What Should a Leadership Retreat Agenda Include?

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

A leadership retreat agenda has to do two jobs at once. It has to give eight or ten senior people a reason to be in a room together for two days, and it has to survive the moment one of them says the thing everybody has been avoiding. Most agendas we see are built for the first job and fall apart on the second. The fix is structural: put the hard conversation on day one, put the decisions on day two, and leave real unscheduled time in between, because that is where the agreement actually forms.

WHAT IS A LEADERSHIP RETREAT FOR?

A leadership retreat is a working session with the day job switched off. Calling it a reward or a kickoff gets the agenda wrong from the first line. The group is there to settle something that email and a standing Tuesday call cannot settle, usually because the conversation needs more than an hour and more candor than a calendar invite produces.

That purpose has to be written down before anything else goes on the agenda. One sentence, agreed by whoever called the retreat: by Thursday afternoon, this group will have decided X. Every session you add afterwards either serves that sentence or gets cut. Harvard Business Review makes a related case from a decade of research on offsites, which found they reshape the informal networks inside a team and that the agenda should be built from what you learn before the retreat rather than from a template.

Ask the group for that input two to three weeks out. Three questions by email is enough: what has to be decided, what will make this a waste of your time, and what do you want to stop doing. The answers write most of your agenda, and they tell you which conversation is the hard one.

WHAT GOES IN DAY ONE VS. DAY TWO?

Day one is for the problem. Day two is for the decision. Running it the other way around is the single most common agenda mistake, and it produces a retreat where everyone agrees pleasantly on day one and then relitigates everything on the drive to the airport.

A two-day shape that holds up:

• Evening before: Arrivals, one shared activity, dinner. No content. People need to have laughed at something together before they disagree about strategy.

• Day one morning: The hardest conversation, in the first working block, with a facilitator who is allowed to interrupt.

• Day one afternoon: The same topic broken into its parts, in small groups. Three or four people per group.

• Day one late afternoon: Unscheduled. Daylight. No optional session that is really mandatory.

• Day two morning: Decisions, owners and dates. Written on a wall where everyone can see them.

• Day two before lunch: What gets communicated to the wider company, by whom, by when. Then end early.

The small-group block is worth defending. Session design people have been making this point for years: the question that decides the format is the number of people and the amount of time they have together. Ten executives in one room for three hours gives you two people talking and eight people waiting. The same ten split into three groups gives you ten people talking.

HOW MUCH FREE TIME IS ENOUGH?

At least two hours in daylight on day one, plus honest gaps between sessions. Not an optional hike that everyone feels like skipping. Actually free.

This is the part that gets cut when the agenda runs long, and it is the part the attendees remember. The pairs of people who walk to the water, the CFO and the head of product who finally have forty minutes, the conversation on a terrace that settles something the morning session could not. At the Breakthrough Energy Fellows retreats we have produced across five cities, including San Diego and Paris, the unscheduled windows did as much work as the programmed ones.

Protect the gaps between sessions too. A fifteen-minute break is a ten-minute break by the time the first session runs over, and a group that is always five minutes behind never relaxes.

WHERE DO MEALS AND EVENINGS FIT?

Structure the first evening. Leave the second one open.

The first night is the one that sets how the group talks to each other for the next two days, and a shared activity does that faster than a dinner table. At the Breakthrough Energy Fellows retreat in San Diego we ran a Mystery Box Cooking Challenge at the Wine and Culinary Center. People who had traded emails for a year ended up arguing about a sauce. The next morning's session started warm.

Meals during the day should be short and seated together, in a room that is yours. A buffet in a public restaurant means the group splits into the same four people who always sit together, and you lose the mixing you paid for. On the second evening, let people choose their own company. By then they have earned it, and the ones who want to keep working will find each other anyway.

One operational note that matters more than it should: collect dietary and accessibility needs at the invitation stage, not the week before. Chasing them late is how a vegan ends up with a plate of sides in front of the COO.

WHAT SHOULD THE EA HAVE IN HAND THE MORNING OF?

Five things, printed and on your phone, because venue wifi is where plans go to die.

• The run of show. Timed to the minute, with the name of whoever owns each block.

• The rooming list. Names, room numbers, arrival and departure times.

• Dietary and accessibility notes. By name, not by count, and already in the caterer's hands.

• The AV plan. What is in each room, who the technician is, and their mobile number.

• The transport schedule. Pickups, drop-offs, and the plan for the executive whose flight moves.

If you are earlier in the process than this, we wrote a companion piece on what to ask before booking a leadership offsite that covers the venue questions, the distance question and the contract clauses that matter. This post picks up after the venue is signed.

And decide in advance who owns the day. If that is you, block your own calendar completely. If it is someone else, say so out loud to the group on the first morning so nobody is quietly looking at you when the projector fails.

FREQUENTLY ASKED QUESTIONS

Q: How long should a leadership retreat be?

Two days and one night covers most of them. One day is a long meeting with a view and the group never drops its guard. Three days is worth it when the team is newly formed or the decision on the table will shape the next two years.

Q: What should be on the day one agenda?

The hardest conversation. Put it in the first working block, while people are fresh and before the group has settled into agreement. Day one is for the thing that could derail the retreat if it surfaces on day two.

Q: How much free time should a leadership retreat agenda include?

Leave at least two hours unscheduled in daylight on day one, plus the gaps between sessions. Executives who traveled in need it, and the conversations that happen in that window are regularly the ones people remember six months later.

Q: Should the CEO present or participate?

Participate. A CEO presenting for an hour turns a retreat into a town hall. If there is a state-of-the-business update, run it the evening before or in the first thirty minutes, then hand the room to a facilitator.

Q: Do evening events need to be structured?

One of them does. A shared activity on the first evening gets a group talking faster than a dinner table does. Leave the second evening open so people can choose their own company.

Q: What should the executive assistant have in hand the morning of?

The run of show, the rooming list, the dietary and accessibility notes, the AV plan with a named contact, and the transport schedule. One printed copy and one on your phone, because the venue wifi is where plans go to die.

WE GET RETREATS DONE.

If a leadership retreat has landed on your desk and the agenda is the part keeping you up, that is the part we are good at. Our corporate event planning services cover the agenda design, the venue, the run of show and the person standing at the back of the room so you can sit down. We handle event production in Chicago and run retreats wherever the group needs to be.

Ask us about a five-city fellows retreat that ended in a cooking competition. Or talk to us and bring your dates.