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31 Questions Every Manager Should Ask in a Skip-Level Meeting
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31 Questions Every Manager Should Ask in a Skip-Level Meeting

November 5, 2020
Rob Lennon
Customer Education Lead at Hugo
Marketer and author with experience spanning a diverse 16 years in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

What makes a good skip-level meeting question depends on what you’re trying to learn.

Do you want to find areas where your managers can improve? Do you need insight into how the team is working together? 

Maybe you want to find out who deserves recognition... Or you’re just looking for common ground to build rapport with your junior employees. 

In any case, achieving the objective of your skip-level meeting requires the right question. So in the following paragraphs, I'll outline questions (along with explanations) categorized by your skip-level objective.

Questions to Build Rapport before Diving In

As I explained in this guide on skip-level meetings, leaders must build rapport with junior employees to have an effective meeting. 

After all, sharing ideas and discussing your manager’s performance with their boss can be nerve-wracking. Building rapport helps establish trust which leads to more useful feedback.

The following is a list of questions you can use to get to know junior employees:

  1. What motivates you to do your job?
  2. Where did you go to college? (OR) Where did you grow up?
  3. What’s the best book, podcast, or movie you’ve recently read, listened to or watched?
  4. (If they have children) How is (name of child) doing?
  5. What do you like to do when you’re not working?
  6. Do you have any trips planned? (OR) Have you been on any trips lately?

The key here is to get them talking and to have fun. If you can find common ground, such as a shared interest, hometown, or college, the rest of the conversation will be much easier. But simply showing interest in people tends to yield better results, even if it’s awkward at first.

Questions to Inform Manager and Team Feedback

As important as building rapport is, your skip-level meetings should be mostly about how you and your team can do better. Scott Boulton, a Human Resources Manager recommends discussing the following questions

  1. What works well in the department right now? (i.e. systems, processes, technology, feedback, etc.)
  2. What needs improvement and/or what obstacles are preventing you from being successful? (i.e. technology, top-level support, more feedback, etc.)
  3. What is one thing, as a department, we need to start doing right away to be more successful?
  4. What is one thing, as a department, we need to stop doing right away to be more successful?
  5. What is one thing, as a department, we need to make sure we continue to do in order to be successful?
  6. What do you need more or less of from your manager or myself in order to be successful as a department and in your role?

As you may notice, all of Boulton’s questions are specific and they require elaboration, not “yes” or “no” answers. In a Harvard Business Review article, Carolyn O’Hara also underscores the importance of being specific and avoiding yes/no questions when soliciting feedback.

For example, she advises against asking general questions like, “Do you have any feedback for me?” Instead, she recommends asking specific questions such as:

  1. What’s one thing your manager or I could improve on?
  2. What’s one thing your manager or I could have done to make that meeting, presentation, or project go better?
  3. How did [name of project] go from your perspective?
  4. What do you think your manager or I could’ve done differently on [name of project]?

Michael Brown, Regional General Manager at Uber also offers the following ideas for questions to ask in skip-level meetings:

  1. What is the morale in the office from your point of view?
  2. How are you feeling about your team?
  3. What obstacles are you facing in your job?
  4. Do you understand the company’s goals and how your team’s goals fit into that picture?
  5. Do you feel like you can do things you believe are right for the business?
  6. Do you think leadership acts consistently with your values?
  7. What would make work better for you?
  8. When was the last time you took a vacation?
  9. What is your sacred space? Do you feel like you have time for it?

Questions to Identify Top-Performers

Praise is a proven and affordable way to improve employee engagement, but how do you know who to praise as a senior leader? 

The Lighthouse blog explains that you can find hidden stars by asking the right questions. Here are a few they recommend using to find out who deserves praise:

  1. Who do you enjoy working with most on your team? Why them?
  2. Who has done awesome work lately? How did they contribute?
  3. Who is an unsung hero in our company? What do they do that deserves recognition?
  4. What is the greatest strength of your team? Who personifies that best?
  5. Who on your team makes those around them better? How do they do it?
  6. If you were forming a new team, who are the people you’d most want on your team? Why them?

As a leader, being at least one organizational level removed from the front lines makes it hard to know who your stars are. These questions help you uncover the unsung heroes you’ll want to invest in.

Start Asking Your Own Skip-Level Meeting Questions

As the leader, you’ll be asking most of the questions. But don’t be afraid to relinquish some control so junior-level employees can provide their perspective on what they think is important. 

And don’t feel as if you must ask a completely canned list of questions. Though a partially uniform set of questions can help highlight patterns, some answers may require deeper exploration than others. So keep your mind open and start uncovering your manager’s blind spots at your next skip-level meeting.


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Rob Lennon
Customer Education Lead at Hugo
Marketer and author with experience spanning a diverse 16 years in retail and SaaS startups across healthcare, mar-tech, and ad-tech, and productivity software sectors.

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