The tech leadership offsite: leading technology teams through change
You're planning an offsite for your technology leaders. Engineering, product, data, infrastructure: they're the people building the change everyone else is talking about. And AI has just moved the goalposts again.
Technology leaders spend most of their time on the systems. The offsite is the moment to spend time on the people: how they lead teams that are stretched, how they work with the rest of the business, and how they keep pace without burning out.
What makes a good tech leadership offsite?
Time on people and leadership as well as roadmaps, honest talk about how the team is coping with the pace of change, and a few clear commitments to take back. The best tech offsites leave leaders with more energy than they arrived with.
Five things to think about before your tech leadership offsite
Is it all roadmaps? Technical planning fills any agenda. Protect time for how you lead, not just what you build.
How is the team really coping? Constant change wears people down. Ask the question, and make it safe to answer honestly.
How do you work with the rest of the business? Many tech teams feel misunderstood. Talk about it, and about what you could do differently.
What does AI change for your leaders? Not just the tools, but what it means for their teams, skills and roles.
What will you stop? Teams can't keep adding. Agree what comes off the list.
Why the Big Bold Mindset fits a tech 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.
No one feels that more than technology leaders. Their charts are redrawn every few months. The offsite is where they can step back 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 tech leadership offsite best.
Five principles for a tech leadership offsite
Redraw the Charts: you can't navigate a new world using an old set of charts. What does AI mean for how we lead?
Strengthen with Safety: people can't own their mistakes until it's safe to. How safe is it to say "I got this wrong"?
Direct Your Attention: your attention is being stolen, so take it back. What deserves our teams' focus, and what's just noise?
Calculate Your Risks: is the safe option really that safe? Where is caution costing us?
Bolster Your Belief: belief is a skill, so train it on purpose. Do our teams believe the plan is possible?
Where a keynote fits in a tech leadership offsite
Technology leaders spend their days deep in detail. A keynote at the start of the offsite lifts their eyes to the bigger picture: how to lead people through constant change, with stories from far outside the tech world.
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.
“You truly inspired our people to think and act differently.”
Caspar has worked with organisations including BAE Systems, Burberry, GSK, Intuit, INEOS Styrolution, Johnson & Johnson, Nuffield Health, Pearson, Sage, Suntory and Thales.
Tech leadership offsite questions
What is a tech leadership offsite?
A meeting away from the office where technology leaders, such as heads of engineering, product and data, step back to agree direction and how they lead together.
What should be on a tech leadership offsite agenda?
Direction and priorities, the impact of AI, how the team works with the rest of the business, and time on leadership and people.
How do you make a tech offsite more than a roadmap review?
Put people and leadership on the agenda, bring in an outside perspective, and keep detailed planning for other meetings.
How do you lead technology teams through constant change?
Be clear on direction, make it safe to raise problems early, and protect your teams from trying to do everything at once.
How long should a tech leadership offsite be?
One or two days. Two days gives time for both planning and leadership conversations.
Should a tech leadership offsite have a non-technical speaker?
Often yes. A speaker from outside the tech world can bring a fresh view on leadership and change, which technical sessions rarely cover.
How do you avoid burnout in tech leadership teams?
Agree what to stop as well as start, make it safe to say a team is stretched, and look after the leaders as well as their teams.
How do you follow up after a tech leadership offsite?
Agree a few commitments with owners and dates, and review them in your regular leadership meetings.
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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