What Are Good Questions for Skip-Level Meetings?

What Are Good Questions for Skip-Level Meetings?

To ensure productive and meaningful skip-level meetings, we’ve gathered insights from top executives and founders on the most effective questions to ask. From inquiring about company culture change to understanding current work and collaboration, explore these nine valuable questions shared by CEOs, COOs, and other business leaders.

  • Inquire About Company Culture Change
  • Enhance Team Chemistry With Feedback
  • Improve Cross-Functional Collaboration
  • Address Challenges Affecting Performance
  • Discuss Upcoming Quarter Changes
  • Eliminate Outdated Metrics
  • Engage in Problem-Solving With the Manager
  • Evaluate Team Progress and Improvement
  • Understand Current Work and Collaborate

Inquire About Company Culture Change

Skip-level meetings are a great way to get an insight into the day-to-day operations of the company. One question you can ask is, “What one thing would you like to see changed in our company culture?” This is a great way to get feedback on how things are going and what can be improved. It also gives employees a chance to voice their opinions and feel heard.

As leaders, we’re often so focused on the big picture that we forget the minor details that can make or break our company culture. So when you’re at a skip-level meeting and there’s a pause in the conversation, ask this question and see what responses you get.

You might hear something as simple as “We need more snacks in the break room.” However, it could also be something more complex like “We need to put a stop to gossiping in the office.”

Whatever the response is, it will give you great insight into how your team feels about their work environment, and it will help you take action to make positive changes.

Luciano ColosLuciano Colos
Founder and CEO, PitchGrade

Enhance Team Chemistry With Feedback

This question seeks feedback directly from the employees on what they feel is necessary to help them enhance team chemistry and be more valuable to their colleagues and overall company success. Asking it gives you an idea of what can be implemented to make communication more streamlined and enhance teamwork while creating a reliable feedback loop.

Liam LiuLiam Liu
Co-founder and CMO, ParcelPanel

Improve Cross-Functional Collaboration

One good question to ask at a skip-level meeting is, “What can we do to improve communication and collaboration between our team and other teams in the company?” This question can help identify areas of improvement in cross-functional collaboration and also show senior leaders that you are invested in improving the overall effectiveness of the organization.

It can help identify potential issues before they become bigger problems and ultimately lead to better outcomes for the team and the company.

Brenton ThomasBrenton Thomas
CEO, Twibi Digital Marketing Agency

Address Challenges Affecting Performance

One question that will prompt employees to be honest with leaders is:

“What are some challenges that keep you from doing your job to the best of your ability?”

Asking this question is a great way to gain insight into what isn’t working and can inform changes that could be made at a higher level to help employees.

Kelli AndersonKelli Anderson
Career Coach, Resume Seed

Discuss Upcoming Quarter Changes

“Are there any major changes coming in the upcoming quarter?” is one excellent question for a skip-level meeting. Skip-level meetings are the ideal transparent environment to get straight answers about the future and stay up to date. Asking this question will show forward thinking and focus on what is ahead, too.

Alexandre RobicquetAlexandre Robicquet
Co-founder and CEO, Crossing Minds

Eliminate Outdated Metrics

I like to ask people to list one metric that we should stop using. As we all know, what gets measured gets managed. The problem is that sometimes we manage based on useless metrics.

Many of these worked their way into the system for a good reason in the past. The problem is that they’ve outlived their usefulness. I’ve found that employees are happy to point out old metrics that they should no longer be evaluated against.

Temmo KinoshitaTemmo Kinoshita
Co-founder, Lindenwood Marketing

Engage in Problem-Solving With the Manager

In a typical organization, the skip-level manager is the person likely to have the most influence on where you are promoted next. Depending on the org structure, while your immediate manager will provide the feedback for your promotion, the skip-level is much more likely to know “where” you will be promoted to.

As a result, this manager will know where things are not going well or things are under-invested in the department. Ask the skip-level manager about this. Ask about the problems they are having. It will show you are interested in solving those problems with them.

Trevor EwenTrevor Ewen
COO, QBench

Evaluate Team Progress and Improvement

This is a great question to ask at a skip-level meeting because it allows managers to give feedback on how they would like the team to progress and what areas could use improvement.

It also gives employees an opportunity to provide their input and highlight any areas they may need additional support or resources. Overall, it helps to create a more open and communicative environment and promotes collaboration.

Scott OrnScott Orn
Chief Operating Officer, Kruze Consulting

Understand Current Work and Collaborate

When attending a skip-level meeting with employees outside of your direct team, it’s difficult to know what to discuss. However, asking “What are you working on right now?” is a powerful question that can help you gain valuable insights into the work being done in the company at various levels.

This question fosters open communication and collaboration while helping you build a better understanding of each team member’s strengths, weaknesses, and contributions to the larger organization. By asking this question, you may uncover common challenges that can be addressed, potential areas for improvement in workflow and process, and opportunities for greater cross-functional collaboration.

Basana SahaBasana Saha
Founder, KidsCareIdeas

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