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How to Add Skip-Level One-on-Ones to Your Management Toolbox

Michael Boufford

Michael Boufford is the VP of Engineering at Greenhouse. He was the first employee/engineer at the company and currently the head of all engineering teams including Product, Customer Solutions, Infrastructure, Automation & QA, Data Science, Security, and IT. He's a regular speaker/panelist at conferences and events including NASDAQ CTO Summit, Wharton Entrepreneurship Conference, and SiriusXM Business Radio.

The problem

As a manager of managers, it is hard to get enough visibility into your direct reports' organizations to provide specific and actionable feedback.

The solution

In my experience, the most useful forum for finding out the “why” and “how” behind what managers are doing has been via skip-level one-on-ones. I have nearly 60 engineers on my team, but I still make sure to find time to meet with each person at least once per quarter. There are a number of benefits to doing this, but in this article I'm going to focus on one angle: finding out what's going on inside of each manager's team so I can offer specific and actionable feedback on how to improve.

Remember that when you’re a manager of managers, your job is the same as it was as a first-level line manager: to make the organization that reports into you more effective through your support, decisions, and processes.

The format

To jump straight to the meat and potatoes, below are a few of the questions that I ask individual contributors during skip-level one-on-ones:

  • Do you feel like you have a clear idea of what you’re doing well and where your areas of improvement are?

  • Do you feel like you are learning? Which skills are you focused on improving?

  • Do you feel like you have a good understanding of your career next steps and what it would take to get there?

  • Do you understand where the team is headed and how what you guys are doing affects customers and the company?

  • Do you feel like you get appropriate recognition when you do a great job?

  • Do you feel like you have the training & resources to improve?

  • What do you think the rest of your team is most concerned about?

  • If you were running the team, what would be the first two or three things you would change?

A caveat...

Many of the managers of managers that I know try to take a shortcut by directly asking an employee “what do you think of your manager?” but fail to recognize the intensely uncomfortable position in which this places the employee. No one wants to be seen as undermining their manager by offering criticism to their manager’s manager. This line of questioning can make employees feel vulnerable to retaliation, and typically results in useless and sometimes apocryphal reviews. I avoid this type of unspecific question like the plague.

Each question I ask in a skip-level one-on-one is designed to provide me with answers about what type of activities are occurring (or not) within the team. When I ask a specific question such as “What professional development activities are you pursuing this quarter?” the employee either has a satisfying answer… or they don’t. If they don’t, I just learned something that I can use to help the manager ensure each person on their team is receiving the appropriate level of support. The same goes for any of the questions I ask during skip-levels.

Why this approach works

Sourcing this type of feedback directly from a manager’s team members removes much of my own subjectivity from the conversation, and provides me with actionable "inside the black box" results to work from. To some managers, having your manager talk to the people on your team might seem unnerving, but not only is this a great practice to ensure support for individual contributors, it’s also great for their managers! A common complaint among middle managers at many companies is that they don’t know where to improve. Properly leveraged skip-level one-on-ones give you exactly the type of information that you need as a leader to provide meaningful support to the managers on your team.

The result? Managers feel like they're getting better every day and the employee feels heard, yielding both higher job satisfaction and improved results for the manager and the employee. As an executive leader, you still have the power to affect the quality of management at every level of your organization—but the first step is to make sure you are gathering enough information to do so constructively.

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