July 2023


Quick Guide: Best 5 Skip Level Meeting Questions (and Dos and Don'ts) 

You might have heard that skip-level meetings hold great potential. But what exactly are skip-level meetings? How do you facilitate them? And which questions should you even ask? Don’t worry, we got you - this article will provide you with a quick guide to skip-level meetings and how to make the most of them.


You might have heard that skip-level meetings hold great potential. But what exactly are skip-level meetings? How do you facilitate them? And which questions should you even ask? Don’t worry, we got you - this article will provide you with a quick guide to skip-level meetings and how to make the most of them. Read along if you’d like to find out more about encouraging questions and supporting tools to bring your skip-level meeting to the next level (pun intended).

skip level meeting on an table with two open laptops

What are skip-level meetings?

Skip-level meetings are all about trust and honest communication, and if used correctly, they can enhance collaboration among employees. A skip-level meeting is one where a manager meets with employees without their direct manager present, usually on a scheduled basis, to support feedback among each other. A manager that would usually talk to other managers thus gets the chance to talk to individual employees by “skipping” a level. 

skip level meeting with two women

Let’s look at an example: say you are a team leader and report to your boss, then a skip-level meeting would be between your team and your boss - hence, the name “skip-level”. Without their direct manager present, employees might feel more at ease when sharing their feedback, allowing their interlocutor to get an idea about the teamwork and leadership skills of the employee’s direct manager. Ultimately, going around the usual hierarchy of the organization can encourage an open dialogue between employees and managers to share insights into their daily life and thoughts at work.

Now that we know what a skip-level meeting is, you may ask yourself: “How do I best implement it?” and “What questions should I even ask?”. Keep reading to find out!

How do skip-level meetings work?

There is no perfect way of implementing skip-level meetings, however, we have done some research and found the best practices for you, to be found at a quick glance with our Do’s & Don'ts checklist.

skip level meeting with one women pointing to a note book


  • Schedule the skip-level meeting in advance to ensure availability
  • Create a welcoming environment and emphasize open communication
  • Prepare yourself: present the agenda, reason for meeting, and the main goals
  • Recognize the teams wins, challenges they overcame, and dedication to growth
  • Take notes: capture the key takeaways and next steps 
  • Follow up with the action items and update your employees about them


  • Interrupting your employee or cutting them off
  • Strictly leading the meeting without the opportunity for open dialogues
  • Creating an environment where judgment has a place
  • Use skip-level meetings without engaging in additional feedback sessions with direct managers
  • Not taking notes: forgetting what has been said and thus not following through with promises 

Skip-level meetings are implemented by managers to gain a better understanding of the state of mind of the employees and the organization. So make sure to stay curious about improvement and to follow up with promises (if you make any).

Sounds like a lot? Not when you take off some mental load by letting an AI-assistant, for example jamie, take notes for you: fully engage in the dialogue with your employee and receive a perfect summary, including action items, so that you never have to take meeting notes again. Stay on top of things by keeping your automated meeting notes all in one place with a trusted virtual assistant of your choice.

Main benefits of skip-level meetings 

Skip-level meetings have plenty of benefits. Communicating them to your employees can encourage them to take part in skip-level meetings - make sure to clearly outline your goals for the respective meeting. Getting insights into your employee's daily life, thoughts, and ideas can optimize their work processes to support them in their productivity. An open dialogue with transparent communication can also uncover pain points or challenges that employees have dealt with or are currently facing - skip-level meetings can thus help managers to become aware and address these factors to promote employee morale and well-being. Showing interest in the individual person behind the employee also supports employee engagement, as they operate in a work culture in which their voice is heard. Utilizing skip-level meetings to build a fostering environment can also help to adapt to employees needs, for example, engagement in training opportunities. Skip-level meetings allow all employees to be heard by the managers, who oftentimes make the significant decisions, so that they can take their perspectives and opinions into account.

skip level meeting with a women and a man standing in front of a whiteboard

Ultimately, the main benefits of skip-level meetings are: 

  • Boosting productivity 
  • Promoting employee growth 
  • Building a culture of trust
  • Employee engagement
  • Talent management and employer retention

Now, how do you get your employees to open up? To share their honest opinion and ideas? And how can you create an environment in which they feel encouraged to explain pain points? How do you empower your employees to voice criticism without them feeling judged or uneasy? Simply read along to find out about the 5 best questions to use skip-level meetings to your advantage.

5 best skip-level-meeting questions for guaranteed success!

Whether you are a leader who is unsure which questions to ask or an employee who is curious about what skip-level questions they might be asked - we curated the 5 best skip-level questions to create and engage in an authentic dialogue with the goal of driving a positive impact in an organization. Besides the usual “How are you doing?”, “What is working well and what isn’t?”, “Any challenges or ideas?”, and “Any way I can support your professional development?”, you can make use of these 5 questions if you’d like to maximize the effectiveness of your skip-level meeting.

skip level meeting between two women

1. Are there any processes or policies you would like to change or have experienced pain points with?

Ask your employee to put themselves in your shoes and ask them where they see potential to grow - encourage them to be as honest as possible about current processes or policies that might need to be updated or adapted. Explain how your priority is to improve the status quo and that realizing recurring pain points of employees help you make important adaptations. Understand where your employee is coming from and ask them why exactly they would change something. (As always), thank them for sharing their honest opinion and assure them that you value their input and will look into possible improvements, if applicable. 

2. Can you give a (recent) example when you have felt that your work or contributions were overlooked at work?

Don’t pressure your employee to give an example if they do not have one - however, this question encourages direct and critical feedback. Leave them some time to think about it and share an example if applicable. When the employee chooses to share an example, make sure not to brush it off - listen to understand their perspective and ask follow up questions to understand what could have been done differently and how you can ensure that a similar situation in the future will be handled differently. Talk them through your thought process and ask if they think your approach would make a positive difference for them and other employees - after all, it is not about guessing what will work but about making it happen together.

3. How could we enhance our current DEI (Diversity, Equity and Inclusion) efforts?

Ask your employee if they would like to share their thoughts about current processes and implementations to foster greater DEI. A study by McKinsey has found that Diversity, Equity, and Inclusion can significantly contribute to not only company growth but also employee satisfaction and retention, thus, managers must ensure that all employees feel welcomed and that they can embrace their differences. 

Emphasize how important DEI is to you, personally and professionally, and that you welcome a differing perspective as it encourages growth. Understand how the direct manager of the employee is promoting DEI currently, what they could do differently, and how you could support them. After all, providing a workplace filled with inclusivity, diversity and equality is the baseline for how employees show up to their workplace and how they treat each other - engaging in a dialogue to ensure this should be a main priority by leadership.

4. How can we contribute to an improved work-life balance and the overall employee well-being?

If you want your employees to stay engaged and present at the workplace, be curious about their ideas and thoughts, while emphasizing that every perspective adds to the learning of the leadership team. The Harvard Business Review (2023) found that employees lay greater emphasis on their work-life balance and that an implementation of respective measures leads to greater productivity and  well-being while reducing employee turnover. You might want to share a personal example of how you facilitate your work-life balance, or what has helped you to reduce stress. You can also ask them if they have specific training they would find useful and interesting to attend, like a workshop about resilience.

5. How can we better support you to show up as your most authentic self at work? 

Asking an open-ended question helps employees to open up, as they leave room for an open dialogue while, in this case, indicating that there is room for improvement. Imagine you are being directly asked how your well-being is - employees would likely refrain from sharing their personal thoughts or might even feel judged or unable to criticize their workplace. Show genuine interest (as you should in every answer) and, if you are the one asking, you can encourage your employee to think about a time they felt their best and a time they felt their worst (they could do this as an activity also after the skip-level meeting - then understanding which factors lead to what experience and emphasizing your full support to drive the positive factors in an environment of psychological safety.

Remember that skip-level meetings are not there to put someone on the spot and drill someone with questions, it’s all about listening with the intent to understand, instead of just listening with the intent to reply

How can I bring my skip-level meeting to the next level? 

Skip-level meetings are used to gain insights into current work processes while fostering a culture of feedback and exchange between employees. They are usually scheduled and recurring, and thus you might find yourself thinking “Not another skip-level meeting” or “How can I make this one better?”. Well, if you have not already gotten inspired by the 5 best skip-level questions or our check-list on how to best implement a skip-level meeting, we have gathered some tips and tricks for you to enhance the quality of your skip-level meeting.

skip level meeting sitting on an table

Switch things around! 

While it is important to implement a sense of structure in your skip-level meetings to get the best results, you can switch it up a bit to prevent stale meetings with no fresh input. Start with a joke, share a quick anecdote, or encourage your employee to share about their weekend plans - informal talk at the beginning creates a calm environment.

Instead of following the same old questions, you can leave some time for asking your employee about their ideas and what they would like to see - whether it is about new ideas for the organization, team workshops to attend or ways of working together, make sure to show genuine interest and don’t shut down bold ideas - remember that a dialogue goes both ways and emphasize that honest feedback is what keeps the ball rolling. 

Tired of the same old (virtual) meeting room? Try a more relaxed and informal environment! Encourage your employee to bring a coffee or tea to the virtual meeting or find a place in your office with a friendly environment, like a terrace in the sun or another informal meeting space. Some managers even like to go for a walk during the skip-level meeting - it really is up to what works best for you and the individual employee.

Use AI-powered tools! 

Let’s be honest, taking notes and being fully present at a meeting can be hard. Even engaging in a feedback meeting and remembering what was said even after a week can be a challenging task when added on top of the usual work responsibilities. Ever thought of using AI to make smarter use of your time by streamlining work processes?

We recommend using AI-powered virtual assistants, like jamie, to help you stay on top of your meeting notes - it summarizes meeting notes for you in just one click and provides you with a professional summary, a full transcript and even action items. Impress your boss by staying on top of your feedback or gathering your notes for all your employees in one place. Try it out now for free here.

Improving your skip-level meeting skills by understanding its impact on an organization and implementing best practices can significantly enhance trust, communication and collaboration between employees. Make use of our “Do’s and Don’ts”- checklist and implement the 5 best questions for a skip-level meeting to get the best results while preparing yourself for success. 

If you are looking for more tips on how to boost your productivity during meetings or the best AI tools to use in meetings, check out our guides and find more information in our blog.

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