friendship help: Hi all. - Help.com

Hi all.

I’ve only made two posts on this site before, but the answers I’ve gotten from them have been great advice and really helped me see things in a new angle. Here it goes:

This coming Thursday I have lunch with my former boss from the university I worked at for 3 years. He is the VP of finance & administration there. I was only a student assistant, meaning I only answered calls, opened the mail, helped schedule meetings a little bit, nothing big. However over the 3 years we did develop a close friendship and I have visited his office a couple times after finishing work and graduating in 2011. I was an economics major and have told him one of my career interests was to follow in his footsteps and be a finance manager.

My question is: how do you guys think I should approach this “lunch” I’m having with him? We scheduled it after I personally gave him a birthday card with $10 in it (lol). He said he would only accept it if he bought me lunch one day, and so we arranged lunch. My dilemmma comes from him knowing I have been on the job search in my field for about 2 months now with not a lot of luck. I definitelly plan on wearing a tie just to avoid underdressing, but should I keep things casually and have conversation like old friends? Or is it possible that I can come out with a job interview due to this lunch with him? Would it be a good idea to email him if I can bring my career documents (resume, cover letter, etc) just in case he wants to talk potential opportunities with me, or just bring everything anyways?

Let me know if you guys need more info. Any advice would help, thanks!!

This open post was written 9 months, 3 weeks ago | V/U/S: 389, 1, 1 | Edit Post | Leave a reply | Report Post


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Zirbel offline Verified User (2 years, 9 months) Long Term User Shouts: 4 #
An Undisclosed Location | 9 months, 3 weeks ago (48 minutes after post)

At least you should start the conversation casually, yes, like old friends. That way you can sound out a bit his situation and possible opportunities for you — if there are any. But if so, and if you feel that’s a good moment for, you can bit by bit sprinkle your interest.
But don’t talk too deeply about the real reasons for your failure on job searching, better plead some reasons which can blandish him a bit — in the way: “You know, there it wouldn’t be for me that nice as it was with you”. Yes, debauch a bit in remembrance of that time with him as a boss.
You know, the whole thing is: To attain your ends by diplomacy! Not by real lying, but with empathy and admiration.
Then either HE will offer you a job (or a job interview) or, unfortunately, there is no opportunity — but don’t ask him directly for a job, to not puzzling him. If ever, ask him later on, after this meeting, by e-mail.

And all together, behave appropriately distant and respectful all the time, not like a buddy, because he is the boss — hopefully your real next one!
Good luck!

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