The neglected skip 1:1

“How on earth could he say those things so confidently when he doesn’t have a clue about what’s happening down here? It’s kind of like the American politicians who used to visit Vietnam, look around a bit, talk to the top brass in the military command, review some statistics, and then proclaim that the war was being won and they could see the light at the end of the tunnel. Right!

Being present allows you, as a leader, to connect personally with your people, and personal connections help you build your intuitive feel for the business as well as for the people running the business. They also help to personalize the mission you’re asking people to perform.

—Ram Charan and Larry Bossidy: Execution: The Discipline of Getting Things Done


One crucial but often neglected meeting in an organizational leader’s meeting toolkit is the skip 1:1—a one-on-one meeting between a manager and her directs’ directs. In other words, it skips a level in the organization.

Frankly, I haven’t been consistent in my career in conducting them. It’s easy not to do them. They are the kind of meeting that you can get away without holding for quite a while without visible negative consequences. Each individual skip 1:1 may provide a bit of value, but they are an incredibly high-leverage activity in the aggregate. Occasionally, you can uncover a severe and otherwise invisible issue that makes all of your skip 1:1s worth it.

Like 1:1s with directs, they are a purposeful business meeting, not just a chance to chat. The purpose is (1) relationship building, (2) information gathering, and (3) a chance to provide affirmation and praise. More specifically, skip-level 1:1s:

  1. Create rapport between you and everyone in your organization. As your team grows, you will have less and less contact with any one individual. Later, as your organization grows, this may be the most substantial conversation you have with an individual that year. Skip 1:1s allow you to build personal connections that can pay dividends later.
  2. Give team members time to ask questions or raise concerns. To a first approximation, zero people in your organization will contact you to ask questions or raise concerns. These meetings are the most successful when you give prompts for potential topics and remind the person that the meeting is mainly for their benefit.
  3. Give you a finger on the pulse of alignment and communication between you and your managers and how that alignment and communication flow down to ICs. Do people understand what your organization is doing? What is the company doing? Do they understand how their work fits in?
  4. Give you a reality check from people on the ground. They can illuminate areas of your organization that you need to pay attention to and lingering issues you may have missed and give you a deeper understanding of the day-to-day work getting done in your organization.
  5. Can uncover places where you are being “managed up” to the detriment of those reporting to that manager. In general, you will hear the perspective of the managers reporting to you more frequently and before the perspective of the people reporting to those managers. This is an opportunity for individuals to give feedback about their manager.


How frequently you hold these meetings depends on the size of your organization. Two guidelines: I do not recommend holding more than one skip 1:1 per week (your time is too valuable) or meeting with the same individual more than bi-annually (their time is too valuable). The idea is to get insight into your organization, not to build strong individual relationships with every individual throughout your team. As in all things, use your judgment.

Things to watch out for

You don’t want to create a situation where you cut your line managers out of communication loops, send mixed messages about your confidence in them, or issue “accidental orders.”

These are real risks, and you should watch out for them. Skip 1:1s are a great tool, but the primary communication channel should always be IC <-> Manager <-> You. That’s what the organization is for. That’s what gives line managers the autonomy they need to do their jobs and helps push decision-making down to the lowest possible level. Issuing instructions undermines your managers.

In fact, Manager Tools recommends against holding skip-level 1:1s because it can undermine your direct managers. (They have a entire podcast about it!]). They recommend a combination of group skip-level meetings, having your directs conduct 1:1s with their directs, and maintaining an open-door policy. All of these are great! That said, I have found skip 1:1s too valuable of a tool to ignore, even with these risks.

So, when you are conducting a skip 1:1, and someone runs an idea by you, asks for your permission to do something, etc., or even, in some circumstances, complains about something, a key thing to ask is, “Have you talked to your manager about this?” You can recommend this as a first step and ask the individual to follow up with you later. For a truly serious situation, you should, of course, act as you see fit.

Sample meeting invitation template

Here’s an example of a meeting invitation:

A chance for us to meet and chat about what’s working and what’s not on our team.

The goal is to help us all work better together and ensure you’re happy and successful working here.

This is meant to be a conversation. I’ll bring a few questions for you, and if there’s anything you’d like to discuss, we’ll start with that. Ideas for improving your team, observations you think I should know about, and feedback on your manager are all good topics. I’m also happy to answer any questions you have for me.

If this time is not convenient, please don’t hesitate to suggest another.

I look forward to talking with you!

Questions for skip 1:1s

The following are some ideas for questions to ask in skip 1:1s:

Organizational Strategy and Processes:

  • What should the organization start doing?
  • What should the organization stop doing?
  • What should the organization continue doing?
  • Are there any process improvements we should consider?
  • Are there any opportunities we might be missing?
  • Are there any areas of the business strategy you don’t understand?
  • What should I know about?

Team Dynamics and Collaboration:

  • How do you feel about the communication in your team and the broader organization?
  • Is this team working poorly with any other team?
  • What do you need from your peers?
  • Who on your team has been doing well recently?

Individual Performance and Satisfaction:

  • Do you feel you get appropriate recognition when you do a great job?
  • Do you have the training & resources to improve?
  • What are the biggest time wasters for you each week?
  • What’s keeping you from doing your best work right now? Are there resources or tools you need that you’re currently not getting?
  • How happy (or not) are you working at the company?
  • Do you see yourself working at our company in three years?
  • What do you like best/worst about the project you are working on?

Managerial Relationship and Feedback:

  • If you were the team leader, what would you focus on (or do more of) and why?
  • Do you have any feedback about your manager—what’s going well and what isn’t?
  • Is your manager giving you enough feedback?
  • How often does your manager cancel 1:1s?

Open-Ended Questions:

What’s on your mind? What questions haven’t I asked that you wish I would?