How to use AI to plan a company retreat (and what to leave to humans)
If you're reading this, the conversation probably went something like this. Your CEO mentioned in a 1:1, just before pivoting to the next agenda item, that the company is doing a retreat later in the year, and could you own that? Maybe it was Slack. Maybe a private DM during an all-hands. Either way, it took about 45 seconds, and now you're responsible for a six-figure event, several months of work, and the small matter of making 50 colleagues feel reconnected to each other and the company.
Nobody handed you a playbook. You're not an event planner. You have a day job. And you have a creeping sense that AI should probably help with some of this, but you're not sure where to start, which tools matter, or whether ChatGPT can actually do anything more useful than draft a generic-sounding agenda.
Here at Basejam, we speak to company retreat planners day in and day out, and increasingly that conversation includes how AI fits in. The honest answer: AI is genuinely useful for parts of the job, near-useless for others, and confidently mediocre at a handful of things if you let it be. This piece is a practical guide to the difference. It's written for the EA, Chief of Staff, or Head of People who's running this alongside their actual role, not for full-time event planners with five tools open at once.
By the end of this, you'll have specific prompts you can copy into Claude or ChatGPT today, a list of named tools worth knowing about, and a clear sense of which bits of the job to keep firmly with the humans.
Where AI actually helps (and where it doesn't)
It's worth being honest about this up front, because most "AI for X" content isn't.
AI is good at: structuring fuzzy thoughts into outlines, drafting documents quickly, summarising long pieces of text, generating first drafts of anything repetitive (surveys, FAQs, welcome notes), and synthesising feedback at scale. Anything where the value is "give me a competent starting point I can refine," AI does well.
AI is bad at: aesthetic judgement (more on that later), local knowledge (the surf instructor everyone in town actually books, the restaurant that handles long tables well), reading a room, surfacing genuinely original ideas, and any task where the value sits in the relationship rather than the artefact. It's also terrible at telling you when it doesn't know; it will hallucinate a confident-sounding venue with the wrong address rather than admit "I'm not sure."
The smart use, then, isn't "use AI for everything." It's "use AI on the bits it's actually good at, so you have time and headspace for the bits only you can do." Which brings us to the timeline.
Before the retreat
This is where AI earns most of its keep. The 90 days between "you own this" and "the team arrives" is mostly a sequence of documents that need writing, briefs that need structuring, and decisions that need framing. AI is good at all three.
The brief: from 45-second ask to one-page document
The first useful thing AI can do for you is turn the hallway conversation into something concrete. Before you book a venue, choose dates, or do anything else, you need a brief: purpose, success criteria, headcount, rough budget, who has final say. Getting this written down protects you for the next three months.
Open Claude or ChatGPT and try something like:
I've been asked to plan a 3-day company retreat for around 40 people, likely in southern Europe, in October. The ask came in a 1:1 with our CEO and lasted about 45 seconds. Help me write a one-page brief I can take back to leadership to confirm before I start spending money. Cover: purpose, success criteria, target dates, rough budget range, who has final say on key decisions, and what input you'd want from them in the next two weeks. Keep it practical and assume the reader is the CEO.
What comes back will need editing, but it'll surface the right questions. "What does success look like?" is a more useful conversation to have at the start than two months in, when the venue is booked and the agenda is half-built.
Themes and agenda drafting
Once the brief is signed off, the next bottleneck is the agenda. A good prompt here doesn't ask for "a 3-day agenda" generically; it gives the AI the context it needs to be specific to your team.
Our team is 40 people split between London (engineering, ops) and Lisbon (commercial). We've just come out of a difficult Q3 and a small reorg. The CEO wants the retreat to feel like a reset and a recommitment, not a strategy offsite. Suggest 5–7 retreat themes that could anchor a 3-day offsite. For each: the theme in one phrase, why it suits us specifically, and 2 ways to bring it to life through sessions or shared experiences.
The output will give you a vocabulary to bring back to leadership rather than starting with a blank page. The themes themselves probably won't be quite right, but they'll spark the conversation that gets you to the right one.
For the agenda itself, lean on AI for structure but treat its specific session suggestions with healthy scepticism. Boompop's testing of ChatGPT for event agendas back in 2023 concluded the outputs were "cookie-cutter and sometimes repetitive – even when you ask for creative and innovative ideas." That hasn't changed much. Use AI to draft the shape; fill in the specific sessions yourself.
Budget line items
This is where AI is most quietly useful and most underused. The mistake most first-time planners make is accepting a budget number from leadership ("let's say £2,000 per person") without testing it against real line items. AI can help you build the actual number quickly.
Build me a line-item budget for a 3-day, 40-person company retreat in southern Europe (think Lisbon or Mallorca). Include accommodation, F&B (with realistic per-person-per-day minimums), AV, transfers, activities, contingency. Use mid-market 2026 European rates. Flag the three lines most likely to creep, and the three most often missed by first-time planners.
The output gives you a defensible budget to take back to leadership, plus a heads-up on the contract clauses that tend to bite (F&B minimums, attrition, AV). Don't trust the absolute numbers; they'll be rough. But the structure and the warnings are reliable.
The attendee intake survey
You'll need one of these. Dietary restrictions, accessibility needs, T-shirt sizes, flight preferences, any reasonable adjustments. Drafting it from scratch wastes an hour you don't have.
Draft a pre-retreat intake form for 40 attendees. Gather: dietary restrictions and allergies, mobility considerations, any reasonable adjustments needed, T-shirt size, flight preferences (direct vs cheapest), one thing they're hoping to get from the retreat. Tone: warm, brief, easy to fill in on a phone in two minutes. End with a clear deadline.
Drop the output into Tally or Typeform. Done in fifteen minutes.
Pre-retreat communications
The welcome doc, the FAQ, the packing list, the Slack announcement. None of these are hard, but they all take time. AI doesn't write them well at first try, but it gets you 80% of the way in one prompt:
Write a pre-retreat welcome doc for 40 attendees of a 3-day company retreat at [venue] in [location]. Include travel and arrival logistics, the day-by-day shape of the agenda, dress code, packing list, who to contact for what, accessibility notes, and what to do on arrival. Tone: warm, clear, not corporate. Assume some attendees have never been to this country before.
Edit, personalise, ship.
During the retreat
Two AI tools earn their place during the event itself, and they're not the obvious ones.
The first is meeting note-taking. If your retreat includes strategy sessions, workshops, or any moment where decisions are being made, you want a record without anyone playing scribe. Granola is bot-free, capturing audio locally on a Mac without joining the call as a bot, which matters when conversations are sensitive. Fathom is the most generous free option for Zoom-based sessions, with unlimited recording and 30-second post-call summaries. Otter is the older incumbent and still solid. Pick one before the retreat, don't try to learn three on the day.
The second is real-time translation for multilingual teams. If you have colleagues whose first language isn't English, DeepL handles documents and live captioning better than Google Translate, and it's particularly strong on European languages. Worth setting up the night before for any team where this is a factor.
A third, more situational use: when an activity falls flat and you need a quick icebreaker or energiser on the fly, whichever AI tool you go to (Claude, ChatGPT, Gemini) is genuinely useful for surfacing options tailored to the group size, time of day, and energy in the room. Better than scrolling through a Google search at the back of the room.
After the retreat
Half the value of a good retreat lives in what happens in the two weeks after it. Most of that is unglamorous synthesis work, which is exactly what AI does well.
Synthesising open-text feedback
You'll send a post-retreat survey. You'll get back dozens of free-text responses to questions like "what worked?" and "what would you change?" Reading them all carefully takes hours; AI does the heavy lifting in minutes.
Below are 38 free-text responses to the question "What worked for you about the retreat?" Synthesise into 5–7 themes ranked by frequency. For each theme: a one-line description, two representative quotes (verbatim), and one concrete suggestion this implies for next time. Do not invent. If something is a single mention, flag it but don't elevate it.
The "do not invent" instruction matters. Without it, AI will sometimes manufacture themes that aren't there. Always read the quotes back against your raw data to catch hallucinations before you share the synthesis with leadership.
Action item extraction
If you used Granola or Fathom for sessions, you'll have transcripts. Run them through Claude or ChatGPT with:
Below are the notes from our strategy session on Day 2. Extract all commitments and action items. For each: who owns it, what they committed to, and any deadline mentioned. Flag anything that sounds like a half-commitment or aspiration rather than a firm action.
You get a clean list to share with the team and chase against. Without this, "what did we even decide?" tends to be the dominant feeling by week three.
The recap email
Drafting the post-retreat company-wide recap is one of those tasks where the blank page is most of the problem. AI gives you a serviceable first draft in 30 seconds, which you then rewrite to add the human texture (a specific moment that landed, a story from one of the activities, a quote from someone whose name everyone knows) that makes the recap feel earned rather than templated.
What AI shouldn't do
This is the section most "AI for X" guides skip, because admitting AI's limits doesn't sell more AI. But it's the most useful part of this piece.
The venue choice. This is the work we focus on at Basejam, and it's exactly the kind of judgement AI struggles with. AI is great at filtering venues against your hard constraints: group size, dates, location, budget. What it can't do is read aesthetic. The difference between a venue that's technically correct and one your team will remember tends to come down to design, atmosphere, and a hundred small details that don't show up in a database. AI can shortlist; humans curate. If you've ever toured a venue that looked beautiful in photos and felt wrong in person, you know what we mean.
Reading the room mid-session. If a workshop is losing the team, AI can't tell you. You need to feel it. Build flex time into the agenda so you can adjust live.
Judgement calls on what suits your team. Whether they'll love a fado dinner in Alfama or find it forced. Whether the morning yoga will land or feel performative. AI has read about both; it hasn't sat in the room.
Vendor relationships. The good caterer who'll move heaven and earth for you next year if you treat them well this year. The local fixer who knows where to find a sound engineer at six hours' notice. AI doesn't have a phone, or twenty years of goodwill in a particular city.
The political bits. Managing the senior leader who wants to add a "quick talk" two weeks out. The colleague who flags dietary restrictions the day before catering closes. The cross-team dynamic that's the real reason for the retreat but isn't in the brief. These need a human in the loop, ideally one with some institutional capital to spend.
A quick tools cheat sheet
For when you want to actually open a tab:
- Writing and synthesis: Claude, ChatGPT, Notion AI
- Meeting notes: Granola, Fathom, Otter
- Surveys and intake: Tally, Typeform
- Translation: DeepL
- Quick visuals (welcome packs, signage): Canva
Pick one in each category and stick with it. You'll be more effective with two tools you know well than ten you half-understand.
The point isn't to use more AI
The temptation, once you start finding AI useful, is to put it in front of every part of the job. Resist that.
The point of using AI for the structured, repeatable, document-shaped bits of retreat planning is to free up time and attention for the parts that actually move the needle: the venue, the room read, the team dynamics, the small details that turn a competent retreat into a memorable one.
If AI saves you ten hours on first drafts, spend three of them on a longer venue conversation with someone who actually knows the property. Spend two on a better agenda revision. Spend one in front of the senior leader you've been avoiding. That's the return.
The retreat your team remembers won't be the one with the slickest welcome packet. It'll be the one held in the right place, with the right shape, where someone clearly put thought into the bits that don't templatise. Those are still your job.
