The Skip-level 1-1

Photo by  Gabriel Sollmann

When I was promoted to Engineering Director, I had no idea what I was doing. It was a role that I had little to no prior experience with, and it took me the better part of 18 months to figure out how to be effective in it. I characterize my performance during that time as being just useful enough to not get fired.

One of the things that helped me ride out those tumultuous times was skip-level 1-1s. Skip-level 1-1s are meetings with folks who are at least two levels away from you. For example, if your direct report is a manager, a skip-level 1-1 would be meeting with your direct report’s reports. As it turned out, skip-level 1-1s became an invaluable tool—one of the things that I feel like I actually got right during my tenure as a senior leader. Among the many benefits, skip-level 1-1s helped me build a stronger relationship with my organization, understand of how my managers were performing, and gain first hand accounts of how my decisions were affecting the people in my organization. So, I thought I’d share a few tips I’ve picked up on how to get started and operate them.

Getting Started

There are two key boxes to check before you embark on skip-level 1-1s. The first is to let your managers know. It’s really important to respect your manager’s sphere of influence. So, before you start meeting with their reports, be sure to give them a heads up. Think of it as knocking before entering. Remember that one of your jobs now is to help your manager be successful. In order to do that, you need to maintain the trust relationship with your direct report.  

The second is to let your entire team know. Receiving an unexpected meeting invite from a Director can produce anxiety. You may not feel important, but that doesn’t mean folks don’t view you as such. So, before you actually start scheduling, find a way to communicate to your entire team that you’re starting a new practice and to expect a meeting invite. Be clear about your intent. I framed my 1-1s as time for engineers to share with me how things were going, what was worrying them, and how we could get better together.  You can put this message in the meeting invite as well so folks don’t forget over time.

Building Trust

Like any 1-1, building trust and safety is paramount to getting value out of these meetings. If you have an opening script for 1-1s with your direct reports, it’s a good idea to give that same script in your first skip-level with someone. This is especially important when taking on a new team. Establish rules of confidentiality. Reiterate the purpose of the meeting. Be a great active listener. For most folks, just knowing that a senior leader is willing to spend the time to listen to their concerns will go a long way.

If you are aware of a recent achievement of this person, congratulate them. If they’ve done something you appreciate, tell them. Acknowledgement is a powerful tool and highlighting positive behaviors is an effective way to encourage more of it.

Conversely, if you find yourself getting negative feedback in this skip-level meeting or disagreement about your decisions, do not get defensive about it. Stay curious and try to get as much understanding as you can from their perspective. The fact is that this person will not have any influence over your decision making authority. Also, there may be enough degrees of opacity that they might not even know you’re the one behind their woes. These are the best types of insights because they will be completely honest. Cherish these glimpses. If you have talking points or context that might repair their misunderstandings, now is the time to deploying them.

Because you probably won’t be meeting with these folks as often as you meet with your direct reports, it might take longer to build a productive relationship. That’s ok. You’re playing a long game here, so don’t get discouraged if these are a little awkward at the start. Remember, the person you’re meeting with may not have ever had a meeting with their boss’s boss before.

Getting Value

Like all 1-1s, some of them will go great and some of them will not. Investing in a bit of preparation can help the both of you get more value out of the meeting. Having an agenda really helps. My skip-levels were usually 25 minutes long of which I primarily let the other person steer for the first 20 minutes, and I reserved the last five minutes to cascade talking points, clarify rumors, and gather data around things I was curious about. Things like: What did you like about the last engineering all-hands? What’s holding your team back right now? Where do you feel uncertain about the company direction?

If you want to take it to the next level, find a way to send those prompts ahead of time so your engineers can prepare. You can do this by placing those questions in the calendar invite, using a shared doc, or whatever other communication channels you employ.

Skip-levels will also give you data with which to practice sponsorship. Because you’re getting face time with your people, you will have a deeper familiarity with their work, interests, and ambitions. And, when stretch assignments or opportunities arise, you will have more information with which to make decisions and influence outcomes.

And, finally, the data you collect in your skip-levels will help you figure out what you and your managers need to work on. Is your management team communicating important company information? Do their teams understand why their work is important? Is your manager building a healthy team environment? Are they avoiding difficult conversations? You will find all sorts of interesting information that will reflect on your manager and yourself in these meetings.


Inevitably, you will hear someone’s struggles and will want to do something. One of the primary rules to abide by in skip level 1-1s is do not preempt your manager. The ability to affect outcomes through your managers is a difficult and vital skill to learn as a senior leader. Skip-level 1-1s will definitely test your discipline in this regard. If engineers learn they can short circuit their manager by taking their issues directly to you, that’s a breeding ground for terribleness for everyone involved. If you find yourself compelled to do something, be very clear with that person about what level of involvement they should expect from you.

I usually try to help folks advocate for themselves by coaching them on how to effectively communicate the issue to their manager. Afterward, you might want to give your manager a heads up that their report is going to be approaching them about an issue. In general, have faith in the management chain and respect the confidentiality of 1-1s. These issues will either become larger problems for your manager or they won’t. But, it’s mostly for your manager to deal with, and most often they are the ones who need to make the decision on whether to live with the problem or solve it.

If you are going to get truly involved beyond coaching and nudging, it’s important to make a commitment to gathering all the data and information you need to make fair decisions. Remember: up until this point you have only heard one side of the story. And I highly recommend that you proceed with caution.


One of the difficulties of managing and leading a large and growing organization is maintaining your humanity. When you get to a team size of 60, 70, or 80, people start to look more like pieces on a board rather than humans. You find yourself wanting to spend more time alone, away from people. And, while that might make your job feel easier, I think we have an obligation to never lose touch with the human cost of our decisions. Over the years, I gained a lot of insights from my skip-level 1-1s that helped me make better choices, but, more importantly, in the end skip-level 1-1s kept me connected to my organization in ways that made me a better, more human leader.

ManagementJason Wong