Maximizing the Benefits of Skip-Level Meetings for Managers and Employees in 2024

By Kyla Mintz

Are you seeking to enhance communication and collaboration within your organization? Do you hope to foster a culture of transparency and trust between employees and senior management? Look no further than skip-level meetings, a powerful tool that can help bridge gaps and pave the way for a more cohesive work environment.

In this blog post, we will explore the ins and outs of skip-level meetings, from understanding their purpose and benefits to preparing effectively and asking the right questions. Join us on this journey to maximize the potential of skip-level meetings for managers and employees alike in 2024.

Key takeaways

  • Skip-level meetings facilitate candid conversations between employees and their manager’s managers, providing numerous advantages.
  • Employees should prepare by understanding the meeting objectives and researching senior management attendees, while managers should create an inclusive agenda to foster open communication.
  • Utilizing carefully crafted questions along with technology can help build rapport, gain insights into areas of improvement, avoid common pitfalls in skip-level meetings & maximize benefits for both parties.

Understanding skip-level meetings


Skip-level meetings are one-on-one discussions between employees and their manager’s manager, bypassing the direct supervisor, to foster open communication and gain valuable insights. Employees and senior managers alike benefit from these meetings, which facilitate candid conversations and foster a culture of open communication and problem-solving.

The traditional hierarchical structure of a company can make it difficult for manager feedback to be shared openly, especially when it comes to the boss’s boss. Senior leaders must create an environment that encourages open and honest communication while making team members feel comfortable and respected. Maintaining a respectful and professional attitude towards both managers is key to maintaining strong relationships with them.

Keep in mind, the direct manager’s presence is better avoided in skip-level meetings. Instead, the focus should be on discussing the enthusiastic conversation you had with your direct manager before initiating the skip-level meeting with the manager’s manager. This format allows for a greater understanding of employee satisfaction and alignment of company goals with employees’ immediate managers, ultimately leading to a more harmonious work environment.

The goals and advantages of skip-level meetings


Skip-level meetings offer unique skip level meeting benefits for both employees and senior managers, including improved alignment, increased transparency, and better understanding of employee satisfaction and company goals. By participating in the next skip level meeting, employees can experience these advantages firsthand and gain insights from their skip level manager when skip level meetings happen.

We will now delve deeper into these benefits for each party involved.

For employees

During skip-level meetings, lower level employees have the opportunity to voice their concerns, share their ideas, and gain valuable career guidance from senior leaders. These meetings serve as a platform for employees to open up about their worries and propose innovative ideas that may not have been considered before.

To make the meeting successful, employees should prepare questions and topics for discussion beforehand and understand the meeting’s objectives. Bear in mind that a skip-level meeting differs from a one-on-one meeting with a direct manager, given its involvement of higher management and focus on broader organizational issues.

For senior managers

Senior managers can use skip-level meetings to gather direct feedback, assess middle-management performance, and identify areas for improvement within the organization. These meetings offer a unique opportunity to evaluate the commitment, performance, and progress of direct reports by obtaining a variety of perspectives and data, while promoting transparency, feedback, and growth.

By fostering trust with employees through open and candid conversations, senior managers can cultivate a positive work environment and encourage a culture of continuous improvement. Additionally, the valuable insights gained during these meetings can be utilized by the senior manager to guide decision-making and drive the organization forward.

Preparing for effective skip-level meetings


Effective skip-level meetings hinge on adequate preparation, where employees and managers concentrate on defining clear objectives, crafting a shared skip level meeting agenda, and fostering open communication.

We will now delve into preparation advice for both employees and managers.

Employee preparation tips

Before attending a skip-level meeting, employees should:

  • Research the senior management attendees by examining their professional profiles
  • Review their prior work
  • Understand their current roles and responsibilities

This will not only enable employees to ask more insightful questions but also demonstrate their initiative and engagement.

Setting clear objectives for the meeting can help employees make the most of their time. Some objectives to consider are:

  • Gaining an understanding of the organization’s goals and objectives
  • Obtaining insights into the senior management’s vision
  • Fostering relationships with senior management

Preparing relevant questions related to these objectives will ensure a focused and productive discussion.

Manager preparation tips

Managers significantly influence the success of skip-level meetings. To start, skip level managers should:

  • Know their employees well
  • Create an agenda that addresses key topics and concerns
  • Collaborate with employees to develop the agenda to ensure inclusivity and transparency.

Encouraging open communication during the meeting is key to receiving sincere feedback and cultivating a positive work atmosphere. Managers should be mindful of how employees may experience the meeting and create an atmosphere that encourages open dialogue, even if it involves discussing challenging topics or issues.

Essential skip-level meeting questions


A well-structured set of questions can help build rapport, gain feedback, and gather insights during skip-level meetings, ensuring productive conversations and valuable outcomes.

We will now delve into some fundamental question categories for these meetings.

Building rapport

Warm-up questions, such as inquiring about team alignment with the company mission or corporate strategy, can help build rapport and open up the conversation. These questions allow participants to ease into the meeting and establish a comfortable atmosphere for more in-depth discussions.

More focused questions can address specific concerns and ideas, allowing employees to share their thoughts on team performance, resource management, and areas for improvement. By creating a balance between warm-up questions and more targeted inquiries, managers and employees can foster a productive and insightful conversation during skip-level meetings.

Gaining feedback and insights

Open-ended questions are crucial for gaining valuable insights and feedback during skip-level meetings. Managers can ask questions about:

This helps uncover information that can drive positive change within the organization.

Employees should also be prepared to share their thoughts on company culture, career development, and any ideas they have for enhancing team performance. By engaging in a two-way conversation, both managers and employees can learn from each other and work together to achieve the company’s goals through effective team feedback.

Avoiding common pitfalls in skip-level meetings


While skip-level meetings offer numerous benefits, they can also present some challenges, such as employees not being forthright, objectives not being well-defined, or communication not being effective. Addressing these issues and fostering a positive atmosphere that encourages open communication and problem-solving is key to a successful meeting.

One of the most common pitfalls in skip-level meetings is using the meeting as a platform for complaints instead of focusing on constructive feedback and improvement. By setting clear objectives, preparing relevant questions, and fostering a collaborative environment, both managers and employees can avoid these pitfalls and make the most of their time during skip-level meetings.

Utilizing technology to enhance skip-level meetings


The use of technology, including video conferencing tools, collaborative note-taking platforms, virtual office software, and meeting agenda templates, can boost the effectiveness and efficiency of skip-level meetings. These tools can streamline the process, making it easier for all participants to stay engaged and focused on the topics at hand.

For virtual skip-level meetings, platforms like Kumospace, the leading virtual office software provider with power AI features, offer conversation intelligence to help assess the talk-to-listen ratio, the words spoken per minute, and the overall sentiment of the call. By leveraging technology, managers and employees can better understand the dynamics of the meeting and work towards creating a more productive and collaborative environment.


Skip-level meetings are a powerful tool for fostering open communication, gaining valuable insights, and aligning employees and senior managers with company goals. By understanding the purpose and benefits of these meetings, preparing effectively, asking the right questions, and avoiding common pitfalls, organizations can make the most of this unique opportunity to strengthen their work environment and drive success.

As we move forward into 2024, let us embrace the power of skip-level meetings to create a more transparent, collaborative, and high-performing workplace. With the right approach, tools, and mindset, the potential for growth and improvement is limitless.

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Headshot for Kyla Mintz
Kyla Mintz

Kyla is part of the Marketing team at Kumospace, where she helps run the social media accounts and creates content. Kyla has many different passions outside of work, including volleyball, traveling, and restaurant dining.

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