This is how you do high quality skip levels:

1. What is going well?

2. What is not going well?

3. What can be done to improve?

Pretty much know what's going on. Anyone who BSes the second question needs to be layered or leave.

Speaking truth to power is rarely easy. Some leaders can take genuine feedback others cannot. Until you have a good pulse on the situation, is it really surprising most people default to inauthentic critiques?

This is why I'm very skeptical on the use of 1-on-1 meetings with management as a means to keep a finger on what's going well or badly in an organization.

If someone is OK with telling management things they don't want to hear, they'll tell management those things regardless of 1-on-1s.

They can’t be done in an in-demand or ad-hoc manner. They need to be consistent over time.

If they aren't consistent then it devolves into what you're saying.

But if you have a relationship with management then you can build a sense of trust based on the contents of that relationship.

Isn't the problem there that management has things they don't want to hear?

Like the whole premise of a skip level is the management hearing more things.

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?

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.

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."

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