I had a terribly incompetent boss when I was in my 20s but he was one of the nicest people I know. I would never ever want to work for him again but I did send holiday cards and kept in touch. Thankfully I did because last year- I applied to a really great job and his wife was on the interview panel. she is awesome and very competent and I think I got the job because of my connection to him. So you never know- its a small world!

Anonymous wrote:I guess the only possible problem with reaching out is if they want to utilize you either as a reference or a point of contact towards a different job. I think you have to ask yourself whether they were just in a job that was a bad fit for them or whether there are other aspects about them that make them a bad fit for any job.

This. Professional contacts have the added complication that personal contacts do not. I'd evaluate whether my outreach could potentially become awkward for either of us. If so, I'd probably hold out at this time. You can always reach out down the road once your former boss is more settled.

I guess the only possible problem with reaching out is if they want to utilize you either as a reference or a point of contact towards a different job. I think you have to ask yourself whether they were just in a job that was a bad fit for them or whether there are other aspects about them that make them a bad fit for any job.

If they are nice people and you don’t work for then of course keep in touch

Why would you want to keep in touch with someone who you consider to be a bad manager and a terrible boss?

What would be sketchy about it? You can like someone as a person and think that they were a bad fit for their job.

I was recruited for a role. Hiring manager sold a sweet deal. I took it.

Bad choice. Boss was inept and a terrible manager. It was like working for someone following the “what not to do” handbook. I left quickly as did many of my peers.

They are a nice person, just horrible at their job. I was told they are in a really bad spot now.

I usually keep in touch with my former colleagues and bosses. It’s important to me to maintain a positive network.

Is it a nice thing to reach out for the holidays and wish them well OR just cross them off the list?

I have no ulterior motives other than I feel bad that they are having a hard time.