How do you handle a boss who can’t stay organized and won’t delegate? I feel like I’m putting out fires he creates everyday.

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Offer to take things off their plate where you think you can help? If they see they can trust others on certain tasks it may help them delegate in the future

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Oh totally! Great advice. I did this initially, but I became disheartened when I didn’t get any responses. Maybe I need to give it another try.

Ooof. Been there.

For me I'm proactive and try not to leave a leadership vacuum for others to fill/fuck up.

That doesn't work always though, for example if they feel the need to 'add value' or take that proactivity as you overstepping.

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Yeah I get caught in that “overstepping” trap. The other option I’ve tried is to ignore the problem until it’s made my problem. But then it becomes my problem at the 13th hour.

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