This article is part of a series on managing managers.

When I was writing my book, I referred to “skip-level meetings” in the text. My copyeditor left me a comment: “What are these? You’ve not mentioned them elsewhere.” It seems that I’ve also previously mentioned skip-level meetings twice on this website without offering any explanation. I’m sorry about that. It seems that I’ve always assumed that people know what they are. So let’s change that.

Skip-level meetings are typically semi-frequent meetings between staff who have a layer in the org chart separating them. It’s a meeting between someone of a given depth m and another of depth m+2. In more relatable human terms, if you were a manager of managers, then a skip-level meeting might involve you having a meeting with one the individual contributors on your direct report’s team.

Don’t worry, I can hear you already: “Another article about more meetings?” Well, yes. But skip-level meetings can pay dividends for you as a manager of managers. They build trust and break down barriers. But before we get into why they’re good, explore the frequency that you should do them, and suggest some example topics of conversation, I’d like to remind you of a particular scene in my favourite television show.

These are for you, McNulty

In a previous article about workplace politics, we highlighted that in particularly old-fashioned workplaces, not going through the proper channels can be problematic. But what do I mean about the proper channels? Well, there is a particularly memorable scene in The Wire (warning: extremely strong language) where Jimmy McNulty, in his usual casually reckless way, talks to a judge about previous murder cases that he feels did not get solved properly. This results in the judge speaking to the Deputy, and then the Deputy calling the Major into his office to explain the situation that he knew nothing about. Hence all of the swearing and the punishment of all-night report writing.

The org chart – whether on purpose or not – can create the expectation of knowledge boundaries where the “proper” way of sharing information is to send it up and down the chain, as McNulty probably should have done with Rawls. However, we all know that this can be counter-productive, bureaucratic and just plain annoying. Sometimes it’s just easier to talk to the person you need to talk to, even if that person happens to be your manager’s manager. 

So why not just have that happening as a regular arrangement? That’s what skip-level meetings are about. You can, with transparency, probe deeper to build rapport, uncover issues, and help your staff grow.

Benefits

There’s a number of benefits for having a culture of skip-level meetings, and those benefits are gained at both ends of the skip-level relationship.

Here are some reasons that skip-level meetings are good for you as a manager of managers:

• They build rapport with the people in your org. Although you could manage entirely through the interface of your managers, your impact, output and availability as a leader is greatly increased by building strong relationships with those in their teams as well. 
• They show that you’re just another human. Sometimes people higher up in the org chart become shrouded in mystery: an important person with a fancy job title that they people aren’t allowed to talk to. However, that’s entirely false. You’re there for them as they fundamentally work for you, so you can show them that you’ve got their back and are open to talk.
• They give you additional insight into how your teams are doing. You don’t have to wait for performance reviews in order to gather a picture of how your teams are doing. By regularly speaking to the staff on those teams, you can build a better picture of how that team functions by looking at it from above and below.
• You get additional insight into how your direct report is performing. Related to the above, you can gently probe into how they feel about their peers and their manager and whether they and their team are getting the support that they need to succeed.
• They demonstrate that you value everyone, regardless of their position in the org chart. By making your time – your most precious commodity – available to more people, you show them that you truly value them. You also show that you don’t entertain politics, where information must always filter through the chain of people in the org chart.

There’s also plenty of benefits for the other member of staff:

• They open the door for fairness and transparency. By knowing that their manager’s manager has time for them, they know that their performance and path at the company isn’t only viewed through the lens of their own manager. 
• They get an insight into what’s going on in other parts of the department and company. Being a couple of levels higher in the org chart, you’ll have access to interesting operational or strategic information about what’s going on in other teams, forming the bigger picture that they’re part of. 
• They get a direct line to give feedback, raise concerns and suggest ideas. Maybe they’ve got suggestions about people, processes, product and tooling ideas that are beyond the scope of their manager to solve. However, you might be just the right person to pick these up and look into them.
• They demystify what goes on at a leadership level. They get the opportunity to lift the lid on what happens higher up the org chart by talking to you about what you spend your time on and what’s important. This not only builds rapport, but it gives them an insight into what the management track might hold for them in the future.
• They allow opportunities for more connections. You may know many more people in the department, so you could make a mentor or mentee connection across different teams, or introduce them to someone that has been working on similar problems before.

So, hopefully I’ve convinced you that they’re a good idea. Now we should think about the practicalities of doing them.

How often should you hold them?

If you have many teams reporting into you, then that’s potentially a lot of people in order to arrange skip-level meetings with. If you’re already having weekly one-to-ones with your direct reports, then you could imagine your calendar becoming even more of a mess than it is already.

A way of tackling this conundrum is to list all of the people that are a skip-level away from you and then bucket them into different meeting intervals depending on the relationship that you want to form with them. I don’t recommend having skip-level meetings weekly, since you’ve already got your direct reports to meet with at that frequency. 

However, you can consider the following intervals:

• Fortnightly: A very small percentage of staff should be in this category. Perhaps you have a few superstars that you see growing quickly, or individuals who are at the core of an important initiative for the department that you wish to lend more support to.
• Monthly: This is a good “normal” cadence. 30 minutes once a month is a good amount of time to check in, catch up and discover what has been going on. Of course, you can always have follow up meetings if anything particularly interesting or worrying arises.
• Quarterly: Some individuals are less chatty, or may not particularly need or want your time (and you’ll know who these people are based on your initial conversations). Checking in once a quarter makes the arrangement more easy going, and enough time passes since you’ve last met for some topics of conversation to arise.
• Occasionally and/or on request: And of course, there may be members of your staff that prefer to have as few meetings as possible and may not get huge value from the relationship, and that’s perfectly fine. You can forgo a planned schedule and just let them grab you when they need you, or vice versa.

The intervals that will suit various members of staff with ebb and flow with time, so don’t be afraid to switch it up depending on which projects you have running, or whether particular staff are going through a period of career growth or a difficult time. Be flexible and offer your support where needed, and work with your direct reports to get this information.

Getting them started

So, get those skip-level meetings kicked off. Before you start causing panic by booking in meetings without any context, perhaps you could send out something like this, after having let your direct report managers know that you’re going to do it.

Hey everyone,

I’m going to start doing skip-level meetings. There’s no bad reason for doing this, in fact, it’s very much for good reasons: I want to get to know you all better, understand what you’re working on more clearly, and – where I can – help you succeed.

What this means is that I’ll be booking in some semi-regular catch-ups where we can have a chat about whatever you want. It can be as formal or as informal as you like. 

Perhaps we could talk about what you’re working on and what I’m working on, or what’s coming up in the future for our teams. We could touch on your career progression, or discuss any concerns that you have about your role or the company.

Your manager knows that this is going to be happening, so don’t worry about that. Also, if you’d rather not do it because you feel you have enough meetings already, then that’s totally fine! Just let me know. But do know that you can come and chat to me at any time.

Best,

A. Manager

This message is written from the viewpoint of a manager getting them underway. But what if you’re an IC and are interested in getting this kicked off?

I’d suggest you start small: speak to your manager about whether you can set up skip-level meetings with their manager. If they’re unsure as to why, then why not just direct them to this article? 

And if you’ve been directed to this article because someone would like to do skip-level meetings with you or your manager, what are you waiting for? Trust me, it’s worth it. Go on.