Good questions to ask a potential new boss?

Question

I first asked this question on Stack Overflow, but it turns out this is a better place for it.

Imagine you were working as a software developer. Imagine that the manager of your team leaves and your company is looking for a replacement. Imagine that as part of the hiring process you had the opportunity to talk with him. You are not the only person doing an interview, and while it is not ultimately your decision whether or not to hire him, you do have an influence. What questions would you ask? What would you talk with him about?

Answer 1

"What is your management style: hands on, or hands off?" Basically you're trying to figure out if they are a micromanager, or if they will treat you like a professional and let you do your job without too much fuss.

"What do you think is your best quality as an employee?" You're asking this to see what sort of quality they tend to respect more in their employees.

"How do you resolve conflicts within your team?" Basically you're trying to see if your potential manager will wimp out at the first sign of trouble or not.

"How would you expect your team to resolve issues and conflicts?" You're asking how they expect the team to function in a crisis.

"Where do you see yourself in 5 years?" Figure out if they are ambitious or not, and possibly if they'll step on you or use you to get themselves ahead.

"What is something you struggle with professionally?" You're trying to see if they have enough self awareness to meet your needs. If you don't care, then don't ask.

Answer 2

Ask him about the programming environments of his recent workplaces. Essentially, do a second-hand Joel test. Observer his reactions, also: if the version control was substandard, what does he think about it? That it wasn't a problem, that it could have been a problem, that it was a problem he couldn't do anything about at the time?

Answer 3

About how many hours per week do you expect your employees to work? Because at the end of the day if a place is a sweatshop, I'm just going to leave anyway, so might as well ask the question up front and if it is a sweatshop then move on to the next one. The prospective boss shouldn't have incentive to lie since if it is a sweatshop and you say you don't like it, then he should know you are going to leave. And if he lied to you, then at least you can say you gave him fair warning....

Answer 4

Tell him to assume that your company scores a zero on the Joel Test.

Get him to arrange the twelve items on the list in a priority order for implementing and justify his answers.

Answer 5

I'd ask about what kind of environments he's worked in before, and ask what he expects of his team.