A skip-level meeting is when you, as a manager, meet with a direct report of someone you manage. So for the person you’re meeting with, it’s their manager’s manager. If you manage three managers, and each of them has three direct reports, there would be nine people you could have a skip-level meeting with. For managers in large organizations, this number could seem overwhelming. If this is the case, try to do it 2-4 times a year, spread these meetings out over several weeks so you don’t have to cram it all into a few days.
The purpose of this meeting is to understand what’s happening at other levels in the organization. This is your opportunity to hear about how they think and feel about the decisions you’re making and the overall vision of the company. Something that you discussed with your direct reports could impact their direct reports without realizing it, yet you may never hear about it.
The difference between this meeting and a typical 1-on-1 with your direct report is that you are not directly managing this person, so be careful not to undermine your own direct report. Your job is to discuss the vision and ideas with them, not make decisions or problem solve.
Sending an invite for a skip-level meeting should be handled delicately. Receiving a 1-on-1 meeting invite from your boss’s boss could send the person into a panic. Did they do something wrong? Are they getting fired? Are you promoting them into their manager’s position? Start by discussing the skip-level meeting with your direct report to get them comfortable with the idea of a skip-level meeting. Make it clear that this is not about a lack of trust in their management, it’s about you becoming a better leader. Then, send an invite with a similar message to their direct reports, along with an agenda so they have context for the meeting and are able to prepare accordingly.