Pick tools a new hire can learn fast

Whenever I choose software for my team, I imagine training someone brand new on it during their first week. If I cannot picture that going smoothly, I take it as a real strike against the tool, no matter how powerful it looks in a demo.

This matters because your stack has to work for everyone who joins later, long after the people who set it up have moved on. A tool that only makes sense to the person who configured it becomes a bottleneck the moment that person is busy, on vacation, or gone. Simple, clear tools spread knowledge across the whole team instead of trapping it in one head.

Ease of learning also tends to predict daily use. Tools people actually understand get used properly, while confusing ones get half-used, worked around, or quietly ignored until they cause a problem.

Try this today: watch the next new hire or team member try to use one of your core tools for the first time, without help. Note where they get stuck, and treat that spot as something to fix or simplify.