Edit: Within 5 minutes of typing this and reading the replies I realized that this is a terrible idea. ;-) Feel free to read and even respond if you'd like, but I think I've gotten all the feedback I need. Thanks to those who replied!!
This is going to be long and kind of rambling, so please be warned! Also please know that I am asking this question with the best of intentions. I'm not trying to get revenge or get anyone in trouble.
I have worked at a company for four years. For most of that time I have been very happy working there. Over a year ago I reached a point where I no longer had to work full time for financial reasons, but I stayed on because I enjoyed it and I really liked seeing the people I work with every day. I have had the same manager for three years. He's a nice guy and, up until about a year ago he was a really great manager. He had his faults, but we all do.
About 8 months or so ago his management performance began to decline. As I see things now, he is trying to wear three hats: executive level, project management, and team management. Also, our team has greatly expanded. In my area alone we have grown from three people to seven in a very short period of time. His old methods of management were just the right mix of hands-on and no micromanagement. However, because he is wearing the executive hat and project management hat, he barely seems to wear the team management hat at all. We rarely see him as he is busy at meetings. This would be fine if he had a structure in place that allowed us to make decisions, communicate, or collaborate without him, but we don't. He seems to assign work willy-nilly, and no one knows what anyone else is doing. As an example, I recently found that five of us were working on the same things, and none of us knew what the others were doing. Also, there is much duplication of effort because there is no one actively coordinating work.
I brought this to his attention about a month ago, and he was receptive to what I had to say, but didn't have a solution. I think he needs help. He needs at least one team lead if not more for the number of people he supervises. He said this was not an option. I see other ways that his management is slipping, as well. I recently had my annual review and it was pretty much the exact opposite of how a review was supposed to be done (I was in management for 8 years and am very interested in management methods). He brought up things I had never heard about before, mentioned hearsay without telling me exactly what the hearsay was or who said it, and then did mention that two of my closest coworkers had complained about me, but wouldn't tell me what the complaint was (if I were my coworkers I would be really upset that he was telling me this). When I asked him to give me specific things I could work on, he couldn't or wouldn't list anything.
In an adjacent group, also under him, two members of the team have been there for a number of years, and a new member was added about a year ago. We can all see (since we have an open office) that he is not doing any work, and the other members of the team have complained that he doesn't do anything. He also comes to work late, smelling of alcohol. Our boss was clueless that any of this was happening because the two established members of the team didn't feel right about complaining to the boss about one of their teammates. But how could our boss have someone work for him for that long and not know that this person wasn't doing anything, and was coming to work drunk?
So here's the question. I am planning to give notice at the beginning of May, with my last day being in the beginning of June. I'm retiring and will be trying to get some part-time, work from home work in my field for at least the next year until I transition into my part-time retirement career. My boss's recommendation would be very helpful to get work. I have thought about going to the VP in charge of our department (this is skipping a level, but the Director between my boss and the VP is worse than useless, and is just part of the problem) to talk about the structural problems in our department and to say that they really need to get my boss some help in the form of team leads.
But there are so many downsides to this I think maybe I should just let it go, leave "gracefully", and keep my boss's good will. I care about the coworkers I'm leaving behind, and this could possibly help them, but I also don't want to "fall on my sword" for no good reason.
What do you think? Would me meeting with her even make a difference, except to make things even more difficult for my boss?