The Customer I Let Go

There's a point with a leaking faucet where you've replaced every washer and it still drips, and you have to admit the problem was never the washer. You knew this two repairs ago and kept going anyway.

I had a customer like that for about a year. Same complaint every few weeks, different words each time, and every time we'd fix the thing they named and the real thing underneath stayed broken. I kept sending people at it. Kept promising the next release would close the gap. It didn't, because the gap wasn't a feature gap, it was that what they needed and what we built were never going to line up, and I think I knew that for months before I said it out loud.

I'd noticed the shape of this for years without a name for it — a small number of accounts eating most of the support time, most of the escalations, most of the late nights, long before I heard the word Pareto attached to it. Knowing the name didn't make the decision easier. It just meant I stopped pretending the math was a mystery.

When I finally told them we weren't the right fit for what they needed, it felt terrible. Not the revenue — that part I could do math on and move past. It was that I couldn't help them, and I'm still not sure how much of that was them not willing to hear what we were telling them versus me not saying it plainly enough, early enough, in a way that gave them a real choice instead of a slow accumulation of disappointment. I land on it being mostly on me. I had the information sooner than they did.

What I've never solved is the timing. Cut it too early and you didn't try hard enough. Cut it too late and you wasted a year of their time along with yours, which is worse, because at least your own time is yours to waste.

If you've ever ended a customer relationship — how did you know it was time, and were you right?