A reader wrote me yesterday:

I just finished your great book Land the Tech Job You Love. I wish I’d had this to refer to when I was job searching over the years. This afternoon I’m going to give my highlighted copy to my brother who is currently in his 4th year of his search for a UNIX Sys Admin job.

My brother’s situation is the reason behind this email. He has 14 years of programming experience (at [big technical company]) and 14 years of UNIX Sys Admin experience (mostly at [company] but the latest 4 years were various short term contract positions). We’re in [big tech city] so there are jobs available. He seems to be able to get phone screens and some interviews but hasn’t been able to land a job. The brutal fact is that he is not very verbal and doesn’t interview well. I also suspect his Sys Admin experience lacks some breadth. It doesn’t help his cause that, even though the subject is taboo, he is in his early 50s (see: The graying of the long-term unemployed).

I would appreciate any thoughts you might have specific to my brother’s situation.

You say he doesn't interview well, and his experience lacks breadth. Sounds like you have the two things to fix right there! :-)

As far as his lack of experience, I'd do as much on my own as possible. I don't know what he has NOT done, but I'm guessing you have some ideas. What do employers in the area want that he's lacking. Do people want him to know LDAP? Set up an LDAP server on your home box. Does he not know enough languages, or maybe the last "new" language he learned as C++? Get a copy of a book on Ruby or Perl or Erlang and start writing some apps. Set up Ruby and Rails on a local server and start learning. Pragmatic has many introductory Ruby titles.

The perception of "This guy is too old" is, I suspect, a vicious cycle. They see him as "an old guy", and then it turns out he knows old skills, which reinforces the "old" part. So he's got to know new skills even more than a kid fresh out of school.

As to interviewing well, I can only suggest practice practice practice, and help him identify the areas that he's weak. Again, I get the feeling you have an idea what these are. Does he not answer questions with enough detail? Then help him practice giving longer answers that focus on business. Or is it just that he doesn't keep good eye contact or speak clearly? Again, practice is key. Maybe you could record a mock interview, with you as the interviewer. Afterward, the two of you can identify and discuss where he can improve. I've also heard wonderful things about Toastmasters for helping people get better at speaking with others.

Let me know how it goes!

Readers, have you had to deal with the perils of job hunting in tech later in your career? How did you handle it? Please let me (and the rest of us) know in the comments.