I’ve got a junior associate who’s incredibly sharp, but she’s terrified of making a mistake. She overthinks everything, asks for approval on every small task, and rarely takes initiative without being prompted. I don’t want to micromanage, but I can see her confidence holding her back. I want to help her grow into her own voice as a lawyer. Any tips on mentoring someone who constantly second-guesses themselves?

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Tell her this. Give her smaller projects and specifically tell her to run with it.

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This is me. I’m here for the tips because I struggle a lot with confidence in lawyering. I just always assume Im wrong since there are so many different perspectives and angles in a case.

I was also like this when I was a junior and it was because I was under an overly critical senior associate in other matters who would be condescending when I asked a question or suggested anything. You sound great but she might work with others who aren’t as supportive as you.

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