Ask who fixes it when it breaks

Before I bring any tool into my stack, I ask a simple question out loud: if this breaks on a busy day, who on my team actually knows how to fix it. If the honest answer is nobody, that tool is riskier than it looks.

This matters because software fails at the worst possible times, usually right when you need it most. A tool nobody understands well becomes a full stop the moment something goes wrong, and you end up waiting on outside support while your work sits frozen. Knowing in advance who owns the troubleshooting turns a scary outage into a quick fix.

This is not about picking only tools with a live chat button. It is about making sure someone on your team, or someone you can reach fast, actually understands how the pieces fit together well enough to get things moving again.

Try this today: pick your most important tool and name the exact person who would fix it if it broke tomorrow. If no name comes to mind quickly, that is your next problem to solve.