The Vacation Test
A leader I coach told me recently about an upcoming trip to Thailand. Two weeks away on a trip she’d been planning for over a year. Then, almost as an aside, she mentioned she’d be taking her laptop.
Keeping my face as straight as I possibly could, I asked why. Her answer came out fully formed, the way answers do when someone’s already justified it to themselves. Other teams don’t pay attention to her out of office, work stalls without her approvals, if she disconnects completely, she comes back to two weeks of backlog and a handful of fires, so bringing the laptop is just easier. She wasn’t complaining; she was describing her reality with the calm of someone who stopped questioning it a long time ago.
Here’s the question I put to her, and the one I want to put to you: what does it say about an organization when its leaders can’t rest without a laptop in the suitcase?
She had told me almost nothing about herself in that answer, but she’d told me everything about her organization.
I call it the vacation test, and it asks one question. Can your best leader be genuinely unreachable for two weeks without anything important breaking?
Not “reachable for emergencies.” Not “just checking messages in the morning.” Completely unreachable. Phone off, laptop at home, someone else holding the keys.
Most organizations fail this test, and the failure is very precise in what it reveals. If work stalls without one person’s approvals, that’s rarely a workload problem - it’s a decision-rights problem. Authority was never really delegated - only the tasks were. The laptop isn’t solving the problem, it’s compensating for it.
None of this is a personal failing, and my client isn’t bad at delegating. She’s operating inside a system where there’s nothing real to delegate to, and the laptop is her rational response to an organizational gap. That’s worth sitting with, because most organizations read the laptop on the beach or taking a call from the runway as commitment. Some even celebrate it. The reframe: a leader who can’t switch off is not evidence of dedication, it’s evidence that your organization has confused a person with a system, and it’s charging the cost of that confusion to her dream trip.
Think about your own team for a moment. Who packed a laptop or their work phone on their last vacation? Who answered a message from a beach, a wedding, a hospital waiting room? When it happened, what did the organization do - fix the thing that made it necessary, or send a thank-you and keep the arrangement?
Most organizations don’t realize they pay for this too. Every approval that waits for someone in Thailand is a decision your organization couldn’t make on its own. Scale that across every hero in the business and you get an organization whose actual operating speed is set by the availability of a handful of individuals. That was expensive before, and now AI transformation is making it a competitive disadvantage.
Passing the test isn’t complicated. Delegate authority, document how recurring decisions get made, then treat every vacation as a live test of your leadership infrastructure. Whatever breaks while someone is away isn’t an inconvenience; it’s your roadmap.
Two weeks is nothing. Any organization that can’t function for two weeks without a specific individual is not being held up by leadership. It is being held together by a person, and people go on vacation, get sick, and eventually leave.
Run the test. Pick your most indispensable leader and write down everything that would stop if they disappeared for two weeks. That list isn’t a measure of how exceptional they are.
It’s a blueprint for everything your organization still needs to build.
If you want the full picture of the patterns behind this, download The Leadership Transition Report 2026, and tell me one thing: who in your organization would fail the vacation test tomorrow? If a name came to mind before you finished the question, you have your answer, and your organization has its next piece of work.