Skip level meetings are one of the most powerful—yet underutilized—tools for fostering transparency, improving team alignment, and driving organizational success.
Skip level meetings are one of the most powerful—yet underutilized—tools for fostering transparency, improving team alignment, and driving organizational success. For senior leaders managing fast-growing teams of 40 to 70 employees, these meetings offer a rare opportunity to connect directly with frontline employees. This connection bypasses the traditional management chain.
But what should you actually talk about in a skip level meeting to make the most of this time?
In this article, we’ll explore:
- The essential topics to cover.
- How to structure these conversations for impact.
- How Meeting For Goals can help you streamline and supercharge your skip level meetings for better outcomes.
If you’re ready to start planning more effective meetings, check out our free meeting templates at https://meetingforgoals.com/meeting_templates. You can also sign up today at https://app.meetingforgoals.com/TenantRegistration/Register to start transforming your meetings.
What is a Skip Level Meeting?
A skip level meeting is a one-on-one or small group conversation. It occurs between a senior leader (like a VP, Director, or C-suite executive) and employees who report to that leader’s direct reports. In other words, it “skips” a level in the reporting hierarchy.
These meetings aren’t about micromanaging or checking in on performance metrics. Instead, they focus on:
- Building trust.
- Gaining unfiltered feedback.
- Connecting employees to the bigger picture of your company’s goals and culture.
Why Should You Care About Skip Level Meetings?
In growing companies, especially those with 40–70 employees, communication can get siloed quickly. As more layers of management are added, it becomes harder for senior leaders to know what’s really happening on the ground. Skip level meetings help restore that connection.
They offer:
- A voice for employees.
- A clearer view for leaders of team morale, challenges, and opportunities for improvement.
When done right, skip level meetings:
- Build transparency.
- Improve retention.
- Create stronger alignment across teams.
Want to run more goal-driven meetings? Visit https://meetingforgoals.com to learn how Meeting For Goals can help.
Purpose of Skip Level Meetings
To get the most out of skip level meetings, it’s important to understand their core purpose. These meetings aren’t just another calendar event—they’re strategic touchpoints that can shape your company’s culture and direction. Here’s what they’re designed to do:
- Open up communication between leadership and frontline employees.
- Break down barriers that prevent honest feedback.
- Surface real-time insights into team dynamics, morale, and operations.
- Reinforce your company’s values, vision, and strategic goals.
Skip level meetings do not aim to bypass or undermine middle managers. Respectfully conducted, they complement management. They give leaders a broader perspective and help ensure that strategy aligns with execution.
For employees, these meetings offer a rare chance to be heard by someone who can make real change. For leaders, they provide insights that might never surface in a report or dashboard.
When employees feel heard and valued, they’re more engaged. Engaged teams are more productive, loyal, and innovative. In fact, according to Gallup, highly engaged teams show **21% greater profitability**.
Meeting For Goals makes this process easier. Our platform offers built-in templates, goal tracking, and follow-up tools. This ensures that skip level meetings are not just conversations—but catalysts for action.
What to Talk About in a Skip Level Meeting
One of the biggest questions we hear from leaders is: “What should I actually talk about in a skip level meeting?” The answer depends on your goals. However, there are a few key areas that every skip level meeting should cover.
Employee Concerns and Feedback
This is the heart of any good skip level meeting. Employees need a safe space to share what’s working—and what’s not. But opening up to a senior leader can be intimidating. Approach these conversations with:
- Empathy.
- Curiosity.
- A non-judgmental attitude.
Here are some helpful topics to explore:
- **Team Dynamics**
- **Workload and Burnout**
- **Communication Challenges**
- **Feedback on Leadership and Processes**
- “What’s one thing you wish leadership understood better?”
- “Is there anything that’s making your job harder than it needs to be?”
- “What’s something you’re proud of that hasn’t been recognized?”
Ask how the team is working together. Are there communication gaps? Is collaboration smooth? Are there any tensions that need to be addressed? Understanding team chemistry can help you identify areas where support or coaching is needed.
Check in on workload balance. Are employees feeling stretched too thin? Are there resource gaps that need filling? These conversations can help you spot inefficiencies before they escalate.
Find out how information flows within and across teams. Are people getting the updates they need? Do they feel looped in on decisions? Miscommunication is one of the most common—and costly—issues in growing teams.
Encourage employees to share their thoughts on management practices, workflows, and company policies. Their input can be a goldmine for improving operations and leadership effectiveness.
Try asking open-ended questions like:
Make it clear that their feedback is valued and confidential. Reinforce that this meeting is about listening—not judging.
Meeting For Goals helps you track feedback trends across meetings. This way, you can spot patterns and take proactive steps to improve.
Strategic Goals and Execution Challenges
Skip level meetings aren’t just about problems—they’re also a great time to talk strategy. When employees understand how their work connects to the bigger picture, they’re more motivated and focused. Use this time to:
- **Reinforce Company Priorities**
- **Check Goal Alignment**
- **Discuss Projects in Progress**
- **Encourage Innovation**
- **Improve Collaboration**
Share updates on company goals, upcoming initiatives, or changes in direction. Help employees see how their work fits into the broader mission.
Ask if employees understand how their individual and team goals support company objectives. If there’s confusion, clarify and realign.
Talk about key projects and what’s going well—or not. Are there roadblocks that leadership can help remove?
Invite employees to suggest improvements to processes, products, or services. Some of the best ideas come from those closest to the work.
Explore how well teams are working together. Are there silos? Could cross-functional communication be improved?
These conversations help you align execution with strategy—and give employees a chance to contribute in meaningful ways. With Meeting For Goals, you can link discussion points directly to strategic goals, assign follow-ups, and track progress over time.
Career Development and Team Culture
Another powerful use of skip level meetings is supporting your team’s growth and well-being. Start by asking about career goals. Where do they see themselves in a year or two? What skills would they like to develop?
These questions show that leadership cares about their future—and is willing to invest in it. Also, take time to talk about team culture. Ask:
- “What do you enjoy most about working here?”
- “What aspects of our culture should we protect as we grow?”
- “Are there behaviors or dynamics we need to address?”
These insights help you maintain a healthy, inclusive, and high-performing culture. Don’t forget to recognize achievements. Celebrating wins—big or small—boosts morale and reinforces positive behaviors.
Meeting For Goals makes it easy to document development goals, track progress, and follow up on mentorship or training opportunities. Want to explore more ways to build a strong team culture? Start using our free meeting templates at https://meetingforgoals.com/meeting_templates.
How to Structure a Skip Level Meeting
Now that you know what to talk about, let’s cover how to structure the meeting for maximum impact. Here’s a simple format that works well:
- **Start with Rapport**
- **Explore Feedback Topics**
- **Discuss Strategic Goals**
- **Talk Career and Culture**
- **Wrap Up with Action Items**
- **Follow Through**
Take a few minutes to break the ice. Ask how things are going, what they’re working on, or what they’re excited about.
Use open-ended questions to explore team dynamics, communication, workload, and leadership feedback.
Check in on alignment, project progress, and collaboration. Share updates and invite input.
Ask about growth goals, team culture, and what motivates them. Offer support where appropriate.
Summarize key takeaways and agree on any follow-ups. Ask if there’s anything else they’d like to share.
After the meeting, document insights and assign any action items. Following through builds trust and shows that you value their input.
Meeting For Goals helps you manage this entire workflow—from scheduling and preparation to follow-up and accountability.
Tips for Running Effective Skip Level Meetings
- Be consistent. Schedule skip level meetings regularly—quarterly is a good cadence for most teams.
- Keep it small. One-on-one or small group formats work best for honest conversations.
- Listen more than you talk. The goal is to understand, not to lecture.
- Avoid surprises. Let employees know the purpose of the meeting in advance.
- Be transparent. If you can’t act on feedback right away, explain why and keep them in the loop.
Want more tips? Harvard Business Review offers a great guide on how to conduct skip level meetings effectively: https://hbr.org/2022/07/how-to-make-your-skip-level-meetings-more-effective.
Conclusion
Skip level meetings are more than just a management tactic—they’re a strategic advantage. For companies with 40 to 70 employees, where complexity is growing and communication can get lost in the shuffle, skip level meetings reconnect leadership with the people driving results.
By focusing on employee feedback, strategic alignment, career development, and team culture, you can turn these meetings into high-impact conversations that drive real change. With Meeting For Goals, you have the tools you need to make every meeting count. From customizable templates to goal tracking and follow-up workflows, our platform helps you run meetings that are focused, effective, and aligned with your company’s mission.
Ready to transform your skip level meetings into a strategic asset? Sign up today at https://app.meetingforgoals.com/TenantRegistration/Register and start building stronger teams, one conversation at a time.
For more tips, tools, and templates, visit https://meetingforgoals.com.