How to Run a Skip-Level Meeting – Purpose, Tips & 5 Must-Ask Questions

A skip-level meeting is exactly what it sounds like: a meeting where a manager speaks directly with employees who normally report to their direct reports, effectively “skipping” one level in the hierarchy.

The purpose is simple but powerful – it gives leaders a way to hear unfiltered feedback, understand the reality of day-to-day operations, and build trust with employees who don’t usually have direct access to them.

According to Gallup’s State of the Workplace report (2024), only 21% of employees feel strongly connected to leadership. That gap is often because communication flows top-down and gets filtered through layers of management.

A skip-level meeting solves this problem by giving leaders a direct channel to employees, showing that they value open conversation and honest insight.

Done well, skip-level meetings make employees feel heard, help leaders catch issues early, and strengthen culture. Done poorly, they can feel like micromanagement or a “gotcha” session. The key is preparation, empathy, and asking the right questions.

The Purpose of a Skip-Level Meeting

At its core, a skip-level meeting serves three main goals:

These meetings are not about undermining middle managers. Instead, they’re a supplement that strengthens alignment across layers of the organization.

Tips for Running an Effective Skip-Level Meeting

1. Clarify the Intent Up Front

Employees may initially feel nervous – after all, meeting with “the boss’s boss” can feel intimidating. The leader should clearly state the purpose at the start: this is not a performance review, it’s a chance to listen and learn.

2. Avoid Putting Managers on the Spot

One of the biggest risks is that employees feel pressured to “complain” about their direct manager. To prevent this, leaders should frame questions around processes, communication, and improvement, not personalities.

3. Create Psychological Safety

Encourage openness by reassuring employees that their feedback won’t be held against them. Leaders should listen more than they talk, take notes, and thank employees for their honesty.

4. Keep It Structured

A skip-level meeting should not feel like a casual chat without direction. Having a clear structure – a few warm-up questions, a main discussion, and a closing summary – helps make the conversation useful for both sides.

5. Follow Up

The most important step is often the one leaders forget: acting on the feedback. Employees will quickly lose trust if they share input but never see any change.

Even small updates like, “I heard this in our meeting, here’s what we’re doing,” build credibility.

Sample Structure for a Skip-Level Meeting

5 Must-Ask Questions in a Skip-Level Meeting

Not all questions are created equal. The best ones are open-ended, neutral, and focused on improvement rather than blame. Here are five that consistently work:

Start with Positives

1. “What’s working well in your team right now that you’d like leadership to know about?”
   Opens on a positive note and shows you’re not only looking for complaints.
2. “What’s one thing your team does really well that other teams could learn from?”
   Highlights best practices and encourages pride in good work.
3. “Where do you feel your work has the biggest impact on the company’s goals?”
   Helps employees see the connection between their role and the bigger picture.

Understand Challenges

1. “What’s one challenge that slows you down or makes your job harder than it needs to be?”
   Surfaces operational bottlenecks you might not otherwise hear about.
2. “If you could spend less time on one task and more time on another, what would you change?”
   Uncovers inefficiencies and hidden time drains.
3. “Do you feel you have the resources and support you need to do your best work?”
   Checks whether gaps in staffing, training, or tools are holding people back.
4. “What’s something customers are saying that leadership may not fully realize?”
   Brings frontline customer insights directly to leadership.

Improve Communication and Leadership

1. “How is communication across the company working for you?”
   Helps identify breakdowns in information flow between teams.
2. “How do you prefer to receive communication or updates from leadership?”
   Reveals whether emails, town halls, or manager briefings actually work.
3. “What’s a recent decision leadership made that helped (or hurt) your ability to do your job?”
   Gives feedback on how big decisions translate to the day-to-day reality.

Encourage Feedback and Ideas

1. “If you were in my position, what’s one change you would make?”
   Invites employees to think like leaders and share practical improvements.
2. “What’s one idea you’ve had recently that could improve how we work?”
   Shows you value creativity and initiative, not just execution.
3. “What’s one thing you wish leadership understood better about your role?”
   Uncovers blind spots and deepens empathy between levels of the company.
4. “What motivates you most in your work here?”
   Helps leaders understand what keeps employees engaged and what risks losing them.
5. “Is there anything you’d like me to know that we haven’t talked about yet?”
   Gives employees a final, open chance to share something important.

Final Thoughts

@vincentsanderson Replying to @sketchychief hope these help! #manager #management #managementskills #leadership #work ♬ original sound – Vincent Sanderson

Skip-level meetings are not about replacing managers or bypassing normal reporting lines. They’re about creating another bridge between leadership and employees – one that allows for honesty, feedback, and connection.

The best leaders use these sessions not as interrogation, but as an opportunity to listen, learn, and show that they care.

When employees see that their input leads to action, skip-level meetings turn from a formality into a cornerstone of trust. And trust, as every strong company knows, is the foundation of performance and culture.