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?

From those questions you can get a good idea of the thought processes that work inside the candidate's head in terms of both technical problem solving and people skills.

I tend to avoid focusing on the technical since a lot of folks can lead you astray here. They sound good on paper and talk a good game but you find out later they are "book smart" but couldn't change a light bulb without calling technical support.

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.