Skip-level Meetings (10 Best Questions & Tips)

Skip-level meetings are normally short and infrequent, but they can hugely impact senior management and individual contributors. The purpose of these meetings is not to diminish managers in between but rather to communicate with those working across various levels of the company and discuss employees’ development, company vision, and strategy.

Before we dive into our best practices and tips, we should understand what a skip-level meeting is, why we should have it, and how managers can prepare for it.

 

First off, what is a skip-level meeting?

It’s a one-on-one session where upper managers meet and connect directly with employees, going past the employee’s direct manager in which they ‘skip’ management level. Essentially, it is to help the upper leaders better understand their team members, establish deeper trust in the company, and gain insight into work challenges faced by front-line employees. 

The purpose of skip-level meetings is rather obvious - to gain unfiltered access to information regarding what’s going on in the company, whether positive or negative. 

 

Are skip-level meetings necessary? 

There is plenty of evidence that shows the benefits of skip-level meetings. Since they are intended for senior managers to share high-level objectives and communicate with employees, they might not connect regularly. Still, it helps build stronger relationships across the company (which is so important for the health and success of the company!).

 

When these meetings are communicated accurately and conducted effectively, they can help:

• Enhance communication flow across every level of the company and reduce top-down communication

• Resolve issues and obstacles, and attain future solutions

• Offer employees the chance to voice their opinions, concerns, and feedback in a psychologically-safe environment and, most importantly, feel heard

• Support leaders in their pursuit of becoming better managers

 

How to prepare for skip-level meetings as an employer or leader?

When you set up the meeting, be sure to approach it with curiosity about how you can help build a stronger relationship between the employee and their manager and the relationship between the employee and the organization. 

During this valuable session, always try to learn how engaged your employee is and how this affects the company's effectiveness. Also, try to collect information that isn’t always readily available to managers. This brings us to the next point - be empathetic and understanding of how your employees might feel, as most would be reluctant to share too much information and be vulnerable with you. So set up the meeting in a comfortable and psychologically-safe environment from the start, get to know them genuinely, and keep the conversation open and honest. 

 

How to approach and make the most out of skip-level meetings?

Here’s an important reminder: While you’re a senior manager in the company, you’re not their direct supervisor. In other words, don’t treat this as a typical one-on-one meeting. Here are a few ways to start and conduct an effective skip-level meeting:

 

#1 Re-establish alignment

Take this opportunity to better understand whether or not the employee is aligned with the company’s goals, vision, and mission. If not, try to explain it to them and correct any misalignments that arise so that your employee knows the importance and impact of these goals. 

 

#2 Discover mentoring opportunities

Skip-level meetings are not the time to diminish or dig up dirt on your managers. Instead, it helps you understand and learn how you can help your middle managers to improve and level up as better leaders in their respective teams.

 

#3 Detect problems

As a senior manager, there is a high chance you won’t know about 75% of your employees' issues. However tempting as it may be, don’t try to solve the big problems first; instead, gain a better understanding of the problems and how many others are affected by them. If there seems to be a consistent pattern across multiple levels, spend time and effort solving the issues.  

 

#4 Listen more actively

Talk less and listen more! Since this is a rare opportunity to interact with your employees, try your best to hear their opinions, frustrations, motivations - everything. This will help you gain insight into improving employee engagement and motivation.

 

10 great skip-level meeting questions to ask as managers

• Is your job what you expected when you accepted it? If not, how has it differed?

• What career goals would you like to achieve in the next 6 to 12 months?

• Do you feel supported in your job?

• What would you suggest to improve cross-functional collaboration?

• What are your work and non-work highlights of the past month?

• What would you do differently if you were in your team's managerial role?

• If you were the company's boss, what would be the first thing you would like to change?

• What’s something you’ve achieved or are proud of this week?

• What’s something past managers have done that has inspired and motivated you?

• What’s one thing you would suggest to improve work culture?

 

As Winston Churchill puts it, "The difference between mere management and leadership is communication." 

 

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