Skip levels that surface real information

Skip levels are easy to mishandle.

Run poorly, they confuse reporting lines. Run well, they are one of the few ways to see the system as it is actually experienced, not as it is summarized upward.

The purpose is not surveillance. It is signal.

As scope grows, more information gets filtered. I lead engineering across Integrations and Platform, with work that also touches developer experience, reliability, and AI-assisted development. Summaries of that work can sound healthy while an engineer is waiting two weeks for an architecture call, or paying the same integration tax the last three customers paid.

Skip-levels are how I catch that earlier.

What I am listening for

I use them to understand:

• where execution feels slower than the plan
• where priorities are unclear
• where coordination pain has become normal
• where someone has ownership in name and not in decision rights
• what a manager may not yet be seeing because they are in the work

I am not collecting a second performance review. I am looking for operating-system gaps: missing specs, review bottlenecks, one-offs that should be primitives, 1:1s that have become status.

How to keep them from going political

Be consistent and explicit. If people do not know why the conversation exists, they will treat it as an audit.

A lightweight format:

• say the purpose in the first minute
• ask system questions, not “how is your manager doing”
• do not overreact to one anecdote
• follow up on patterns
• close the loop when a pattern is real, without turning the skip-level into a gossip channel

Useful questions look like the 1:1 questions, aimed at the system:

• What is more complicated than it should be?
• Where do you wait on a person instead of a default?
• What would you own if the decision space were actually yours?

What I do with the information

If three people describe the same friction, that is not a people story. That is a missing platform, a missing review layer, or a missing planning artifact.

Legal Intake taught me to make execution inspectable. Skip-levels are a people-shaped version of the same idea: do not wait for the dashboard to go red.

Treat the information with care. Isolated complaints stay isolated. Repeated structure gets a system change. That is how skip-levels stay useful instead of becoming a second management chain.