[alwaysbeconsing]

Isn't the necessity of skip meetings itself a pathological sign? The only thing you legitimately need to talk to your manager's manager about is things your manager can't handle -- i.e. mostly problems with and/or praise for your manager. Everything else should go through your manager, or what are they there for?

[rrrrrrrrrrrryan]

How do you know that your direct reports are doing their jobs well if you never talk with the people they're managing? Just take their word for it?

"Yes boss, all my subordinates are happy and think I'm doing a stellar job at managing this team."

[Spooky23]

Depends on the org and the situation. Sometimes the guy a level up has a broader perspective.

Like anything, ymmv. If it’s setup as a way to rat out your boss in a deep org, that’s stupid. If it’s a way for the director to establish relationships with some of the ICs, that can be productive.

[rqtwteye]

When communicating through a middleman you always lose information or it gets distorted. There is definitely value in talking to upper levels directly.