The leadership away day: ideas for leading your team through change
You're planning a leadership away day. It's a rare chance to get your leaders out of the building and out of the day-to-day. Usually because something is shifting: a new strategy, a new structure, new pressure on results.
The risk is that you spend the day doing what you do every week, just in a nicer room. The opportunity is to step back, think differently and come back as a team pulling in the same direction.
What makes a good leadership away day?
A clear purpose, real conversations about what's changing, and time to think rather than report. The best away days end with a shared direction and a few small steps everyone owns.
Five things to think about before your leadership away day
Why are we going away? If the answer is "we always do", start there. A clear purpose changes the whole day.
What are we avoiding? The topic nobody has put on the agenda is often the one that matters most.
Who does the talking? If the most senior person speaks most, the room learns to wait. Plan for every voice to be heard.
Is the day for thinking or for updates? Updates can go in an email. Protect the time for thinking together.
What changes on Monday? Agree before you leave who will do what, and when you'll check.
Why the Big Bold Mindset fits a leadership away day
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 leadership away day is where a team gets the space to redraw those charts. Away from the noise, leaders can look at what's really changing and decide how they'll lead through it.
The Big Bold Mindset® is built on 21 principles, each with a practical tool. These five fit a leadership away day best.
Five principles for a leadership away day
Figure Out Focus: are we looking at the past, the present or the future, and where should we be looking?
Bolster Your Belief: belief is a skill, so train it on purpose. Do we really believe in where we're heading?
Agree on Values: which of our values do we live, and which are just on the wall?
Master Your Emotions: master your emotions, or they master you. How are we really feeling about the change ahead?
Inch Yourself Forward: what's the smallest step that would make a real difference this month?
Where a keynote fits in a leadership away day
Many teams open their away day with an outside voice. A keynote at the start lifts the room out of the day-to-day and gives everyone the same starting point: why the old charts no longer work, and what it takes to lead people through change. The conversations that follow are sharper for it.
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 away day, 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.
“The Big Bold Mindset® has truly inspired me in my own leadership. We used it in our leadership meeting the following week. We applied the 'Wearing Hats' technique to envision our future organisation, and the 'Why / Why Not' workshop to explore how to accelerate our growth in the Nordics.”
Caspar has worked with organisations including BAE Systems, Burberry, GSK, Intuit, INEOS Styrolution, Johnson & Johnson, Nuffield Health, Pearson, Sage, Suntory and Thales.
Leadership away day questions
What is a leadership away day?
A day out of the office where a leadership team steps back from day-to-day work to think about direction, priorities and how they lead together. It's also called a leadership offsite or leadership retreat.
What is the purpose of a leadership away day?
To give leaders time and space to think about the big picture together: where you're going, what has to change, and how you'll take people with you.
What should you do on a leadership away day?
Start with the one thing that has to be different afterwards. Then make room for honest conversation about the change you face, agreeing priorities, and clear next steps.
How do you make a leadership away day engaging?
Get people talking rather than watching slides. Bring in an outside perspective, mix up who speaks, and work on real issues.
How long should a leadership away day be?
One day works for most teams. Two days, with an evening together, gives time for harder conversations.
Should you have a guest speaker at a leadership away day?
An outside speaker can say what's hard to say from the inside, and give the team a shared language for the rest of the day.
How do you follow up after a leadership away day?
Agree a few small steps with owners and dates before you leave. Check them at your next leadership meeting, not at next year's away day.
Is a leadership away day the same as an SLT offsite?
Very close. An SLT offsite is usually the most senior team; a leadership away day often includes a wider group of leaders.
What's the difference between a leadership away day and a leadership retreat?
An away day is usually a single day, close to home and focused on the business. A retreat is longer, often residential, with more time for reflection.
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.
Offsite and retreat guides
Leadership offsites
SLT offsite · Leadership offsite · Executive team offsite · Strategy offsite · Tech leadership offsite
Leadership retreats
Leadership retreat · Retreat themes · Retreat ideas · How to plan a retreat · Retreat agenda