Skip Level Meeting: What Questions To Ask? - Peter Boolkah

The skip level meeting is an invaluable tool for managers to understand better what’s going on in their team. It allows them to connect with employees who may not be directly reporting to them and gain insights into how the team works that they might otherwise miss out on.

However, knowing what questions to ask during these meetings can be difficult.

This blog post will explore critical questions you should ask your team members to ensure you get the most from skip-level meetings.

What is a Skip-Level Meeting?

A Skip-Level Meeting is when a senior manager meets with their direct reports, as well as the direct reports of those employees. Doing so allows the senior manager to get an overview of the work environment from their subordinate’s perspectives and the people they manage. This helps create an open dialogue between different levels of management and encourages honest feedback, which can help identify challenges and opportunities.

Ultimately, a Skip-Level Meeting aims to increase productivity and efficiency for the organization. It’s an opportunity for the senior manager to understand better what is happening in their organization and how they can best support their team.

The benefits of Skip-Level Meetings go beyond just improving communication. They help build trust between levels of management, as well as encourage collaboration and cross-functional learning. This increases employee engagement, which has an overall positive effect on business performance. Additionally, having a senior manager show their presence in the organisation’s day-to-day operations can help motivate employees and make them feel appreciated.

In conclusion, Skip-Level Meetings are a great way to bridge the gap between different levels of management. Creating an open dialogue allows for honest feedback, which can help improve the work environment and business performance. They also develop a sense of trust, collaboration, and appreciation that helps employees stay motivated. Ultimately, these are all critical elements for any successful organization.

So if you’re looking for ways to bridge the gap between different levels of management and increase productivity, then Skip-Level Meetings could be the perfect solution. Try it and see how you can impact your organisation’s performance.

Benefits of Skip-Level Meeting

Skip-level meetings are a great way to ensure that communication from the top echelons of the organization reaches even entry-level employees. For example, IBM has used skip-level meetings to foster relationships between senior leaders and their teams. These meetings allow senior leaders to build rapport with their team members and get direct feedback from them on how they’re doing.

Moreover, skip-level meetings can provide employees with a sense of trust and accountability that one-on-one meetings may not be able to achieve. This is why IBM has found such success with their implementation of this practice. Skip-level meetings create an environment where everyone feels connected and valued by the organization’s leadership. So if you’re looking for ways to improve communication within your organization, consider implementing skip-level meetings. It may just be the answer you’re looking for!

Skip Level Meeting - Peter Boolkah

Specific Questions to Ask in Skip-Level Meetings

Regarding skip-level meetings, managers need to ask the right questions. These should be questions that focus on the big-picture goals and objectives of the organization as well as any potential next steps needed to achieve them. For this reason, key questions to consider asking in a skip-level meeting include:

  • What is the primary focus of the organization?
  • How is the team doing in terms of reaching their goals and objectives?
  • What can be done to improve overall performance?
  • Are there any new initiatives that need to be implemented?
  • What have been this team’s biggest successes and failures over the last year or so?
  • Is there any additional support that the team needs to be successful?
  • What are the manager’s thoughts on moving forward with this team?

By asking these questions, managers can better understand what is happening within their organization and where improvements or next steps must be taken. In addition, it allows them to provide helpful feedback that can help the team reach their goals and objectives more effectively. As such, skip-level meetings are an essential part of any organization’s success

8 Ways to Prepare for a Skip Level Meeting as an Employee

1. Know who you’re meeting

Knowing who you’re meeting in a skip-level meeting can help make the conversation more productive. It’s essential to be mindful of your role as an employee and be prepared to answer questions if possible. Knowing who is on the other side of the table can also help you feel more confident when talking about yourself and your work. Preparation is vital to having a successful 1 on 1 meeting with your boss and their boss. Doing some research beforehand can help you understand the purpose of the meeting, which will help you prepare effectively.

This is also an excellent opportunity to make sure that all parties involved are on the same page about expectations and any potential issues that may arise. These steps can help ensure that everyone works together towards shared objectives. Additionally, being aware of who else is in the room can help you to understand what each individual brings to the table and how it might affect the conversation. This knowledge is invaluable for ensuring your skip-level meeting is as productive as possible.

By preparing for a skip-level meeting, you can gain essential knowledge about those attending the conference. This enables you to be better equipped for any discussions that may take place and allows you to communicate your ideas, achievements and goals effectively. Being prepared can help increase your confidence going into the meeting and make it easier for everyone involved to work together towards a successful result.

2. Have a list of things you love

When you have a skip-level meeting, it’s essential to be prepared. One of the best ways to do this is by listing things you love about your job and why it’s such a fantastic opportunity for growth. This could include anything from the people you work with, the projects you’re working on, or even just the overall environment of your workplace. Having a list of positive things to focus on can help put you in the right mindset for the meeting and make it easier to discuss any issues.

Furthermore, having this list handy can be a great resource to refer back to if you feel overwhelmed or need extra motivation during the meeting. It can also be used as evidence of all the excellent work you’ve been doing, which can help to demonstrate your value to upper management. So don’t forget to list what you love about your job – it could enable you to ace your skip-level meeting!

3. Know your goals and progress

As an employee, preparing for a skip-level meeting is vital to ensuring you and your manager get the most out of it. Knowing your goals and progress is essential because it allows you to provide more detailed information on how you’ve been working towards them. It also gives your manager a better idea of where you are in terms of development and what future goals might need to be set.

Additionally, having that information handy can help make the meeting more productive by allowing for better conversations and understanding of the objectives. Reviewing your progress is a great way to show that you’re invested in ensuring you reach your goal. Lastly, it shows respect for yourself and your manager by presenting yourself in the best possible way. Preparing for a skip-level meeting is essential to demonstrate that you’re responsible for your career development and growth!

The bottom line is that preparing for a skip-level meeting will help ensure that it’s productive and beneficial to you and your manager. A clear understanding of your goals and progress can help make the process smoother and more organized while demonstrating your commitment to reaching those objectives. So don’t forget to take the time to get yourself ready for the meeting and make sure you’re putting your best foot forward.

4. Share roadblocks you experience

Skip-level meetings offer significant potential benefits for both the employee and the organization. For employees, it allows them to break the ice with their managers’ manager, better understand their role in achieving organizational goals, and clear any roadblocks they may be experiencing. It also helps the organization by allowing for knowledge sharing across departments and establishing clearer objectives at each level. For these reasons, coming prepared for a skip-level meeting is beneficial.

Employees should look into their current tasks and responsibilities and any challenges they may have encountered recently that could be shared with the higher-ups to ensure a productive meeting and maximize the potential benefits for everyone involved. If you’re preparing for a skip-level meeting, take the time to carefully consider any potential roadblocks you have encountered and the best ways to communicate them effectively. Doing so will help ensure successful outcomes for all parties involved!

5. Have suggestions for what could be improved

Skip Level Meetings are a fantastic way for employees to feel heard and appreciated. It allows them to share their experiences, suggestions and ideas with higher-level managers without going through a chain of command. This is important as it gives employees a platform to express how they feel about specific topics that could potentially help the company improve in some way or another. A Skip Level Meeting is an excellent way for employees to feel empowered and their opinions are valued. It also allows them to build relationships with the upper management team, which can be beneficial in future situations.

Ultimately, it’s an opportunity for all involved parties to benefit from each other’s views and gain insight into different perspectives. Companies must take advantage of these meetings and create an environment encouraging employees to have their say. By doing this, companies can show employees that they value their opinions and consider them when making important decisions. It’s also an excellent way for employers to get feedback on improving the working environment for everyone. So if you’ve attended one of these meetings recently, share your thoughts on what could be improved and how it might benefit the company. Your opinion matters!

6. Ask questions about work and life

A skip-level meeting is an important opportunity for employees to ask questions and get a better understanding of their work and life. It allows them to hear from senior leaders in the organization about the big picture and will enable employees to voice their concerns or ask questions they may not have been able to otherwise.

This insight can be invaluable, giving employees a better understanding of the organization and how they fit in. Plus, it’s an opportunity to learn more about workplace culture, which can be extremely helpful when navigating challenging tasks or projects. Ultimately, a skip-level meeting can help employees become stronger and more successful. So make sure you take advantage of this opportunity!

7. Reach out to team members for what to expect

Attending a skip-level meeting can be intimidating, especially if it’s your first one. However, reaching out to team members who have attended one can help you prepare for the meeting. They can give you information about what to expect and provide valuable insight into the purpose of the meeting. Attending these types of meetings is essential as they offer the opportunity to hear directly from your company’s leadership and understand the goals they have set for the team.

It is also an excellent way to stay informed on any changes or initiatives that might affect you as an employee and help ensure your success at work. Taking the time to ask questions and listen attentively during these meetings can help you build relationships with important stakeholders, learn more about how decisions are made, and understand the company’s vision for the future. So don’t be afraid to ask questions, and make sure you’re getting the most out of your skip-level meeting!

8. Ask for feedback

Skip-level meetings are essential for employees to contact their supervisors or even higher-level executives directly. It offers open communication and feedback, allowing employees to ask questions, provide ideas, or voice concerns without pressure from other team members. This direct line of communication benefits both the employee and the organization as it allows for more honest dialogue and encourages them to develop creative solutions. It also allows employees to feel like their opinions are respected and heard, which can help build morale and boost engagement. Having skip-level meetings is essential to creating an open organisational culture where everyone feels supported and valued.

Furthermore, it can be a great way to get to know colleagues at different organisational levels. It offers an opportunity for employees and supervisors to build relationships outside of their respective teams, fostering a sense of collaboration and support. Additionally, it can help clarify projects or initiatives as the higher-level executives may have more insight into how they should be carried out. In effect, skip-level meetings are a great way to facilitate two-way communication and collaboration across the organization.

skip level meeting in office

Setting the Stage for a Meeting

During the meeting

Set aside any distractions and focus on the task at hand. Listen carefully and be open-minded about other people’s ideas. We’re all here because we want this meeting to succeed, so let’s ensure we are all working together as a team. Let’s work together to ensure our questions are answered, and everyone’s ideas are heard. Let’s make sure we are making decisions that will benefit the group. Let’s strive for collaboration, efficiency, and success!

At this point, reviewing the agenda and objectives we have set out for ourselves would be helpful. We can then break down these objectives for each task so that we can move forward in an organized fashion. We should also ensure everyone understands the functions and is prepared to contribute ideas.

If there are any questions or concerns, now would be a good time to address them. It’s essential that everyone feels comfortable enough to speak up and have their voices heard. Let’s ensure everyone is on the same page and working towards a common goal.

Let’s keep our conversations focused and productive, and don’t forget to take breaks if needed. We want to ensure this meeting is successful and efficient, so let’s do our part!

Following up

Now that you have the groundwork, it’s time to prepare for the meeting. If you haven’t already done so, update your contact list with all the relevant stakeholders and invite them to join in on the discussion. Keep everyone informed by sending email reminders and providing any necessary materials beforehand. On the meeting day, please arrive a few minutes early and be prepared to greet everyone as they come. Have all of the required materials on hand, including an agenda that clearly outlines the objectives of the meeting.

Stay focused on the plan during the session and keep discussions on track. Make sure each decision is made with consensus from all parties involved, and take notes so you can refer back to them later. Finally, thank all participants for their time and input before wrapping up the meeting. With these steps in place, you should now have a thriving setting for your meeting that will lead to productive outcomes and meaningful results.

What NOT to Do in a Skip-Level Meeting

It’s also important to remember that a skip-level meeting is not the time or place for criticism — positive or negative. While you may have some feedback about the team’s performance, this should be reserved for one-on-one conversations with individual group members. A skip-level meeting aims to create an open dialogue between all levels of leadership and foster mutual understanding. Keeping criticism out of the conversation will help maintain trust and collaboration.

Additionally, it’s essential to focus on solutions rather than problems. This is not the time to complain or point fingers — instead, strive to identify opportunities for growth and improvement as a group. Finally, keep your comments brief and relevant so everyone can stay on track and get the most out of the meeting. Considering these points will help ensure your skip-level meetings are productive, positive experiences for everyone involved.

Final Thoughts

Skip-level meetings can be a great way to gain invaluable insight into the inner workings of your business. Not only do they help you build relationships with employees at all levels, but they also provide an opportunity for honest feedback and open dialogue about how things could improve.

When it comes time to hold skip-level meetings, questions like those listed above are vital in helping ensure that everyone’s voice is heard and taken seriously. By keeping these tips in mind when preparing for your next meeting, you can rest assured knowing that you have done everything possible to ensure it goes as smoothly as possible and provides real value to yourself and your team members.


What is the purpose of skip-level meetings?

Skip-level meetings are designed to create a space for employees at all levels of the organization to come together and discuss challenges, successes, and opportunities. This type of meeting enables everyone in the company to have direct access to management, which can help foster a sense of connection and camaraderie between teams.

Additionally, these meetings provide an invaluable opportunity for leadership teams to hear feedback from the frontline and better understand their employees’ perspectives. This can lead to improved decision-making, increased employee engagement, and improved business outcomes. Skip-level meetings are essential for any organization that wants to ensure meaningful communication between leadership and its employees.

Overall, skip-level meetings create an environment where all levels of the organization can exchange ideas openly and collaboratively. By investing in meaningful conversations, companies can build better working relationships and encourage employee engagement. In short, skip-level meetings are an essential part of any business’s strategy for success.

Who initiates a skip-level meeting?

Typically, the senior or executive leader initiates a skip-level meeting. This type of meeting can be organized to check team morale and progress on projects, get employee feedback, or even show recognition for good work. It’s an excellent way for executives to keep their finger on the company’s pulse and build relationships with employees at all levels.

By hosting a skip-level meeting, leaders can better understand how their decisions will affect employees on the ground and what challenges they’re facing. Plus, it helps create an open dialogue between leaders and their staff, allowing for honest feedback without fear of repercussions. It also serves as recognition to those who may not often receive recognition from upper management.

Skip-level meetings can be conducted one-on-one or in small groups, and they don’t have to be restricted to just the employee’s direct manager. Executives should try to reach out to employees from all company levels, including those who may not directly report to them. Doing so will give executives a more comprehensive view of the company.

Ultimately, skip-level meetings should empower employees and allow them to voice their opinions and ideas in an open, safe environment. When done correctly, these meetings can provide valuable insight for upper management and help foster strong relationships between the company’s leaders and workforce.

Are skip-level meetings good or bad?

Skip-level meetings have both pros and cons. On the one hand, they can allow leaders to hear directly from employees at different levels without any filter. This may help create a more transparent culture in the workplace that encourages honest feedback. On the other hand, some employees might feel uncomfortable speaking up in front of their superiors or peers, which could lead to a lack of trust and communication. Ultimately, it’s up to the company to decide whether skip-level meetings benefit their team.

If leaders take the time to create a supportive environment where everyone feels comfortable sharing their thoughts, these meetings can be an effective way for employees to have their voices heard. Executives should also make clear that any feedback shared in these meetings will remain confidential. This can create a sense of trust between the company and its employees, fostering better relationships and improving morale at work.

In summary, skip-level meetings have both advantages and disadvantages. It’s important to weigh both carefully before deciding what is best for your team. With thoughtful planning and implementation, they can effectively build a more open and trusting relationship between leaders and their staff.

How do you make the most of your skip level 1-on-1s?

Skip level 1-on-1s can be a great opportunity to gain a strategic perspective on the organization and get closer to front-line employees. To make the most of your skip level 1-on-1s, here are some tips:

  • Make sure you set aside plenty of time for each meeting so that you can go into detail and get to know the person in front of you.
  • Ask probing questions and take lots of notes to remember key points from each meeting.
  • Create a relaxed atmosphere conducive to open discussion, where people feel safe speaking candidly.
  • Make time for informal interactions as well – this will help your team members feel comfortable enough to open up about their experiences.
  • Follow up with the people you meet to check in on progress or provide additional support if needed.

By making the most of your skip level 1-on-1s, you can help create a more connected and engaged organization that can better reach its goals. So don’t neglect this important opportunity!

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