"I have been doing very well in my new EA/Hybrid role. I work for absolutely one of the most disorganized individuals I have ever encountered. Brilliant, but horrifically disorganized. To the point where she blows the the binder system, the different color folder system, and I could go on. But the worst of them all is a lack of clarity in desired results, so that many times, we have to repeat a process 2-3 cycles before her team finally comes close to something she "may" want. HR has told me, she is the type that just wants to sign it and let me take control and its done. The issue is, I've tried this to some degree but find she is also the type that tends to quickly judge a person and dismiss a person and it depends on the day. I am sure some trust issues are there. Her favorite statement is..."It's the same old process that doesn't get any better." I believe that I can help here, but I am at odds on how to organize my day to stay on top of hers. For one thing my Executive Assistant role is a hybrid where I do a number of other items as well. But I believe support of her has become critical to the unit. How would you go about assisting "the disorganized on paper and in thought" executive?"
It's good to hear from you again. I'm so glad you are doing well! Congrats! I edited your question for privacy and brevity's sake. I hope you don't mind. I do believe all your concerns are justified and it's normal for you to feel the way you do. You provided enough examples for me to get a clear understanding of what the situation is like. To answer your question, I think of the movie Jerry Maguire and that famous line, "Help me help you." The problem is your boss doesn't want the help and doesn't want to improve. Not only is that evident of her actions, but also what she said point blank, "It's the same old process that doesn't get any better." While it is true that the assistant is there to keep the executive organized and on top of things, this only works when the executive GIVES that power to the assistant and realizes admin stuff should be the domain of the assistant because the executive should be doing the executive thing - leading the team, innovative ideas, business strategy, forecasting etc. While I wholeheartedly believe the assistant should also "train" their executive to be an executive if your boss has trust issues and is so fundamentally disorganized that they don't even know how they want to carry our their OWN role, it's hard to change anything.
Another prime directive of the assistant is to make the executive's life easier so the best you can do is carry out your job in the disorganized way she likes to function. It's your job to bend to their style, to function to their liking, to make things easier on them. While I agree it doesn't make any business sense at all, I think most realize how flighty and a handful your boss can be. Most also realize it's the executive who manages the team, so any shortcomings are really the responsibility of the boss. You will have a job for life if you can somehow make them like you, comfortable with you and bring a smidge of ease to their lives even though the larger problems will not be solved.
Executives and companies are so busy as it is, everyone never has enough time. There will constantly be a ton of problems. If you can focus on getting stuff done without the emotional aspect showing (annoyance, rolling of the eyes, complaining to your boss) and without making the situation worse, that's all you can ask for. If your boss is super flighty and doesn't deliver results, they may not have a job for long. At some point, unless one is brilliant like Steve Jobs, years down the road, executives will no longer be in the industry and will be ousted. Until then, teams will be built around the brilliant executive looking for that great match who can put up with all their difficult ways.
I have said this before - you can only control your own thoughts, behaviors, actions, and life. Do what you can with your boss, but realize they don't want to change or improve. You'll have to weigh which duties are more important to take care of immediately and perhaps stay over time to catch up on other tasks. Perhaps you can delegate smaller tasks to interns or anyone below you, but ultimately you will be responsible for them/their work as well. Your role will continue to be a juggling act as your boss has all the power and ultimate final say. You probably have and will continue to feel that you are constantly "undoing" any of their mistakes or bad decisions. Overall, I think if you've lasted this long, you've managed to cope pretty well. Keep it up and I hope you get promoted soon!