How to prepare your team before going on holiday episode artwork

EPISODE · Aug 5, 2026 · 8 MIN

How to prepare your team before going on holiday

from The Leader's Kitbag

Over the next few weeks, a lot of us will be packing the work bag for the last time before heading off on holiday. And if you're a leader, there's a good chance you'll be carrying a quiet, nagging worry alongside the suncream and the out-of-office: what's going to happen while I'm gone?In this episode of The Leaders Kitbag, I explore why how your team performs in your absence tells you more about your leadership than almost anything they do while you're stood watching.I take you back to my second tour of Iraq, when a period of leave landed me away from my team during the busiest, most volatile stretch of the entire deployment. What I found when I got back taught me something I still talk about today: one of the real tests of your leadership isn't how things run when you're in the room. It's how they run when you're not.A lot of leaders read a smooth-running team the wrong way. When things tick along fine without them, it can feel uncomfortable - almost like a sign they're not needed. It's the opposite. A team that performs well in your absence is a sign you've trained, developed and supported them well enough that they don't depend on you being there.I share a few simple, practical things you can do now to set your team up to succeed while you're away, so you can actually switch off on holiday - and come back to find things went brilliantly without you.In this episode, you will learn:Why how your team performs in your absence is one of the clearest tests of your leadershipWhy a smoothly running team while you're away is a sign of strength, not a threatThe warning sign to watch for if things fall apart the moment you step backPractical steps to prepare your team before you go on leaveHow to actually switch off on holiday without worrying about workBen's Key TakeawayIt's easy to read a smooth-running team the wrong way while you're on leave, and feel like you're surplus to requirements. But that's backwards.A team that thrives in your absence hasn't happened by accident. It's the result of work you've done well before you left: delegating clearly, making priorities visible, and making sure people know who to turn to when you're not there.Scan ahead, start that work now, and you'll come back from holiday to find your team did just fine without you - because you set them up to.Want to learn more about how to be a leader?The expression of interest form is now open for the next cohort of my 'Leader in Me' programme.If you're ready to:Build confidence and capability as a leaderBreak free from firefighting and become more proactiveLearn how to inspire your team and deliver results…Find out more here.

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