How can I reconnect with someone I haven't spoken to in years?

Write an introductory letter ( include you previous connection ) or cover letter with your resume. Address it to the individual hope for the best.

Getting together for coffee is good place to start. I would advise that you do not bring up your job hunt; let her ask that question naturally. Otherwise your ulterior motive will be pretty transparent. It is sorta a tacky thing to do, so try give it some extra tact. Now get out there and work your network!

There’s no way of reconnecting without it being obvious that you want a job with her – so just be straight with her, but be open and sound pleased to be talking to her again.

Tell her that you were researching her organization for a job opportunity and you were so pleased to see that she was working there too.

I give @marinelife a GA. You don;t want to appear to be stalking her. She may not wish to reconnect. But at least you are looking for the job and it is “unrelated” to your knowing her. It intimates that you are not expecting her to interfere in the job process.

Are you on LinkedIn? It’s intended for professional networking (even though to some extent it seems to have evolved into yet another social site). You could connect with her that way and send a message of inquiry through the LinkedIn channels.

It seems as if you couldn’t have known her very well. If you were good friends, I think it would feel natural to you to call her up informally and just say you were wondering if you could discuss any opportunities within her organization.

If you’re not too sure how she viewed your past relationship, it might be best just to apply and let her recognize your name when she sees it. If you were to interview and even be hired as a result of her influence, it could be awkward for both of you.

It’s not clear why you can’t just pick up the phone and call or simply send an e-mail. My suggestion is: the more personal the better. I would call. Be prepared to leave a message. Write out exactly what you want to say. Ask the person for a 20-minute informational interview about the company.

Just in case:
If your relationship with this person ended poorly and you were at fault, call and apologize. Admit that you were an idiot, irresponsible, or whatever the situation calls for. Most people won’t argue with (or reject) an apology that includes the words “I was so stupid.” Then let this job opportunity pass. The last thing you want is for someone to think you’re just being nice/making contact because there’s a job opening involved. (Otherwise, years have passed, and you still haven’t changed.) Then contact your acquaintance if there’s an opening in the future.

Good luck!

(I think that was a whole 3 cents.)

@give_seek Well put!