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My manager left the company 3 years ago. I have been on good terms with him. I kept in touch with him for a few months after he left. Then other things became a priority, and I unintentionally neglected to remain in contact with him.

Now, I am looking for a job change, and one of the options I am looking for is an opportunity to work with him again. I am fairly certain he would be happy to have me in his team (or at least, he "wouldn't mind").

If I just call him and say, "I am looking for a job change. Would you consider me in your team?", it would sound rather selfish, and I am not comfortable doing this.

How do I resume contact with him with this goal in mind, with minimum awkwardness?

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    I'm afraid that your question will not remain open on TWP, so I'm not really sure that migrating it there will be helpful for you. This very much focuses on your interpersonal relationship with your ex-manager, so, while I usually respect the OP's request for migrations, I'd like to hold off in this case. Please let me know that this works for you.
    – Catija
    Commented Nov 3, 2017 at 18:20
  • OK, that's fine with me. Thanks!
    – Masked Man
    Commented Nov 4, 2017 at 0:22

3 Answers 3

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There's nothing wrong with getting back in touch because you're looking for work. In fact, I'd recommend against random "hey how are you it's been a while" contact that slowly morphs to "oh yeah btw I'm looking for a job." It's dishonest and it doesn't fool anyone.

However, straight up "can I come work for you?" is very direct and may leave the old manager feeling pressured or unable to decline, resulting in potential embarrassments to you both like an interview you could never succeed in. Instead, be clear that you are looking for work and asking for help, but don't ask your manager to hire you. If the manager happens to be hiring, or to be in a position to open up a space for you, you don't need to suggest such a thing - a good manager can think of that themselves.

I would probably email something like this:

Hi [name], hope this finds you well. A lot has been going on for me these past few years, and I'm looking for a job change, so I'm reaching out to people I've enjoyed working with in the past. If you know of something available that would suit me, I'd really appreciate any introductions or information you can provide. Since we last worked together I've [learned C++, shipped 3 commercial products, been promoted to senior DBA, taken on more project management, whatever] and I'm looking for a role where I can [continue to learn and grown, lead a team, get into Internet of Things work, speak at conferences several times a year] and [some other thing you want.] Are you aware of anything?

Key points about this email are that it lets your manager know how you've grown since your last communication, and describes the position you want. Don't make your manager do all the work of figuring out what would be good for you. In addition to avoiding the pressure of directly asking for a role with the manager, this approach also means that the manager can tell you about "a great opportunity with a friend of mine" without it being some sort of consolation prize to make up for not having a job to offer you.

Depending on the response you get you could elaborate that "I really enjoyed working for you and it would be really cool if there was an opening at your firm" but I wouldn't include that in the first email.

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    Please, don't use "hope this finds you well". This is a signature greeting of spam and phishing emails. Besides, it is similarly disingenuous as as the phrase "hey how are you it's been a while", which you yourself reject.
    – Martin Vegter
    Commented Nov 4, 2017 at 9:34
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    Your phishes may vary, I suppose they use it because it's perfectly normal and ordinary to do it. And if you can't see the difference between one sentence of greeting at the start of an email vs several different emails that don't mention the job hunt just a desire to "catch up" before finally mentioning the true motivation only after an in-person meeting - well I suspect you offend people quite often without realizing it.
    – Kate Gregory
    Commented Nov 4, 2017 at 18:02
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    @MartinVegter Just because a phrase is used in spam and phising emails doesn't mean it's not an acceptable greeting, especially when it's genuine. It seems logical that when you're contacting someone you got along with, you hope they are well. The disingenuous nature of starting a conversation first lies in misdirection: it makes it seem like you're contacting them to hear about them but then it becomes clear you were actually just looking for a job. To me that's quite a difference.
    – Cronax
    Commented Nov 7, 2017 at 15:47
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How do I resume contact with him with this goal in mind, with minimum awkwardness?

I think the best thing you can do is send him an email asking how he is doing. If you're close enough maybe even a phone call, this would be a stronger approach versus an email. Once you are comfortable that the relationship is intact, then you could ask them to be a reference for you.

By asking if they will be a reference, if they are still comfortable with you, they may offer up any opening they have influence over on their own, and you may not have to ask.

If you have successfully reconnected, and they don't offer, then ask them about potential opportunities within their organization. By doing this in a general indirect manner, you're allowing your contact to decide whether or not they want to work with you again. Basically, you are attempting to elicit either "Hey I have an opening" or "I know someone who does" type of response.

Good luck!

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  • The Ladders recommends this approach. A reference is easy for a former manager to do, and you're asking for a favor, not a job. That, I think, is easier to respond to and puts that manager in the right frame of mind. As a former supervisor, I can say this: I remember the good ones pretty well. I also remember the bad ones really well. It's the mediocre ones that don't stick out.
    – baldPrussian
    Commented Nov 5, 2017 at 1:01
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I think the best way to raise this with your old boss is to send him an email or call to check in, mention you're looking for a new job, and suggest meeting up for coffee or lunch to catch up if he has any openings. If he takes you up on it, then you go, catch up, and have a nice time (also, definitely offer to treat your boss, since you're asking for a favor). A politely worded email would work too, but face-to-face contact makes it easier to re-establish a rapport, especially if it's been a while.

Honestly, if you got along well before, I think it's just a matter of re-establishing communication. Most people I know would be happy to help out an old colleague that they got along well with.

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    I am not sure what this offers over the other answers provided.....
    – user1856
    Commented Nov 3, 2017 at 17:43
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    @MisterPositive fair enough, they weren't there when I started typing. I can remove this one
    – captaingabbeh
    Commented Nov 3, 2017 at 18:35

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