How Should an Employee Prepare for a Skip-Level Meeting?

Opening up a skip-level meeting invite from your boss’s boss might leave your palms sweaty and your stomach queasy. Or maybe you’re even a bit excited. It’s hard to know what to expect if it’s your first time. How should you prepare for a skip-level meeting?

Here’s the good news: A skip-level meeting can tip the scales in your favor. If you’re prepared, it’s a chance for you to feel seen, connected to leadership, and more confident in your role and prospects. 

So, take a deep breath, keep reading, and learn how to prepare for the before, during, and after of your skip-level meeting.

Good management makes a difference. According to Gallup’s State of the Global Workplace Report, people working in companies with poor management strategies are 60% more likely to be stressed than people who have access to a positive workplace culture. That’s not much of a surprise. But brace yourself: Employees in these negative work environments experience “a lot of stress” about 30% more often than the unemployed. 

Companies that want a better understanding of their company cultures and business initiatives need a finger on the pulse of employee engagement. The purpose of skip-level meetings is for leadership to gain feedback about management performance and what it’s like for employees to do their jobs. To get that feedback, your boss’s boss invited you to a one-on-one meeting that bypasses your direct manager. 

These meetings aim to open communication channels, offer you direct access to senior managers, and share insight into broader company goals. Data collected from these skip-level meetings often affects leadership decision-making.

Skip-level meetings have many benefits—they are not meetings you should decline. You’ll get the chance to encourage rapport with senior management and build trust, which is valuable when company reports show turbulence. Plus, you can share your team’s accomplishments, paint a picture of your team’s alignment, request resources, and position yourself for growth.

As with most virtual team meetings, it’s typically management’s responsibility to set the agenda and share where and when your skip-level meeting will happen. But knowing what to expect helps you feel calmer and more prepared. Most skip-level meeting agendas balance individual development, team feedback, and company goals, with intentional time allocated for open discussion and goal setting.

When you receive the agenda, consider creating a Loom screen recording that includes data and thoughts about the topics from the agenda. This allows you to practice and review your performance—and generate a resource you might share with the manager.

The agenda could include discussions on career development goals, team challenges, employee feedback on management, company objectives, and any roadblocks. A good agenda will also include these elements:

• Meeting time and location

• Attendees

• Roles given to participants

• Prioritized list of items to be discussed

• Duration for each topic

• Action items framed as targeted skip-level meeting questions

• Goals to be achieved

• Supporting documents

A skip-level meeting agenda could look like this:

Skip-Level Meeting Agenda Template

Date: [Insert Date] 

Time: [Insert Time] 

Location: [Insert Location/Virtual Link] 

Attendees: [Employee Name], [Boss’s Boss Name]

Introduction (5 minutes): Personal check-in, an overview of meeting goals

Company strategy and goals (10 minutes): Discuss company vision, initiatives, alignment

Team feedback (10 minutes): Discuss team dynamics, challenges, leadership insights

Employee development (10 minutes): Share career goals, ask for advice on growth

Roadblocks and biggest challenges (10 minutes): Discuss obstacles, request guidance

Next steps and follow-up (5 minutes): Agree on action items, schedule future check-ins

Closing remarks (5 minutes): Express gratitude for the opportunity

Knowing the time constraints can help you prioritize feedback so your conversation is productive.

Now is your chance to leave an impression and create an open path for future communication. But it’s not just about showing up. You should be prepared to keep the conversation flowing and cover all your bases. Start here before you jump into goal setting:

1. Do homework. Explore the manager’s LinkedIn and chat with colleagues who have met with them.

2. Get the lowdown on logistics. Scope out the meeting format, venue, and what tech you’ll need.

3. Say hello. To give context before the meeting, use Loom to record an introduction where you share your role’s day-to-day responsibilities and a few memorable nuggets about yourself.

Think of your video intro as a bite-size asynchronous chat. Your skip-level manager can view the Loom recording when they have a second and then drop comments and reactions directly on the video. This introduction can help you both feel more comfortable, resulting in a more effective skip-level meeting.

Set goals for the meeting

Never go into the meeting without predetermined goals. According to Gallup and WorkHuman’s report findings, progressive companies encourage employees at all levels to give feedback and recognition. It’s a good meeting practice to give and receive both. Here’s how to prepare goals for your skip-level meeting:

• Make lists. Highlight wins, career aspirations, accomplishments, and any work-related issues.

• Be curious. Prep questions about the company, your role, and the manager’s responsibilities. 

• Share information. Submit any materials or reports ahead of time needed to guide the discussion.

• Clarify objectives. Set clear goals for feedback, career advice, or understanding of the company.

• Identify action items. Anticipate further discussions, needed resources, or decisions from the meeting. Having these in mind helps you steer the conversation effectively.

• Understand the manager’s role. Realize they need to build relationships, gain insight into the team and organization, and get feedback about the managers they manage or even about themselves.

Communicate effectively during the meeting

The day of the meeting is here. Maybe your heart’s pounding with excitement. Or maybe your mind’s racing with worry that you’ll forget your talking points. 

The Harvard Business Review describes the self-doubt or worrying employees often feel—whether it’s about looking like you’re “trying too hard” or even wasting a senior manager’s time. It’s a valid concern. After all, sharing feedback with your manager’s manager requires a delicate balance. Overstep, and you might be seen as bypassing your immediate supervisor. 

The meeting’s tone—conversational or structured—will guide how in-depth or formal you should be. Use active listening so you can tap into the underlying tone. You’ll want to be diplomatic, choosing your words carefully to navigate the conversation like this:

• Prepare mentally. Show up as your proactive, eager-to-improve self. Although you have a clear agenda, stay flexible and let the conversation flow naturally.

• Manage time well. Since you frontloaded a Loom intro video, you can spend less time on the small talk and use the meeting to dig deeper into learning and offering feedback.

• Share your experiences. If you’ve been with the company for a while, share valuable insights about past challenges. It shows you’re a problem solver committed to improving the company.

• Take notes or record the meeting. It's essential to keep track of takeaways, action items, and advice. If you’re in a video meeting, use Loom to record it while screen sharing and get a digital record for reference.

• Participate actively. If you’re too caught up in note-taking, you might miss out. Stay present and contribute meaningfully by recording the meeting and catching extra details later.

• Clarify and confirm. Ask for clarity on and confirm action items or expectations for follow-up. This can include setting timelines, identifying responsible parties, or scheduling further discussions. 

If you’ve used Loom to record your meeting, you can use it to check your notes or add more details to your notes from the recording. You can also share the link with your skip-level manager for their reference as part of your follow-up.

Follow up after the skip-level meeting

Ever feel like you’re taking on too many meetings throughout the week? Research by Fellow indicated that 40% of managers have more than 15 hours of meetings each week: stand-up meetings, walk-and-talks, lunch meetings, and so on. That means they spend almost 40% of their time in meetings. When you tack on reviewing meeting follow-ups, it’s easy to understand that they’d have meeting fatigue. You don’t want to add to the overload, so here’s how to follow up effectively:

• Understand expectations. Know who will send a recap or action items after the meeting.

• Send a thank-you email. Say something like, “Thank you for meeting with me today. I appreciated your insights on [specific topic], and I’m excited to work on [action item or next step].”

• Recap action items. Share takeaways with your boss’s boss for alignment and accountability.

• Set timelines and track progress. Review progress on your action items and make good on commitments made during the meeting.

• Stay engaged. Take the initiative to send periodic updates on broader company initiatives or personal goals to keep the conversation alive.

Consider sending a Loom video if you need to share your meeting notes. It’s a quick, effective way to add context while respecting your skip-level manager’s time. You can record and share a personalized video with the click of a button. Since Loom videos are also quick and easy to view, your boss’s boss isn’t likely to ignore them and won’t have to spend precious time reading a lengthy email.

Let your skip-level manager know you’re also open to receiving feedback and questions via Loom videos. They’ll appreciate how Loom makes this task much quicker. 

Loom doesn’t just benefit your manager—it saves you time, too. Loom AI polishes your videos by removing silences and filler words like “uhms” and “uhs.” It also creates titles, chapters, and summaries, and it can turn any video into a document, like meeting notes. This means you can skip the part where you parse through the transcript to create your own document—Loom automatically does this for you. You can then go through and tweak the document to your preferences.

Skip-level meetings don’t have to leave you feeling anxious. The right tools can help you connect with senior leadership, feel heard, and boost your confidence in your role. 

Loom can help you with all stages of your skip-level meeting. Start off by introducing yourself or connecting with a Loom video. Next, prepare for your meeting by recording your screen while running through the brief. Then, share the link so your skip-level manager has all the context they need. Then, you can use Loom to record the meeting itself for future reference so no important details fall through the cracks. 

Loom is an effective medium for post-meeting follow-up communications and action items. You can have a chain of ongoing Loom discussions as you both check items off the action item list. Or maybe your boss’s boss asked to see an example of one of your projects. Using Loom, you can record your screen as you explain your process and the end result.

Want a meeting sidekick that makes you look good? Enhance your preparation for skip-level meetings with Loom.