· 9 mins · Productive Meetings

4 skip-level meeting questions (and tips to fuel your next meeting!)

Skip-level meetings are a goldmine for employee feedback. Here are four skip-level meeting questions to add to your agenda.

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Skip-level meetings are often short and infrequent, but pack a punch in terms of impact on both senior management and individual contributors. These meetings aren’t meant to undermine managers in between, but rather to connect those working across multiple levels of the organization to discuss an employee’s growth, company strategy, and share feedback.

Before we get to our skip-level meeting agenda template, here are a few things you might be wondering about, including:

You can also jump to the skip-level meeting template.

Let’s get started!

What is a skip-level meeting?

A skip-level meeting is a one-on-one meeting where upper managers meet directly with employees, bypassing the employee’s direct manager, essentially “skipping” a level of management to connect directly with employees. (Get it? 😏)

The goal of a skip-level meeting is twofold:

  • For employees to gain insight into company goals, objectives, and strategies.
  • For senior leaders to create a shared space for employees to discuss career progression, professional goals and give feedback.

Who is responsible for the skip-level meeting agenda? 

The best skip-level meetings happen when both employees and senior leaders contribute to a shared agenda. And in terms of timing, most skip-level meetings are 30 to 45 minutes on a bi-monthly or monthly basis. While the meetings might be shorter than a typical one-on-one, the impact is tremendous (when done well).

Are skip-level meetings bad?

When done properly, no, they’re actually great. As mentioned, skip-level meetings are not a time to get feedback from employees on their direct managers. That kind of feedback should be brought up between the direct report and manager directly.

Skip-level meetings are intended for senior leaders to share high-level strategy and connect with employees they might not connect with regularly otherwise. It’s an opportunity for senior leaders to build better relationships and connections across the organization. Fabian Camargo, Engineering Management Coach puts it best:

When done well, skip-level meetings can: 

  • Improve the communication flow across all levels of the organization
  • Support managers in their pursuit to be better leaders
  • Build better skip-level relationships, making senior leaders less “scary” and more approachable to employees
  • Provide companies with more ways to exchange feedback across the organization
  • Give employees the opportunity to share their ideas, thoughts, and feedback in a psychologically safe environment, and ultimately feel heard

How to prepare for a skip-level meeting as an employee

One of the objectives of this meeting is to improve alignment across the organization. Camargo shares that:

“Skip-levels can be helpful to make sure the messages are consistent between the employee, manager, and the skip-level manager.” 

Fabian Camargo, Engineering Management Coach

This meeting is also a means for reducing top-down communication within an organization, giving employees ample opportunity to voice concerns, ideas, and anything else that’s top of mind. After all, when did a game of broken telephone end with the same initial message successfully? Never.

Preparation tips for employees

If you’re in the employee seat during a skip-level meeting, here are some ways in which you can prepare:

  • Change your mindset. Treat this meeting as an opportunity to learn more about how senior leadership is thinking about and approaching org-wide objectives.
  • Don’t be afraid. While the person you’re meeting with is more senior within your company, it doesn’t mean they’re not there to help and provide anything from clarity to guidance and support.
  • Seek alignment. Leading up to the meeting, think about ways in which you can better understand the business priorities of your skip-level manager. Use this time to share your priorities as well and see how both can better align. This is also a great time to align on expectations that you have of the company and vice versa.
  • Use your time wisely. This is the chance for prized time with a leader you otherwise might not have access to. Use this as an opportunity to learn and prepare by reflecting on your journey at the company and what you want your future with the business to look like.
  • Prepare questions and talking points. If you want this meeting to be effective, it’s important that you show up prepared, be it adding your questions in advance or truly understanding what you’re hoping to get out of the meeting and communicate that with your leader. (A one-on-one meeting software like Hypercontext, is a great tool to help).

Speaking to the last point, if you’re not sure what questions to ask, you can pick from our list!

Questions to ask your boss’s boss during a skip-level meeting

  • What mentorship opportunities are there available for me?
  • What skills do you think our team is lacking?
  • How can I help train and support others in the company?
  • Who in the company do you think I can learn the most from?
  • How are we progressing on our goals as a company?
  • What big changes are coming down the pipe in the next 6 months?
  • What’s something you wish we did better as a team?
  • What are we doing to make ourselves stand out in the market?
  • What’s worrying senior leadership right now?
  • How can I get more involved in workplace culture?
  • Are there any aspects of our culture you wish you could change?
  • What’s worrying you most?
  • What’s your biggest challenge as a people leader?
  • What would it look like for our team to knock it out of the park?

Want more? Check out these 121 one-on-one questions!

How can leaders prepare for skip-level meetings?

Approach this meeting with a curiosity around how you can help strengthen the relationship between the employee and their manager, as well as the relationship between the employee and the company.

This is your opportunity to gather useful information on how things are going, straight from the front-line. During this time, do your best to learn how engaged your employees are, and how this is impacting effectiveness – in other words, get the information that isn’t always readily accessible to leaders.

Be thoughtful around how employees might feel, and aware that he/she might have difficulty sharing opinions and being vulnerable with you. It’s your job to make sure you foster that environment both by setting the pretext for your one-on-one before and during your meeting.

How to approach this meeting

One thing to remind yourself is that, while you’re a leader within the organization, you’re not their direct manager. Don’t treat this as a typical one-on-one meeting. Instead, here are some other ways you can approach this meeting:

  • Seek alignment. Use this time to better understand whether or not employees are aligned to the company goals in the ways you need them to be. Do they understand the importance and impact of each goal? Use this opportunity to correct any misalignments that pop up.
  • Discover coaching opportunities. While this is not a time to dig up dirt on your managers, it is still a great opportunity to learn about different areas in which you can level up and coach middle managers who report into you.
  • Uncover blockers and pain points. As a senior leader, you likely won’t know about 75% of the problems your employees face. From lack of resources to misalignment within the team. Don’t use this time to try and solve the big issues, but rather gain a deep understanding of the issues and how many people are affected by them. If there’s a consistent pattern across multiple employees, spend the necessary time needed to fix the problems.
  • Talk less. Listen more. This is a great opportunity to gather feedback from individuals who you don’t interact with on a day-to-day basis. Use this time to listen to their goals, problems, frustrations, motivations, all of it. This will help you better understand how to keep your workforce engaged.

Skip-level meeting questions for managers

  • What professional goals would you like to accomplish in the next 6 to 12 months, and what makes you say that?
  • Do you feel supported?
  • Is your job what you expected when you accepted it? If not, where has it differed?
  • What are your work and non-work highlights of the past month?
  • What’s a big, audacious goal that you’d like to achieve this quarter?
  • If you were managing the team, what would you do differently?
  • How could we improve cross-functional collaboration at [your company]?
  • If you were the CEO, what’s the first thing you’d change?
  • What’s something you’re proud of that happened this week? This month?
  • What’s something past managers have done that’s inspired and motivated you?
  • What’s one thing you would recommend to improve our workplace culture?

💰 Bonus skip-level meeting questions 💰

  • What is everyone around me neglecting to share with me?
  • What’s one thing we could do as a company that would impact your personal life?
  • What’s one thing we can do to improve the performance of the team?
  • Who is one person in the company that you’d like to learn more from?
  • Who deserves a shout-out?
  • Is there anything that would be productive for me to re-explain to your team?
  • How do you feel about the balance between your individual work vs. managing?
  • Do you have any questions that, if answered, would help you in your day-to-day?

Skip-level meeting agenda template

If you’re struggling to add questions to the agenda, use these four essential agenda items to fuel your conversations:

  • What are you LEAST clear about – in terms of our strategy and goals?
  • What professional goals would you like to accomplish in the next six to 12 months, and what makes you say that?
  • Are you happy in your role? What could make it better for you?
  • What’s one thing we should start, stop and continue doing as a company
Skip level agenda template

Run your skip-level meetings in Hypercontext

What you should do now

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