Leadership retreat agenda: a sample two-day plan you can adapt
You're writing the agenda for your leadership retreat. It's tempting to fill every hour, because every hour is expensive. But a packed agenda leaves no room for the conversations that make a retreat worth it.
This sample follows a simple order: see the future, face today honestly, decide what matters, then agree the first steps. Adapt it to your team.
What should be on a leadership retreat agenda?
An opening that sets the purpose, time looking at the future, an honest look at today, the few decisions that matter, time on how the team works together, and clear next steps. Leave space to walk, talk and eat together.
A sample two-day leadership retreat agenda
See the future, face today honestly, decide what matters, then agree the first steps.
Day 1
Morning: Open with the purpose of the retreat, then an opening keynote to lift everyone’s thinking.
Late morning: The future: what will we see, hear and feel five years from now?
Afternoon: Today as it really is: what's changed, and what are we avoiding?
Late afternoon: Walk and talk in pairs, with one question each.
Evening: Dinner together, with no agenda.
Day 2
Morning: The big decisions: the few priorities that matter, and what you'll stop doing.
Late morning: How we work together: what builds trust here, and how we'll disagree well.
Afternoon: Monday: three small steps, each with an owner and a date.
Close: Each leader says one thing they'll do differently.
A one-day version: open with the purpose and a keynote, spend the late morning on the future, the afternoon on priorities, and finish with next steps.
Five things to keep out of the room
Updates. If it can be read, send it before you go.
Laptops in every session. Attention is the scarcest thing leaders bring.
Every topic at once. Three conversations done well beat ten rushed ones.
The same voices every time. Plan for the quieter leaders to be heard.
Decisions with no owner. If nobody owns it, it won't happen.
Why the Big Bold Mindset fits
The order of this agenda follows The Big Bold Mindset®: imagine a better future, see today as it really is, then close the gap.
It's built on 21 principles, including Redraw the Charts, Build Your Trust and Inch Yourself Forward, each with a practical tool.
Where a keynote fits
First thing on day one. A tailored keynote sets the tone, gives leaders a shared language and makes every session that follows sharper.
Built for your team, not taken off the shelf
Every audience is different, and every leadership team is facing its own set of issues. So no two of Caspar's keynotes are the same.
Before the day, Caspar does a deep dive into your world: what's changing, what matters most to you, and what you need people to think and do differently. Where it helps, he speaks to several of your senior leaders to get a wide view of what's really going on.
Then he crafts a keynote specifically for your retreat, applying the Big Bold Mindset principles that fit your challenges. Not the talk he gave last week, but one built for your team.
About Caspar Craven
Caspar Craven is the creator of The Big Bold Mindset® and a leadership keynote speaker. He has spoken at events in over 38 countries, for over 400 organisations going through change.
Before speaking, he spent five years at KPMG Corporate Finance, was CFO of a fast-growth tech company through its sale to private equity, and co-founded and sold a tech business. He has sailed around the world twice: first in the BT Global Challenge, then as skipper with his wife and three children under ten.
His lesson from both worlds: put people first and the results will follow. See Caspar's keynotes.
“Exactly on point for our top global leaders! The learnings will resonate long past our meeting.”
Caspar has worked with organisations including BAE Systems, Burberry, GSK, Intuit, INEOS Styrolution, Johnson & Johnson, Nuffield Health, Pearson, Sage, Suntory and Thales.
Leadership retreat agenda questions
What should be on a leadership retreat agenda?
The purpose, the future, an honest look at today, the key decisions, how the team works together, and next steps.
How do you structure a two-day leadership retreat?
Day one for looking out and looking honestly at today. Day two for decisions, how you work together and next steps.
What should you do on the first day of a leadership retreat?
Set the purpose, lift everyone's thinking with an outside voice, then look at the future before getting into today's problems.
How much free time should a leadership retreat have?
More than you think. Walks, meals and evenings are where trust gets built.
When should the keynote speaker be on a leadership retreat agenda?
Usually first thing on day one, so the keynote sets the tone for everything that follows.
How do you end a leadership retreat?
With clear next steps, each with an owner and a date, and one commitment from each leader.
Can a keynote be tailored to our leadership team?
Yes, and it should be. Caspar starts with a deep dive into your challenges, often speaking to several senior leaders, then builds the keynote around what matters most to your team.
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