I've been in a situation where I had to work directly with a good CEO (plus board, C-Levels, and a lot of middle-management) and problematic middle-management was the actual problem.
It was almost like parody:
- CEO wanting people to leave at 5 sharp, middle-management inventing work and forcing people to do overtime and telling people "he's the CEO, he can leave at 5, he doesn't know we have a lot of work to do".
- Bureaucracy and inefficiency, with everyone complaining about it, but whenever CEO pushed back on that same bureaucracy, the discussion would be hampered by one or two people fillibustering the meeting to force the status quo.
- People going to golf courses or resort trips paid by vendors and then pushing for a vendor that costs 100k/year. This one was so blatant that I was surprised said person wasn't fired.
- CEO and C-Levels taking suggestions from the trenches, and the board loving it, but middle-managers laughing about the suggestions behind the CEOs back, right after the meeting. This one stung because a few of those were suggestions I made and he presented as his own on my request.
This is the kind of stuff that HN people would go "Chesterton Fence" but was just fucking corruption and schoolyard bullying from middle-management.
Obviously the company didn't grow in the period, and the CEO resigned and left for much greener pastures.
In the end the only lesson I learned is that the CEO should have laid-off those people.
And that the CEO should make more money because childcare is hard work.
Funny thing is that I'm a middle manager myself.