>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.
If you're telling your skip level something that you haven't or wouldn't tell your direct manager, that is an indication that you are failing to communicate with your direct manager. That in itself is worth the skip level person knowing.
For this is less about being careful, and more about not going off on a spontaneous rant, which honestly, isn't a good idea to do for the chain of command anyway. Spontaneous rants are for your peers. Deliberate communication up and down the COF.
> 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.
I agree with this, and disagree with the parent comment's framing of this as "going outside the chain of command", but I do think that if you have a healthy relationship and open communication with your direct manager, I can't think of many reasons not to tell your direct manager something before telling your skip-level (or above), as a courtesy and an opportunity for them to address the issue first but not because of some rigid expectations around "command structure".
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.
This is half true. When I was an employee I viewed the chain of command as existing for my benefit, not my manager's. If some random bigwig wanted me to do something for them I would direct them to my manager. It wasn't my job to arbitrate between differing management demands on my time.
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.