In small companies (especially startups), where HR may not really exist or the HR person may be the main violator, how do you deal with inappropriate behavior. If a person has been there a long time and is "too important to fire" how do you handle them?

At a startup I left because of this, my boss had been there since day 1. He was a nightmare. The last straw was when he took out his anger at a home issue on me and made fun of me for being upset. HR told me they couldn't do anything about him.

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OP, just validating that this is indeed unacceptable. One tip for startups - even when it's not time-effective or cost-effective to change things (and for a senior software engineer it's probably most efficient to just go elsewhere) - depends on the size of the startup, but you could make sure the board knows what's going on. Privately ping the investors on the board (find their contact info somehow) and make it clear that your manager drove you away. The board is ultimately the boss of the boss of the boss, and they see a ton of companies good and bad. If they notice that an executive or manager at the company they've funded is being a jackass and driving people away, they'll take note and pressure will be applied. And, since the network of investors is a bit different from the network of folks who directly manage you, if you privately ping them it's less likely to affect how you're viewed by any of the folks who hire and evaluate you at future gigs.

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