Skip-Level Meetings

Skip-level meetings are one of the critical keys to successful management at levels of remove. And yet many people skip or undervalue them. I know, I’ve been there. No one wants to add yet more meetings to their calendar, especially the type that are often without an agenda. Still, if you want to build a strong management team, understanding the people who report to those managers and maintaining a relationship with them is hard to avoid.

What is a skip-level meeting? Put briefly, it is a meeting with people who report to people who report to you. There are a few different ways that people hold these meetings, but their purpose is to help you get perspective on the health and focus of your teams. However you choose to hold them, keep this purpose in mind.

One form of skip-level meeting is a short 1-1 meeting, held perhaps once a quarter, between the head of an organization and each person in that organization. This tactic accomplishes a couple of things. It creates at least a surface-level personal relationship between you and everyone in your organization, which keeps you from viewing them as “resources” instead of human beings (something that is a risk in managing large organizations). It also gives those individuals time to ask you questions that they may not feel are worth scheduling a meeting themselves to ask. These meetings are most successful when you provide prompts about potential topics, and remind the person that the meeting is largely for his or her benefit. Each person should come prepared to focus on what he or she is interested in talking to you about.

Some suggested prompts to provide the person you are holding the skip-level 1-1 with include:

What do you like best/worst about the project you are working on?
Who on your team has been doing really well recently?
Do you have any feedback about your manager — what’s going well, what isn’t?
What changes do you think we could make to the product?
Are there any opportunities you think we might be missing?
How do you think the organization is doing overall? Anything we could be doing better/more/less?
Are there any areas of the business strategy you don’t understand?
What’s keeping you from doing your best work right now?
How happy (or not) are you working at the company?
What could we do to make working at the company more fun?

The 1-1 doesn’t scale forever. If a quarter has, say, 60 working days, and you have 60 people in your organization, doing one a quarter with each member means you have one every day, or five a week for 12 weeks. This gets worse and worse the more people there are in your organization, and at some point it doesn’t make sense — at 1,000 people you’d be doing nothing but these 1-1s, assuming you worked 40 hours a week. However, if you have a smaller organization, dedicating time every quarter to each person does have some benefits.

If you have a larger organization, or are impatient with the idea of adding more unstructured 1-1s to your schedule, there are other ways to get skip-level time. I used to hold skip-level lunches with whole teams, where I would buy lunch for the group and we would talk about whatever was going on. I tried to do these a couple of times a quarter for each team. This has many of the benefits of the 1-1 meeting, in terms of making you more familiar to the team members and vice versa. It doesn’t give you the focus to give career coaching to individuals, but it does help you get a sense of the group dynamics and get feedback directly from the teams.

Of course, people act differently in group scenarios, and when you are the Big Boss they may feel uncomfortable complaining in front of others about problems they’re having with their manager, even when this person isn’t in the room. Many of my lunches served as little more than chats about random technical matters, but I could get a sense for where the team believed their focus needed to be, and I got to answer some detailed questions about the company’s strategic focus, the work other areas were doing, or upcoming projects they were interested in hearing more details on.

In the group setting, these questions can be used to draw out information:

What can I, your manager’s manager, provide for you or your team? Anything I should be helping with?
Is this team working poorly with any other teams, from your perspective?
Are there any questions about the larger organization that I can answer?

For me, the skip-level lunches provided familiarity, which in turn generated more willingness for people to come to my office hours and cover more sensitive 1-1 topics there, whether by their request or, occasionally, by mine.

The purpose of this skip-level process, beyond maintaining trust and engagement, is to help you detect places in which you’re being “managed up” well, to the detriment of the team under that manager. Having people who manage up well in your organization is always a hard situation to detect and respond to. These individuals get to you first, so you hear their perspective before you hear anything else, and you’re predestined to think they’re in the right and to support their decisions. Skip-level meetings are a chance to hear the other side of the story, to get a reality check from the people on the ground.

At this level, you’re constantly making tradeoffs between investing in expensive engagements, such as 1-1s, that can provide deep value but cost you in time and energy, or casual engagements that are more efficient in terms of your time but provide less detailed information. You won’t get it perfectly right. There will still be times when you hear too late about a project that’s suffering, or a manager who’s failing his team, or a team member who’s causing problems for others. Invest some time in learning how to maintain these indirect relationships.

Don’t underestimate this process, even in the case where you know the skip-level reports well. There’s no guarantee that you will keep your close ties with a team just because you used to manage them directly. Managers commonly slip up here when they already have personal relationships and plenty of history working together, so they feel they don’t need to do extra work to keep in touch with those teams directly. I’ve been there and made this mistake. This philosophy sometimes works for a short period of time. But as the teams slowly change, the relationship changes. And even if the team members haven’t changed, they won’t always come to you with problems they have with their manager. Refer back to “Ask the CTO: The Fallacy of the Open-Door Policy” for the reasons why.