We got a question from a reader:

It looks like I’m going to be interviewing for my new lead, a person who is more senior than I am. This person may end up being my boss. What questions should I ask during the interview?

You want to find out if they are going to be a good mentor who can lead the team to building good things in a liveable environment that helps your career. But you also need to make a good impression on them because they may be your boss (who is also covertly interviewing you). This led to an interesting discussion, here are some suggestions we came up with:

What percentage of your time do you think will be technical work, inter-team program management, project management (scheduling, budgeting and resource allocation type work), or people management? Which of these do you prefer and why?

Essentially, what do they think they’ll be doing? This should match what your team thinks they will be doing. The second part of the question is also important: what do they want to do? Does it match with what they will be doing?

Do you have a people management philosophy? What is it?

Ideally, they have read some books and have some buzzwords that they can share with you. Mostly the goal is to figure out if they have a reasonable general plan but one that doesn’t involve taking over the world from day one.

Do you have a project management philosophy? What is it? How do you approach planning and scheduling? What is your position on ambiguity?

Again, you want an educated plan without a hard-line about your project. If they are already planning to re-do everything you’ve spent your last six months on, well, that’s a red flag.

How do you feel about failure? There is a lot of good from letting people learn from their own mistakes but that takes time and can be catastrophic if ignored for too long. How do you draw the line between letting someone learn lessons and helping them (unasked)?

This ties in with people and project management philosophy but is more specific.

How do you deal with non-cooperation? How do they deal with the inevitable frustrations associated with working with independently minded engineers? Do they need to build consensus to make decisions?

On one hand, building consensus is good. Having people personally buy into a decision makes them happier with the work. On the other hand, design by committee is usually the lowest common denominator. So how does the interviewee deal with getting smart people, people who have more history and knowledge than they do, going in the same direction? This is not a one word answer and should lead to examples from their past.

Speaking of examples from the past, you might as well start reading their resume and ask some specifics, maybe along the lines of this:

Can you walk me through a project you were a lead of? What were some of the challenges? Do you have an example of a time when your idea wasn't implemented on this project? What happened?

Projects should not crash and burn. Other people should not be called out as jerks and idiots. In fact, no name calling at all. Ideally, everyone is acknowledged as doing the best they can with the information and skills they have. And hopefully your interviewee can admit being wrong and handling it gracefully.

We have problem X. The design team develops a strategy that will solve the issue permanently. You go to management and they suggest a route that is technically naive and potentially dangerous. What do you do?

Managers are not there only to manage you. A large part of their job is to protect you. Make sure they understand that.

How important is team togetherness? How important (and often) do you want to have events like offsites and lunches and beer.

Hopefully they talk about team building as a way to ensure communication lines be left open and then launch into something reassuring about work-life balance and not requiring all of your time.

What is the best way to tell you that I feel like I'm being micromanaged? And what do we do if that happens? What are some good ways to communicate that I’m unhappy in general?

Some people like data and want you to make a graph. Some want you to struggle through until you are really fed up. Some want to wait until a set one-on-one time to catch up. Others like casual coffee. This question will prove useful if they really are going to manage (even mentor) you. Ideally the interviewee has some nice tactical advice about how they like to work. The worst answer here is “I don’t know” and the best answer is whatever you prefer doing.

If it is a real manager role, have you ever fired anyone? What was that like? How did it come about?

Good managers will sometimes get stressed, possibly emotional about this question. Firing people, even laying them off, sucks. It is an indication of personal failure to find the good in the people that work for you. Bad managers cackle gleefully, enjoying their power. I’d leave it until late in the interview. Or skip to something reasonably technical after.

Should everyone be allowed to choose their own computer environment (OS / compiler / tools)?

The answer to this is “no”. Teams waste precious time and money supporting three or more development environments because of individual preferences. Choose one and accept that the grass will always be greener and someone will always complain it isn’t their choice.

What is your favorite interview question for technical hires such as myself?

If the question is “what does i++++++ evaluate to?” or anything involving goats and cabbage, then run away. You want to see something that is a good judge of technical ability. Ideally, you’ll see something you can come up with an answer to but remember you aren’t on trial here. You can say “huh, that’s interesting, what do you look for in the answer?” to get them to explain it further.

Why are you leaving your current job?

If you have time, this is always entertaining. But everyone expects this question and probably has practiced an answer that makes them sound good. And you can’t really say “Wow, you sound heroic in your quest for this job but, really, why are you leaving your current job?” Instead, let us leave you with this suggested question:

Tell me about the last two people who worked for you that left the company. Why did they leave?

While the color commentary here is mine, the discussion of good questions included Christopher Svec, Christopher White, Andrei Chichak, Alvaro Prieto, and myself.