A director walked into the office one morning and announced we were overhauling the entire IT infrastructure — every laptop, every server, Windows to Mac, top to bottom. The chief systems administrator got pulled in to build a financial model with finance. Budgets, projections, forecasting, the whole enchilada.
Nobody in that room asked the one question that mattered: why. Our existing setup wasn’t even two years old. Still under warranty. Working fine. There was no ticket, no outage log, no evidence anything was actually broken. As far as anyone could tell, the entire trigger was a stray comment — someone senior, at some point, wondering out loud why we weren’t on Macs yet.
That comment never asked for an infrastructure overhaul. It probably wasn’t even really about laptops. But “why aren’t we on Macs” got quietly swapped for “how do we modernize our systems” — a much easier question, and a much more exciting one for a director trying to make an impression. He had budget. He had the appetite. He had a fix that looked decisive from every angle. So he built it.
My team spent that entire summer migrating a perfectly functional infrastructure to a new one, at a cost north of a couple million dollars. Mac server infrastructure, back then, was genuinely rough — we even ended up on Mac wireless routers and keyboards, if you can believe that. It was exhausting, unnecessary, and by the end of it, nobody could point to a single problem that had actually been solved. We got praised for flawless execution. That summer was just busy work.
I don’t think that director was foolish. I think he did what most of us do the instant a problem-shaped thing appears in front of us — reach for the fastest, most tangible fix available, because having an answer feels like leadership, and sitting with an unresolved question doesn’t. The Mac comment gave him something to point to. Something to build, launch, and get credit for. What it didn’t give him was an actual problem worth solving.
You’ve felt a version of this yourself, probably more recently than you’d like. A colleague brings you something that sounds simple, and you’re already three steps into a fix before they’ve finished the sentence. I used to run into this constantly in my coaching practice — a client would open with some mundane, everyday challenge, and within five minutes it was obvious there was something else entirely underneath it. The job wasn’t to solve the stated problem fast. It was to resist doing that long enough to find out if it was even the real one.
Most expensive mistakes don’t look like recklessness from the inside. They look like competence. Like someone finally taking charge.
Before you fix the next thing that lands on your desk — pause. Ask what’s actually going on before you ask how to make it go away. Sometimes you’ll dig and find a real, gnarly problem worth solving. And sometimes, if you’re lucky, you’ll find there was no crux at all — which means there was never really a problem. Just a comment nobody bothered to question.