Skip-Level Meetings: A Powerful Leadership Tool

As an HR leader for almost twenty years, I’ve spent a lot of time coaching managers and leaders on engagement and performance.

One of the strongest tools I give to leaders is the skip-level meeting. They’re an opportunity for you as a senior leader to connect deeper into your organizations and get a less-filtered view of life on the frontlines.

Hopefully, you’re already having regular one-on-one meetings with managers and they have check-ins with their direct reports. But how often are they connecting with the people two or more levels below them?

Do you understand what they care about, their pain points, their reasons for excitement and motivation, and their opinions of your managers? 

In this article, we’ll focus on how to have impactful skip-level conversations, the value they can bring to your organization, and give a template for conducting one.

What is a skip-level meeting?

A skip-level meeting is a conversation between a senior manager and someone who reports to one of their direct reports (i.e. individual contributor). The mid-level manager is not in the meeting, they’re skipped over to talk to lower-level employees.

The purpose of skip-level meetings is to encourage transparency, feedback, and learning that will ultimately help guide decision-making. They also create more visibility, build rapport and trust, and foster better relationships between a leader (who may be more hands-off) and front-line employees.

Benefits of skip-level meetings

Skip-level meetings are powerful for both the leader and the team. 

When done right, you’ll get more insight into the team, what's important to them, and any opportunities to improve the work environment or spark change. 

The employee walks away with a sense that you care about them, want to support them in their careers and day-to-day work, and are open to feedback (you “get it” more after the conversation).

One leader I worked with recognized through skip levels that a new organizational structure wasn’t working. They could only get this information through direct feedback from the team because the managers weren’t sure how to present the feedback, given their position in the new structure. 

Another leader I know finds skip levels to be extremely effective for hearing market feedback from team members who talk directly to clients. They’re able to ask direct follow-up questions and get their heads around the client conversations, instead of getting the feedback second-hand through managers.

Conducting a skip-level meeting

If this is the first time you’re considering holding skip-level meetings, or this is new for your organization’s culture, there are a couple of things you can try to ease people into the concept of speaking to their boss’s boss.

1. Have your manager tell the team in a team meeting that you will be holding skip-level meetings and what to expect in them. This shows they’re bought in and excited for them, and it’s not something you’re doing to exclude them or go behind their back (no “gotcha” moments).  
2. Then you can reach out to the team with an email or Slack to reinforce the goal of the meetings, the agenda, and how they tie into your company values or culture (“As you know, one of our values is about learning, so I want to learn from you and see what we can be doing differently or strengthening on our team”) and next steps (example: “I’ll be reaching out to each of you individually to set up time”).
3. Depending on your culture, and how uncomfortable or different this may feel for your team members, you may want to consider a group exercise first. Try taking the team out to lunch (perhaps virtually) to create a more casual space for open dialogue to start, then move to one-on-ones in the next cycle.

Skip-level meeting questions

For the actual conversations, it’s important that you have some leading questions but also create the space for open dialogue and let the conversation go in the direction the employee takes it!

Here are some specific questions to help guide the conversation: 

1. On a scale of 1-10, how has this month been for you? What would have made it a 10?
2. What are you most excited about right now in your role or for this team (or company)?
3. What worries you or what are you most concerned about?
4. What is a recent win that you had?
5. What is a roadblock that you’re currently facing?
6. What is going on for the team that you think I might not be aware of (or not know enough about)?
7. Do you know the company's goals?
8. What do you appreciate the most about your manager?
9. What do you wish your direct manager did differently?
10. What can I be doing differently as the leader of this department?
11. How can I help you with your career goals?
12. What other feedback did you have that we didn’t talk about / or / What question didn’t I ask that you wish I had?

In addition to these leading questions, make sure to again cover the purpose of the meeting and open with some general chit-chat to ease into the conversation (“How was your weekend?”, for example).  

Following-up

After you’ve held your conversations, make sure you do some follow-up work as well! You want to ensure the team feels heard and that you took in their feedback to make some changes (or why you didn’t implement anything new if it didn’t make sense).

The worst outcome is that you have these conversations and people think they were just for show, so close the loop!

1. Send out thank you notes after the meetings with a couple of key takeaways and action items you had from the conversation.
2. Tie any action back to those conversations. Referring to them in team meetings or when announcing changes or new initiatives, “Because of the feedback I heard during my skip-level meetings….” or “Thanks to the insight from the team…”
3. Reference any key topics when you meet with them again to continue the conversation, “Last time we spoke you mentioned X, has that improved or how is that going?”

Cadence

Depending on the size of your organization, and how fast it changes or evolves, I’d recommend a quarterly or twice-yearly cadence for skip-levels.

This is so you have the opportunity to act on any suggestions brought up, move fast on improvements, and get follow-up feedback if any changes had the impact you intended.

Be a present leader

Being a strong, present, vulnerable, and available leader has never been more important.

While employees leave managers and companies who don't care about them, they also stay at companies where they feel heard, valued, and supported. 

They stay with managers and leaders who take the time to reach out and listen and act on their feedback and make them feel heard.

Skip-level conversations are a great way to build trust, gather feedback, increase employee engagement, and retain top employees.

Some further reading:

• How to increase employee engagement
• How to go from manager to coach
• How to run effective one-on-one’s
• How to conduct a better performance review
• Best employee communication software
• Four Leadership Lessons From The Early Days Of Abebooks
• What Is Succession Planning? How To Develop Your Next Leaders

Related Podcast: The Secret Code To Exceptional Leadership (with Ian Mills from Transform Performance International)