[JohnFen]

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.

[solarmist]

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.

[maxerickson]

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.