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Best Questions To Ask Your Boss’s Boss During a Skip Level Meeting

In this article, we’ll be demonstrating the importance of this meeting format, explaining the benefits your business can expect from running quarterly skip-level meetings.

The Hugo Team
The Hugo Team
The team transforming meeting productivity
Best Questions To Ask Your Boss’s Boss During a Skip Level Meeting

The majority of workers will have to face a range of different meetings in their typical week. From team meetings on a Monday to ensure everyone knows what they’re doing that week to one-on-one feedback sessions with a manager - 37% of employee time is spent in meetings.

One less typical format of meeting is the skip-level, which represents a shift in an employee’s traditional schedule. Within these meetings, employees will have the opportunity to chat with senior management, skipping over their own senior managers in order to chat to their manager’s manager. 

In this article, we’ll be demonstrating the importance of this meeting format, explaining the benefits your business can expect from running quarterly skip-level meetings. 

In this article, we’ll be walking you through the following topics:


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What is a skip level meeting?

A skip-level meeting is a slight alteration of manager-employee one-on-one meetings. Instead of talking to any senior leaders in your team, you’ll be skipping one level of leadership and talking directly to your manager’s manager. 

Depending on where you’re located in the company, this can have you talking to anyone from a supervisor to a regional department leader, or even a CEO or co-founder.

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Are Skip-Level Meetings bad?

The central idea behind skip-level meetings is to create more effective lines of communication across your business. There is nothing bad about them, when run correctly.

Instead of compartmentalizing people down into individual teams, skip-level meetings ensure that there are more fluid communication paths across the company. 

While upper management can seem like a shadowy set of figures that are off doing something supposedly important, a skip-level meeting gives a team member the opportunity to become more familiar with the people they work for. Additionally, these meetings work inversely,y allowing senior leaders to become familiar with all the different members of teams they are inadvertently leading.

There are several positive reasons for hosting skip-level meetings:

  • Healthy Relationships - Lower-level employees can often feel like they're not an important part of the team. By giving them the opportunity to make their voice heard with skip-level meetings, they’ll be more engaged at work and have a much healthier relationship with the company as a whole.
  • Career Guidance - When talking to your boss’s boss, if you’re going to stick around in that company for a while, then your main goal is most likely to move up the ladder. Who better to give guidance and advice on doing this than someone who’s already reached a higher point than you have. The insight that team members can gain from skip-level meetings is invaluable. 
  • Foster Transparency - Communication between levels ensures that everyone has a better understanding of exactly how the company runs. Opening these lines of communication that are traditionally closed ensures that a team gets more information about the organization that they exist within and how it works. 
  • Receive Feedback - Skip-level meetings also provide an opportunity to give feedback about your manager to a higher level, helping everyone to get a clearer picture of how things feel for the team that someone is leading.

Everyone deserves recognition and an opportunity to feel supported in their role. Skip-level meetings are the perfect opportunity for everyone to feel connected within an organization, fostering a much healthier working culture. 

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Who normally participates in a skip-level meeting?

Depending on the organization itself, a skip-level meeting could technically include every single employee, right from new trainees up to the CEO. While skip-levels do normally favor people moving upwards, they also provide CEOs and other leading positions the opportunity to refine their management and leadership skills and get feedback on middle-management.

If one of your company goals is to improve your organization’s culture, then you should try and get as many people as possible involved in your next set of skip-level meetings.

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How To Run Effective Skip Level Meetings

Although there is a range of useful benefits to these meetings, they also take a great deal of preparation to set up. Typically, skip level meetings happen once every one or two quarters, just due to the sheer volumes of meetings that need to be set up.

Here are two central tips for setting up flawless skip-level meetings:

  • Establish the Reason
  • Plan Ahead

Let’s break these down further.


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Establish the Reason

Skip-level meetings can be conducted in one of two ways, each benefiting one party more than the other.

  • Format One, favoring upper management - These meetings are mainly to find out how middle-level management is handling their teams. Within these meetings, everyone is given a full promise of anonymity and therefore is much more likely to speak their minds. If you want honest insight into how certain managers are performing, then you should make this the purpose of the skip-level meeting, ensuring anonymity and allowing people to share their honest thoughts about the employee’s direct manager. Be sure that these types don’t turn into a witch hunt, keeping honesty and problem-solving at the center of your meetings.
  • Format Two, favoring the team - These are directly structured to allow a team member to discuss their job and career with their manager’s manager. This form of meeting doesn’t necessarily have to be anonymous as it is less about feedback and more about future planning. These meetings will help with employee engagement, boost their clarity about how to move up the company, and aid with team structure.

When deciding on which format of skip-level meetings you want to use, you should first consider what the company’s goals are when hosting these forums. If you’re looking to create a more positive and productive work culture, then the second is more apt. Yet, if you want to find out about how a certain senior manager is performing and gather feedback, then the first format is more in line with the company’s vision.

Be sure to establish the reason for the meeting before sending out invites. This also goes another one-on-one meeting that you host, ensuring everyone has access to an agenda. If you’ve not run a one-on-one before, then take a look at this template by Hugo.


Plan Ahead

One of the easiest ways to make sure that the skip-level meetings that you plan out are effectively conducted is to plan ahead. There are a lot of moving parts to these meetings, including the time, date, and location that they are going to be held.

A method of getting around the difficulties associated with the logistical puzzle that is a skip-level meeting is to shift them online. The world has quickly become familiar with online meetings, and this particular forum is perfect for this new format. By using a tool like Hugo, you’ll be able to schedule meetings that are directly synced with everyone’s work calendars.

Additionally, within those meeting invites, you’re able to attach a skip-level meeting agenda that makes sure all the attendees know exactly what’s going to occur in the meeting. By using an online meeting tool, you’ll also avoid the hassle of booking out meeting rooms and ensuring that everyone can physically get to their meetings.

In order to host the best skip-level meeting possible, remove any of the barriers you can - that includes location.

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Skip-level meeting questions to ask a senior leader

Let’s cover some rapid-fire questions that you can ask your boss’s boss during your one on one meeting. Remember to write the skip-level meeting questions that you like down on the skip-level meeting agenda before the meeting occurs, so everyone has enough time to prepare.

Take a look at this sample agenda for a formal meeting:




While some skip level managers like to focus on questions around their personal life, we wouldn’t directly recommend this. While knowing what their dream vacation is or what they do in their free time can build rapport, it doesn’t always good ideas to flow. Especially when looking for more feedback or a direct report about progress, these questions should be avoided.

  • What did you study in college?
  • Where did you grow up?
  • What was your career path to getting to this point?
  • How do you think the company is going to change in the next 5 years?
  • What do you think are the most important skills that I can develop if I want to succeed in this environment?
  • Do you think the company is inefficient in a certain area? If so, why?
  • What kind of manager feedback do you think could most help my boss?
  • Do you have any feedback on the {last project} our team finished?
  • Have you noticed any difference between out team’s goals and other teams?
  • How long have you been in this profession?
  • How do you go about giving team feedback?
  • How best do you think I can win over team support when proposing a project.
  • What skills of your own do you value the most?
  • What’s the difference between your current position and my upper manager?
  • What is the biggest challenge in your position?

These skip-level meeting questions will ensure that you can touch on the company’s direction, your own career development, and how to forge better leaders in the future. With a wide range of skip-level meeting questions, you’ll be able to hone your idea of what your team needs by talking with your boss’s manager directly. 

When working with direct reports between an employee and a skip-level manager, you allow individual contributors to make their voice heard, giving front line employees more time with managers two steps above them.

No matter if you choose some of the above questions or make your own, making sure you’re ready for the meeting is key. Be sure to prepare for a skip-level meeting ahead of time, getting your talking points in order to ensure that your meeting goes as smoothly as possible.

Final Thoughts

Skip Level meetings provide an invaluable resource for boosting your team’s work ethic, creating strong communication lines within your organization, and gathering feedback on manager performance. No matter why you want to start skip-levels, they’ll provide a range of benefits that will instantly pay off for your company. 

If you’re looking for a definitive list of skip-level questions that you can ask, then we recommend our 101+ Skip-Level Meeting Questions guide on Hugo. 

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