How to Run Skip-Level Meetings

What are skip-level meetings?

Skip-level meetings are held between a founder, or a senior leader, and employees under middle-management.

Essentially, you’re meeting with your direct report’s direct reports.

Skip-level meetings are about tackling departmental silos and information turf wars by enabling a free flow of information. Regular communication with leaders and decision-makers helps employees believe that their feelings and contributions are valued.

This type of meeting is a great way to build trust within your company and provide a level of transparency that many other companies don’t. As an executive or senior manager, you have a unique responsibility to ensure that all staff members are satisfied in their roles and contributing to company goals.

What are skip-level meetings meant to achieve (and how can they go wrong)?

Skip-level meetings are a great way to build rapport with employees at your company and help them feel seen in their roles by more than just their direct managers.

The purpose of the meeting is to get honest feedback from your employees and create better relationships across your organization. It’s also about keeping leaders from missing critical information about how their company actually runs.

The purpose of a skip-level meeting is not to determine a manager’s effectiveness in their role or listen to your skip-level team members vent about their leadership.

An effective skip-level meeting helps you understand how team members feel about the company, their roles, their goals, and how you can improve employee satisfaction and retention.

Let’s say you’re a startup founder, and until last year, you oversaw every department in your organization. You’ve recently taken a step back to focus on growth, but you don’t want to lose focus on the well-being of the people helping you build your company.

Skip-level meetings are a great way to quickly and personally tune back into your organization, serving as a pulse check and providing an opportunity to gather innovative ideas.

However, this isn’t just another opportunity to schedule a meeting to suck up people’s time. Too many meetings can be highly disruptive. To combat this, have a clear objective in mind before adding skip-level meetings to your employees' already-swamped calendars, such as checking the temperature following a hectic period.

Or, hold your skip-level meetings asynchronously. This allows people to share their contributions without losing too much productivity time—but more on that later.

First, let’s discuss a few benefits of skip-level meetings and how they can go wrong.

Pros and cons of skip-level meetings

Skip-level meetings are a great way to learn more about your contributors and ensure they’re happy with their work environment. There are a few different pros and cons to keep in mind and help ensure your skip-level meetings are successful.

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Pros	Cons
Improve transparency in communication Lower-level employees don’t always have direct access to senior leaders, so skip-level meetings provide an outlet to talk to their boss’s boss. Build trust in your employees and help them realize their work matters to the bottom line.	Knowing who to meet from large teams Does your company have hundreds of employees? Even when conducting meetings asynchronously, meeting with everyone would take entirely too much time. Speak to your managers to decide who would be the most valuable to speak with from each team.
Keep employees happy and engaged Disengaged employees report miserable working experiences. Create a line of communication with leadership that helps employees feel more engaged at work, leading to better satisfaction.	Miscommunication during meetings Be aware that you won't have all the information your managers have, so you'll be missing context. Avoid committing to anything without speaking to their direct manager first. After all, the goal is not to override your team leaders but to assist them in discovering pain points.
Promote new ideas and initiatives Employees may have had ideas to help the company’s bottom line that they haven’t felt comfortable bringing up yet. Give front-line employees an outlet for bringing up these suggestions.	The potential for undermining your middle managers Don’t let your skip-level meetings turn into a vent session for employees – you’re not here to listen to gossip about your managers. Stick to your agenda and don’t let the conversation get derailed.
Discover obstacles you were unaware of The managers directly below you may not have been aware or forthcoming with some of the problems your team is facing. Uncover roadblocks you may not have known about otherwise with skip-level meetings.	Meeting overload kills productivity Your employees could already be suffering from meeting overload. Don’t impede their productivity with yet another meeting. Prioritize asynchronous communication methods for your discussions.
Align employees with your long-term goals and vision Skip-level meetings can be great ways to get your team excited about long-term goals and how they can contribute. Be sure to set a part of the meeting aside to cover the team’s goals.

Start with the basics: Create your skip-level meeting agenda

Don’t head into your skip-level meetings without an agenda. These types of meetings can be sensitive (especially if you end up meeting with disgruntled employees), and you want to keep the conversation on the right track.

Create an agenda document for each skip-level meeting and have each person you meet contribute to it (especially when holding an asynchronous skip-level meeting). Add questions you want to ask and send the document to the employee ahead of time so they can prepare their responses.

You can also send a voice message or screen share with Yac, asking the employee to add in their own questions. Using voice communication helps you avoid any misunderstanding about the process.

Break the agenda into sections, like building a connection with the employee, discussing feedback and ideas, and talking next steps. Be sure to emphasize that you are not making decisions in this meeting but that you will discuss things to implement with their manager(s).

Let’s get back to our startup founder example. It’s now been a few months since you’ve had your hands in each department in the company, and you want to make sure that goals are still being met, employees are still happy, and your company mission is well-known.

You’ll focus on these objectives as you create your agenda and send them to your shortlist of representative employees in a screen share. It might sound something like this:

“Hey Matt, here are a few questions I’d like to cover to get to know how you’re feeling about working with us and if there’s anything we can do to make your day-to-day run smoother. I’d also love your input on an initiative we’re running next quarter. Please can you think about these questions here in the doc and send me a Yac back with your answers by Friday?”

With Yac, you can even record this on your phone while on the go.

As the skip-level meeting host, keep your objectives in mind when creating your agenda and deciding which specific employees to meet with.

Here’s a sample agenda template you can use:

Add in your list of questions, then leave a space open for adding the next steps at the end of your meeting. Duplicate your agenda for each team member you end up meeting with.

Must-ask skip-level meeting questions

Stay on track with a list of specific questions. To keep your meetings from taking too much time, stick to the top five to seven questions you’re most interested in learning the answer to and add them to your agenda.

Here is a shortlist of skip-level meeting questions to get you started:

What do you think about the company’s mission?
What projects have you most enjoyed working on?
What is the biggest obstacle you face in your day-to-day responsibilities?
What suggestions do you have for improvement in the company?
How could we better leverage your skillset?
What should we start doing as a company?
What should we stop doing as a company?
What are your goals for the next 18 months years?
How can we help you reach those goals?
Are you happy in your role? If not, how can we make you happier?
Is there anything I can do to help you succeed in your role?
What is your favorite or least favorite part of working at this company?

How to hold a successful skip-level meeting (and how asynchronous communication comes into play)

If you’re considering having a skip-level meeting, let’s talk through the steps to its success—and to ensure it doesn’t take up a ton of your time.

With these steps, you can easily hold an asynchronous meeting that helps you gather the data you’re looking for without being a major time suck.

Communicate beforehand

Let your managers and your skip-level team members know that you’ll be holding these meetings, especially if it’s the first time you’ve tried this type of team meeting. The easiest way to do so is with an asynchronous voice note with a tool like Yac.

Be transparent about what they can expect and why you’re doing this, so your managers understand the purpose and are kept informed.

Make sure you’re not holding these in response to some kind of issue. There are more appropriate ways to determine if an employee or a manager is underperforming.

Instead, consider having skip-level meetings at a half-yearly or yearly meeting cadence so your leadership team knows when they will come up again.

Lighten everyone’s calendar with asynchronous meetings

Depending on how many direct reports you have and how many direct reports each of them have, you might be facing a lot of meetings. And when your employees are attending an average of 21.5 hours of meetings per week as it is, you don’t want to put added stress on their plates.

To lighten the load and make sure you’re not interrupting everyone’s workday, hold them asynchronously. This way, people can fit your skip-level meeting into their schedule where it makes the most sense.

Here’s a quick how-to for conducting a successful asynchronous skip-level meeting:

Send your agenda via Yac (you can link your Google Doc or Notion page in the message). Set expectations and explain the purpose for your meeting.
Explain that your questions in the meeting template are a guide for your conversation and give them some time to think about their response to each (a day or two should be fine).
Leave space for your meeting attendee to input their questions or concerns.
Once the attendee has submitted their questions, begin the conversation over voice messages. Ask the first question in a private 1-to-1 and ask your employee to reply in a thread.
Follow up in the same thread if you have any additional questions or comments about the response.
Continue asking questions, giving each new one its own heading to keep track when it comes time to review your chat.
Share your findings with the necessary stakeholders to continue working towards organization-level goals.
Pass along to managers any relevant insights that may support your employees, such as better-fitting roles or identified leadership potential.

Let’s head back to our startup founder example one last time. You’ve just asynchronously met with someone from your marketing team to see if they’re happy with a new process. You’ve received loads of great feedback, and you’re looking forward to discussing the new ideas with the marketing director.

Your next steps are to compile all your notes into a single source of truth you can share with the team leader. You’ll want to collaborate on the next steps to put these ideas into practice, so be sure to include a section for this in your document.

Build rapport

This might be your first time meeting with these employees directly, so starting with small talk can be a great way to kick these meetings off.

If you’re holding synchronous meetings, spend a few minutes getting to know each other a little better. You can even make this the first item on your agenda.

If you’re doing these meetings asynchronously, record a voice message sharing a bit about yourself, your weekend, your hobbies, or anything else. Then share a personal message with each of your meeting attendees in a 1-on-1 and encourage them to do the same.

Even as a skip-level manager, it’s a good idea to have a better understanding of who works for your company and what they enjoy doing outside of work.

Ask for feedback and ideas

Ask your questions and see what ideas each team member has to improve things on their team or help them succeed better in their role.

Because you’re not on the front lines like a lot of these employees, you likely have a much different idea of how certain processes work. Take what each team member has to say to heart, especially when talking about roadblocks.

You want to foster an environment that helps everyone get their best work done, so take note of any common themes so you can discuss them with their direct managers.

Be sure to also note any ideas or suggestions for new projects. It’s easy to lose track of ideas if you have multiple meetings, so be meticulous about attributing ideas to the right people. This way, you know who to reward for an outstanding contribution. You’ll also know who wants to be involved or even lead the next project.

Debrief team leaders

After you’ve held all of your skip-level meetings, set aside time to discuss your findings, ideas, and feedback with managers on the team.

Consider sending an async screen share to other leaders to discuss insights and issues (if there are any). Or, as we mentioned before, you can easily compile all of your main discussion points into a document so you can all work on the next steps at convenient times.

To really make the most of your skip-level meetings, make sure that something comes of them. Show your employees that their feedback is being heard and changes are being made, otherwise they may be less forthcoming in future meetings.

Key takeaways:

Skip-level meetings are a great way to keep your ear to the ground and understand how your employees feel about the company. However, they can be time-consuming, so you want to consider how asynchronous communication can help streamline the process.

Use async to free up calendars and ensure your team remains productive, even while valuable conversations are being held.

Take advantage of tools like Yac that can help you run seamless asynchronous meetings, minimizing calendar events and increasing productivity while keeping your employees happy.