As your company grows, you begin to notice the change. You might have once known what everyone was working on. Now, you’re hearing about problems weeks after the fact or feeling a disconnect between what your leadership thinks is happening and what people are actually experiencing on the ground. Your managers may claim that all is well, but you have a hunch there’s more to it. This “information gap” is normal, and a skip-level meeting is one of your most powerful tools to bridge this gap.
What is a skip-level meeting
A skip-level meeting is exactly what it sounds like: a meeting where high-level executives bypass the middle layers of management and speak directly with rank-and-file employees.
For example, an engineering supervisor would talk to the engineers who report to their engineering manager.
It's almost always one-on-one, not like an all-hands or town hall meeting. This format is crucial for creating a safe place where employees can be honest. It's also important to be clear on what they are not. It does not serve as performance feedback for the employee. Nor is it a secret "check-up" designed to ruin a middle manager.
When handled correctly, a skip-level meeting serves as a tool for understanding an organization's health, gathering unfiltered feedback, and turning high-level strategic goals into real-world practice.
What is a skip-level meeting for
As a top manager or founder, any information that comes to you will have to pass through the filter of your subordinates; this is their job. However, before you are too quick to act on what they say, talk to the people who are on the front lines. They may have an entirely different view, and one that needs to be heard.
- Builds trust: Skip-level meetings show employees that senior leadership is accessible and genuinely cares about their experience.
- Uncovers hidden issues: An employee might never tell their direct supervisor about unclear team goals or burnout. However, they may be willing to share those insights with a senior leader who can see the big picture.
- Bridges the gap between leadership and employees: It links up the "why" of company strategy with the "how": the day-to-day task structure. You find out what's working and what’s not, directly from those doing it.
- Boosts workforce retention: When people feel heard and know they have a direct line to top management, their involvement and loyalty improve remarkably.
How to conduct effective skip-level meetings
Running effective skip-level meetings means more than just setting up an appointment. Knowing how to run a skip-level meeting is a well-thought-out process that brings real value to both the company leadership and rank-and-file employees.
Step 1 — Create a meeting agenda
A skip-level meeting agenda helps ensure consistency. By preparing one, employees will appreciate that you respect their time. This plan will also guide your discussion, making sure you don't miss important topics.
You can rely on Plaud Note to create a good meeting agenda. Plaud Note’s meeting templates can help you save time. You can create a standard agenda for your skip-level meetings and then simply reuse it in subsequent meetings.
Step 2 — Prepare open-ended questions
Prepare broad questions to avoid killing the discussion with "yes" or "no" answers. These questions also prompt storytelling and the sharing of details.
Below are some of the best skip-level meeting questions:
- "How can leadership better support you?"
- "What's something we're doing right now that you think is a waste of time?"
- "If you were in my job, what is the first thing you would fix?"
- “What do you most enjoy about working on your team? What is the most difficult part to navigate?"
- "Are you getting what you need from your direct manager to be successful?"
Step 3 — Invite employees personally
Avoid releasing impersonal, cold calendar invites. The first thought an employee has after receiving such an invite from a top leader is: "Am I in trouble?" Instead, personally invite them with a warm, clear email to set the right tone from the start.
This is an example of a good personal invite:
"Hi [Name], I'm scheduling informal 30-minute chats with all the members of the team. This is a regular part of how I stay connected with everyone in the organization. It's not a performance review, just a chance for me to learn from your perspective. I'd love to hear what's going well and what's not."
Step 4 — Automate meeting notes
In the meeting, your only task is to listen and be there. How can you do that if you're spending all your time either looking down into a notebook or typing? It may break the connection and make the employee feel like he is just feeding you data.
This is the biggest challenge of one-on-one meetings. You cannot fully participate when your hands are stuck taking notes for both sides. With the help of a device such as Plaud Note, that problem is solved. You put it on the table, focus on the discussion with your subordinate, and develop a real rapport. The device records and transcribes the whole meeting, so that nothing is lost. In addition, it automatically summarizes key points for you to reference later.
Step 5 — Communicate next steps
The meeting may be over, but it certainly shouldn't just end in a black hole. The employee needs to know that their thinking was heard. This doesn't mean that you have to promise them everything they want. Be candid with them. If they share a good idea, say, "That's a great point. I will bring it up at the next board meeting." If they share a problem, say, "Thank you for telling me that. I will look into it." This principle of accountability is crucial to building trust.
Step 6 — Send a thank-you email
Within 24 hours, send a short, private note. It provides closure and reminds your employees of their contribution. It can be a simple one-liner to make them feel valued and respected:
You can say: "Thank you for chatting with me, [Name]. I'm deeply grateful for your perspective."
Challenges in running skip-level meetings
These meetings are powerful, but that doesn't mean they're easy. Here are the common hurdles and their possible solutions.
- Employee discomfort: Most employees feel anxiety, uncertainty, and have unclear expectations when meeting a senior leader. They are nervous about what to say and may fear their boss will find out.
How to overcome: Over-communicate the purpose (it's not a trap!) in your invite. This directly addresses unclear expectations. Start the meeting with a simple icebreaker to reduce discomfort and build rapport.
- Bias toward outspoken employees: It's easy to mistake a quiet employee for an employee with no problems. You may only get feedback from the most outspoken people.
How to overcome: Use open-ended questions to draw out quiet employees. Give them silence to think. To initiate participation, you can use anonymous feedback tools.
- Manager resistance: The middle manager (your direct report) is the person most likely to feel threatened. They will think you are "checking up" on them or undermining their authority.
How to overcome: Be transparent. Communicate with your managers before and after the meetings so they understand the purpose. Frame it as a way to help them: "I'm doing this to find out how I can better support you as a leader and what resources your team needs."
- Scheduling and time constraints: For the company leadership, these meetings are a huge time commitment.
How to overcome: Keep the meetings short—30-45 minutes is plenty. Batch your employees by team, and schedule them at a time that's outside of the employee's peak work hours.
Turn conversations into insights with Plaud Note
You held 10 skip-level meetings, each lasting between 1.5 and 2 hours. Now what? The true task is translating each separate conversation you have into actionable points.
This gap can be bridged by Plaud Note and Plaud AI. Instead of reading all the transcripts by hand, the AI can analyze conversations in one go. It generates action items that make your meetings actionable fast.
You can dig deeper with the Ask Plaud feature. This allows you to ask the AI questions across all your past records. For example, you could type "Search all meetings for 'Tool X'" to find every mention, or ask "What are the main suggestions for improving onboarding?" Plaud AI will search your records, find the keywords, and give you synthesized insights and recommendations. Plaud Note helps you spot these patterns and lay out a clear path for improvement.
Conclusion
A skip-level meeting is far more than just a calendar entry. It is a crucial communication channel that, if handled properly, fosters trust, lets hidden problems emerge, and keeps an expanding company together. These meetings are not something that you'd "like to have," they're a necessity for any leader wanting to determine the pulse of their organization. With a clear process and the right equipment, you can turn these simple chats into one of your most powerful tools as a leader.
FAQ
Are skip-level meetings good or bad?
They present a good leadership tool. The only time they become "bad" is when they are not run properly: for example, when used to undercut a manager, when feedback isn't kept confidential or shared generously, and when there is no action ever resulting from the feedback, which soon erodes trust.
How common are skip-level meetings?
These are common and considered best practices within healthy, large organizations, especially in the tech industry. Growing startups are also increasingly adopting skip-level meetings as they scale, so that senior leadership does not become isolated.
How often should I hold a skip-level meeting?
It depends on the size of your team. A good cadence for most senior leaders is to meet with each skip-level employee once or twice per year, which allows you to build a relationship and track progress over time.
What are the don’ts in a skip-level meeting?
Do not use the meeting for performance reviews. Make sure not to overpromise. Most importantly, do not go to the employee's direct manager and say, "Jane told me that." All feedback must be anonymous and shared only as general themes.
