by Leon Rosenshein

Tell Me About A Time When ...

I’ve been doing interviews for a while now. And one of the questions I like to ask candidates, of all levels, is to tell me about a time when they made a mistake that had significant impact. I find that there’s a lot of signal in the answer. There’s information on how self-aware the candidate is, what they find important, and how they respond to mistakes, both in the moment, and afterwards.

Because one of the follow on questions, if it doesn’t come up in the discussion, is “What did you, or anyone else, do to try and make sure it didn’t happen again?” And the response to that question has even more signal. It says a lot about how the candidate can generalize from specifics and how they think about the future. Answers can range from “I learned to do/not do X before I Y” to defining team/org processes as a way of reducing the likelihood of the issue to tooling with automated validation that prevents bad things from happening.

It’s those tools and automated validations that have the most impact on the future, and that’s what I really want to see in a candidate. Even with the most junior candidates or college interns I can end up having an interesting discussion of how a whole class of problems can be prevented. We can talk about Post-Incident reviews and root cause analysis and what you do when you find the root cause.

Because when it comes down to it, especially if you want to be able to get a good night’s sleep, how you prevent issues is more important than how you deal with them.