I have a large organization that I’m responsible for. With so many different projects and layers of management, it’s really easy for me to get out of touch with the people doing the work of building products. It’s also easy for me to be a distant, unknown figure. To partly address both of these problems, I do regular skip levels with people in my reporting chain. Right now, I have it set up to be at least a half hour twice a year with every manager and senior individual contributor. I used to do most of these in person when I visited the various offices, though it’s all via video conference right now because of COVID-19.

I have a simple, informal agenda. Half of that agenda is for me. I want to know how the person is doing, both psychologically and professionally. I want to know if they have concerns about how the organization is running and being led. I want to solicit feedback on their manager to help me better coach them. I am not there to give instructions; that would undermine both the purpose of the meeting as well as their direct manager’s role.

The other half of the agenda is for them. What changes do they want to see? What do they not understand or disagree with in how the organization is running? What questions can I answer and explain? What do they want advice on? How can I help them be successful, both in their current role but also with respect to their professional goals? I emphasize that I want to serve them in the meeting. If something is important to them to bring up with me, I will consider it important enough to discuss with them. I try to establish a safe, casual tone from the beginning, emphasizing that I am there to help them and to become a better leader.

When I have a skip level with a particular person for the first time, I explain all of this. I also assure them that I’m available beyond the regular schedule. The schedule sets a minimum, not a maximum. It’s also not the only way to communicate. I want them to email me or chat or set up another meeting if they need to, so I try to make sure the ice is broken so they feel comfortable doing that.

I’ve been doing things this way for years, though some of the logistics have changed as my organization has grown and circumstances have changed. I think it’s working. This is a difficult thing to collect data on. The desired effects are that members of the organization feel like their needs are attended to and their concerns are heard, and that I am a more effective leader. Anecdotally, I have evidence for the former. As for the latter… I can only hope.