The EA's Guide to
Planning the CEO's Offsite.

If you're an EA or Chief of Staff, this guide exists because you asked for it. Not in so many words — but in the 200+ phone calls we've taken over 14 years from people in your role who inherited an offsite planning assignment two weeks before a board meeting, a Monday morning, or a redeye flight.

Here's what we've learned watching this specific buyer navigate this specific problem.

The decision that gets made wrong most often

Most CEOs delegate the offsite to an EA with a budget number and one sentence: "I want it to be good." That's the first problem. Without a more specific brief — what does the CEO want the team walking out of this thinking? — you're shopping blind.

Before you talk to a single vendor, get the CEO to answer one question: "What's the one conversation you want to hear at dinner on the second night?"

The answer to that question tells you the venue, the agenda, the facilitator, the room layout, the music, and whether there's a fireside at all. It's the Rosetta Stone of the whole event.

The three offsite formats you need to know

1. The Alignment Offsite

Leadership team, 8–15 people, 2–3 days. Goal: get on the same page about strategy for the next 12 months. Best when there's been a change — new board member, new CFO, new product line.

What to optimize for: a room small enough that no one can hide. Round tables or U-shape. A facilitator who can handle conflict without letting it escalate.

2. The Expansion Offsite

Leadership + next layer down, 25–60 people, 2 days. Goal: align the broader leadership bench with the strategy the exec team already set.

What to optimize for: breakouts that are facilitated (not self-organized). Real exposure to the exec team — not just on-stage presentations.

3. The Incentive Offsite

Top performers across the org, 50–300 people, 3–4 days. Goal: recognition, retention, cultural reset.

What to optimize for: a destination that feels earned. Specific, not generic. Avoid anywhere that says "luxury resort" in the URL.

The vendor vetting questions the planner never wants you to ask

1. "What's the most recent event you produced, and can I talk to that client?"
2. "Who specifically will be on the ground the day of? Are they senior enough to make decisions when something goes wrong?"
3. "Walk me through the last thing that went wrong on an event and how you handled it."
4. "What's your process when the CEO changes their mind about something 48 hours before the event?"
5. "How are you compensated? Commission on vendor bookings, flat fee, or markup?"

If the answers to #3 and #4 are vague, keep looking. Great producers have dozens of war stories and handle change orders without emotional escalation.

The budget conversation that should happen before anyone proposes anything

Most RFPs include a number. Don't give your number away unless you know what you're getting for it.

Instead, share the business outcome you need and ask the producer to come back with a range. "We need our leadership team walking out aligned on strategy, energized, and talking about this 6 months later. What does that cost for 12 people, 3 days, in New Orleans?"

A producer who gives you a single number is guessing. One who gives you a range — and explains what changes between the low and high end — understands the work.

The Little Black Book

Once you know the destination, our Little Black Book has the tactical intel: private dining rooms with transport logistics, booking windows, and curator notes on 17 cities including New Orleans, Austin, Nashville, and San Francisco.