Should I Stay or Should I Go Now...

I work directly with him on a lot of stuff. He intentionally cuts her out of it, as he's been doing it with me since before she was promoted... and she has zero expertise in my area.

I've been doing it with him long enough that I know what he will want before he wants it... and can do 90% of what he needs to do for him without him having to give me any guidance. I also know exactly what he will want to see to make decisions... and usually I can guess what decisions he will make. So I can guide him through all the decisions he needs to make, with recommendations that are already 90% "correct," and have at my fingertips all the info he will want to reference to close the decisions on the spot.

I definitely have value to him... but it's specific to my specific area of expertise. He does not want to lose me and have to start from scratch with somebody new who has to learn all the lessons I've already learned. He also knows that while she understands my value, she's also annoyed by it. So while I'm sure he was annoyed with her for playing games with my bonus, I'm sure he was not surprised by it either.
I’m curious.

He knows he fucked up with the previous hire (who had to be fired).

Why is he chickenshit to do what he needs to do regarding your “boss?”

Firing her appears to be the option.

Are you a public company? Is she in the C-suite? Was her predecessor in the C-suite?
 
I’m curious.

He knows he fucked up with the previous hire (who had to be fired).

Why is he chickenshit to do what he needs to do regarding your “boss?”

Firing her appears to be the option.

Are you a public company? Is she in the C-suite? Was her predecessor in the C-suite?
We are a $2B division of a public company. He is part of the parent company's executive leadership team, she is not. His last screw up was very public and he took a hit for it with corporate politics at the parent company level. He does not seem to want to risk it again... I also suspect he likes that she knows her job is only because of his backing... and that keeping it is based on keeping him happy.
 
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