Hi! I'm not sure if my question matches this category, but I wasn't sure where else to put it.

I've been a contractor for almost 2.5 years. I want my company to finally hire me. It's too difficult to deal with the taxes, the no benefits, the no PTO, etc.

I'm a little bit leery to ask my boss for various reasons. Is it ok or not to go to HR instead? The HR person is really helpful. I just don't want my boss to feel slighted.

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Maybe go to HR with a hypothetical, inquiring about the process and what your options are. Then say you need a moment to think about it and have a conversation with your boss

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This is one of those situations where I would pretend to not really know the right next step. You can go to HR with that approach “I’m not sure if you’re my next stop, but this is what I’m interested in doing..” and if your boss asks, same thing “I didn’t realize I could just talk to you about it… idk why I thought I had to go to HR.” That’s usually my approach to avoid stepping on toes at least.

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