Ever felt like there’s a disconnect between leadership and the rest of the team? Well, there’s one type of meeting that is like the ultimate ultimate weapon for closing that gap; the skip-level meeting.
In this guide, we’ll show you how to organize skip-level meetings to bring employees out of their shells and share their insights. Use our guide to help your team feel more connected, heard, and motivated than ever.
What exactly is a skip-level meeting?
A skip-level meeting is when someone in senior leadership meets directly with employees who don’t report to them, “skipping” the manager in between. A skip-level meeting can be a powerful tool to break through the usual layers of hierarchy and get a more honest, unfiltered view of what’s happening across the company.
In general, a skip-level meeting won’t involve your middle managers. The focus is definitely not to undermine middle management, but to build deeper connections between employees and people at the top. Leaders get a clearer sense of how their strategies are playing out on the ground, and employees get a chance to be heard, ask questions, and share what’s really working (or not working) in their day-to-day.
They can be informal, one-on-one, or small-group conversations. Organizing a skip-level meeting at the right time can catch issues before they get a chance to grow. At their best, they give leadership a full understanding of team dynamics, while employees are able to open up and express themselves freely.
How you can organize the perfect skip-level meeting
Skip-level meetings work best when they’re thoughtful, intentional, and built on trust. A quick calendar invite isn’t enough; you must make a few preparations to maximize the strength of a skip-level meeting.
So if you’re looking to organize the perfect skip-level meeting for your teams, we’ve got every aspect covered below.
1. Know your purpose before you book the room
Skip-level meetings can be a powerful tool, as long as they are more than just ticking a box on a sheet. Really get to grips with your goal well beforehand. What is the underlying purpose of the meeting? Are you checking in on team morale? Gathering feedback about a recent change? Exploring how different departments collaborate? Deeply knowing your purpose helps you ask the right questions, steer the conversation, and (most importantly) avoid turning the meeting into awkward small talk.
Get into the mindset that helps you ask more specific questions. Instead of “How’s everything going?” ask, “What’s one thing that’s working really well in your team, and one thing that’s slowing you down?” The more intentional you are, the more valuable your skip-level meeting will be for everyone. So in short, know the meeting’s purpose!
2. Keep it casual (not chaotic!)
This isn’t a job interview or a quarterly review, so try to skip the stiff vibe. A relaxed tone puts people at ease and opens the door for honesty. That doesn’t mean showing up unprepared, though. Have a few friendly questions or conversation starters in your back pocket, especially if the person you’re meeting isn’t naturally talkative.
You could even think about more casual settings, too, like walk-and-talks, coffee chats, or even hosting the meeting during an offsite can create a special atmosphere that’s remembered long after. You want employees to feel safe, heard, and open - not like they’ve been suddenly called into the principal’s office.
3. Don’t use it as a surprise performance review
This one’s big. A skip-level meeting should feel like a two-way dialogue, not a secret audit. If employees walk in expecting a friendly chat and walk out feeling like they’ve been assessed, you’ve lost trust before you’ve built it. Steer clear of reviewing KPIs or critiquing performance unless that’s explicitly the meeting’s purpose (which it rarely should be).
Remember: one of the main goals for a skip-level meeting is to learn exactly how things are running on the ground. That includes things like what’s working, what’s broken, and how people feel about their work. Think of it more like being a curious observer than a boss with a checklist. If anything performance-related does come up, make it clear you’re gathering context, not giving grades. Keep the focus balanced between looking at past mistakes that need improving and the future goals you’re aiming for. Stay in the present moment with your teams, they’ll feel better for it.
4. Give people a heads-up (and set the tone early)
While most of us do love a surprise gift or birthday party, we can’t think of anyone who likes a mystery meeting invite with workplace higher-ups. To avoid unnecessary nerves, let attendees know exactly what the meeting is about and why it’s happening. A simple message like, “I’d love to hear your perspective on how things are going in the team,” goes a long way. It tells them this isn’t a disciplinary chat or a backdoor performance review, and the meeting will be a place where their voice is heard.
If you take a bit of time to set the tone and let everyone know it’s a safe space, you’ll get much better results. Encourage everyone to ask the kind of questions that forge new meeting ideas. When people know what to expect, they’re more relaxed, more open, and more likely to give you something real, not just what they think you want to hear.
5. Don’t forget the middle managers
Skip-level meetings work best when they’re not treated like secret missions. Let middle managers know that the meetings are happening and be transparent about the purpose—reassure them it’s not a workaround to undermine their role. You’re simply looking for unfiltered insight, and you’ll be sharing back relevant themes or feedback in a constructive way.
You really need to make sure your middle managers still feel looped in (rather than left out). This way, they’re far more likely to support the process—and even encourage their teams to be open. Skip-level meetings are about strengthening communication across layers, not cutting anyone out of the conversation.
6. Prepare a few open-ended questions
While you want the meeting to feel relaxed, that doesn’t mean winging it. A few well-chosen open-ended questions can be the difference between a meaningful conversation and an awkward silence. Focus on prompts that encourage reflection and generate new meeting ideas. Here are a few to try:
- “What’s something you wish leadership understood better?”
- “What’s a recent challenge your team faced—and how did you handle it?”
- “If you could change one thing about how we work, what would it be?”
Keep it light where possible, but leave room for deeper insights. Good questions show curiosity, and they’re often the fastest route to real, valuable feedback.
7. Listen like you mean it
It’s crucial to remember that in a skip-level meeting, you’re there to listen, not just lead the conversation or jump into fix-it mode. One of the quickest ways to shut someone down is to interrupt, over-explain, or immediately defend a decision they’re questioning. Skip-level meetings rely on trust, and trust starts with truly listening. That means letting people finish their thoughts, asking follow-up questions, and showing you’re present.
There might be times with a little bit of silence, but that’s fine when everyone feels comfortable, and can even lead to more thoughtful and honest insights. Take notes and make eye contact when it reassures. When people feel truly heard, they open up more. And when leadership shows curiosity instead of defensiveness, employees are far more likely to be themselves, which is exactly what you want from a meeting like this.
8. Keep it confidential - but not forgotten
Honest feedback doesn’t happen unless employees know their input is safe. Make it crystal clear that what’s shared in the room stays in the room. You can still share themes or insights more broadly, but anonymize anything that could trace back to a specific person. The goal isn’t secrecy—it’s psychological safety.
That said, don’t let feedback vanish into a black hole either. Summarize key points, identify patterns, and turn insights into meaningful follow-up actions. This balance of confidentiality and visibility is where trust really grows. People will come back to future meetings more willing to speak up, knowing they’re not just being heard, but respected.
9. Don’t try to “fix” everything on the spot
It’s tempting to jump into problem-solving mode the moment you hear something you can “fix.” But resist the urge. The real purpose of a skip-level meeting is to gather insight, not to start trying to fix the entire world. If someone shares a pain point, thank them for their honesty and let them know you’ll follow up after looking into it properly. That pause gives you space to check with middle managers, get more context, or spot wider trends.
Immediate fixes might feel satisfying, but thoughtful, coordinated changes are what actually move the needle. So instead of reacting in the moment, focus on listening, absorbing, and making a plan. Show your team you take their input seriously, and that you’re thoughtful about what comes next.
10. Be consistent with your cadence
If you want real results, you’ll need to build consistency into your approach. Think quarterly check-ins, offsite meetings, or rhythmically timed meetings that sync with team goals or review cycles.
Whatever your meeting cadence, make it clear to employees that these meetings aren’t just “a one-time thing.” That predictability helps people prepare, reflect more deeply, and take the meetings seriously.
By getting your meeting cadence right, you’ll build better relationships, track feedback themes, and see progress between conversations. Plus, knowing when the next skip-level is coming up gives employees a chance to surface feedback in a more timely, structured way. Trust doesn’t build in a single session, it needs to grow with each meeting and each exchange.
11. Follow up and follow through
A great skip-level meeting doesn’t end when the call does. What you do next matters just as much as what was said. Take time to process everything you heard, look for common themes, and (this part is key) circle back. Let people know what you’re doing with the information they shared. Even small follow-ups like “We’re exploring that last meeting idea now” or “Here’s how we’ve acted on your feedback” can go a long way.
When employees see that their input leads to real outcomes, trust skyrockets. On the flip side, skipping the follow-up makes it seem like the meeting was just for show. Show them you’re not just listening—you’re listening with the intent to learn, grow, and act.
Level up skip-level meetings with an offsite retreat
Skip-level meetings are perfect for bridging the gap between leadership and employees. They can uncover insights that don’t always make it to the surface. But if you really want those conversations to flow? Take them on an unforgettable offsite retreat.
A Surf Office team retreat gives your office superstars the perfect environment to connect without distractions. Casual skip-level chats over coffee or structured team-building activities, everything is designed to bring your people closer together, naturally.
Here’s what we offer:
- Stress-free transfers? We got you! ✅
- Quality-assured accommodations? Check! ✅
- Engaging team-building activities?Our speciality ✅
- Restaurant reservations? That's on us! ✅
- Expert retreat planning assistance? Of course, we have this covered! ✅
- Onsite support, tailored to your needs? Absolutely ✅
Not only this but we also have access to 160+ locations around Europe, APAC, the US, Latin America, and now Africa, meaning the sky is your limit when it comes to choosing the right location for you and your team.
Spaces are limited, so get in touch with us today!
