100 Skip-Level Meeting Questions (+ Free Agenda Template)

According to Scott Boulton, human resources leader, “one of the more effective tools that a manager can employ is the use of a skip level meeting.”

Not only do skip-level one-on-one meetings help managers and managers direct reports, but they also foster a better workplace for current and future employees. 

“Over the years, I gained a lot of insights from my skip-level 1-1s that helped me make better choices. But, more importantly, in the end skip-level 1-1s kept me connected to my organization in ways that made me a better, more human leader.” – Jason Wong, leadership coach and former senior director of engineers at Etsy.

So, without further ado, let’s learn what a skip-level meeting is, 100 questions to ask during a skip-level meeting, and how to prepare for a skip-level meeting! 

• What is a skip-level meeting?
• 50 questions to ask your boss’s boss
• 50 questions to ask employees
• Skip-level meeting agenda template
• How to prepare for a skip-level meeting

What is a skip-level meeting?

A skip-level meeting is a one-on-one meeting with your manager’s manager. Hence, the meeting is called a skip-level meeting because it skips your manager to meet with their direct report. 

According to Boulton, “Skip level meeting is one where a manager’s manager meets with employees to discuss department concerns, obstacles, opportunities for improvement, etc. with a focus on maintaining and/or improving overall communication.”

Here are some of the key benefits of skip-level meetings:

• Foster positive relationships between all levels of the organization
• Gauge performance of managers
• Evaluate employee satisfaction 
• Receive feedback to help managers become better leaders
• Build trust and rapport between all levels of the organization
• Foster transparency and open communication between all levels of the organization

50 skip-level meeting questions to ask your boss’s boss

Here are 50 questions to ask your boss’s boss during skip-level meetings:

• Questions to foster trust
• Questions about strategy
• Questions to gain feedback
• Questions about career development 
• Questions about alignment

Questions to foster trust:

Beginning the interview by fostering trust is important. One way to do this is by asking friendly questions to get to know each other. 

Here are 10 example questions to ask to foster trust:

• What do you like to do in your free time?
• What is your favourite book, movie, or podcast?
• Do you have a big family?
• What is your dream vacation?
• What is your dream job?
• Where were you born?
• Where do you live?
• What did you study in school?
• What would you do if you won the lottery?
• Are you a morning person or a night owl?

Questions about strategy

Picking your boss’s direct report’s brain on their strategy will allow you to see the company’s direction. 

Here are 10 example questions to ask about strategy:

• In what direction do you see the company going in the future?
• Does this team support the companies mission? How or how not?
• Do you agree with the strategies that our team is currently using?
• What other strategies could our team implement?
• Which strategies do you feel are most effective?
• Which strategies do you feel are least effective?
• Do you think our team is a good size to achieve these goals? If not, do you think our team needs to downsize or upsize? 
• How do you think upper management can help us improve our strategies?
• Do you think our team is maximizing its resources?
• What other resources/processes do you think our team should implement to have more effective strategies?

Questions to gain feedback

While your boss’s boss likely wants to gain feedback on your boss, it’s also important for employees to ask questions about feedback about themselves. 

Here are 10 example questions to ask to gain feedback:

• What questions can I ask my manager to receive the most feedback?
• What kind of feedback is most effective to give my manager?
• How often should I be asking for feedback from my manager?
• How often should I give feedback to my manager?
• Can you provide me with feedback on [last project your team did]?
• How can I give feedback to upper management?
• How can I ask for feedback from upper management?
• What improvements do you recommend to better our processes?
• Which one do you think was most successful of all the projects our team has completed in the last [quarter/year]? Why?
• Do you value team projects or independent projects more?

Questions about career development 

Getting a sense of upper management’s career development and growth will give you an idea of what you need to do to move up in this company. 

Here are 10 example questions to ask about career development:

• When you started at this company, what position did you have?
• How long did it take you to get to your current position?
• What was the process like to get to the position you have now?
• What skills do you value most for leaders?
• When appointing leaders, is there a specific skill/trait that you look for?
• What would be your biggest challenge with this position?
• Is there an opportunity in the future for me to advance in this company? 
• What are your goals at this company?
• What goals can I implement to help me advance my career at this company?
• Are there any specific responsibilities I can ask my manager for to help me advance my career?

Questions about alignment

Ensuring that you align with the company’s goals and values is important because it allows you to see if this is a place where you can grow. Additionally, according to Harvard Business Review, “clear visibility among corporate, employees’ and supervisors’ goals leads to sharply improved financial results.”

Here are 10 example questions to ask about alignment:

• What projects would you like our team to prioritize this [quarter/year]?
• What do you want our team to achieve this [quarter/year]?
• Does our team reflect the companies values?
• Does our team achieve company goals?
• What is the most important thing our team can do this [quarter/year]?
• How can our team improve to achieve company goals?
• How can our team better contribute to the company?
• What other teams have similar goals to ours? 
• How can our team work with other teams to achieve common goals?
• Can you suggest ways I can better align with company goals and values?

50 skip-level meeting questions to ask employees

Here are 50 questions to ask employees during skip-level meetings:

• Questions about manager feedback
• Questions about employee satisfaction
• Questions about employee productivity
• Questions about team communication
• Questions about problem-solving skills

Questions about manager feedback

According to Marcus Buckingham, Harvard Business Review contributor, ​​“great managers know and value the unique abilities and even the eccentricities of their employees, and they learn how best to integrate them into a coordinated plan of attack.” 

Here are 10 example questions to ask about manager feedback:

• Does your manager foster a psychologically safe environment? Give an example of how or how not?
• Does your manager provide you with the necessary resources to succeed?
• How does your manager act under pressure?
• Does your manager prioritize tasks well?
• How does your manager encourage your team?
• Does your manager address your team’s needs and concerns?
• Does your manager treat all employees equally?
• What are your manager’s areas for improvement/growth?
• What is your manager’s biggest strength?
• Does your manager ensure that you always have work to do?

Questions about employee satisfaction

Gauging employee satisfaction will showcase employees’ issues and ways to address them to make your company a better workplace. Additionally, happier employees will result in less turnover. 

Here are 10 example questions to ask about employee satisfaction:

• Would you recommend this company to your friends as an employer?
• Do you feel excited about coming to work?
• Are you proud to be working for this company?
• Are you satisfied with your current compensation and benefits?
• Do you enjoy working with your team?
• How can we help improve your engagement at work?
• Is there anything else you would like to share that you find important to your employee experience at this company?
• What is your favourite thing about your job?
• What is your least favourite thing about your job?
• Are you happy with your current role/responsibilities?

Questions about employee productivity

Understanding what makes your employees productive will help you foster a productive environment. For example, if you see a trend in more productivity in the morning, you may avoid scheduling meetings at that time to allow employees to get work done during those hours. 

Here are 10 example questions to ask about employee productivity:

• What are your top priorities right now? What can we do to help you with this?
• What percentage of your time do you spend in meetings vs. doing deep work?
• What would you like to spend more time on?
• What would you like to spend less time on?
• When do you get your best work done? Morning / Afternoon / Evening?
• How do you like to organize your day?
• What are the biggest time wasters for you each day/each week?
• How do you know that you’ve had a productive day?
• How could I help you be more productive?
• Are there any software, tools, or resources that you think you could benefit from?

Questions about team communication

According to Harvard Business Review, “companies that communicate effectively had a 47% higher return to shareholders over a five-year period (mid-2004 to mid-2009).” Thus, it’s important to foster good team communication. 

Here are 10 example questions to ask about team communication:

• Does your team communicate well with other employees? Give an example.
• Does your team communicate well with customers? Give an example.
• Are your team members active listeners?
• How do your team members take feedback?
• How do your team members give feedback?
• How do your team members act when talking in a group/presenting?
• Do your team members use work-appropriate vocabulary while at work?
• Does your team create a welcoming atmosphere for you to communicate in?
• Does your team communicate well with your manager?
• Does your team communicate well with other teams?

Questions about problem-solving skills

Although managers always encourage reaching out to them when a problem arises, managers also appreciate self-dependable teams that can problem-solve on their own. 

Here are 10 example questions to ask about team problem-solving skills:

• Does your team ask for help when there is a problem?
• Does your team suggest ways to fix the problem? Give an example.
• How does your team act when a problem arises?
• Does your team evaluate the consequences of their decisions before making them? Give an example. 
• Is your team open to suggestions when problem-solving?
• Can your team problem-solve under pressure? Give an example. 
• Does your team problem-solve quickly?
• Are your team’s problem-solving skills effective most of the time?
• Does your team solve problems on their own before going to upper management?
• Does one team member take the lead when problem-solving?

Skip-level meeting agenda template

How to prepare for a skip-level meeting

Now that you’ve got 100 example questions to ask let’s learn how to prepare…

Tips to prepare if you’re meeting a senior leader

If you’re having a skip-level one-on-one meeting with a senior leader, it’s important to show appreciation for their time. This will demonstrate that their time is impactful as it allows employees to share comments and concerns with upper management.  

“If you are aware of a recent achievement of this person, congratulate them. If they’ve done something you appreciate, tell them. Acknowledgement is a powerful tool and highlighting positive behaviors is an effective way to encourage more of it.” – Wong.

Tips to prepare if you’re meeting your direct report’s report

If you’re meeting with your direct report’s report, it’s a good idea to talk to your manager beforehand. Ask them any questions you may need to know before going into the meeting and find out what feedback they are most interested in. This will ensure that you’re getting the most out of your skip-level one-on-one meeting. 

Here are a few more tips to help you prepare:

• Create an agenda before the meeting
• Have questions ready
• Practice with another employee or friend
• Ensure you have the proper tool to take effective meeting notes (Fellow is an excellent resource for this)

Parting advice

“When used consistently and effectively, skip-level 1:1s are a great, two-way tool for both of you and the team,” says Steven Sinofsky, business and product development leader. 

So, follow the above tips to come prepared and ask the above questions to have an effective and productive skip-level one-on-one meeting.