Navigating skip-level meetings can be a tricky but rewarding endeavor, as it leads you to uncover hidden gems of insights and foster a culture of open dialogue between managers and employees. Like any skilled leader, it's crucial to traverse the skip-level terrain with finesse.

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).

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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.

Skip-level meetings are intended for senior leaders to meet with employees in one-on-one meetings, without their direct reports (manager) present. These meetings usually take place once a quarter and provide both senior managers and employees a chance to exchange feedback with each other.

A senior manager who would usually talk to other managers thus gets the chance to talk to individual employees by “skipping” a level, thus removing the level of direct reports.

Without their direct supervisor present, employees might feel more at ease when sharing their feedback, allowing senior management 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 senior managers to share insights into their daily lives and thoughts at work.

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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.

Boosting Productivity

Getting insights into your employee's daily life, thoughts, and ideas can optimize their work processes to support them in their productivity.

Promoting employee well-being

 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 become aware and address these factors to promote employee morale and well-being.

Employee engagement

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.

Talent management and employer retention

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 significant decisions so that they can take their perspectives and opinions into account.

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How To Start Skip-Level Meetings?

There is no perfect way of starting and implementing skip-level meetings, however, we have collected some guiding tips, that can help you, as a senior manager, as well as your employees to prepare for and kick off your next one-on-one meeting with ease.

Inform all relevant parties

Remember, skip-level meetings are all about transparency and feedback sharing. So why not start off by letting everyone know that you would like to implement skip-level meetings in your organization? This means, that both employees and their direct supervisor should be informed about your intentions.

The last thing you want to do is have a team leader think you are talking to a team member behind their back. Or worse, have employees feel like they are in trouble when receiving an invitation to a skip-level meeting in their calendar.

To make things easier for you, we have prepared an email template for you to use to contact employees about your intentions:

Prepare For A Skip-Level Meeting

Preparation is key for effective one-on-one meetings between a senior-level manager and an employee. Being prepared will not only positively impact how focused and productive the discussion will be, but also allows the senior manager to approach the skip-level meeting with a clear understanding of the employee's background, achievements, and challenges.

This knowledge helps in building trust and demonstrates a genuine interest in the employee's perspective.

Thus, here is a checklist for senior leaders before stepping into their next one-on-one meeting:

1. Understand the employees' background: Familiarize yourself with their career trajectory, achievements, and experiences within the organization.
2. Analyze Recent Performance and Feedback: Examine the employee's recent performance reviews and feedback. Identify areas of strength, potential growth, and any specific feedback provided by their direct manager or team members.
3. Identify Current Responsibilities: Gain a clear understanding of the employee's current role and responsibilities. This includes projects they are working on, key tasks, and any recent accomplishments or challenges.
4. Define Meeting Objectives: Clearly define the goals and objectives of the skip-level meeting. Whether it's understanding team dynamics, addressing specific concerns, or seeking feedback on organizational processes, having a clear purpose is essential.
5. Anticipate Follow-Up Actions: Anticipate potential outcomes of the meeting and plan follow-up actions. Be ready to address concerns, provide support, or recognize achievements.

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Ensure all insights are documented

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 that the information you gain during the meeting is well documented.

Taking notes and staying focused during the meeting sounds like a lot to handle all at once? 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.

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Dos And Don'ts For Skip-Level Meetings

To ensure that your one-on-one meetings are not only productive but also foster a positive and open culture, it's essential to be mindful of certain dos and don'ts.

Let's explore the key practices that can elevate your skip-level meetings and some pitfalls to avoid, ensuring that this managerial tool serves its purpose of bridging communication gaps and nurturing a collaborative organizational environment.

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5 Best Skip-Level Meeting Questions For Guaranteed Success!

Whether you are a senior manager 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.

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

Ask your employees 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 helps 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. 

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

Don’t pressure your employees 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.

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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. 

Emphasize how important DEI is to you, personally and professionally, and that you welcome a differing perspective as it encourages growth.

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.

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4. How can we contribute to an improved work-life balance and 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 implementation of respective measures leads to greater productivity and well-being while reducing employee turnover.

You can ask them if they have specific training they would find useful and interesting to attend, like a workshop about resilience.

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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.

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 - 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. 

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How Can I Bring My Skip-Level Meeting To The Next Level? 

Well, if you have not already gotten inspired by the 5 best skip-level questions or our checklist 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.

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. 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.

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.

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Use AI-powered tools! 

Let’s be honest, taking notes and being fully present at a meeting can be hard. 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. Try it out now for free here.

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Mastering Skip-Level Meetings

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.