When is it appropriate to report your boss and how should I do it?

To be clear, I am not ever a person who “reports” people or makes issues. I prefer to handle things on my own or talk to the person directly but this has just become ridiculous and I need some advice.

Aside from her general lack of expertise and experience in what she is supposed to be doing, she just isn’t making an effort. This has been a problem for over a year but before covid we had the staff to cover. Now it’s just me and her due to downsizing. She is constantly pawning shared tasks onto me. I have tried to talk to her about it and logically frame questions like “ok which task would you like me to prioritize” and she just says “figure it out.” When I need to ask clarifying questions I can’t get hold of her. We have three hour meetings before calls with clients and vendors so that I can bring her up to speed on issues and so that she knows the actions that have been taken and can give updates. Also, she is completely unstable and tells me WAY too much about her personal life to the point where I know that she destroyed her ex-husband’s girlfriend’s car when she found out she was pregnant (incidentally, her ex and his girlfriend work for the same company...it’s a HOT MESS and I have no idea why she wasn’t fired for that).

All of that would be tolerable because I love my job and I love my other colleagues and I love her boss. But, the past week she has been even more MIA than usual and she missed a major deadline and I had to get on at 6:30 this morning to finish before our deadline. Then, this morning we’re on the call with vendors and executives and her boss asks her to demonstrate and share her screen and she says “I’m going to have ____ share her screen because I seem to be having connection issues” so I share my screen and present the reports. Meeting done.

But then, she messages me afterwards through company messenger and said “thanks for that, couldn’t share my screen because I’m at the pool. Didn’t realize I’d have to present or I would have been on.” WAIT WHAT????? So not only are you at the pool on company time when you should be working, but you are handling meetings and talking confidential client business IN A PUBLIC POOL?? (She is not scheduled off today).

THEN she tells me I’m going to have to approve my own paycheck today because she won’t be back on her computer before the deadline. She is asking me to commit a fireable offense or not get paid. I told her no I will not do that and she is going to have to figure it out. She said she’s going to have her boss do it and lie and say she’s still having connectivity issues.

It’s getting to the point where I have documented so many lies, erratic behavior, and violations (I save everything) that I think I need to report this to her boss. Especially because she’s just admitted to flagrantly stealing time and breaking confidentiality laws, and potentially interfering with me getting paid on time. However, the executive I need to talk to is fairly new, I don’t know him very well, And I don’t want it to seem like I’m trying for a power grab or being petty. He already knows about my boss’s messy divorce because it’s been brought to HR and my boss received an informal warning. How do I approach this? Do I not report and just continue to let her bury herself? Do I need to report to someone else? Any advice is greatly appreciated. I’m trying to handle it as professionally as possible.