What is a Skip-Level Meeting?

As a company grows, a dangerous gap begins to form. In the early days, you knew every employee’s name and exactly what they were working on. As you add layers of management, you become insulated. Information travels up the chain of command, but by the time it reaches your desk, it has been polished, sanitized, and filtered. You stop hearing the truth.

This is where the Skip-Level Meeting becomes a necessary tool. A skip-level meeting is a meeting between a manager’s manager and the employees who report to that manager. For a founder, this usually means meeting directly with individual contributors or junior managers, bypassing their direct VPs or leads.

The goal is not to spy. The goal is to pierce the bubble. It is an information gathering exercise designed to help you understand the ground truth of your company culture and operations.

Middle managers are human. They naturally want to present themselves and their teams in the best possible light. Consequently, they often hide bad news or downplay structural problems until it is too late.

If you rely solely on your direct reports for information, you are playing a game of corporate telephone. A skip-level meeting allows you to get raw data. You hear about the broken coffee machine, the confusing software license, or the morale issue that your VP forgot to mention.

This direct line of sight allows you to detect patterns. If one person complains about a process, it might be an isolated incident. If five people in different skip-levels complain about the same process, you have a structural failure that requires your attention.

The biggest risk with skip-level meetings is how they are perceived by your middle managers. If not handled correctly, your managers will feel like you are undermining their authority or conducting a witch hunt.

To avoid this, transparency is required. You must tell your managers ahead of time that you are conducting these meetings. You must explain that the goal is to understand the organization better, not to evaluate the manager’s performance.

Furthermore, you must never make decisions in a skip-level meeting. If an employee asks for a raise or a change in strategy, you must not say yes. If you override your managers in these meetings, you emasculate them. Your standard response should be, “Thank you for that feedback. I will discuss it with your manager.”

These meetings should not be interrogations. They should be listening sessions. The dynamic is awkward by nature because you are the boss’s boss. To get honest answers, you need to ask specific, open ended questions.

Instead of asking “Is everything good?” which invites a polite “yes,” ask specific questions:

• What is the one thing that slows you down the most?
• If you were in my seat, what is the first decision you would make?
• What are we doing that we should stop doing immediately?

Skip-levels are the antidote to the ivory tower effect. They remind you that your decisions have human consequences. They help you retain high performers who might otherwise feel invisible.

However, you must filter what you hear. Employees lack your context. They might complain about a lack of resources without knowing the budget constraints. Your job is to listen, synthesize, and then verify the facts before you act.