How can I get more comfortable with confrontation?
Anonymous
How can I get more comfortable with confrontation?
I'm leaving a job where my boss' discomfort with addressing issues lets problems fester and leads good employees to leave. My new position will involve management of direct reports and contractors. My old position didn't involve direct management, but I ended up de-facto managing several people and contractors who were giant headaches because they weren't doing their jobs, and I had no authority to do anything about it beyond documenting and scrambling to fill in the missing pieces. When I'd ask my boss for help, she would tell me 'just ignore it'. Ignoring it meant a few all-nighters making up for coworkers slack to get deliverables completed, so I found a new job.
I don't want to be this kind of boss, but conflict and confrontation don't come naturally to me. I'm a recovering people pleaser who has learned boundaries but I still struggle with keeping them and can give people the benefit of the doubt a little too often. I would love some tips or thoughts on how to professionally and proactively identify and manage pain points before they fester and get worse.


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