Earlier quoted context omitted.
>I see no reason why you'd have to be more careful in those meetings than the 1:1 with your manager The first thing that comes to mind is you wouldn't want to tell your skip level manager anything that you wouldn't (or haven't already) told your direct manager. That's going outside the chain of command and creates political and organizational issues that no one will appreciate.
> That's going outside the chain of command and creates political and organizational issues that no one will appreciate. I'd refuse to work anywhere that cares about chain of command. Managers are for bookkeeping purposes, not commanding. If your manager doesn't let you talk to the people you need to talk to to get things done then it is a very toxic environment.
Of course this isn't a hard rule, if I'm having a conversation with my skip-level and some topic happens to come up that I haven't spoken with my manager about before, I'm not necessarily going to hold back just because of that, I can follow up with my manager later. But if something's bothering me or I have some feedback or something like that, I'd generally chat with my manager about it before anyone above them.