily smarter. They were just honest about the uncertainty, stayed curious, and didn't pretend the map existed when it didn't. That's the job now. AI is in that same weird liminal space — powerful enough that ignoring it is a real risk, but still raw enough that overconfidence is its own trap. So you stay humble. You experiment. You read the things that make your brain hurt a little. You build the systems, watch what breaks, fix it, and build again. You bring people along who are skeptical, because they'll catch the things you're too excited to see. Spring feels right for this. Everything starting over. Green coming back through the gray. The year finally admitting it has some ambition. First day of spring, new title, same uncertainty — just a little more comfortable with it than before. — Steve ☘️