How to plan a leadership retreat: eight steps that make it work
You've been asked to plan a leadership retreat. It's a big investment of time and money, and everyone will judge it by one thing: did anything change afterwards?
Most of what makes a retreat work is decided long before anyone arrives. These eight steps cover what matters most.
How do you plan a leadership retreat?
Decide what has to be different afterwards, ask your leaders what they need, choose a theme, then shape the days around thinking rather than reporting. Bring in an outside voice, protect time to connect, and plan the follow-through before you go.
Eight steps to plan a leadership retreat
Decide what has to be different afterwards. Write it in one sentence. Every other decision follows from it.
Ask your leaders what they need. A short conversation or a few questions in advance. You'll find the real issues faster than any planning meeting.
Choose a theme. One that names the change your leaders face, with a question to carry through the retreat. See leadership retreat themes.
Pick the right place. Far enough from the office to switch off, with space to walk, talk and think.
Shape the days around thinking. Keep updates for email. Give the best hours to the conversations that matter. See a sample leadership retreat agenda.
Bring in an outside voice. A keynote at the start lifts leaders out of their day-to-day thinking and gives everyone a shared language.
Protect time to connect. Meals, walks and evenings build the trust that makes the hard conversations possible.
Plan the follow-through before you go. Decide how you'll capture commitments and when you'll check on them. Put the date in the diary now.
Why the Big Bold Mindset fits a leadership retreat
The Big Bold Mindset® is a way of thinking for achieving big bold goals in a changing world. Its starting point is simple: you can't navigate a new world using an old set of charts.
A retreat is where leaders get the space to draw new ones. The Big Bold Mindset® is built on 21 principles, each with a practical tool.
Where a keynote fits
An opening keynote sets the tone for the whole retreat. It gives leaders stories and ideas to come back to, and a shared starting point for the conversations ahead.
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.
“Refreshing and incredibly impactful. Really made our conference different. The team loved him!”
Caspar has worked with organisations including BAE Systems, Burberry, GSK, Intuit, INEOS Styrolution, Johnson & Johnson, Nuffield Health, Pearson, Sage, Suntory and Thales.
Planning a leadership retreat: questions
How far ahead should you plan a leadership retreat?
Three to six months is common. Good venues and speakers book up, and leaders' diaries fill quickly.
How long should a leadership retreat be?
Two to three days is typical. It gives time to slow down and for deeper conversations.
How many people should attend a leadership retreat?
Small enough for every voice to be heard. Most leadership retreats work best with a single leadership team.
What should you include in a leadership retreat?
Time on direction, honest conversation about change, time to connect as people, and clear next steps.
How do you get leaders to engage at a retreat?
Work on the issues they care about, ask what they need beforehand, and keep updates out of the room.
Should you hire a keynote speaker for a leadership retreat?
A keynote at the start can lift the whole retreat, especially when it's tailored to what your leaders are facing.
How do you measure the success of a leadership retreat?
Check the commitments a month later. Ask what leaders are doing differently, not just whether they enjoyed it.
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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