Alternatively, I've met plenty of people who are so desperate to climb the ladder that, even knowing full well their deficiencies, they climb to a level where those deficiencies become detrimental for everyone around them.

If you aren't a good organizer, and climb into an organization centric position, that's 100% on you. If you aren't a good leader and take a coordinating position, that's on you. If you aren't good at lining up blind screws, and you knew that was a core competency for your job when you took it, that's on you. It's not that I expect you to be "smart enough to overcome" whatever you're bad at, but you shouldn't be in positions where something you're bad at, but can't overcome, is a major part of your duties.

At that point, yes, I'm going to be "mean" and directly point out your deficiencies.

Can you tell I had a fun meeting today?