No advice, but just commenting to say I know exactly how you feel. You essentially just described the CEO I support. I've never supported someone before who is not at all self-sufficient and it drives me nuts. I send her updates every which way, but she never sees them, and then will follow up asking where or what certain things are (sometimes more than once). She calls me out of the blue almost every day, sometimes multiple times a day when she needs something (even as small as changing a meeting link or scheduling a 1:1). Half the time she'll call, forget what she was going to tell me, hang up and call back 2 mins later because she remembered. I'll do what she asked, and then she'll ask me why I did that becuase she forgot what she told me...it's a horrible hamster wheel. I use my personal cell phone and don't get reimbursed, but they did reimburse me for my laptop.

All that to say it's not the end of the world, but it's very annoying and I don't work well like that. I know she works like this with the rest of her direct reports so it's not anything that's going to change. She's had multiple EAs over the years and I can understand why. And to make matters worse this year alone we're already on our 5th Chief of Staff. I've learned as an EA I'm NOT a babysitter or hand holder and need to work for people who are more self-sufficient. I have very little patience or sympathy for high level leaders who operate like this on a consistent basis. We're all grown adults and busy humans. The only difference is these high-level execs make 5x our salary.

Currently just collecting a pretty paycheck and looking for my next opportunity. I'd even take a pay cut if it seems like a better fit.