While 1-1s facilitate communication between a team member and their manager, skip levels should facilitate communication between a team member and their manager's manager. These meetings between a senior leader in the company and their "skips" serve to promote communication across the leader's whole team, not just their direct reports. It also gives the skips an opportunity to get to know their senior management, ask questions, and/or clarify their understanding of company or functional objectives.
It's important to note that the following are not purposes for the skip level meetings:
To check in on the performance of a manager by "going around them."
To manage priorities, career management, or perform any duties typically handled by a team member's direct manager.
Conducting skip level meetings
Skip level meetings should be held at least quarterly. Whether or not you choose to organize them more frequently is at your discretion, and likely impacted by the number of skips you have.
Skip level meetings can be conducted one-on-one or in groups of no more than 10-15 (to encourage participation). You may prefer one approach over the other, or if you have too many skips one-on-one meetings may not be feasible.
If you're able to do one-on-one skip levels, we recommend the first meeting with each skip be similar to a coffee chat - a free-form discussion with the intent to get to know each other.
Aside from any of these free-form initial skip levels, subsequent meetings should have a clear agenda. The first portion of the agenda should include anything you want to update or reinforce with your skips - review strategy, remind the team about areas of focus, etc. After that, there should be ample time for questions from the skips.
Don't worry about repeating information in skip level meetings. One of the most common reactions managers have after they conduct skip levels is to say "I thought everybody knew that!" Remember that messages often have to be shared several times in several ways before they are communicated effectively.
Skip level meetings can also be a great place to solicit feedback from your skips. SKS questions, among other feedback mechanisms, make solid agenda items.