How to prepare for a skip-level meeting as an employee

TL;DR: Skip-level meetings give you a chance to build visibility with senior leadership. Prepare by documenting your recent wins with metrics since your last skip-level meeting, identifying systemic friction worth escalating, and researching your skip-level leader's priorities. During the meeting, quantify successes, frame challenges as objective insights with proposed solutions, and ask about team priorities and your professional development. Afterward, send a brief summary and keep a searchable record of commitments. Granola helps with meeting preparation, templates, and enhanced notes so you can stay present and still document outcomes.

Skip-level meetings give you a chance to shape how senior leadership sees your work, your team, and your potential. The challenge is staying present during the conversation while capturing what matters. This guide shows how to prepare your notes, document outcomes, and keep a searchable record so each conversation builds on the last.

This guide covers how to prepare notes for a skip-level meeting, what to capture during the conversation, and how to document outcomes so the meeting compounds over time.

The strategic value of skip-level check-ins

Why managers schedule skip-levels

Understanding why the meeting exists changes how you show up. Senior leaders use skip-levels to stay connected to daily operations and team dynamics as organizations grow. These meetings help executives understand what's actually happening on the ground and identify patterns they can't see from their atltitude.

Leaders also use these meetings to build relationships with people who do not report to them directly, get feedback about the managers who report to them, and identify rising stars. When executives run them thoughtfully, skip-levels strengthen middle managers rather than undermine them, a point Spinach.ai makes in its guidance on the format.

It's important to agree on a cadence that works for everyone involved. Quarterly check-ins are a reasonable example, though the exact frequency matters less than consistency. A set schedule makes skip-levels a normal part of how leadership stays connected.

What sets skip-level meetings apart

A regular 1-on-1 with your manager covers status, blockers, and day-to-day work. A skip-level widens the lens: organizational context, career development, and systemic issues your direct manager may not have the authority to fix.

That difference requires you to shift your mindset. Instead of passive status reporting, treat the meeting as active, strategic engagement. The focus isn't recounting your sprint. You are there to connect your work to priorities your skip-level leader owns, and to surface patterns they cannot see from their altitude.

For the manager's side of this equation, see our guides on how to run a skip-level meeting and skip-level agenda templates.

How to prepare for a skip-level meeting

Note preparation makes the difference between a forgettable check-in and a conversation that moves your work forward. Run through the following skip-level preparation checklist before your meeting.

• Document recent wins with specific metrics
• Identify systemic challenges with specific, actionable solutions
• Research leader's priorities from all-hands and announcements
• Prepare open-ended questions about team priorities and your development
• Define your goals for the meeting before you walk in
• Tell your direct manager the meeting is happening

Document your recent project wins

Skip-level leaders see dozens of people across the organization, which means you need to stand out. A list of activities is forgettable, but quantified outcomes stick. "We shipped the onboarding redesign" is a status update. "We reduced churn by 12% after shipping the onboarding redesign" is a contribution they can repeat in a leadership meeting.

Pull your wins from the last two quarters and attach a number to each: revenue influenced, cycle time reduced, churn moved, adoption gained. If you work in research or discovery, count decisions changed by your findings, not interviews conducted.

Identify challenges worth escalating

The hardest preparation skill is separating personal grievances from systemic friction. Frame feedback around patterns and systemic issues rather than personal complaints, focusing on organizational impact. "I'm overworked" is a grievance. "Customer research requests doubled this quarter with no added headcount, which is delaying discovery for the Q4 roadmap" is an organizational insight.

Also, come with suggestions, and not just problems. Indeed's career guidance recommends developing specific, easy-to-implement solutions for any issue you raise. As an individual contributor, you are well positioned to describe the reality of getting work done. IEEE Spectrum points out that senior leaders are often disconnected from that day-to-day experience, which makes your grounded perspective genuinely valuable.

Prepare your skip-level meeting notes

Tooling pays off here. Our pre-meeting briefs surface open threads from your last conversation with this person, relevant context, and agenda points worth revisiting, so you walk in with continuity instead of starting from scratch every quarter. You can also use our 1-on-1 template to structure your agenda before the call.

Our overview video shows the notepad workflow end to end, and Chris and Sam explain the design philosophy behind it in this conversation.

Research your manager's recent priorities

Your skip-level leader has their own scorecard. Find it. Review company all-hands notes, recent announcements, and their public statements, then ask yourself which of your wins maps to what they care about. IEEE Spectrum recommends asking the skip manager directly what their priorities are and how your work contributes.

If you have met this leader before, query your past notes. Our chat with your meetings feature lets you ask "What did we discuss in my last skip-level?" and get source-linked answers from the actual conversation.

What to capture in a skip-level meeting

Structure your notes across three lanes. This template balances self-advocacy with organizational value:

Quantify your recent successes

Lead with outcomes, not effort. Executives think in results:

• Weak: "I've been doing a lot of customer research."
• Strong: "The discovery sprint we ran in June killed two features before engineering spent a quarter building them."

Address systemic friction and roadblocks

Frame challenges as objective insights. Aggregate feedback before sharing it and present it as a pattern: "I've observed an autonomy gap across the team and I'd like us to work on delegation clarity" invites engagement in a way that individual accusations never do, per our skip-level agenda guide.

Get clarity on current team priorities

Ask how your work aligns with where the team is going. This signals strategic thinking and gives you information you cannot get from your direct manager, who may filter priorities through their own lens.

Identify your professional blind spots

Ask for feedback on areas you cannot see yourself. Workhuman suggests asking whether the leader has noticed areas where you could improve. Framing this as growth rather than weakness reads as confidence.

Questions to ask in a skip-level meeting

These tips come down to one principle: ask questions that connect your daily work to executive priorities.

Mapping your work to team objectives

• "How does my work on customer research align with the team's Q4 priorities?"
• "What would you like to see more of from our team?"
• "What are the top three priorities for the product organization this year?"

Goals for your professional development

• "What skills are most important for someone in my role to develop over the next year?"
• "What does a strong promotion case look like at this level?"
• "How do you see my role evolving within the company?"

Deel's question list recommends asking about specific milestones for career advancement, which turns vague ambition into a documented path.

Linking daily work to executive priorities

• "How do you see customer research contributing to this year's priorities?"
• "What are the core values the company prioritizes, and how do they impact decision-making?"

Common pitfalls to avoid in skip-level meetings

Don't blindside your direct manager

Transparency is the foundational rule. The US Chamber's guide notes that the manager being skipped should know the meeting is happening, its purpose, and what will be discussed. Tell your manager in advance and ask if there is anything they would like you to raise. Afterward, share a summary. Radical Candor recommends sharing notes right after the meeting, which keeps the conversation from feeling like it happened behind anyone's back.

Frame feedback as objective insights

Skip-levels are not venting sessions for complaining about your direct manager unless something is seriously wrong. Your skip-level leader will protect their direct report by default, and any complaint without a specific action you have already taken gets filed under "this person can't handle working relationships". Without structure, these meetings turn into demotivating venting sessions, as HR practitioners warn.

Review your recent work performance data

Expect questions about your performance. Review your recent metrics, shipped work, and feedback so you can speak confidently without notes in front of you. Being vague about your own contributions undermines everything else you prepared.

Best practices for documenting skip-level insights

Capture commitments and action items

Follow-through builds credibility. If your skip-level leader commits to raising a resourcing issue or connecting you with a peer team, that commitment only exists if you write it down. Capture action items during the meeting without losing presence: jot rough notes on the moments that matter and let the details get filled in afterward.

Build a searchable record of takeaways

One skip-level is a conversation. Five skip-levels over two years are a career narrative. Our searchable archive lets you query across every past conversation: "What did I commit to in my last skip-level?" or "What themes keep coming up?" One reviewer noted you can search across all past meetings instantly, which turns isolated check-ins into cumulative documentation of your growth.

Let Granola add the missing context

We designed Granola to work differently: your rough notes guide the enhancement, so the output reflects your priorities. Write "career path discussion" and Granola finds every related moment in the transcript and adds the relevant quotes. Your notes stay in black, AI additions appear in gray, and you control what stays. Our overview of the AI notepad approach explains the mechanic, and Granola Chat handles follow-up questions across meetings.

"Granola was a very simple tool to set up and start using, It has been extremely useful in making notes on calls with prospective customers as well as team meetings, and allows me to focus on the conversation with confidence, that the important points are being noted." - Tom S. on G2

For sensitive conversations, our transparency features include an automatic in-chat notification and a video watermark, and our consent guide covers when to use them.

Turning meeting insights into action items

Communicate skip-level results clearly

Send your direct manager a short summary: what was discussed, what was agreed, and what you are doing next. This closes the transparency loop and keeps trust intact.

Document and clarify meeting agreements

Send a follow-up email to the skip-level leader within 24 hours. 15Five notes that follow-up reinforces credibility and maintains momentum. Keep it to three elements:

"Thanks for the conversation today. My key takeaways: [topic 1], [topic 2]. On my side, I'll [action item] by [date]. Looking forward to continuing this next quarter."

Document your skip-level outcomes

Store the notes, action items, and commitments in a searchable archive so you can track progress and prepare for the next conversation. Our Zapier integration lets you push action items into your task system, and our MCP connector lets your other AI tools work from your meeting context.

Try Granola for free. Download the Mac or Windows app, connect your calendar, and run your next meeting to see it in action.

FAQs

How often should skip-level meetings happen?

Aim for at least quarterly, though Yale ITS recommends establishing whatever cadence works for everyone. Consistency matters more than frequency.

Should I tell my manager what I discussed?

Yes. Share a brief summary of key topics and action items, since transparency prevents your manager from feeling blindsided.

What if I don't have anything to say?

Prepare questions about team priorities, organizational direction, and your professional development. There is always something to learn from a senior leader.

Can I decline a skip-level meeting?

We don't recommend declining, since skip-levels create career development opportunities. If you have concerns, raise them with your direct manager first.

How long should a skip-level meeting last?

Typically 30-45 minutes. Prepare enough material to fill the time, but prioritize a quality conversation over covering every agenda item.

Key terms glossary

Skip-level meeting: A meeting between an employee and their manager's manager, bypassing the direct reporting line to discuss strategy, development, and organizational health.

One-on-one: A recurring private meeting between two people, usually a manager and direct report, covering status, blockers, and development.

Organizational alignment: The degree to which an individual's or team's work supports the company's stated priorities and strategy.

Professional development: The skills, experiences, and milestones an employee pursues to grow in their role or advance their career.

Action items: Specific commitments made during a meeting, with an owner and usually a deadline.

Institutional memory: The accumulated knowledge of past decisions, conversations, and commitments that persists beyond any individual's tenure.

Enhanced notes: Meeting notes where your rough jottings are filled in with transcript context, keeping your structure while adding supporting detail.