What Should an Executive Assistant Ask Before Booking a Leadership Offsite?

By Megan Cary, Senior Executive Producer | PC Events + Experiences

Booking a leadership offsite is rarely in anyone's job description, and it is almost always on someone's plate anyway. The questions below are the ones that decide whether the two days run quietly or whether you spend them behind the AV table.

Ask them before you sign. Most of them cost nothing to ask and a great deal to discover late.

WHO IS THE OFFSITE FOR, AND WHAT SHOULD IT DECIDE?

Start here, because the answer sets the headcount, the room and the length. An offsite for eight people deciding next year's operating plan is a different booking from an offsite for forty people hearing it.

Write down the one decision the group has to walk out with. If nobody can name it, the agenda will fill with updates, and updates are what email is for. There is a strong case for taking the team out of the building, and it gets stronger the more specific the reason is.

HOW FAR FROM THE OFFICE IS FAR ENOUGH?

Far enough that nobody can pop back for an afternoon meeting. That is the real test.

An hour's drive or a flight both pass it. Six blocks does not. The offsites that get hollowed out are the ones close enough that three people slip away at two o'clock, and by day two the room has lost its quorum.

We have run leadership retreats for clients all across the country and globe: D.C., Dallas, Boston, San Diego and Paris. The San Diego retreat ran a Mystery Box Cooking Challenge at the Wine and Culinary Center. Distance was doing work in every one of them.

WHAT SHOULD THE VENUE HAVE THAT A HOTEL MEETING ROOM DOESN'T?

Daylight. A room you can reset without moving to a second space. Breakout corners that are out of earshot. A place to eat that is not the room you have been sitting in all day. Somewhere outside to walk.

Ask the venue directly about the ceiling height, the natural light, and whether the room next door is booked. The list of what planners are asking venues for has shifted toward exactly these things, and most sales sheets still lead with square footage.

For the University of Chicago Booth Family Office Summit, we organized 200 attendees across a day and a half at the Rubenstein Forum, with a VIP dinner in the Skyview Room overlooking the city. The dinner being somewhere other than the meeting room was not a flourish. It was the thing people remembered.

WHO OWNS THE DAY-OF SO YOU DON'T HAVE TO?

You focus on your executive. We'll handle everything else.

That line is the whole answer, and it is worth being literal about what it means. Someone has to hold the run of show, meet the AV crew at seven, chase the catering headcount, move the transport when a flight slips, and notice that the second breakout room is twelve degrees colder than the first. If that someone is you, you are not in the room with your executive.

Our event management work exists for this. One producer onsite, one point of contact for the venue and every vendor, and a run of show that has been through its fourth revision before anyone arrives.

The job is to make sure nothing reaches the executive assistant on the day. If she is answering a question from the AV crew at nine in the morning, we have already lost.

Patrick Crosson, CMP, DES, Chief Experience Owner, PC Events + Experiences

WHAT HAS TO BE IN WRITING 2-3 WEEKS OUT?

• The run of show. Final, with the names of whoever is speaking and for how long.

• The rooming list. Names, arrival times, departure times, and who is sharing ground transport.

• Dietary requirements. Collected, confirmed back by the venue, and re-confirmed the day before.

• The AV plan. Who is bringing what, and who is paying for what the venue brings.

• The weather contingency. For anything outdoors, with a call time for the decision.

• The contract clauses that bite. Attrition dates, cancellation terms, and the last day to drop rooms without penalty.

Two weeks out is also the last comfortable moment to change the room set. After that, you are paying for labor, not for furniture. If you are lining up vendors at the same time, these are the questions to ask vendors that most planners skip.

FREQUENTLY ASKED QUESTIONS

How far from the office does a leadership offsite need to be?

Far enough that nobody can go back for an afternoon meeting. That is the only distance rule that matters. In practice, it means either a drive of about an hour, or a flight. A hotel six blocks from the office looks efficient on paper and gets raided by calendars by lunchtime on day one.

How far ahead should we book?

Three to six months for a group under fifty, longer if the dates are in January, February, September or October. Smaller groups are easier to place late, but executive calendars are the real constraint, so the date usually has to be held before the venue does.

Who runs the day so the executive assistant does not have to?

A producer who is onsite, holds the run of show, and is the single point of contact for the venue, the AV crew and the catering team. If the answer to that question is you, the offsite has not been resourced. The point of bringing in a producer is that you sit in the room with your executive instead of behind the AV table.

What should be in writing 2-3 weeks out?

The final run of show, the rooming list, dietary requirements, the AV plan with who is bringing what, the transport schedule with arrival and departure times, and the contingency for weather if any part of it is outdoors. Four weeks out is also when the attrition and cancellation clauses stop being theoretical.

What does a leadership offsite cost?

It moves with headcount, destination, number of nights, and how much production the general session needs. Ask for a range against your headcount and your dates before you shortlist venues.

Should we do a site visit?

Yes, and send somebody who will notice the things a floor plan does not show. A site visit is how we found that the Cancun awards dinner planned for the resort dunes sat in the heat and the smell of seaweed, which moved the whole evening indoors three months out. A floor plan would never have said so.

WE GET OFFSITES DONE.

If an offsite has landed on your desk and you would like someone else to hold the run of show, that is what we do. Hotel and venue sourcing, the producer onsite, and the contingency you hope not to need, in Chicago and wherever your executives are flying.

Ask us about an offsite that changed venues three months out. Our who we are page says the rest.