How would you reach out to a former boss to catch up while also indicating subtly that you are possibly interested in returning

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I would just ask them to lunch or coffee, and hope they open the door to you coming back when you're together in person. If they're in another office, you could see if they have time for a call and hope for the same. If they don't mention anything and the firm/group is receptive to boomerangs, I think it's fine to be direct about the reasons you want to return. Worst case scenario, the group isn't hiring or they aren't interested, but then at least you know for sure.

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Did you go in house or to another firm, and did you exit with your relationship intact?

SD1 nailed it, although I might be a little more overt. The question how you’re doing will for sure come up. I would answer “you know, it’s been pretty good. Nice people and interesting work. But I’m starting to think I might have made a mistake in leaving and wanted to know if there might be a path back to your team at some point.” Understand that they might have a full queue at the moment that limits their ability to rehire you now. But even if that’s the case turnover creates opportunities. If they like you and your skills and know they can rehire you at some point without paying a recruiter, that’s a huge bonus for them. And don’t sweat the look of returning to the place you left. It happens. It’s one reason never to burn bridges when returning. Partners understand it and are flattered to hear that their grass is the greenest after all.

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