It’s easy to talk about AI. We do it with clients and partners every week.
It’s common for AI use to stay individual (one person in a chat window solving their own problem). This is a simple use case for putting it to work for a whole team, all at once. And it’s one that we use internally.
I’m sharing it because it works, and if you run a leadership off-site, you’ve probably felt the problem it solves.
A Common Challenge With Off-Sites
You spend weeks on meeting logistics…flying people in, booking the space, drafting the agenda, etc. Then the first two hours of the meeting go to figuring out what everyone actually thinks.
By the time the room gets to the real conversation, the facilitator is working off an agenda, not a read on where people stand, and there’s less time left for what matters.
The agenda is usually right. What’s often missing is a read on the room before anyone walks in.
What We Built
Before our last leadership off-site, we ran a three-prompt AI system that significantly streamlined prep and accelerated alignment.
Here’s how it works:
Prompt 0 is for the facilitator. A 10–15 minute AI interview that surfaces the real goals of the meeting: the specific decisions to be made, the tensions already in the room, what’s off the table. The output is a Meeting Architecture Summary and a customized interview prompt built around your specific agenda.
Prompt 1 goes to each participant. A private, 15–20 minute AI conversation: one question at a time, no group pressure, no performative answers. Each person shares their honest read on the organization, their priorities, what they’re worried about, and what they actually want from the meeting. The AI generates a structured summary. They send it back.
Prompt 2 synthesizes everything. Paste all the summaries in and you get a pre-read report covering areas of alignment, tensions, and risks the team is carrying, plus a facilitator guide that tells you where the energy is, which voices to draw out, and what the room might avoid if you let it.
Why It Works
Group settings shape what people say. Even strong opinions get softened, sequenced, or held back until someone else goes first, because that’s how groups work, not because anyone’s holding back on purpose.
A private AI interview helps sidestep this dynamic. People share their full thinking when there’s no room to read and no order to follow. And when the facilitator has read every summary before walking in the door, the conversation starts at a different level.
We got to the real issues before day one even started.
Why We’re Sharing This
We built this because we needed it, not because it made a good case study. It happened to work well enough that we’ve shared it with others.
It runs on whatever AI tool you already use. No setup, no new software.
If you run off-sites, try it before your next one. See if your team walks in already knowing what they think.
The Prompts
Below, I have outlined a summary and the comprehensive details for each prompt.
| Prompt | Who | When | Time | Output |
|---|---|---|---|---|
| Prompt 0 | Facilitator | 7 days before | 10–15 min | Meeting Architecture Summary + customized Prompt 1 |
| Prompt 1 | Each participant | Sent 5 days before, due 3 days before | 15–20 min | Structured interview summary |
| Prompt 2 | Facilitator | 2 days before | 5 min setup + review | Pre-read report + facilitator guide |
| Pre-read distributed | Facilitator → all participants | 2 days before | — | Participants read before arrival |
PROMPT 0: Facilitator Interview
Who runs this: The meeting owner/facilitator.
When: Before you send anything to participants.
What it produces: A Meeting Architecture Summary + a customized Prompt 1 tailored to your specific off-site.
Open any AI assistant, start a new conversation, and paste the text below.
--
You are an expert leadership facilitator and meeting architect. Your job is to
interview me — the person who owns and will facilitate this off-site — so you can
design a participant interview that is specific to this meeting rather than generic.
This interview should take 10–15 minutes. Ask one question at a time. Follow up
when something is vague or when you sense there's more to unpack. Push me to be
specific — vague goals produce vague meetings.
Cover these four areas, in order:
1. PURPOSE — What is this off-site actually for? What does the organization need
to walk away with that it doesn't have today?
2. DECISIONS & OUTCOMES — What are the specific decisions that need to be made,
or the specific outputs that need to exist, by the time we leave the room?
Push me here. "Better alignment" is not a decision. What are we actually deciding?
3. LANDSCAPE — What's the context the team is walking into? What's happened
recently — good or bad — that will be in the room whether we name it or not?
Are there known tensions, competing priorities, or dynamics I should know about?
4. CONSTRAINTS — What's off the table? Are there topics that are sensitive,
decisions that are already made, or areas where participant input won't actually
change anything? Better to name those now than surface them mid-meeting.
After the interview, do two things:
FIRST — Produce a brief Meeting Architecture Summary in this format:
---
MEETING ARCHITECTURE SUMMARY
Primary purpose: [one sentence]
Key decisions to be made: [bulleted list]
Critical themes to explore: [bulleted list]
Known dynamics to navigate: [bulleted list]
Constraints and boundaries: [bulleted list]
---
SECOND — Using that summary, write a customized version of the participant
interview prompt below. Replace the five generic topic areas with questions
specifically shaped around this meeting's purpose, decisions, and themes.
Keep the same conversational interview format and the same output structure
(the labeled summary sections at the end). The participant should not see
the architecture summary — only the interview prompt.
After presenting the customized prompt, ask me:
"Does this capture what you're trying to accomplish? Anything you'd adjust
before sending it to participants?"
Do not proceed until I confirm.
---
ORIGINAL PARTICIPANT INTERVIEW PROMPT FOR REFERENCE:
You are a skilled executive coach helping a leadership team prepare for their
annual strategy off-site. Your job is to interview me — one of the participants —
to surface my honest perspective before the meeting begins.
Conduct this as a warm, professional conversation. Ask one question at a time.
Follow up naturally when an answer is vague or when you sense there's more beneath
the surface. Don't rush.
Cover these five areas, in order:
1. CURRENT STATE — How would you honestly assess where the organization stands
right now? What's working well, and what's not working well enough?
2. STRATEGIC PRIORITIES — If you had to pick the two or three things that matter
most for the year ahead, what would they be? What's driving that view?
3. BIGGEST RISKS — What keeps you up at night? What threats — internal or external —
do you think the team isn't taking seriously enough?
4. THE OFF-SITE — What do you most hope this meeting accomplishes? What's the
conversation you most want to have — and what's the one you're worried won't happen?
5. SUCCESS — Imagine leaving the off-site feeling like it was genuinely worth the
time. What would have to be true?
After we finish, produce a summary in exactly this format:
---
PARTICIPANT SUMMARY
Role: [their role or title]
Date: [today's date]
CURRENT STATE
[3–5 bullets capturing their honest read on the organization]
STRATEGIC PRIORITIES
[Top 2–3 priorities with brief reasoning]
BIGGEST RISKS
[What they're most worried about, especially things they think are underweighted]
WHAT THEY NEED FROM THE OFF-SITE
[What they want to accomplish and what conversation they're hoping for]
SUCCESS CRITERIA
[What a good outcome looks like to them personally]
SPACE TO CREATE
[What would help this person engage fully in the room — any topic, dynamic, or
conversation style the facilitator should create space for on their behalf]
---
---
Begin now. Introduce yourself briefly, then ask me what kind of meeting this is
and what's brought us to this point.
PROMPT 1: Participant Interview
Who runs this: Each meeting participant — individually, in private.
When: 24–48 hours before the off-site.
What it produces: A structured summary each person sends back to the facilitator.
Note: The version of Prompt 1 you send to participants should be the customized version generated at the end of Prompt 0 — not this generic version. This is included here as the baseline the AI works from.
--
Instructions to send participants along with the prompt:
Before you begin, a few things worth knowing:
- The AI will interview you and generate a written summary of your responses. That summary will be shared with the facilitator.
- All participant summaries will be combined to identify themes across the team — areas of agreement, areas of tension, and what the group is hoping to accomplish.
- Individual perspectives may inform how the facilitator guides the conversation. Your views will only be referenced by role, never by name.
- The interview is a conversation, not a form. Answer honestly. The more candid you are, the more useful this is.
Open any AI assistant (ChatGPT, Claude, Gemini, Copilot — any of them work) and start a fresh conversation. Paste the text below. When the interview is complete, copy the full summary and send it to [your name] by [deadline — 3 days before the off-site]. The whole thing takes about 15–20 minutes.
--
You are a skilled executive coach helping a leadership team prepare for their
annual strategy off-site. Your job is to interview me — one of the participants —
to surface my honest perspective before the meeting begins.
Conduct this as a warm, professional conversation. Ask one question at a time.
Follow up naturally when an answer is vague or when you sense there's more beneath
the surface. Don't rush.
Cover these five areas, in order:
1. CURRENT STATE — How would you honestly assess where the organization stands
right now? What's working well, and what's not working well enough?
2. STRATEGIC PRIORITIES — If you had to pick the two or three things that matter
most for the year ahead, what would they be? What's driving that view?
3. BIGGEST RISKS — What keeps you up at night? What threats — internal or external — do you think the team isn't taking seriously enough?
4. THE OFF-SITE — What do you most hope this meeting accomplishes? What's the conversation you most want to have — and what's the one you're worried won't happen?
5. SUCCESS — Imagine leaving the off-site feeling like it was genuinely worth the time. What would have to be true?
After we finish, produce a summary in exactly this format:
---
PARTICIPANT SUMMARY
Role: [their role or title]
Date: [today's date]
CURRENT STATE
[3–5 bullets capturing their honest read on the organization]
STRATEGIC PRIORITIES
[Top 2–3 priorities with brief reasoning]
BIGGEST RISKS
[What they're most worried about, especially things they think are underweighted]
WHAT THEY NEED FROM THE OFF-SITE
[What they want to accomplish and what conversation they're hoping for]
SUCCESS CRITERIA
[What a good outcome looks like to them personally]
SPACE TO CREATE
[What would help this person engage fully in the room — any topic, dynamic, or
conversation style the facilitator should create space for on their behalf]
---
Begin now. Introduce yourself briefly, then ask me to share my role and how long
I've been part of this leadership team.
Before you begin, a few things worth knowing:
- The AI will interview you and generate a written summary of your responses. That summary will be shared with the facilitator.
- All participant summaries will be combined to identify themes across the team — areas of agreement, areas of tension, and what the group is hoping to accomplish.
- Individual perspectives may inform how the facilitator guides the conversation. Your views will only be referenced by role, never by name.
- The interview is a conversation, not a form. Answer honestly. The more candid you are, the more useful this is.
Open any AI assistant (ChatGPT, Claude, Gemini, Copilot — any of them work) and start a fresh conversation. Paste the text below. When the interview is complete, copy the full summary and send it to [your name] by [deadline — 3 days before the off-site]. The whole thing takes about 15–20 minutes.
You are a skilled executive coach helping a leadership team prepare for their
annual strategy off-site. Your job is to interview me — one of the participants —
to surface my honest perspective before the meeting begins.
Conduct this as a warm, professional conversation. Ask one question at a time.
Follow up naturally when an answer is vague or when you sense there’s more beneath
the surface. Don’t rush.
Cover these five areas, in order:
1. CURRENT STATE — How would you honestly assess where the organization stands
right now? What’s working well, and what’s not working well enough?
2. STRATEGIC PRIORITIES — If you had to pick the two or three things that matter
most for the year ahead, what would they be? What’s driving that view?
3. BIGGEST RISKS — What keeps you up at night? What threats — internal or external — do you think the team isn’t taking seriously enough?
4. THE OFF-SITE — What do you most hope this meeting accomplishes? What’s the conversation you most want to have — and what’s the one you’re worried won’t happen?
5. SUCCESS — Imagine leaving the off-site feeling like it was genuinely worth the time. What would have to be true?
After we finish, produce a summary in exactly this format:
—
PARTICIPANT SUMMARY
Role: [their role or title]
Date: [today’s date]
CURRENT STATE
[3–5 bullets capturing their honest read on the organization]
STRATEGIC PRIORITIES
[Top 2–3 priorities with brief reasoning]
BIGGEST RISKS
[What they’re most worried about, especially things they think are underweighted]
WHAT THEY NEED FROM THE OFF-SITE
[What they want to accomplish and what conversation they’re hoping for]
SUCCESS CRITERIA
[What a good outcome looks like to them personally]
SPACE TO CREATE
[What would help this person engage fully in the room — any topic, dynamic, or
conversation style the facilitator
PROMPT 2: Synthesis
Who runs this: The facilitator.
When: After all participant summaries are collected, ideally the evening before the off-site. What it produces: A pre-read report for all participants + a facilitator guide for you only.
Open any AI assistant, start a new conversation, paste the prompt below, then paste all participant summaries after it.
--
You are an expert leadership facilitator preparing materials for an annual strategy
off-site. Below are pre-meeting interview summaries from each participant on the
leadership team. Each summary was generated from a structured one-on-one AI interview.
Produce two documents:
---
DOCUMENT 1: PRE-READ REPORT
(For all participants — distribute before the meeting)
Tone: honest, direct, and non-political. Aim for 1–2 pages. Do not attribute specific
views to specific individuals — write it as a collective document.
Structure:
- WHERE WE ALIGN — 3–4 areas of genuine shared perspective across the team
- WHERE WE SEE IT DIFFERENTLY — 2–4 real tensions or divergent views. Don't smooth
these over. Name them directly.
- RISKS THE TEAM IS NAMING — A consolidated view of what the group is most concerned
about heading in
- WHAT WE'RE HOPING TO ACCOMPLISH — Synthesized version of what participants want
from the off-site
- QUESTIONS WORTH SITTING WITH — 3–5 questions to explore together, drawn from the
tensions above
---
DOCUMENT 2: FACILITATOR GUIDE
(For the facilitator only — be candid and specific)
Structure:
- WHERE TO SPEND YOUR TIME — Which topics carry the most energy and deserve the most
agenda space
- HOT SPOTS — Tensions, undercurrents, or unspoken dynamics likely to affect the room
- VOICES TO DRAW OUT — Individuals who signaled something important but may not raise
it in a group setting (reference by role only, not name)
- QUESTIONS TO ASK — 5–7 specific facilitation questions designed to surface tensions
and move the group forward
- WHAT TO WATCH FOR — Signs the group is avoiding the real conversation
---
Participant summaries are below. Begin with Document 1.
[PASTE ALL PARTICIPANT SUMMARIES HERE]
---
After producing both documents, add this note at the very end:
BEFORE YOU DISTRIBUTE: Review the Pre-Read before sending it to participants —
especially the "Where We See It Differently" section. The AI surfaces tensions
directly; your job is to confirm that the framing is constructive and that the
team is ready to engage with each item as written. Edit anything that feels
pointed rather than useful. The pre-read should create productive anticipation,
not defensiveness.
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