Leadership Offsite Ideas: How I Would Plan the Day

For me, a leadership offsite is one day where the people who run a company step away from running it, so they can practise running it better.

It is a lovely idea, honestly. A day off the treadmill, and a day on purpose.

But, I find the agenda usually fills up before anyone has decided what the day is for.

I have done this myself. More than once.

What should a leadership offsite actually be for?

I think a leadership offsite should be built around one behaviour you want to see more of on Monday morning.

One behaviour, one single thing. Choosing it is probably the most useful hour of the whole planning.

A strategy review together is a good thing to have, and I would keep one in the day.

But, for me, the offsite earns its place when people leave doing something slightly differently, and talking about it differently too.

Small and specific.

“Raise the disagreement in the meeting itself” is a behaviour you can watch for. “Better alignment” is a hope, and a perfectly decent one.

Leadership offsite ideas I would actually use

These are the five ideas I keep coming back to when I plan a leadership offsite day.

• Pick the behaviour first, then the venue. The resort can wait a week. The sentence for Monday can't.
• Play something before you discuss anything. A simulation gives the room a shared story to point at, so nobody has to point at each other.
• Give the game real tension. Scarce resources, private goals, a clock. Rules small enough to learn in 10 minutes.
• Spend as long on the debrief as on the game. The game makes the moments. The debrief turns them into decisions.
• Leave with one commitment per person, written down. Then someone checks on it two weeks later, in a normal meeting.

Why play a game at a leadership offsite?

It is fair to be sceptical here. Senior people have sat through a lot of icebreakers, and I have run a few rubbish ones myself.

But, a well-made simulation gives me something a discussion rarely does.

It shows how the team actually behaves under pressure, live, in the room, with everyone watching the same thing.

In Ripple Effect, five leaders run one company, and their decisions land on each other's desks.

Nobody needs a slide on interdependence after that. They have just felt it.

And that shared hour becomes the reference point for the rest of the day. “Remember round three?” does a surprising amount of work by the afternoon.

If you want to see the range, I wrote up the leadership simulation games I have designed for rooms like this.

How long should the game and debrief be?

For a one-day leadership offsite, I would give the game 90 minutes and the debrief 90 minutes.

That looks lopsided on paper. It is the right kind of lopsided, for me.

Because without the debrief, a good game is probably just a nice morning, and a nice morning fades by Wednesday.

I use a loop I call EPPA for that part. Have a look at the EPPA debrief loop if you want the steps.

A sample leadership offsite agenda

Here is the shape I would start from, and then bend to fit the team.

• 9:30 Arrive, coffee, one sentence each on what they hope changes.
• 10:00 The game, 90 minutes.
• 11:30 Break.
• 11:45 The debrief, 90 minutes.
• 13:15 Lunch.
• 14:15 The real strategy question, worked through using the language from the morning.
• 16:00 One commitment each, written down and read aloud.
• 16:30 Close.

What I would leave out

Paintball and trust falls have their place, and plenty of teams have a lovely time with them.

But, for a leadership offsite, I would leave out anything the team can't link back to Monday.

And I would cut the third keynote. I say this as someone who has been the third keynote.

Fewer sessions, more air.

Who should run the day?

I think someone from outside the team should run it, so the most senior person gets to play instead of host.

That could be an L&D lead from another function, or an outside facilitator. Either works, honestly.

If executive team building is closer to what you need, I wrote more on executive team building.

Questions people ask me about leadership offsites

How many people can play a game at a leadership offsite?

Ripple Effect seats five leaders at a table. For a bigger group, I would run several tables side by side.

Should a leadership offsite be away from the office?

I think yes, if you can manage it. A different room makes it easier to behave a little differently.

What should happen after the offsite?

Check the written commitments two weeks later, in an ordinary meeting.

That small check probably matters more than the whole day, for me.

Plan the day backwards from Monday morning, and most of the agenda sorts itself out.

And if your team already has an offsite format it loves, keep it. They probably know something about their own room that I don't.

With love from Bengaluru, this is Arvindh saying over and out.