e-mail to old boss

so I interned for this small consulting firm a couple summers ago and had a pretty good boss who was extremely friendly and seemed like he would help me later on in my career. at the time, I thought I would keep in touch with him after my stint was over, and see if he had any positions within his advisory firm later on after I had graduated. the biggest mistake I made was, was that I never sent him an e-mail or checked up to see how he was doing in the past 2 years after my tenure was over. I feel like a jackass now because I am currently looking for jobs all over the place and nothing seems to be going my way. I really feel that if I got back in touch with him, he would help me out--if not, at least guide me in the right direction. I am not really sure how to approach this email, as I am very eager to get in touch with him and see if he has any way of getting me in contact with the right people. I don't want to sound like an asshole either since I haven't contacted him within the past couple years nor do I want to sound desperate (but then again it may come down to that). please, if anyone has any advice or has had to do something like this in the past, let me know. it would be greatly appreciated.

Thanks again!

 

I'd ask him if he wants to go get coffee. I mean, you pretty much have to re-establish the relationship and I'd just be forward and honest with him about what you want/need.

I'd also wait to see what other people say, though, as well :-p

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He was a college kid at one time, and probably realized that you had other things on your mind the last couple years. I agree with setting up a time to get coffee and lunch, although with this job market and your current position, he is going to know what you are looking for, unless he is oblivious.

Be honest and straightforward.

 

Don't apologize.

Don't come off as desperate.

Don't lie or hide anything.

Also, reach out to him first, before going off the deep end. Just make the first e-mail a very short one regarding your intentions. You can get into more detail after some back and forth.

Your best chance is sincerity with a sprinkle of nonchalantness.

 

E-mail them and give them under the premise that you want to give them an update on what you have been up to for the past year and a half, but don't show your cards. Then (assuming they are in the same location as you…if not set up a call), ask to set up a lunch or coffee meetings where you lay out your cards. Steer the tone of the meeting so they will ideally ask you if you need help. However, if you are unsuccessful in maneuvering the meeting that way, bring it up.

 

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