The leadership offsite: how to plan one that actually changes things
You're planning a leadership offsite. Maybe it's your whole leadership team, maybe it's the leaders in your function. Either way, you're taking busy people away from the day job, and you need it to be worth it.
Most offsites are remembered fondly and forgotten quickly. The ones that change things have a clear purpose, real conversations and a plan for what happens next.
What makes a good leadership offsite?
A clear reason for going, honest conversations about what's changing, and a few agreed next steps with owners. The best leadership offsites change how the team works together, not just what's on the plan.
Five things to think about before your leadership offsite
What's the one outcome? Write it down before you book the venue. Everything else on the agenda should serve it.
What's the real conversation? Every leadership team has one they keep putting off. The offsite is the place to have it.
Is this a team, or a group of leaders? Leaders who each run their own area can forget they're also a team. Make time for how you work together.
How will you hear every voice? The loudest voices fill the space. Plan for the quieter ones too.
What will you check in a month? Agree it before you leave, and put the date in the diary.
Why the Big Bold Mindset fits a leadership offsite
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 offsite is the team's chance to check its charts. Away from the day job, leaders can see where their thinking is out of date and agree how they'll lead from here.
The Big Bold Mindset® is built on 21 principles, each with a practical tool. These five fit a leadership offsite best.
Five principles for a leadership offsite
Figure Out Focus: we don't all look at time the same way. Who in this team looks to the past, the present or the future?
Put People First: a happy boat is a fast boat. What do our people need from us right now?
Unleash Your Superpowers: those around you already know your superpower. What does each of us bring to this team?
Strengthen with Safety: people can't own their mistakes until it's safe to. How safe is it to speak up here?
Harness Your Habits: lead yourself first, one habit at a time. Which one habit would make the biggest difference to how we lead?
Where a keynote fits in a leadership offsite
Many leadership teams open their offsite with an outside voice. A keynote at the start shakes the team out of its usual way of thinking and gives everyone a shared starting point. The conversations that follow are braver 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 offsite, 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 offsite questions
What is a leadership offsite?
A meeting away from the office where a leadership team steps back from day-to-day work to think about direction, priorities and how they lead together.
What is the purpose of a leadership offsite?
To give leaders time to think together about the big picture, have the conversations the day job crowds out, and agree how they'll lead from here.
What should be on a leadership offsite agenda?
Start with the one outcome you need. Then make time for the real issues, how the team works together, and clear next steps. Keep updates out of the room.
How do you make a leadership offsite engaging?
Work on real issues, not hypothetical ones. Mix up who speaks, bring in an outside perspective, and leave room for conversation.
How long should a leadership offsite be?
One or two days works for most teams. Two days gives time for the harder conversations and an evening together.
Should you book a speaker for a leadership offsite?
An outside speaker can challenge the team's thinking in ways that are hard from the inside, and give everyone a shared language for the rest of the offsite.
Why do leadership offsites fail?
No clear purpose, too many updates, and nothing agreed for afterwards. Within a week it's business as usual.
How do you follow up after a leadership offsite?
Agree a few small steps with owners and dates before you leave. Check them at your next leadership meeting.
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 · Executive team offsite · Strategy offsite · Tech leadership offsite · Leadership away day
Leadership retreats
Leadership retreat · Retreat themes · Retreat ideas · How to plan a retreat · Retreat agenda