A Guide to Successful and Pleasant Skip-Level Meetings

I don’t know about you, but my blood used to curdle when I got an invitation for a meeting with my boss’s boss. Often, those leaders were people I rarely interacted with who held the meetings because they had heard that it’s good to have them, which all amounted to an utterly awkward affair that both of us could not wait to end. I did not know what questions to ask during a skip-level meeting or how open and honest I could be. And in general, it was difficult for me to see the benefits of skip-level meetings.

Now, as a manager of managers, I am cognizant that some of my team members view my invitations for a skip-level meeting with a certain level of trepidation. At least initially.

But I firmly believe in the benefits of being connected with each and every one of my teammates, so I try to make it as easy and productive as possible for all of us.

What Are Skip-Level Meetings?

Skip-levels are meetings between a higher level manager and their non-direct reports. These meetings are a great opportunity to ask questions, provide feedback, discuss new ideas and above all – connect on a human level.

What Are The Benefits Of Skip-Level Meetings?

No matter how well the communication flows within your organization, there is always some distortion. I make it a point to receive information from the managers in my team about how each employee feels and performs at any given moment, but there is nothing better than to hear it straight from the horse’s mouth.

Another major benefit of skip-level meetings is that it facilitates smooth downstream communication. Discussing any decisions, changes or plans that I am implementing directly with each impacted team member allows me to provide further context, explain and address any concerns.

The opportunity to speak with higher-level leaders allows employees to be heard and feel they impact the way of work and the organization. I often find that the best ideas for improvement and enhancement come during conversations with the people who are actually doing the work.

Regular skip-level meetings also give employees confidence that if there is an issue their direct manager cannot or would not handle, they have a place to reach out for support. No matter how idealistic and positive we may want to be, the truth is that flawed manager-employee relationships constitute a significant source of work dissatisfaction and diminished motivation.  After all, we all know the saying, “employees do not leave a company. They leave a manager”. No matter how cliched, it does have some truth to it.

Sharing the same goals and values is paramount to the success of a team. But for those shared values to persist, they need to be communicated often and through different channels. Skip-level meetings are a great way to remind and demonstrate the values you want your team to have.

And there is, of course, the simple curiosity and human connection. I am lucky enough to work with over 60 individuals from 14 countries with different experiences, stories and personalities. Being able to talk to them regularly gives me a glimpse into diverse lives and cultures. And teaches me a lot of unexpected things.

How Often Should You Have Them?

I find that ad-hoc skip-level meetings can be a powerful management tool. Every time there is a decision I have announced to the team that I know would cause tension, or when there is a performance or personal issue with any of my team members, I make it a point to have a direct conversation with them. This could be a bit tricky as their direct manager may see it as interference, so it is essential to have full alignment before scheduling the conversation with the employee.

But to establish trust and reap the skip-level meetings’ full benefits, they should not occur only to address issues. They work best if used as a regular pulse-check, and their frequency should depend on the topics and areas that will be discussed. They should not be so close together that it makes them tedious and boring, and at the same time, if they are spread too far apart, it might be hard to build and maintain a proper connection.

I find it most efficient to have skip-level meetings with my non-direct reports, people managers every two weeks. This allows me to stay close to the operations, provide them people management coaching and advice, and address any needs they have faster without them having to go through our team’s whole hierarchy.

I meet with the rest of my team members once a quarter. It used to be twice a year, but it turned out that was not often enough. So many things would have changed between our meetings that it was difficult to pick up the conversation where we left of, and with some of them, it felt as if we are meeting for the first time every time. Definitely not enough to build a trusting and fruitful relationship.

How To Limit The Discomfort?

As mentioned, skip-level meetings can be a source of discomfort for both parties. Depending on how prepared we are and how to conversation starts, there is definitely lots of potential for awkwardness and uncomfortable silences there.

But there are some ways that can help us mitigate it to a certain extend. And the first one is to acknowledge it. Pretending that there is no discomfort often brings additional tension to the situation. And I have found that bringing the topic out in the open normalizes it and is usually accompanied by a sigh of relief as if my colleague was holding their breath until then.

It is essential that the intent of the meeting is very clear from the start. What are the objectives we are trying to accomplish during the conversation, and what is expected from each participant should be outlined and discussed. Preferably even before the meeting itself.

Another factor that I overlooked for a while (with the unfortunate result of a lot of stress for some of my team members) is predictability. For a time, my skip-level meetings were not reoccurring at a regular interval but scheduled whenever I could find a break in my agenda. In my mind, it went like, “oh, I finally have time to meet with some of my teams; let’s organize some meetings.” Until one or more of the managers came back with me with, “Lisa freaked out because she saw you invited her to a meeting. She thinks she has done something wrong.” In those situations, Lisa was usually a new member of the team who did not know me and had never had a manager three levels up want to speak to her for no particular reason. Still, it was a lack of acknowledgment on my end of her potential perceptions.  Since then, I have set my skip-level meetings at a regular cadence and ensure that each new hire is warned that I do like to chat with them.

And then, showing vulnerability always helps. For the conversation to become a real human connection rather than a simple listing of updates, we as managers should show up as humans and not merely as abstract leadership figures. This also means not hiding our flaws or insecurities, no matter how scary it may be.

And then again, sometimes, despite all our efforts to make the skip-level meeting an enjoyable and fruitful conversation built on trust, it does not work, and the employee does not open up. And that is fine, don’t push it. After all, those interactions’ primary purpose is to provide our team members with the opportunity to share ideas, concerns, or issues. If they don’t feel the need or do not desire to do that, it is their right not to.

What Questions to Ask in a Skip-level Meeting?

In some meetings, the conversation just flows. There are many topics to discuss, many stories to tell, and there is not much need to guide the discussion. Other times, it is not that effortless, and I like to have a plan to fall back on.

In this article, you can find a significant number of questions to ask during a skip-level meeting, and you can pick the ones that best suit your needs. My approach is quite simple.

I have a few basic questions I ask during skip-level meetings that I find are usually enough to fuel the discussion and help us uncover the most important focal points: What was the best thing that happened to you at work over the last quarter? What was the worst? What can we improve in the way we work? What do you need from me, your manager and our organization?

I try to devote as much time of the conversation as possible to those questions and the topics that stem from them, but I do also ensure that I provide some updates on upcoming initiatives or plans. And, of course, interweave our team values in the whole conversation.

Those meetings are also a great time for employees to ask their questions. These usually revolve around their performance, the future plans of the organization and their possible career progression.

Conclusion

Apart from all else, skip-level meetings are a great tool for keeping teams aligned and going in the same direction. It is up to us as managers to turn them from a dreadful and uncomfortable event to a discussion that brings learnings and value for both participants. And this is not that hard if we plan, are authentic and acknowledge all emotions brought about by the meeting.