I have to give tough feedback and warning to one of my employees for making people around uncomfortable (ie: making fun of veganism to a veg indian lady, calling me and other managers "bro", telling me he had a crush on me years ago, gossiping and complaining about other peers because they aren't "fun")

Any suggestions. My strategy is to spin in about the importance of respect (being a core company value) and suggest a course about workplace harassment.

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No need to spin it. Start by saying this is going to be a difficult or serious conversation to set the tone. Recap the behavior or off color topics using the rule of what could be seen/heard if it was recorded. Tell them it's not ok and you expect x going forward (or expect they will not do y). They may be defensive or try to negotiate. Tell them it isn't negotiable and reiterate expectations.

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This is the answer. Don’t sugar coat it, no need to do a Freud analysis on why the person acts they way they do. They need to be told the way you speak to and speak about your colleagues is not acceptable and their behavior needs to change or they will be finding a job elsewhere.

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Is this the first conversation you've had with this person on this topic? If so,, I'd recommend thinking about why he might be doing this and not defaulting to the automatic assumption that it's rooted in intentional disrespect. I mean, sometimes it actually is, but other times it can someone trying to form connections via jokes and camaraderie but going about it in all the wrong ways. After he shares, I'd let him know that--whatever his reasons may be--it's not going over well, it's hurting his perception, and the behavior needs to change. Unless he's been outright offensive, I would stop short of using the phrase harassment because in my experience people get ultra paranoid and defensive when they hear that term, stop listening, and go into self-protection mode. Lest you think I'm siding with someone being awful, just a heads up that I'm not. Big time feminist here. Just trying to make sure your message is heard and lands because that's really the ultimate goal.

Also think it's important to set a tone by calling out even the microaggressions. It makes the bigger conversations easier when everyone knows the expectation is to check yourself even when there "no harm" or "always been that way".

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