Tips on interviewing a prospective boss?

November 1, 2019 1:29 AM

I am a software engineer working on a team without a manager. I'm going to be part of the interviewing process for my new boss. I have worked for bad bosses before and want to make every effort to not work for one again. So, askme, do you have any tips for how to interview candidates who may become your direct superior?

Things I've already done:

I've ensured that all of my 15 colleagues will meet the candidate for a semi-structured lunchtime discussion.

Things I want from a boss:

A person who can cultivate a high-trust team.

Someone who can sort noise from signal in an extremely chaotic organization and who can help migrate the larger organization towards less chaos.

Someone who is cognizant and responsive to the concerns of the minority folks on the team.

Someone who's able to make a concrete and ongoing commitment to operational excellence.

Someone who understands the exact value of process and can determine when the ROI on process is negative.

Someone who can make decisions.

posted by anonymous to Work & Money (12 answers total)

Sure. As an individual, just listen to what the candidate says in response to others. Listen to how they say it. To whom they direct the answer. Whom they give short shrift responses to. See who they honestly respect, and who they'd rather ignore. Because the only thing you're going to get out of someone over a lunch discussion is a sampling of their people skills.

Management skills are almost impossible to gauge unless you yourself have those skills and have been trained to interview for them. And even then it's still a crap shoot because there's no stake in an interview like there is in a six month long project with people yelling at you because shit is broken.

A free-for-all lunch meeting is not the place for the 15-20 minute long scenario breakdowns that are necessary to get a handle on management skills.

Are you interviewing any women? Any people of colour? Anyone over 30?
posted by seanmpuckett at 4:54 AM on November 1, 2019 [7 favorites]

Respectfully disagree with seanmpuckett about only getting people skills. Ask behavioral interview questions, but do it in a way that's a bit more respectful and less direct since this might be your boss. "Hey, we get a lot of fires that detract from organizational strategic goals. How have you handled that in the past?"

You're not going to get a perfect read, but you're absolutely going to be able to sift out the "management platitude" types from the "get stuff done" types. People that have done it have specifics to talk about -- how'd they prioritize, how'd they communicate expectations, how'd they manage the really bad fires. People that just expect 60 hour weeks and staff to do it themselves are going to give you some BS about pulling together as a team and motivation and rah rah.

Please note, though, that meeting all 15 team members is something to benefit the candidate, not your team. Conducting an interview well is a skill, and opinions from poor interviewers are about as worthwhile as opinions from poor anything.
posted by bfranklin at 5:42 AM on November 1, 2019 [6 favorites]

Management is primarily a job of delegation and communication, so ask them about situations where these are carried out. In particular, how they have functioned as liaison to groups outside the team and within.

Ask them for an example of handling disagreements.

Praise vs. (constructive) criticism.

Ask them how many weeks of maternity / paternity leave their current employer provides.
posted by nickggully at 6:18 AM on November 1, 2019 [3 favorites]

First, I'd caution against negative interviewing - don't interview someone based on the faults of previous bosses, interview them based on skills, values, and experience.

So for some of your things - for looking for approaches to diversity you can ask how they have supported creating diverse teams in the past - looking for hiring practices, etc. If they have no answer this is a sign. A behavioural question really focuses on things like "tell me about a time you..." "Could you share an experience or two that you've had in building diverse teams?" -- it takes answers out of the theoretical.

"Have you ever been in a situation where you felt there was too much emphasis on process? How did you determine whether there was a way to streamline?" Etc.

For creating order in a chaotic company, there are definitely some behavioural questions you can ask, but I think it is important, especially if you yourself have never been a manager, to temper your expectations here unless you have a particularly small or flat organization. That said, it might help your interviewee(s) to get a sense of what they are walking into to ask about their experience in those kinds of situations.
posted by warriorqueen at 7:40 AM on November 1, 2019 [1 favorite]

As a software engineering manager who also interviews peers, more junior managers and SE's all the time, this "I've ensured that all of my 15 colleagues will meet the candidate for a semi-structured lunchtime discussion" part worries me. What do you expect to get out of this interaction? Will you be asking all 15 for their feedback? How will one person's feedback be weighted against others? This is way too many people to be making a decision.

(Also - will this person be managing all these people? IMHO, that's way too big a team for a single person to manage, but not the question here... )

I would ask situational type questions: "Tell me about a time you've had to manage disagreement in the team. What was the result? What would you do differently next time, if anything?". Or "Tell me about a time where you've had to manage many disparate asks coming into the team in with conflicting dates. How do you prioritize? "

"Tell me about a time when you've stepped into a new team before as their manager. How did you get up to speed? How do you engage with the team and it's individuals? What sort of questions did you ask? What would you do differently this time if given the opportunity"

But I second warrierqueen's comments about tempering expectations if you've never managed before. Managing a team is a completely different skill set, career path and set of goals vs those of the software engineers. And not all SE's who make the shift realize this and should be making the shift, which is why sometimes SE's get horrifically under-qualified managers. But what's important to you may not necessarily be aligned with what's important to your new manager's bosses, and it's important to keep that in mind.
posted by cgg at 8:59 AM on November 1, 2019 [4 favorites]

Behavior is surprisingly stable over time. If you ask about how they handled previous situations, that's likely how they will handle similar ones in the future. You can look for the factors they take into account, communication style, etc.
posted by wnissen at 9:16 AM on November 1, 2019

I've been the person doing the hiring of this person three times in the last six months, and have involved their future teams in different ways. I've also been on panels to hire people that will manage me.

Seconding cgg about that lunch. I wouldn't recommend that model. It's the very rare manager who can do well in that context (plus eat so they can get energy for their afternoon interviews). I would recommend picking a few taste makers to do a 2-3 person lunch max and whose read will be appreciated by the rest of the team. My guidance for lunches is always "your job is to look for red flags, not to get a positive read. Just have a normal lunch with someone and let me know if something goes weird."

For your interview, I would look to integrate with the broader interview panel. What can you evaluate that no one else can? Or what is not covered that you think is important to the team? Your responsibility to your team is to say "I think this process will hire us a manager that can help us all succeed." That's not just about your interview, it's about the entire system and its values. In my past versions of this, the member of the team has usually done technical interviews because that's the thing they can do better than me or other management-type interviewers. But then I'm covering mentorship and performance management since that's a thing I spend more time on. You have a stronger voice on topics where you're an expert than in topics where the stakes are high for you (i.e. "will they help me get promoted" or "will they solve org conflict that's important to me in a way I like").

Also be aware that you probably don't have a real veto. If a hiring committee gets a whiff of "this person is resentful of this hire in general and looking for reasons to bounce candidates" they will hire over you in a heartbeat. If you're measuring the same skills as someone more senior on the panel, the hiring manager will tend to trust the more senior person. Try to build trust that other interviewers are asking good questions and have the same judgement as you about what a good answer is and get them into a spot that reflects your values. But be careful about pushing too far out of your lane.
posted by heresiarch at 1:51 PM on November 1, 2019

Take a few minutes during the discussion to observe how the candidate responds to women, people of color and similar exemplars of diversity. Are their questions taken seriously, or dismissed? Are they talked over or ignored?
posted by SemiSalt at 3:38 PM on November 1, 2019 [5 favorites]

Get their take on each element of the Joel test.

Ask if they've heard of crockford, cunningham, and fowler. And what about it.

Have them contrast risk management under waterfall, scrum, and kanban. See what happens.

Have them articulate what their idea of a high performing engineer is.

Full-stack vs focused competency.

Mountain dew or diet Coke.
posted by j_curiouser at 7:20 PM on November 1, 2019

They should be able to do the jobs of the employees they are managing.
posted by xammerboy at 10:12 PM on November 1, 2019

I had the opportunity to interview prospective bosses before, and one question that is very illuminating is "Tell me about a time you had to let someone go."
posted by radioamy at 9:39 PM on November 2, 2019 [1 favorite]

I'm a software engineer manager myself with a fair amount of hiring experience and I think there's some great advice in this thread. I agree that the semi-structured lunch discussion with such a large group of people is probably not going to be a great format.

Like j_curiouser, I like the Joel Test, and think it's a good topic to bring up. Bonus points if they recognize it. If not, have it ready and walk through it with them, or at least the items on it most important to you and your team.

I also really like radioamy's question: "Tell me about a time you had to let someone go."

I would also bring up Agile Scrum. It sounds like your team is headed in that direction. Point out that a lot of engineers are skeptical, if not outright hostile, toward it. What has been your candidate's experience?

I only have one additional suggestion: Have you read Daniel Kahneman's Thinking, Fast and Slow? I recommend reviewing this short passage from it on interviewing:

http://txti.es/kahneman-interviews

I think you're on the right track in enumerating the specific competencies you are looking for in your ideal candidate. Are they shared by your team and the rest of the organization?
posted by klenwell at 9:42 AM on November 3, 2019