6 ChatGPT Prompts for Skip-Level Meetings

Skip-level meetings are one of the most valuable tools a senior manager has. They’re also one of the most awkward for everyone involved.

The person running the meeting wants honest feedback about how the team is doing. The person attending is trying to figure out what to say without throwing their manager under the bus. The manager in the middle is wondering what’s being said about them. Nobody is fully comfortable.

That awkwardness is actually the point. Skip-levels work because they create a direct line between senior leadership and the people doing the work. Information that gets filtered through layers of management often loses its edge. Problems get softened. Concerns get reframed. By the time feedback reaches the top, it barely resembles what people actually think.

Skip-levels cut through that. But getting useful information out of them takes preparation on both sides. Without the right questions, the senior leader gets polite non-answers. Without the right framing, the attendee either says too much or plays it too safe.

These ChatGPT prompts for skip-level meetings cover both perspectives. Three for the senior manager running the skip-level, three for the employee attending one. Whether you’re trying to get honest feedback about your organization or trying to give honest feedback without creating problems for yourself, there’s something here.

If You’re Running the Skip-Level

Prompt 1: Prep Questions That Surface Real Feedback

The default skip-level questions get default answers. “How’s everything going?” produces “Good, busy.” You learn nothing.

The problem is that most people don’t walk into a meeting with their boss’s boss ready to share unfiltered opinions. They’re cautious. They’re reading the room. They’re trying to figure out what you actually want to hear. Your job is to ask questions that make honesty feel safe.

The prompt:

I'm preparing for a skip-level meeting with a [job title] who reports to [manager name/role]. This person has been on the team for [duration] and works primarily on [area/project].

Help me prepare 8-10 questions that will surface honest feedback about:

How well the team is functioning

Whether they have what they need to do good work

Their manager's effectiveness (without making it feel like an interrogation)

Their own growth and engagement

I want questions that invite real answers, not polite ones. Avoid anything that sounds like an HR survey.

Why this works: Generic questions signal that you’re checking a box. Specific questions signal that you actually want to know. ChatGPT can help you find the angle that opens people up instead of shutting them down.

Adjust by adding context about what you’re actually trying to learn. If you’ve heard rumblings about workload, say so. If you’re evaluating the manager for promotion, that shapes what you ask. The more context you provide, the more targeted the questions become.

Prompt 2: Find Patterns Across Multiple Skip-Levels

One skip-level is a data point. Five skip-levels from the same team are a pattern. The problem is that you forget the details of conversation one by the time you finish conversation five.

This is where most senior leaders lose value from skip-levels. They have the conversations, nod along, and then struggle to recall specific themes when it’s time to act. If you’re doing skip-levels right, you should leave with a clear picture of team health. That requires synthesizing everything you heard.

The prompt:

I just completed skip-level meetings with 5 people on [team/manager]'s team. Here are my notes from each conversation:

[Paste notes from all meetings]

Help me identify:

Themes that came up multiple times

Potential concerns that need follow-up

Positive patterns worth reinforcing

Anything that contradicts what the manager has told me

Summarize the overall health of this team based on what you see.

This turns scattered notes into something actionable. You’ll spot things you missed in the moment. If three out of five people mentioned unclear priorities, that’s a pattern worth addressing. If everyone praised the team culture but one person hinted at burnout, that’s worth a closer look. For more on capturing meeting details you can reference later, see our guide to ChatGPT prompts for meeting notes.

Prompt 3: Debrief With the Middle Manager

Here’s where skip-levels get tricky. You heard things about a manager’s leadership, workload decisions, or communication style. Now you need to share that feedback without betraying confidences or making the manager defensive.

This conversation can go sideways fast. Share too much and you burn trust with the team. Share too little and the manager doesn’t get feedback they need. The goal is to help them improve without creating paranoia about what their team said behind closed doors.

The prompt:

I need to debrief with [manager name] after completing skip-levels with their team. Here's what I heard:

[Summarize themes, not individual quotes]

Help me plan this conversation. I want to:

Share the feedback in a way that's constructive, not accusatory

Protect the anonymity of individual team members

Be direct about concerns without damaging our relationship

Give them a chance to share their perspective

Draft talking points I can use. Tone should be supportive but honest.

Frame it around patterns, not people. “Several people mentioned wanting more clarity on priorities” lands differently than “Sarah said you keep changing direction.” The first is useful feedback. The second creates a target. For more on delivering tough feedback effectively, our prompts for difficult employee conversations cover the framing in more depth.

If You’re Attending a Skip-Level

Prompt 4: Prepare What to Say (And What Not To)

Your manager’s boss wants to meet with you. You’re not sure what they’re looking for. You don’t want to say too much or too little.

The anxiety is normal. Skip-levels feel high-stakes because they are. What you say might shape how leadership sees your team, your manager, or you. That’s a lot of pressure for a 30-minute conversation.

The prompt:

I have a skip-level meeting with [senior leader title] coming up. I report to [your manager]. I've been in this role for [duration] working on [main responsibilities].

Help me prepare by thinking through:

What topics are appropriate to raise vs. what I should handle directly with my manager

How to give honest feedback about my experience without venting or complaining

2-3 things I want them to know about my work or the team

Questions I could ask them to make this useful for me too

I want to come across as thoughtful and professional, not political or naive.

This helps you walk the line between honest and appropriate. The skip-level is not the place to unload every frustration, but it’s also not useful if you just say everything is fine. The best approach is prepared candor: know what you want to say before you walk in.

Prompt 5: Give Feedback About Your Manager Without Making It Weird

They’re going to ask about your manager. That’s part of why skip-levels exist. The question is how to answer honestly without saying something you’ll regret.

The instinct is either to protect your manager completely or to finally say what you really think. Both extremes are wrong. Overly positive makes you look like you’re not paying attention. Overly negative makes you look disloyal or difficult. The goal is constructive honesty.

The prompt:

In my skip-level, I'll probably be asked about my manager. Here's my honest assessment:

What's working well: [list specifics]

What I wish was different: [list specifics]

Help me figure out how to talk about the "wish was different" parts in a way that:

Sounds like feedback, not criticism

Focuses on impact rather than personality

Doesn't make me look like I'm going around my manager

Give me 2-3 ways to phrase this that are direct but professional.

The difference between “My manager micromanages everything” and “I’d love more autonomy on projects where I’ve proven I can deliver” is the difference between venting and feedback. This prompt helps you find the second version.

Prompt 6: Follow Up After the Meeting

The skip-level ended. Now what? Most people just go back to work and forget about it. That’s a missed opportunity.

A brief follow-up does two things. It puts you on the senior leader’s radar in a positive way. And it forces you to actually process what was discussed instead of letting it fade into the background noise of your week.

The prompt:

I just finished a skip-level meeting with [senior leader title]. Here's what we discussed:

[Paste your notes or summary]

Help me:

Draft a brief thank-you message that references something specific from our conversation

Identify any commitments I made that I need to follow through on

Note anything I should share with my direct manager about the conversation

Flag any topics worth revisiting in future skip-levels

Keep the thank-you under 4 sentences. Professional but not stiff.

Most people don’t follow up after skip-levels. That’s exactly why doing it makes an impression. It takes five minutes and signals that you took the conversation seriously. Similar to how you’d prepare for a regular 1-on-1 meeting, the value comes from treating it as a real conversation worth documenting.

Tips for Better Results

• Give context about the relationship. A skip-level with someone you’ve known for two years is different from one with a new hire. The dynamic matters, and ChatGPT can adjust its suggestions if you tell it where things stand.
• Be specific about what you want to learn or share. “Help me prepare for a skip-level” is too vague to get useful output. Say what you’re worried about, what you’re hoping to learn, or what you want them to walk away knowing.
• If you’re the senior leader, tell ChatGPT what you already know about the team. It helps generate questions that probe deeper rather than covering ground you’ve already covered.
• If you’re the attendee, be honest with ChatGPT about your frustrations. It can help you translate raw feelings into professional language, but only if you give it the real version first. Don’t sanitize your input and expect useful output.

Common Mistakes

Using skip-levels as a performance check on the middle manager.:

That’s not what they’re for. If you have concerns about a manager, address those directly. Skip-levels are for understanding the team’s experience, not building a case.

Going in without specific questions:

“So, how are things?” is a waste of everyone’s time. You scheduled the meeting. Come prepared.

Sharing individual feedback with names attached:

The fastest way to make sure nobody tells you anything useful again. People need to trust that candor won’t come back to bite them.

Treating it as a venting session if you’re the attendee:

One or two constructive concerns are useful. A list of grievances makes you look bad and doesn’t actually solve anything.

Forgetting to close the loop:

If someone raised a concern and you did something about it, tell them. If you couldn’t act on it, explain why. Silence after a skip-level teaches people that speaking up doesn’t matter.

Frequently Asked Questions