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The Skip Level Meeting Questions You Need to Prepare!

There's no rule book when it comes to asking skip level meeting questions; it all depends on what information you as a manager are trying to find out, and what is the purpose of the meeting. Often referred to as skips, a skip-level meeting is a gathering between the upper manager and an employee, literally skipping the employee's direct manager. Holding these types of meetings is a useful approach for C-level managers to get to know their team members more and for employees to better grasp their team's objectives in relation to those of the company.

Benefits of Skip-level Meetings

A skip-level meeting enhances communication, and even though the manager is the main driver of the meeting, skips should always be a two-way street. It's best to start with a casual chat, asking the invited employee how their week is going, what they did on the weekend, what plans they have for the upcoming weekend, etc. Starting a skip-level meeting in this way allows for a casual lead into the actual meeting, and ensures you don't overwhelm the employee by diving in too fast. Once the casual part of the meeting is over, you can start to shift into work-related topics.

A skip-level meeting differs quite a bit in format, as compared to other types of remote meetings because of the particular goal that is set for it. Essentially, the goal of this meeting is to establish a conversation between two people who are part of the same team but rarely see each other. Communication is key to any team and company; that's why skips are highly recommended for startups and larger companies where employees often don't have the chance to interact with higher management.

Improve communication

If you're getting started on the skip-level meeting game, it's important to set a comfortable environment. Meeting with the boss of your boss could be quite scary at first, so that's why knowing which skip level questions for boss' to ask is crucial, to ensure the employees become comfortable. Skips provide higher management and employees with the opportunity to improve communication and get to know each other personally and professionally.

Below are a few skip level meeting questions you can use to break the ice:

  • Did you always know you wanted to be/work in [job position/department]?
  • What activities do you do in your free time?
  • Where did you study?

Gain new insights

C-level executives sometimes don't get the full picture of what happens within the company at a team level. When issues arise that potentially affect individual employees or overall team performance, they're often not aware. Skip-level meetings are ideal for talking about everything that happens inside the team, good or bad.

It's not always easy to get employees talking about their teammates or direct manager, which is why it's crucial to ask the right questions.

  • What is working well in the team? (Processes, team, technology, work schedule...)
  • What needs improvement? (Support, more feedback, better tools, more work flexibility...)
  • Does the current workspace arrangement aid your productivity?
  • As a department, what do we need to continue doing in order for you to be successful?
  • Do you feel supported by your current manager (and myself)? Is there anything that you think we could improve?

Kick-off skip-level meetings

Let's kick off skip-level meetings the right way, rather than giving your employees a panic attack with no-context calendar invites. We advise you to speak to the whole group or send an email explaining the reasoning behind holding skip-level meetings and what your aim is with them. Another way to inform your team of the upcoming round of skip-level meetings is to invite them each to a Complish discussion. From within a discussion, you can write out your meeting agenda, and allow invited employees to comment on the points prior to the meeting.

Skip level meeting agenda

Creating a skip level meeting agenda will help you before, during, and after the meeting. Doing this, not only helps organize the meeting, but ensures that you tackle all the important matters you need to cover. Also, creating a meeting agenda serves as a place to take your meeting minutes, essentially a summary of all the points discussed and actions to take from them.

Whether you're running in-person, online or asynchronous meetings, Complish can help you set up a skip level meeting agenda to run successful skip-level meetings.

Skip level meeting invitation email sample

If you decide to send out written communication rather than speak directly (face to face or online) with your team members, you can use a skip-level meeting invitation email sample that you can tweak to adapt to your company's style and tone of voice.

What to talk about in a skip-level meeting

If it's your first time holding this kind of meeting, it's fair not to know what to talk about in a skip-level meeting. It could be a good idea to firstly meet with the team's directing manager and ask for some facts about each team member on a professional and personal level, so you have something to start with before jumping into the questions.

Asking the right skip level meetings questions

Skips should focus on how the manager and their team can do better, thus asking the right skip level meeting questions is crucial. To make the skip more productive, it's advisable to come up with at least 5 questions each, manager and employee. Having the questions beforehand helps set up a meeting agenda and allows you to draw all the information and knowledge out of the meeting.

Skip level questions to ask your employee

With the initial casual chat, the employee will feel more relaxed and comfortable and look at the meeting more as a casual chat rather than a performance review. To get to know the day to day, personal goals and overall perception of the company and their team, we have come up with 10 skip level questions to ask your employee:

  • Which of the projects that you have worked on have you enjoyed the most?
  • If you were in my shoes, what changes would you apply to the team? (people, management, tasks...)
  • Is there anything (tool, platform, support) that would make your work easier or help you be more efficient?
  • Are you clear on the team's goals?
  • Are you clear on the company's goals?
  • How's your relationship with your direct manager? Is there anything I can help you with?
  • Are you happy with your current position? Is there anything that you'd change about it?
  • What are your goals in the next 3 to 5 years?
  • Do you feel like you have grown throughout the time that you've been with [company]?
  • Is there anything that [company] isn't doing that you'd like to implement? (can be company culture, activities, social impact, perks and benefits...)

Skip level questions to ask managers

As we mentioned before, these meetings are a two-way street. This means that employees should have a list of skip-level questions to ask higher management. They shouldn't be afraid to ask these questions, so it's important to set the stage and create that open forum for them. If they have doubts about what to ask, you can provide them with the following questions as a guide to get them thinking.

10 questions to ask your leader:

  • What ideas would you wish that we put in practise in the future?
  • What should our team prioritise when the next quarter starts?
  • What can I do to help in other company matters?
  • How did you like the last project we worked on? Did it bring the results you were hoping for?
  • How can I receive more detailed feedback from my manager?
  • Is there any way I can help newcomers in the company?
  • Is there something that you wish we did better as a team?
  • What's the biggest challenge you face as a leader?
  • Are there any openings for more junior/senior/management roles coming up?
  • Are the company's goals being reached?

Asynchronous Skip-level Meetings w/ Complish

While, in terms of format, online skips aren't that different from those that happen face to face, asynchronous skip-level meetings can be a challenge for both parties. If your team is scattered around different time zones and scheduling a video call is an impossible mission, you can asynchronously run skips with Complish's discussion feature. Discussions are collaborative documents within Complish in which you can invite users into and set a schedule (or not) so that those invited know by when they hop in to the discussion.

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