Unlock Team Potential with Skip-Level Meetings

Jason Hall

Published On: September 24, 2020

Categories: Career, Professional Development 0

Advancing your career in leadership will eventually have you leading larger and more complex teams. Usually, the larger team will be referred to as a department, business function, or organization. Hopefully, you’ve already had great success establishing the best practice of having regular one-on-one meetings with your direct reports, but with a more complex organization, those one-on-one meetings alone might not be enough.

There are at least five common problems that can persist with a more complex organization. (I use the term “persist” here as a reminder that they are an ongoing concern.)

  1. Time for one-on-ones
  2. Erosion of trust
  3. Climbing (or falling) off the pedestal
  4. Skill inventory
  5. Grandparenting

Only one of these problems is self-explanatory, so let’s expand on each a bit.

Time for One-on-Ones

Any time I talk about one-on-one meetings, I make sure to mention that you should schedule in-depth one-on-ones with your direct reports. I make this distinction because of this first problem with complex teams. You are only one person. You have demands on time coming from multiple angles, and there simply isn’t enough time to devote the same level of personal attention you give your direct reports to every person within your department. You will generally have several or all of your direct reports leading smaller teams, and they should schedule in-depth one-on-one time with each of the employees on the team they lead.

You still need to build relationships with the individuals who make up the broader team you lead, but how do you scale little ol’ you? You still need to sleep, eat, and have something resembling life outside of work. A practice that works well for engaging regularly with folks on your team who aren’t your direct reports is the skip-level meeting.

The name implies “skipping over” a manager to speak directly with an individual contributor. It is not the best name because it implies that you should not be talking to someone. Do not let the term confuse you. In fact, call these meetings whatever you like—just do them.

Skip-level meetings should be scheduled for a shorter duration and further apart. I set mine for 15 minutes, and I do them monthly with each employee on my team. You might discover people who need a little extra or a little less along the way, and you can adjust them as needed.

The format of the skip-level meeting is like that of the one-on-one meeting. It should be friendly, open, and—most importantly—all about the individual you’re meeting with. During skip-level meetings, you will learn amazing things about the people on the team you are leading, and you will be presented with multiple opportunities to help them serve your customers and develop their careers.

The solution to the time problem is spreading the meetings out and keeping them focused. Try to get each team member thinking about what they would like to discuss ahead of time. Once you have had enough skip-level meetings with someone to build trust and remove some of the anxiety, you’ll find they look forward to them, and they’ll have plenty to discuss with you in future meetings.

If you are wondering how skip-level meetings can scale to an organization of hundreds or thousands, I’ll let you know when I get there. Rotating skip levels should work for you until your organization is around 50 people. Beyond that is outside the scope of my experience, but I’m looking forward to working that out down the road.

Erosion of Trust

This one sounds scary doesn’t it? It can be quite scary if you schedule skip levels without the necessary prep work.

Your direct reports are often leaders in development. They are proud of what their team accomplishes and often secretly very proud of being the person that led the team to those accomplishments. If you establish skip levels without discussing it with your team leaders first, you risk damaging the trust you’ve worked so hard to build with them.

Make sure you discuss with the managers you lead the reasoning behind establishing a skip-level meeting cadence. It will prevent the very human behavior of your team leaders filling in the missing parts of a story with negativity, and it is a great way to introduce this topic for a future in which your direct reports are leading a more complex organization.

Climbing (or Falling) Off the Pedestal

Once your org chart lists you with two or more levels in your downline, it is likely that you will be placed onto a pedestal by one or more people in your department. Do not confuse this with respect. I am sure you are highly respected by your team but being placed on a pedestal is different. It can be bit destructive, whereas mutual respect is highly constructive.

The problem with living on a pedestal is that you are still human, and you will make mistakes. The higher you are placed on the pedestal, the farther you fall when you get it wrong. Skip-level meetings give you the chance to be seen and known as a person. Use the time to expose innocuous vulnerabilities you might have, so the individual team members remember that although you are more experienced and likely more resilient, you experience many of the same struggles they do.

For example, my entire team knows that I struggle with managing my weight. Some of them can relate, and we often discuss that mutual struggle during our skip levels. It has little to do with what I can provide for them or the company, but it’s always a reminder that I’m a fallible person with real flaws.

At all costs, avoid getting comfortable on the pedestal. Once you decide that the pedestal is where you belong, you are one step away from disassociating with your team through arrogance. Skip levels can help keep you grounded by ensuring time for you to listen intently to what’s important to employees at the individual contributor level.

Skill Inventory

Do you truly know what skills you have available in your department? What about strengths and abilities that are often referred to as soft skills? Is someone adept at teaching others? Is someone skilled at organization and project management? Maybe you have someone with a natural talent for public speaking?

You should always be curious about your team’s skill inventory. It helps you organize in a balanced way so that people have diverse skillsets and are complementary to each other within a business function. And it lets you know where to turn to meet business needs as they arise.

A great skip-level meeting idea is to take job history from an employee’s resume and have them tell you about what they did in each instance. Ask if there is anything they loved about that work and anything they didn’t like. The account you get during your skip-level meeting will be much different than what you get from an interview due to less anxiety and nervousness. Through this discussion, you will learn all about the skills in your team’s arsenal, including the skills they did not think to list in the resume.


Grandparenting is a term I use to describe a specific behavior pattern. When a parent becomes a grandparent, there is often a dissonance between how they interact with their child versus how they interact with their grandchild. Grandparents are fun! They always take you neat places and feed you junk food. But grandparents are still parents to their children. Grandparents create a very positive and special relationship with grandchildren, but in many ways, their direct children are then taken for granted.

Grandparenting makes sense in a family environment. As a parent myself, I know I’m looking forward to not having to “be the villain” at times anymore. However, grandparenting does not always work well in an organization. In fact, in an organization, grandparenting can start to resemble favoritism. The leader (grandparent) appears to favor the individual contributors (grandchildren), and they can appear to be taking their direct reports (children) for granted. Grandparenting is not implicitly a bad thing. (I have literally said to a group of people before, “just think of me as your fun uncle.” I was not quite ready to call myself a fun grandfather, yet!) But you have become aware of this behavior and actively manage it.

Grandparenting can lead to a situation in which your direct reports feel neglected, or even abused, but those reporting to them feel elated to work with such fun and positive leadership. If you find yourself wondering, “Why do most people love everything I do, but the people right next to me are having a tough time?” you might be grandparenting too much.

Skip-level meetings provide an outlet to properly frame grandparenting. The skip level is a good time to practice grandparenting—if you are going to do it at all, do it then. Skip-level meetings are also less visible to the rest of the team due to the one-on-one format, which prevents the issue of someone mistaking a public act of endearment for favoritism.


One-on-one meetings with team members are an essential part of modern leadership practices. The skip-level meeting is a type of one-on-one designed to help you build meaningful relationships with the individual contributors in your complex organization. They help you avoid the pitfalls associated with time management, build trust with your team leads, hop off the pedestal you might have been placed on, inventory your team’s skills, and manage the impact of “grandparenting.”

You can get started with skip levels right away. Be sure to talk it over with your direct reports who are managing teams themselves and then get the meetings scheduled.

Jason has worked in technology for over 20 years. He joined SentryOne in 2006 having held positions in network administration, database administration, and software engineering. During his tenure at SentryOne, Jason has served as senior software developer and founded both Client Services and Product Management. His diverse background with relevant technologies made him the perfect choice to build out both of these functions. As SentryOne experienced explosive growth, Jason returned to lead SentryOne Client Services, where he ensures that SentryOne customers receive the best possible end to end experience in the ever-changing world of database performance and productivity.