A friend of mine has asked me to recommend him for a position at a company I used to work for. I like him, but I do not think he'd be a good fit for the position based on his past work experience and interests. What should I do?
I don't want to damage my relationship with him. Adding to that is the fact that he's been unemployed for almost a year, which (to me, who has a bit of S in him) makes it more difficult for me to say no. If he had a job, I could say something like "wait for a better opportunity".
I also don't want to damage my reputation within my network by appearing to be someone who does not make thoughtful recommendations.
I know there may not be an elegant solution to this (although if there is, I'm all ears).
-DB

There are friends...
...and there are friends. Have you ever had a frank talk with him, about his skills and job search? Have you recommended the interview series? If not, well, you know to next time a friend is unemployed. That would provide the foundation for the conversation you need to have.
A true friend, like a good boss, is frank about such matters. What if he gets the job and then flounders or fails? And does your reputation matter to him? One would hope so.
You need to tell him that you have reservations about giving a recommendation, and be specific about the job/skills mismatch.
And that is the key to a successful conversation: it's about the match, not about him personally.
Good luck.
John Hack
Good advice
Thanks for the advice, John. I know I can't take the easy way out.