How to Prepare for a Skip-Level Meeting (With Tips and Questions to Ask)

When I meet with our CEO, I come prepared. I have the open action items from our last conversation ready to review. I've gathered updates on the metrics and initiatives they asked me about. My agenda is set before I walk in the door. Why? Because I want them to know I value the time we spend together, and I want to make every minute count.

That's exactly how you should approach your skip-level meetings.

A skip-level meeting is a rare opportunity. You get direct access to a leader two levels above you, someone who can influence your career trajectory, advocate for resources your team needs, and make decisions that affect your daily work. Most employees only get a handful of these conversations each year. The question is: will you make them count?

The employees who stand out in skip-levels aren't necessarily the loudest or the most accomplished. They're the ones who show up prepared, ask thoughtful questions, and follow through on what they discuss. They treat the meeting like it matters, because it does.

The challenge is staying organized across multiple skip-levels over time. What did you discuss last quarter? What action items did you commit to? What questions did the executive ask that you should follow up on? An AI meeting assistant like Fellow captures every conversation so you can walk into your next skip-level knowing exactly where you left off.

Want to impress in your next skip-level? See how Fellow helps you prepare with instant access to past meeting notes and action items.

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What is a skip-level meeting?

A skip-level meeting is a one-on-one conversation between you and a leader who is two or more levels above you in the organizational hierarchy. The name comes from "skipping" over your direct manager to meet with their boss (or higher).

For example, if you report to a team lead who reports to a director, a skip-level would be a meeting between you and that director. Some organizations also conduct skip-levels with VPs or C-suite executives, depending on company size and structure.

These meetings typically happen quarterly, though some companies schedule them monthly during periods of change or for high-potential employees. Unlike your regular one-on-ones with your manager (which focus on day-to-day work), skip-levels are about bigger-picture topics: your career aspirations, your perspective on the organization, feedback on company processes, and ideas that might not surface through normal channels.

Why do skip-level meetings matter for your career?

Skip-level meetings matter because they give you visibility with leaders who influence promotions, project assignments, and organizational decisions. Your direct manager knows your work, but senior leaders often don't, unless you create those touchpoints.

These conversations also give you a chance to share perspectives that might get filtered or softened as they travel up the chain. If you see a process that's broken, a tool that's slowing your team down, or an opportunity the company is missing, a skip-level is your chance to share that directly with someone who can act on it.

From a career development standpoint, skip-levels let you discuss your long-term goals with leaders who have broader visibility into opportunities across the organization. Your manager knows what's available on your team. A senior leader knows what's available across the entire department or company.

Spencer Norman, VP of Engineering at Privy, described what makes skip-levels valuable from a leadership perspective:

"I found skip-levels to focus, at least the best ones, to focus more on career goals, career aspirations, kind of longer arc goals and things like that." This tells you exactly what to bring to the conversation.

How to prepare for a skip-level meeting

Preparation is what separates a forgettable skip-level from one that advances your career. Here's how to show up ready.

Review your past conversations

If you've had previous skip-levels with this leader, review what you discussed. What action items did you commit to? What questions did they ask? What topics did they seem most interested in?

This is where an AI meeting assistant becomes invaluable. With Fellow, you can search your AI meeting notes or use Ask Fellow to query past conversations: "What did I discuss with [executive name] in our last meeting?" You'll walk in with full context instead of trying to reconstruct conversations from memory.

If this is your first skip-level with this leader, do your research. Review their recent all-hands presentations, read any company updates they've shared, and understand their priorities. Showing that you pay attention to leadership communication signals engagement.

Prepare updates on previous commitments

If the executive asked you about something in a previous conversation, come with an update. Did they ask about a project you were working on? Bring the results. Did they suggest you explore a new skill or opportunity? Share what you've done.

Following through on past discussions demonstrates reliability and shows you take these conversations seriously. It also gives you easy talking points that naturally flow from your shared history.

Identify 2-3 topics you want to discuss

Don't wait for the executive to drive the entire conversation. Come with your own agenda items. Consider:

• A career goal you'd like their perspective on

• A challenge you're facing that they might have insight into

• An idea for improving something in the organization

• A question about company strategy or direction

Having your own topics prepared shows initiative and ensures you get value from the meeting even if the executive's questions don't cover what matters most to you.

Prepare specific examples and data

Senior leaders appreciate specificity. Instead of saying "things are going well," come prepared to share a specific accomplishment. Instead of saying "we have some process issues," describe a concrete example and, if possible, a proposed solution.

Quantify your impact when you can. "I reduced the onboarding time for new customers by 30%" is more memorable than "I've been working on improving onboarding."

Write down your questions in advance

It's easy to forget what you wanted to ask when you're in the room with a senior executive. Write your questions down beforehand and bring them with you. This also signals preparation.

Good questions to have ready include questions about company direction, their career advice, opportunities they see for your growth, and how you can better support organizational goals.

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What questions should you ask in a skip-level meeting?

The questions you ask shape how senior leaders perceive you. Thoughtful questions demonstrate strategic thinking, curiosity, and engagement.

Questions about company strategy and direction

These show you're thinking beyond your immediate role:

• What are the biggest priorities for the company/department this quarter?

• How do you see our team's work contributing to those priorities?

• What challenges is the leadership team most focused on solving?

• Are there any upcoming changes I should be aware of or preparing for?

• What does success look like for our organization over the next year?

Questions about your career development

Skip-levels are ideal for career conversations because senior leaders have broader visibility:

• Based on what you know about my work, what skills should I be developing?

• What experiences would help me prepare for [role you're interested in]?

• Are there projects or opportunities coming up that might be a good fit for my growth?

• What did your career path look like, and what would you do differently?

• Who else in the organization would you recommend I connect with?

Questions about how you can contribute more

These demonstrate initiative and a growth mindset:

• What could I be doing that would be most valuable to the team right now?

• Is there anything I'm doing that I should do more of, or less of?

• Are there any gaps on the team or in the organization where I could help?

• What do the highest performers in roles like mine do differently?

• How can I better support my manager's success?

Questions about their perspective

Senior leaders have context you don't. Tap into it:

• What's something you wish more employees understood about how decisions get made?

• What do you look for when identifying high-potential employees?

• What's the most common mistake you see people in my role make?

• How do you think about balancing short-term delivery with long-term career growth?

• What's changed most about this company since you joined?

What to expect during a skip-level meeting

Knowing what to expect reduces anxiety and helps you show up as your best self.

The tone is usually conversational

Skip-levels are not performance reviews. Most senior leaders use them to build relationships and gather unfiltered perspectives. Expect a conversational tone, often starting with casual topics before moving to substance.

You'll likely be asked about your experience

Common questions from executives include: What do you enjoy about your role? What challenges are you facing? How is your team functioning? What could the company do better? What are your career goals?

Prepare thoughtful answers to these questions. Avoid generic responses like "everything's great." Share specific observations, both positive and constructive.

You might be asked about your manager

This can feel awkward, but it's normal. Senior leaders use skip-levels partly to understand how their direct reports (your manager) are performing. Be honest but professional. Focus on behaviors and impact rather than personal criticism.

Frame feedback constructively: "I'd love more clarity on priorities when things shift quickly" is better than "My manager doesn't communicate well."

There may be silence, and that's okay

Senior leaders often pause to think. Don't rush to fill every silence. If they ask a question and then wait, take your time to give a thoughtful answer. Pauses show you're being reflective, not reactive.

How to follow up after a skip-level meeting

What you do after the meeting matters as much as the meeting itself.

Send a brief thank-you note

Within 24 hours, send a short email thanking them for their time. Reference something specific you discussed and any action items you committed to. This keeps you top of mind and demonstrates professionalism.

Document key takeaways

Write down what you learned, any advice they gave, and any commitments you made. If you use an AI meeting assistant like Fellow, your notes are already captured, but review them while the conversation is fresh to highlight what matters most.

Follow through on your commitments

If you said you'd do something, do it. If the executive suggested you talk to someone, reach out. If they recommended a book or resource, engage with it. Following through is how you build credibility over time.

Prepare for the next one

Start a running document of topics for your next skip-level. When you encounter something worth discussing, whether it's a win, a challenge, or a question, add it to the list. You'll never scramble for talking points again.

Teams at Shopify, HubSpot, and Motive use Fellow to stay prepared across all their meetings. Read their stories →

Skip-level meeting preparation checklist

Use this checklist before every skip-level:

One week before:

• Review notes from your last skip-level with this leader

• Identify 2-3 topics you want to discuss

• Gather updates on any previous action items or commitments

One day before:

• Write down your questions

• Prepare specific examples or data points to share

• Review any recent company communications from this leader

Day of:

• Arrive a few minutes early (or log in early for virtual meetings)

• Have your notes accessible but don't read from a script

• Bring something to take notes with

After the meeting:

• Send a thank-you message within 24 hours

• Document key takeaways and action items

• Add topics for the next skip-level to your running list

Common mistakes to avoid in skip-level meetings

Only bringing complaints

Skip-levels aren't venting sessions. If you have concerns, share them, but balance criticism with constructive suggestions. "Here's what's not working, and here's an idea for how we might fix it" is much more effective than a list of grievances.

Being unprepared

Walking in without topics, questions, or updates signals that you don't value the meeting. Senior leaders notice. Preparation demonstrates professionalism and respect for their time.

Talking only about your immediate work

While it's fine to share what you're working on, don't let the entire conversation focus on tactical updates your manager could provide. Use skip-level time for bigger-picture discussions: career growth, organizational feedback, strategic questions.

Being afraid to share your perspective

You were invited to this meeting because leadership wants to hear from you. Don't give safe, filtered answers out of fear. Thoughtful honesty (delivered professionally) is what makes skip-levels valuable for everyone.

Forgetting what was discussed

If you can't remember what you talked about last time, you'll repeat the same conversations and miss opportunities to demonstrate follow-through. Use an AI meeting assistant to capture your skip-levels so you can review them before your next meeting.

Frequently asked questions

What is the purpose of a skip-level meeting from an employee's perspective?

Skip-level meetings give you direct access to senior leaders who can influence your career trajectory, advocate for your team's needs, and provide perspective on company strategy. They're an opportunity to share your ideas with decision-makers, get career advice from leaders with broad organizational visibility, and build relationships beyond your immediate reporting structure. Making a strong impression in skip-levels can lead to new opportunities, mentorship, and increased visibility.

How should I prepare for my first skip-level meeting?

For your first skip-level, research the leader you'll be meeting with by reviewing their recent communications, presentations, and stated priorities. Prepare 2-3 topics you'd like to discuss, including at least one career-related question. Think through how you'll answer common questions like "What do you enjoy about your role?" and "What challenges are you facing?" Practice summarizing your current projects concisely. Arrive with specific examples that demonstrate your contributions and impact.

What if my skip-level meeting feels awkward or forced?

Some awkwardness is normal, especially in your first few skip-levels. Reduce tension by coming prepared with questions and topics so you're not relying entirely on the executive to drive conversation. Start with lighter topics before diving into substance. Remember that senior leaders do many skip-levels and are used to putting people at ease. If the conversation stalls, asking for their career advice or perspective on a company initiative usually opens things up.

Should I talk about problems with my manager in a skip-level?

You can share constructive feedback about team dynamics or processes, but avoid making it personal or venting about your manager. Focus on specific behaviors or situations rather than character assessments. Frame feedback in terms of impact: "When priorities shift frequently without explanation, it makes it hard to plan my work effectively." If you have serious concerns about your manager, a skip-level may not be the right venue. Consider HR or other appropriate channels.

How do I make a good impression in a skip-level meeting?

Come prepared with specific topics, questions, and updates on previous discussions. Show that you think beyond your immediate role by asking strategic questions about the company or department. Share concrete examples of your impact rather than generic statements. Follow up on any commitments you make. Send a brief thank-you note afterward. Over time, consistent preparation and follow-through build your reputation as someone senior leaders want to invest in.

Can AI help me prepare for skip-level meetings?

Yes. An AI meeting assistant like Fellow records and transcribes your meetings so you can review exactly what was discussed. Before your next skip-level, you can search past conversations or use Ask Fellow to query your meeting history: "What action items did I commit to with [executive name]?" This ensures you never forget important context and always show up prepared to follow through on previous discussions.

Make every skip-level count

Skip-level meetings are rare opportunities to connect with leaders who can shape your career. Don't waste them by showing up unprepared or forgetting what you discussed.

Fellow is the secure AI meeting assistant that captures every conversation across Zoom, Google Meet, Microsoft Teams, and in-person meetings. Review past skip-levels instantly, track your action items, and walk into every meeting knowing exactly where you left off. SOC 2 Type II certified, HIPAA compliant, and we never train on your data.

Stop scrambling to remember what you discussed. Start showing up prepared for every skip-level. Try Fellow free →