A Lesson in Recommendations

Early in my MSP days, I recommended a project management tool to a client because it was the one everyone in my network was using.

Six months later she called to tell me her team had quietly gone back to spreadsheets. Nobody hated the tool. It just never fit how her crew actually worked - how they billed, how they escalated, how half her staff needed things written down and the other half needed things said out loud.

I'd sold her the popular answer instead of the right one, because I hadn't looked at her business closely enough to know the difference.

That call sat with me longer than most. It's the reason I don't lead with tools anymore - with clients or with AI. I lead with the shape of the business first, and let the tool fall out of that, even when it means saying "I don't know yet" in the first meeting.

That's the same instinct that pushed Toodlebox toward AI in the first place - not chasing the trend, but the same old problem showing up again in a new form.