Skip-Level Meeting Questions to Ask Your Boss’s Boss - Docket

Skip-Level Meeting Questions to Ask Your Boss’s Boss

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What is a skip-level meeting?

Do you ever feel like you would love to meet with your manager’s manager? As you’re working your most challenging every single day at the job, don’t you sometimes wish you could meet the person in charge of your direct boss? With skip-level meetings, that dream becomes a reality. A skip-level meeting is held between a manager’s manager and their employee, without the manager being present. Other names for skip level meetings are skip-level 1-on-1s. These meetings can be very effective for many different reasons. They are commonly used for a boss, or skip-level manager, to get an unfiltered view of what’s happening around the organization. Now that you know the answer to: “what is a skip level meeting?” Now let’s take a few more advantages of these meetings:

Gain new insights

A skip-level interview, or meeting, can be extremely effective because it allows each party to gain useful insights. As employees may work in the trenches every day, executives may not even know what it’s like. Alternatively, lower-level employees may never realize what even happens in the seat of an executive. Having these meetings can be an excellent way for both parties to learn what happens within the organization as a whole.

Can solve issues

Often, things may happen in an organization that the executive team has no idea about. And while they can involve small problems, these issues are often pretty major. And if an employee doesn’t have the resources to let their voice be heard, problems can fly under the radar. But with the help of a skip-level meeting template, employees can talk one-on-one with a manager to voice any issues that they see within the organization. The template, along with others, can be used in a free trial of Docket which we invite you to start today.

Can lead to growth

While there are many skip-level meetings pros and cons to consider, one of these meetings’ leading benefits involves the growth potential. And while that means growth for the lower-level employee, the growth potential is also for the manager. When an employee sits down in one of these meetings, they can gain knowledge, insights, and valuable information from the manager. On the other hand, the manager may also gain valuable information and may even learn something about the organization that they had no idea about.

How do employees prepare for a skip level meeting?

While developing the right skip-level meeting agenda questions to ask your boss’s boss is a significant first step, there are some other tips to keep in mind. Check out these tips below:

Know what’s on the line

One key factor to remember is that these meetings can be a massive step for your organization and your career growth. That being said, you want to ensure you prepare properly and have a goal before stepping foot inside that meeting room.

Get ideas and feedback

Given the importance of these meetings, it’s best to get ideas from others before talking to your boss’s boss. While other colleagues may have been in your shoes previously, they can give you great insights on what to expect and prepare.

Schedule the right way

On some occasions, the employee may be the one to invite these skip-level managers to the meeting. To ensure you have a clean, professional document or email for the invitation, we recommend using a skip level meeting invite template. It’s also best to research one on one meeting request email sample documents to see if you’re on the right track.

Skip level meeting questions to ask your manager

If someone has been fortunate enough to sit down with their manager’s manager for a meeting, they may have no idea what questions to ask. After all, this can place them in a very vulnerable position, especially if your manager’s manager is a very reputable, important person. However, to get the most out of these meetings, you want to prepare yourself with the right questions. That being said, you’ll want to have a skip level meeting template that lists out all of your questions.

Questions to ask your boss during skip level meeting

Preparing for these meetings can be stressful. Take a look at these questions to ask your manager’s manager:

What made you start or join the company?

This is a very open-ended question that can spark a lot of conversation and engagement.

What first made you interested in this industry?

Since most people love to talk about themselves, this question can really get the meeting off on the right foot.

Where did you grow up?

These meetings shouldn’t only involve talking about work. That being said, you should have a few questions like this one that dives into their personal life. Although it’s simple, this is one of the best questions to ask the skip-level manager.

Frequency of skip-level meetings

Given that a skip level meeting synonym is a skip level 1-on-1, these meetings can benefit many aspects of any organization. Depending on the organization’s size, it may work best to have schedule skip-level meetings quarterly or semi-annually for maximum success. Organizations should design skip-level meeting agendas document for employees and be sure also to schedule these meetings On the employees’ behalves. If, however, skip-level meetings are not a part of an organization’s culture, an employee should consider reaching out on their own. Asking their manager directly is a good first step. From there, a skip-level meeting invitation email sample like this one can be effective: 

Hi {Skip-Level Manager First name},

My name is {First Name}, and I work with {manager first name} as {title}. If possible, I’d like to schedule 30 minutes to learn more about your role at {company name}. I’d love to hear more about your journey and see if you had any tips on my career growth.

 I generally have a stand-up meeting each morning and a standing team meeting on Tuesday afternoon. Are you available {1-2 proposed times}?

Thank you,

This short and to-the-point skip-level meeting invite sample has the potential to change the life of an employee. The template, along with others, can be used in a free trial of Docket which we invite you to start today.

About the Author

Heather Hansson

Heather is VP of Product and Chief of Staff at Docket. She enjoys leading cross-functional teams to work together on vision, strategy, and implementing solutions that help people work and live better. When she isn’t helping rid the world of wasteful meetings with Docket, Heather likes to run, take violin lessons with her son, and spend time with her family.

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