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Executive traveler and private office coordinator in a Manhattan hotel suite with city skyline
Journal
CLIENT JOURNEYS
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September 7, 2026

Four Lines From a Chief of Staff

An offsite for forty, from the four line brief it arrived as to the single invoice it left as, and the questions asked before anyone quoted anything.
Justin Keeperman
Justin Keeperman

This is an example brief, composed from the way offsites of this shape are actually run rather than from one identified company. The decisions in it are the real ones.

Know before you go

  • The shape: forty people, three nights, nine departure cities, October in Europe.
  • Lead time: six to nine months. A buyout needs longer than a block.
  • Settle early: the arrival window, block or buyout, and who signs it off.
  • What drives the cost: the spread of departure cities, the buyout premium, and the one big evening.
  • Where it usually goes wrong: a first working morning scheduled too early after a travel day.

How it arrived

Four lines from a chief of staff. Forty people, three nights, somewhere in Europe in October, needs to feel like a reward and still get eight hours of work done.

That is a good brief. It has a number, a window, a region and a tension. Most of what follows is resolving the tension.

What we asked before quoting anything

Five questions, and none of them were about hotels.

Where are the forty people flying from. Who has to be in the room for the working sessions and who is optional. Is there a number, or a number you would go past for the right thing. Who signs it off, and what do they need to see. And what went wrong at the last one.

The last question is the useful one. It was the answer to that, not the brief, that decided the property.

Air from nine cities, one arrival window

Forty people leaving from nine cities is nine separate problems that have to become one arrival. We worked backwards from a two hour window on the Tuesday afternoon, because a welcome dinner where a third of the room walks in at nine is not a welcome dinner.

Three people could not make the window without an overnight. They came a day early, which cost three room nights and saved the first evening.

Block or buyout

At forty people in October, a buyout of a smaller property was within reach of a block at a larger one. We priced both.

The buyout won, and not on price. It won because a group that has the whole house stops behaving like guests. The bar stays open, the sessions run late without a conversation with a duty manager, and nobody is negotiating for the terrace.

Meeting space that actually works

The usual failure is a beautiful room with no natural light, or a beautiful room with too much of it and no way to see a screen. We looked at both rooms in person, at the hour they would be used.

Eight hours of work happened across two mornings rather than one long day, which nobody asks for and everybody prefers. The afternoons were free, which is what made it feel like a reward without anyone having to say so.

The evening people remember

One. Not three. The budget for three good evenings, spent on one that was genuinely good and two that were relaxed and cheap, produces a better week than three competent ones.

One invoice

Air, rooms, ground, meeting space and the evenings on a single statement, coded the way their finance team already works, reconciled once.

The chief of staff never chased a supplier. That was the actual brief, underneath the four lines.

What we would change

We would build in a slower first morning. The group landed Tuesday afternoon and started work at nine on Wednesday, and the room was flat until eleven.

Have an offsite to place?

See how we work with principals, family offices and executive teams, or send us the headcount, the window and what went wrong last time.

What makes a good offsite brief?

A headcount, a window, a region and the tension you are trying to resolve. You do not need a hotel shortlist. The most useful line you can add is what went wrong at the last one.

Do you work inside an existing travel policy?

Yes. Cabin rules, hotel caps and approval thresholds are set once and booked to. Where something falls outside policy you hear about it before it is booked, not after.

Is a buyout usually better than a room block?

Not usually, but often at thirty to fifty people in shoulder season. The reason is behavioural rather than financial. A group with the whole property stops negotiating for space and the evenings run properly.

How does billing work?

One statement covering air, rooms, ground, meeting space and events, coded to match how your finance team already works, so it reconciles in one pass and stands up to whoever signs it.