Most leaders wait until the last minute to set up their holiday break.
But in my coaching practice, I’ve found that the key isn’t what you do while you’re “on” vacation – it’s what you do the two weeks before you even pack your bags.
Here are a few “get-ahead-of-it” ideas I share with C-Suite clients.
➡️ Create a Two-Week-Out Plan.
Decide now what must be done, what can be delegated, and what can simply wait. Upfront clarity minimizes pre-holiday stress more than anything else.
➡️ Set expectations early.
Draft your out-of-office message now – this week – and align your team with it. In your absence, who do people contact, and for what? When people know how to operate while you’re away, they’re empowered to keep things moving without you.
➡️ Hold “mini-me handoff meetings.”
In 10 minutes, ask your key team members:
“If something urgent comes up, how would you handle it without me?”
This transfers *thinking* – not just tasks.
➡️ Identify your holiday hijackers.
What usually pulls you back into work mode? Email? Group chats? Unaligned colleagues? Plan the guardrails now.
➡️ Schedule your re-entry time today.
Block the first morning (or day) back for “reset and review.” It prevents that dreaded post-holiday overwhelm.
The most successful leaders don’t just take a holiday – they prepare for one.
What pre-holiday strategies would you add to this list?
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