Skip-level 1-on-1s are the concept of you, as a leader of multiple teams, of meeting directly with people who report to people who report to you. This is sometimes a very delicate topic, because you may make your direct reports, or the people you’re meeting with (who work for them) nervous about disrupting the chain of command, but I find it’s very worthwhile to navigate this delicate issue, to ensure that your leaders and managing their people well.

• They should be conducted at least annually (every 6 months can be valuable, depending on your organization’s growth rate and leadership maturity of the leaders in your group) with everyone who is 2-3 levels below you on the org chart
• The immediate supervisor should be notified before the meeting is scheduled
• The skip-level person should not commit to anything or do other things to ‘break’ the chain of command, such as promising binding things (e.g. promotion, training)
• The skip-level person should send out an email within 5 calendar days after the skip-level, sent to the immediate supervisor with notes from the discussion (high level recap)
• Draft Agenda to consider for these meetings:
  • Welcome to the team! (Note: This item is if this employee is a relatively recently hired employee)
  • Chat about their background before joining your group
  • Share some of my background and history
  • Chat about current role/responsibilities
  • Chat about frustrations/areas for improvement you see within the group
  • Chat about your career goals/interests