In the past, when I have been in this position (auditioning a new lead-programmer, section-lead, department-lead, and once a VP of Engineering), I start off trying to find who they are and what they have been doing --

• Where did you most recently work?
• What did you like about it?
• Why are you leaving?
• What do you expect get Here that you couldn't get at your previous job?
• Do you have any children?
• Do you have pets?
• What are your favorite relaxation techniques?
• When did you last take vacation? Where did you go?
• Are you a hacker? What's your favorite Language and Operating system? (Sort of a hand-grenade....)

• What's your opinion on over-time?
• At your last job, how often did you hold staff-meetings? How long did they last?
• What do you think of off-site team-building exercises?
• Did you socialize with your team an your previous job?
• Do you see yourself having a problem managing someone who is five/ten/fifteen/twenty years older than you (OGB's favorite)?
• How do you handle intra-team conflicts? (John refuses to maintain Mary's code because "It's Yucky!")
• Same question; inter-team conflicts. ("We can't deploy the code tonight because the Sys-Administrators won't give us root access to the production servers.")
• How do you handle unreasonable demands from your management? (hand-grenade number one)
• What kind of Upper Management behavior would lead you to resign? (hand-grenade number two)

Watch for waffling answers and tick them in your notes as something to come back to later. (I always take notes on a pad of paper during the interview process. It keeps me from fidgeting and keeps the Interviewee honest.)

The second round of questions is exploration of places where I got weasel words and waffling answers the first time around. I'm trying to get information from them, not put then on the spot -- 'That was interesting, what you said about xxxx, can you expand on that?' -- but I want to know why they waffled. Basically, I need a Manager who has intelligent opinions and the moxie and juice to be able to defend them in a civilized conversation. And, in this litigious age, I want the answers to the Hand-Grenades to leave me feeling comfortable with the candidate's ethics.

At the end of the interview, I should know if I'd be comfortable introducing this candidate to my Dog, my Mother, and my Sister. And coincidentally, I should have found out whether there is anything that might make working in the same room with them a bit sticky. I have had a Candidate who couldn't stand 'Rock and Roll' and said so in the interview. I pointed out the usefulness of headphones. Later I introduced her to the introductory riff in "Jumpin' Jack Flash"(the Rolling Stones), the bass-line in Credence's "Heard It Through the Grapevine", and the coda of Mark Knopfler's 'Speedway in Nazareth' (I quote: "It's almost Bach-ian in the way the multiple lines play off each other -- Is all Rock and Roll this good?").

If I can't get that level of comfort fairly quickly, then either there is something wrong with the candidate (down check, next Interviewee please), or their answers are so interesting that I didn't get through my full list of questions. In that case, I negotiate with H/R for another time-slot later in the day, or invite the Candidate out for a beer and conversation after H/R is done with them. (Note: this is a somewhat insidious interview technique -- get a couple of pints of Bass Ale in the candidate and see where they go....)

Bear in mind, that a Reasonable Manager (no, this is not an oxymoron) will not try replace the primary language of a shop overnight, or even over a couple of years. The last thing a New Broom wants is to start a project that will fail. And replacing Perl with anything else is not a simple proposition (been there, done that, didn't have no fun, and the t-shirt doesn't fit). A New Manager wants to keep the new job. So, for the first six to eighteen months a Reasonable Manager will pick on problems that are winnable. You get to assist them in determine which problems are winnable....

Do you have any children?

It may be a regional thing (state/country), but the candidate might claim that this question is trying to get information about their age and/or marital status. If you're in a large enough organization to have an HR department, it might be worth asking them for guidelines about the types of questions to avoid.

And I'll agree on the 'why are you leaving' (or 'why did you leave', as the case may be). It can also be a hand grenade question, as sometimes people will just go off talking badly about the company/people they used to work with. For management jobs, I'd expect the answer to be mostly diplomatic.

...

Another question that I seem to keep getting asked is 'have you ever been fired from a job, or left because you were told you were going to be fired?' (mostly for security forms, as opposed to in an actual interview, though) I just remember the question, as I get to answer 'Yes', and in the follow up 'why?' I get to answer 'use of sarcasm'

I suggest you try to design some behavioural questions based on the attributes you're looking for in a boss. For a manager, I'd focus more on communication, leadership, supervision, organizational and delegation skills than technical ones.

Apart from interviewing him/her one-on-one, I'd further ask the applicant to give a technical whiteboard presentation to all members of your team and allow power of veto to any team member (this is what Peopleware calls an "Interview Audition"). I'd also have at least two other team members interview him/her one-on-one.

Here's a random selection of some of my favourite interview questions:

• Why did you choose your current career? Ice-breaker: lets the person talk about their past and how they got to where they are. Helps you understand them and their goals/values.
• What are you good at? Bad at? Strengths? Weaknesses? Put the candidate at ease by telling him/her about your strengths and weaknesses. Again, a good ice-breaker, hopefully allowing you to break down the barriers and know what the person is truly like.
• What motivates you? Describe a specific situation when you were very motivated to perform a task. Describe a situation when you felt unmotivated.
• What two projects are you most proud of and why?
• What are your favourite tools? When you start a new job, what tools do you immediately download and install?

You liked your old boss right?

Write a list of reasons and make questions around them.

Don't limit yourself to him being Perl friendly. You could end up with a Perl friendly lunkhead for a boss

You liked your old boss right?

Honestly? Not particularly. The man was entirely prepared to make the two Perl programmers on his team port all of the production Perl code (much of which has run without issues for years) to .NET because "Perl is unmaintainable."

We only talked him out of it by escalating to his boss and explaining that (a)neither of us knew .NET well enough, (b)the UNIX scripts were not likely to be successful as .NET applications, and (c)we don't like spending time and money to fix stuff that's not broken.

Updates:

• 20070808 : added "all". Makes much more sense now.
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Besides the topics that eyepopslikeamosquito mentioned, the generic 'what was your most miserable failure?' with a followup of 'what would you have done differently, in hindsight?' can give you some insight into a person's personality.

From the last time I had to hire someone, here are the generic questions that I asked:

• Tell us about yourself (note -- forces them to summarize their resume to what they think is important)
• What is your most proud accomplishment, and why?
• What action do you most regret, and why?
• What is the worst job you've ever had?
• What goals do you have in your career?
• What are your long term goals?
• What motivates you?
• What is your greatest weakness?
• What specific skills and experience do you feel set you apart from others who might have applied for this job?
• Why do you want to work for (insert organization)?

update: fixed a typo.

Anyone have ideas on what to ask during the interview to increase the chances of a clueful (and Perl-friendly) boss?

I view the interview process for a potential boss pretty much the same as for a subordinate. I too have been both a manager and the (barely) managed! :-)

My favorite interview questions to ask that can help you generate more questions are:

• What is the project you worked on in the past that was your favorite? And why was it your favorite?
• What technical hurdles did you encounter and how did you go about resolving them?
• What political and human factor issues did you run into and how did you go about resolving them?

Getting a feel for a candidate's project management skills (using the questions I've posed as a springboard) is not a bad thing either.

One final question I ask after they've gone through their "dream project" discussion is " was the project a success or a failure and what made it such?" The range of types of answers you get are fairly enlightening and can give you more insight into how the person thinks. And finally, "how did you handle handing this project off to others after you were completed?" can be an eye opener as well. Quite often you find out the person never handed their pet project off but in fact used it as a means to justify their existance where they were at.

Just some thoughts.

My last thought: be fluid in your interviewing strategy and adapt to what you find. Avid the temptation to follow as script because you might miss something if you are not adaptable.

• Take the time to talk to employees even if you're busy, if you know it's important
• Main job: make sure your team is able to work - defend them from "upper" management, who usually have no clue about what your people are working on or how they should go about doing their jobs.
• Stick up for your team members if they are right, fight for them if necessary, unfortunately often it is (better equipment etc)
• Quit if you can't ethically stand for how you or your team are treated etc

• Why is it warmer in the summer?
• What are the cycles of a 4 stoke engine?
• How does a duckbill platypus bear its young?