I ask this question in every interview I have with someone who has at least as much experience as I do. I ask this when I’m interviewing job candidates and also when I’m the one applying for a new position. I don’t really care about what that engineer’s name is or where they worked. I ask this question because it seems to be unheard of enough that most don’t have a canned response and it consistently spurs insightful conversation.
As interviewer, I ask senior software engineers this question. When they explain why, I listen for several points. Do they really know why that person was the best they’ve worked with? If they can barely explain why, I take it as a hint that this person has less experience working with others than I’d hoped for. If you can’t explain why a great engineer is great, how do you intend to get there yourself? I understand the sort of chicken and egg situation that arises when you ask someone to describe why someone is so great at something – they can’t answer, because if they could, wouldn’t they know the secret sauce and be just as great? Instead, I want to hear the impact that engineer had on the interviewee: How well did they teach you? What did you learn? Are the answers to these questions superficial? Is the interviewee able to realize the impact this person had on them or are they reaching for the first ex-coworker they can think of? Are the reasons compelling and align with who I’m hoping to hire? After all, the hero in this person’s head is who they’ll look to for inspiration technically and behaviorally. I want to interview the person in their head vicariously through them.
And, dear god, do they offer themselves as the answer to the question?
When I’m interviewed, I really make it a point to ask this question to whomever manages people at the company I’m in talks with. It takes 0.02 seconds to realize whether an answer is geniune and thought-out or canned and fake, and I think that’s a nice barometer for the amount of respect I’ll receive as an employee. When I get a thoughtful response, I listen for all kinds of hints. Were they the best because of the wrong reasons? I have my expectations for a company and manager and some times it’s clear those aren’t going to align well with the what the interviewer perceives as good. That’s ok, and I think it’s important to notice those discrepancies as soon as possible. Please don’t say the best engineer you’ve worked with or hired was the greatest because they worked long hours and never gave you bad feedback. Instead, I’m hoping they tell me about how well this engineer worked with others or how they were able to lead a team through tough projects with minimal intervention – that sort of stuff sparks my attention. Someone managing people should be able to answer this question indepth without hesitation.
Someone’s willingness to point out specific people and give them praise also stands out to me. It’s wonderful that someone would have such nice things to say about a co-worker, past or present, and in my book it’s an indicator of good character.
I usually like to interject with further questions to lead them down deeper paths. I love hearing specific examples of times when someone was great. I know interviewers and interviewees enjoy this question because I’ve been told so by many people. Who doesn’t like to reminisce from time to time? It’s a delightful way to chat about what makes software development fun while also digging for insight about a person or process. I’d bet this question could be tailored to almost any field, really. Who’s the best product manager you’ve worked with? Who’s the best salesperson you’ve worked with? It’s a very wide-open question that leads to deep conversation.