“Wait, I have a meeting with my boss’s boss? Why? What am I even supposed to say?”

That was the text a colleague sent after receiving an unexpected calendar invite. She wasn’t being dramatic – just genuinely puzzled. It wasn’t a performance review. No project deadline loomed. She wasn’t “in trouble”.

“Not sure how this is going to be useful,” she added.

That reaction is more common than you’d think.

Many people are sceptical of skip-level meetings. They feel awkward, unclear, or even political. But that hesitation often causes people to miss what could be one of the most underused opportunities in their professional lives.

In this week’s post, let’s take a closer look at skip-level meetings: what they are, why they matter, and how to make the most of them – whether you’re an employee or a senior leader.

What Is a Skip-Level Meeting?

A skip-level meeting is a conversation between an employee and someone a level (or more) above their direct manager. It’s not about bypassing anyone – it’s about expanding lines of communication that would otherwise stay closed.

Why is this necessary?

In any organization, information tends to travel through layers. Along the way, it gets filtered, softened, or sometimes lost entirely. Likewise, employees often don’t have direct access to senior leaders – the ones making decisions that impact their work.

If you’re an Employee: Making the Most of a Skip-Level Meeting

Let’s go back to that groan – “Why am I meeting my boss’s boss?”

Here’s the short answer: It’s an opportunity.

Not the cheesy, “network your way up” kind. But a real chance to understand what matters at the next level, share your perspective, and build relationships that can shape your growth.

What you can Gain

• A window into strategy. Senior leaders see patterns. They’re looking around corners. A skip-level meeting lets you understand not just what the company is doing, but why. That helps you make smarter choices in your day-to-day work.
• Visibility without self-promotion.. A skip-level meeting gives you a chance to be seen – not by broadcasting your achievements, but by showing up prepared, thoughtful, and engaged. When a senior leader hears how you think, what you’re working on, and how you’re contributing, they begin to associate your name with value. That kind of visibility is subtle but powerful. It’s not about bragging – it’s about being on their radar in a meaningful, authentic way.
• Candid feedback. Sometimes your direct manager is protective, busy, or just unsure what feedback to pass along. This is your chance to ask directly: “How does my work show up at your level?”
• Career clarity.  Want to grow? Ask what skills matter at the next level. Ask what gaps you could fill. Don’t just assume hard work will get noticed – it rarely works that way.

How to Prepare

“Play it by ear” is not the right approach for a skip-level meeting. Going in unprepared will make your senior manager feel like you wasted their time. You will be unlikely to get a second meeting!

Here are six recommendations to help you get the most out of your skip-level meeting:

1. Loop in your manager (yes, really).

Don’t go behind anyone’s back. Let your manager know you’ve been invited (or want to request a meeting) and be clear about why. “I’m hoping to understand our team’s role in the broader strategy” is a solid reason. When you handle this openly, it builds trust—not suspicion.

2. Define one clear goal.

Senior leaders are generally short on time, so it’s best to keep the discussion focused and productive. What do you hope to achieve? Clarity on the company’s strategy? Feedback on recent work? Guidance on specific challenges? Information on growth opportunities? Be clear about your objective.

3. Ask good questions.

A skip-level meeting is only as good as the quality of questions asked. Using your primary goal as the launchpad, craft thoughtful questions to guide the conversation. Here are some examples (you can find plenty more through research – or better yet, create your own).

What are the top goals/challenges for the company right now? How can I/my team align more closely with these?

• In the context of the company’s growth, how do you see my/my team’s role evolving in the future?
• What is one gap you think I/my team could fill? Are there any upcoming initiatives I/we can contribute to?
• Could you share your feedback on [recent project]? How does senior leadership perceive my/my team’s work?
• How can I grow in my role to better support my team and the organization? What skills/experiences would be most valuable?
• What are some market trends/players that we should be watching closely?
• What is your advice on pitching new ideas and projects at this time?

In general, aim to ask questions that reveal hard-to-access information, show your willingness to learn and grow, and reinforce your commitment to helping your team and company succeed.

4. Listen more than you speak.

In her piece in the Harvard Business Review, renowned career coach Melody Wilding advises following the 70/30 rule during skip-level meetings:

Regardless of what you want to get out of the conversation, your primary job is to listen… aim to speak 30% of the time, while allowing your boss’s boss to speak for 70% of the time. By listening more, you avail yourself of their experiences and insights and can more easily pick up on non-obvious nuances.

5. Show appreciation and accountability.

Small actions make a big impression, like sending a thank-you email or sharing a quick summary of how you plan to move forward based on their suggestions. If you promised to come back with a clarification or additional information, be sure to follow through.

6. Be consistent.

Building a long-term relationship will require consistency on your part. Check if it would be possible to set up a conversation every quarter or six months, based on the senior manager’s convenience, and get your meeting on the schedule.

If You’re a Senior Manager: Leading Skip-Level Meetings with Intent

Now let’s flip the lens.

If you’re a senior leader, skip-level meetings aren’t just a people practice – they’re a leadership necessity.

Too often, the view from the top gets cloudy. You see outcomes, not the frictions underneath. You see data, not the effort behind it. These meetings bring the real story into focus.

What You can Gain

• Keep a finger on the pulse. As you become more senior, it’s easy to become disconnected from frontline challenges and sentiments. Skip-level conversations allow you to keep in touch with ground realities.
• Foster alignment. The more senior you are, the more access you have to top-level thinking. By sharing this vision not just with your direct reports but also with junior employees, you can create much-needed alignment on priorities.
• Enable support. Are teams further down the chain of command getting the support they need? Or are their requests getting overlooked due to poor communication, wrong assumptions or perhaps even your own resistance? As you deepen your understanding of the situation, you may discover gaps or imbalances that need to be rectified.
• Demonstrate care. Sitting down one-on-one with skip-level reports sends a clear message: that you value them and want to help them succeed. This goes a long way towards strengthening your leadership credentials.

How to Do it Well

Here are seven suggestions to help you leverage skip-level meetings:

1. Take the initiative.

Some companies do organize annual/half-yearly sessions to connect senior managers with employees. Even if your organization doesn’t have such a mechanism, you can be proactive and start holding your own skip-level meetings.

2. Loop in your direct report.

Don’t bypass the middle manager (your direct report) during the process, as this could create tension and resentment. Give them a heads-up, explain your intentions, and ask if there’s anything they’d like to share with you before the discussion. You could even encourage them to conduct their own skip-level meetings, both upwards and downwards.

3. Set the agenda.

What is your key goal for the session? To build rapport or check blind spots? To share guidance or get feedback? Let employees know in advance so they can prepare accordingly. (Keep in mind that most people are unfamiliar with the concept of skip-level meetings, so you may need to clarify doubts.)

4. Be sincere.

Come to the conversation from a place of care and goodwill. Be genuine in your efforts to engage participants, listen actively and share useful insights.

5. Build trust.

At the start, employees may feel hesitant due to the larger-than-usual power imbalance. Put them at ease by emphasizing that this is a dialogue, not an interrogation. Show curiosity and be open to their perspective. Enhance confidence by being consistent. Take special care to avoid rescheduling or cancelling these meetings.

6. Don’t undermine the middle manager.

Ensure that the line of communication between team members and their immediate supervisor stays open. When a relevant issue comes up, remember to ask, “Have you talked to your manager about this?” Don’t promise big moves without consulting the manager. After the meeting, share non-sensitive insights with the manager to co-create solutions.

7. Follow through.

If you do commit to something – information, resources, opportunities – then make it happen. No action means no credibility. As leadership coach Lina Reinhard notes:

For you as a leader, this may be your 5th skip-level meeting for the week; for the person sitting across from you, it may be the only one this quarter. People remember what you commit to, so follow through on it.

What Organizations Gain: Using Skip-Level Meetings as a Strategic Tool

Most companies say they want open communication, engaged employees, and aligned teams. But many rely on surveys, dashboards, or one-way updates to get there. Skip-level meetings offer something those tools can’t: real-time, human-to-human feedback that cuts through the clutter.

Here are five ways organisations can leverage them more effectively:

1. Make them part of the operating rhythm.

Instead of treating skip-levels as ad hoc or optional, formalize them. Create lightweight expectations for senior leaders to hold regular conversations with employees 1–2 levels below. Whether it’s quarterly or biannually, a consistent cadence makes it easier to build trust and momentum over time.

2. Train for the nuance.

Skip-levels aren’t intuitive for everyone. Equip leaders and employees with the mindset and tools to approach them well. Offer guidance on what to talk about, how to prepare, and how to follow-up. The goal isn’t to script the conversation – it’s to set it up for success.

3. Use them to identify and remove friction.

Themes that surface across skip-level meetings can reveal common friction points: unclear priorities, poor tooling, slow decision-making, or ineffective communication. When leaders spot patterns early, they can act before small issues spiral into systemic problems.

4. Spot and support emerging talent.

People often shine in skip-level conversations in ways that don’t show up on performance reviews. Maybe it’s the way they connect dots. Maybe it’s how they frame problems or advocate for their team. These conversations give leaders a better lens into potential – and let them support growth proactively.

5. Bridge the trust gap.

In organisations where there’s distance between leadership and teams, trust can erode quietly. Skip-levels help rebuild that bridge. Not by adding more layers of communication, but by removing some – if only for 30 minutes at a time. They remind people that leadership isn’t out of reach, and that their voice can be heard.

Final Thought: Beyond the Org Chart

Skip-level meetings aren’t about skipping over people. They’re about skipping misunderstandings. Skipping assumptions. Skipping the slow erosion of trust and context that happens when communication gets too filtered.

They’re a tool – underused, undervalued, but incredibly effective.

For employees, they offer a direct path to insight and impact.

For leaders, they provide clarity that no canned updates can deliver.

For organisations, they can become part of a system for listening, aligning, and adapting.

So the next time someone groans, “Why am I meeting my boss’s boss?” – maybe the better question is:

What opportunity might I be missing if I don’t?