Best Skip-level Meetings Questions to Ask Your Team and Managers

Are you a senior leader at an organization? Do you worry about improving the communication between you and your employees? Are you concerned about the performance of your managers? 

If you answered yes to those questions, you should try skip-level meetings. 

Skip-level meetings are touted for improving the communication flow among the rank and file of an organization. There is often a gap between direct reports supervised by managers and the senior leaders to whom these managers answer. Skip-level meetings are a remedy to that situation.

By having one-on-one interactions with direct reports, you can get first-hand insights into what goes on at the grassroots level of your organization. You will be able to get feedback about your managers, determine if your employees are enjoying their role, any challenges they may be facing, and generally, areas of improvement.

If you want to try skip-level meetings and you’re clueless about what kind of questions you should ask, this article was written for you. I have highlighted the best skip-level meeting questions to ask your team as a senior leader. Since skip-level meetings are a two-way interaction, I have also underlined questions that direct reports can ask senior leaders. 

Skip-level meeting questions to ask your team

Asking the right questions makes your skip-level meetings more effective. It is crucial to lay out questions that you’d like to ask your employees. Don’t wait until you call them into your office or join that zoom meeting before you think of questions. You are both taking out of your time, so aim to ensure that it’s worth it.

The questions must be purposeful and aimed at eliciting specific responses or building trust between you and the employee. You should ask questions to build rapport and trust, gain feedback, and evaluate performance.

Questions to build rapport and trust

You would agree that having a meeting with a senior leader can make an employee a little anxious. As a senior leader, it behooves you to reduce the tension in the room.    

How do you do that? By asking questions to build rapport and a level of trust. These questions should be personal and unrelated to their role and the organization. It’s a way to show the employee that you’re human too and that you’re interested in their life beyond work. 

Skip-level meetings shouldn’t be too formal. Building rapport and trust at the start of the meeting is best for setting the tone. It equally motivates the employee to communicate freely and honestly with you. This way, you can get genuine responses to your questions and not responses motivated by fear

Here are questions you can use to build rapport and trust as you kick off your meeting:

  1. Where did you go to college? Where did you grow up?
  2. What do you do outside of work?
  3. Do you have any hobbies? What do you do for fun?
  4. What motivated you to join our organization? 
  5. If they have any kids, spouses, or siblings, you can ask: How are your kids? How is your spouse? How is/are your sibling(s)?
  6. How did you spend your last vacation?
  7. What drives or motivates you?
  8. If around a festive season: Do you celebrate [name of holiday]? How did you celebrate it? How will you celebrate it?
  9. What’s your favorite song at the moment? Who’s your favorite artist?
  10. Do you read books, listen to podcasts, or watch movies? Which is your favorite?

Be careful not to get carried away and spend too much time building rapport. It’s just a precursor to the main questions about feedback and performance. Regardless, take this section seriously. Establishing personal connections with your employees is an effective team management technique.

Questions to gain feedback

Feedback is the breakfast of champions.” - Ken Blanchard, Ph.D., management expert, and best–selling author.

What’s a skip-level meeting without getting feedback on your managers and the work environment. In fact, gaining feedback is one of the primary reasons for skip-level meetings.

Because you’re somehow far from the action, it would be difficult for you to get wind of what goes on between managers and direct reports and the general perception of the work environment. Skip-level meetings come to the rescue! Below are some questions you can use to derive feedback.

  1. What’s the best part of working with your manager?
  2. What’s the hardest part of working with your manager?
  3. Do you think your manager could have handled a situation better?
  4. Which recent situation do you think your manager handled effectively?
  5. Do you feel your manager is approachable?
  6. What process(es) in our organization are you less satisfied with?
  7. What do you enjoy most about your role?
  8. What system can be implemented to improve your productivity at work?
  9. Do you ever feel not carried along by your manager or team?
  10. How can the organization improve your work/life balance?

Questions to evaluate performances

As a senior leader, you should want to know how your employees are performing individually. Who’s putting in the most effort? Which team member is underperforming? What may be the cause of this underperformance? And so on.

It shows that you’re interested in learning about how you can improve team performance. 

Here are questions you can ask:

  1. Which team member do you enjoy working with the most? Why?
  2. Do you think there is enough collaboration within your team?
  3. Do you feel your team is overworked or underworked?
  4. If you were to lead your team, what would you do differently?
  5. What’s the biggest challenge your team faces?
  6. Who are the most valuable people on your team? And why?
  7. Who do you consider a high performer in your team?
  8. What do you like most about working with your team?
  9. What can the organization do to improve your team’s efficiency?
  10. What do you think your team does really well?

With these questions, you can easily identify top performers within teams. Do well to give them the recognition and praise they deserve. As for the underperformers, discover what’s wrong and encourage them.

Skip-level meeting questions to ask your managers

You’ve been informed that you have a skip-level meeting with a senior leader at your organization. Although your leader will ask most of the questions, you don’t want to go into the meeting without having your own questions. 

Not to worry, here’s what to ask in a skip-level meeting as an employee:

  1. What’s worrying senior leadership the most right now?
  2. Are there any mentorship opportunities available for me?
  3. Where do you see this organization in the next few years?
  4. What do you wish we did better as an organization?
  5. What’s your biggest challenge as a leader?
  6. What’s your career trajectory like? How long did it take you to get to your current position?
  7. What skill do you value most in leaders? 
  8. What career advancement opportunities are available to me in this organization?
  9. What do you think about our team’s performance?
  10. When appointing leaders, what specific skill(s) or character traits do you look out for?

Having questions of your own shows that you prepared for the meeting and that you’re committed to learning. And this will leave a good impression about you on the senior leader.

Potential pitfalls of a skip-level meeting

The majority of opinion on skip-level meetings is predominantly positive. People lean towards the pros most of the time. 

But, it’s not all positive. There are potential dangers associated with skip-level meetings that are usually not in the spotlight. Let’s examine some of them. 

  1. Hidden agendas:

As a senior leader, you will be meeting with several employees across your organization. Some may be sincere and honest in their interaction with you; others may not. It may be difficult to tell who’s honest and who’s not.

It is not strange to find employees with hidden agendas make incorrect statements about their managers, teammates, and the work environment. Acting on this information can result in adverse consequences for the team or the organization. 

I would suggest that you scrutinize negative feedback gotten from employees before acting on them. You can juxtapose feedback from employees to see if there’s consistency. 

  1. Perceived favoritism:

For large organizations with many employees, it may be difficult to meet with every employee. As a result, senior leaders tend to pick and choose who to meet. This is a risky thing to do as it may give off a sense of favoritism within the organization. Employees will definitely notice, and it may escalate. 

So, make sure you meet with everyone. I know, it seems like a herculean task. But consider it the price you pay for keeping your team together. 

How can you make this possible? Shorten the time allocated to each employee. If you used to spend 30 minutes with one person, reduce it to 15 minutes to accommodate more employees. Further, reduce the frequency of the skip-level meetings. Suppose you used to meet with employees once in 2 months; you can limit it to once a quarter. That way, you wouldn’t feel too overwhelmed. 

  1. Possible misinterpretation of words:

During skip-level meetings, employees tend to share ideas with senior leaders to get their opinion. A simple “This sounds like a good idea” could be easily interpreted as an approval to implement such an idea when it’s not really the case. Instead of seeking approval from or further running it by their direct managers, some employees choose to work on the idea based on the comment of the senior leader. 

This situation is risky as managers could interpret it as the senior leaders undermining their authority; because ordinarily, managers are to give approvals to the direct reports. 

Similarly, leaders can misconstrue statements made by employees during skip-level meetings and vice versa. Therefore, it is necessary to be clear and straightforward in your conversations. Also, seek clarity when needed.

  1. Not handling feedback on managers properly:

Employees tend to share their concerns about their managers during skip-level meetings, some of which may be unsolicited. How you act on this feedback is important. Be careful not to act in a way that may heighten tension within the organization's rank and file. 

At the same time, try to do something about the concern. So that the employee wouldn’t think you don’t regard their complaint. If the concern is about a conflict that can be resolved by the manager and employee without you interrupting, direct the employee on what to do. That way, you’re respecting the authority of the manager.

However, where it requires a higher authority, please step in.