Send Your Key Person on Leave
You find the broken parts of a role while they are still cheap to fix, when the person who holds it takes their leave.
By James Schramko · Updated November 2026
You have someone the business leans on. It might be an operations manager, a bookkeeper, or the one person who knows where everything is. They rarely take a holiday, and part of you is relieved.
That relief is costing you. I saw what it can hide on many occasions, back when I worked for other people. Here are two that come to mind.
What Turned Up When They Left
In one job I inherited, I was going through the profit and loss and found advertising fees for a residential investment property. The person who had held the finance role had been running personal accounts through the company. Nobody found it until their employment was terminated, and then a whole lot more came out.
The second was at a dealership. One person never took holidays. When they finally went away, the business found all sorts of things that shouldn't have been there.
The Person Who Never Leaves
The person you suspect least is often the one who makes sure they never go away. Covering their tracks takes time and energy every day, and so does covering for the parts of the job they can't do. Either way they need to be at the desk.
Most people who skip their leave are honest. Whatever is hidden in a role, honest mess or worse, stays hidden while the same person sits on it every day.
A role that is always staffed never gets tested. The tasks get done, or look done, and nothing reaches you. You judge the role by how few complaints you hear.
Meanwhile the leave balance grows. The person feels they can't go, because things fall over when they do. You feel you can't spare them, for the same reason. Both of you have just described a problem in the business, and both of you are calling it loyalty.
What the Gap Shows You
When someone steps out, three kinds of things turn up.
Some tasks only they know how to do. Nobody else has the login, the contact or the steps.
Some tasks were being done badly, or had stopped being done, and nobody above them knew.
Some tasks should never have been theirs. They picked them up years ago and the job grew around them.
Each one is cheap to fix when you find it in a quiet week with the person due back on Monday. The other way to find it is the day they resign or get sick, with no notice and no handover.
Make It a Rule
Don't let people accumulate annual leave. Everyone takes what they are owed, every year, and the key people take it in a block.
A long weekend hides everything, because the work waits for them. A week or two is long enough for the regular jobs to come around while they are away.
Put the dates in the calendar months ahead and tell them plainly why. The business needs to see how each role runs with its owner out of the room. Say it to the whole team so nobody reads it as a sign they are in trouble.
While they are away, they are away. If they answer messages from the beach, you learn nothing.
While They Are Away
Keep a list. Every time something stalls, a customer asks a question no one can answer, or a report fails to arrive, write it down with the date.
Fix the small ones on the spot. Hold the bigger ones for the day they come back and go through the list together.
The list describes the role. Treat it that way when you sit down with them. Most people are relieved to hand over the parts they were holding together alone.
Self-Diagnostic
Who in your business has the biggest leave balance?
When were they last away for a full week with no contact?
If they left tomorrow for two weeks, what are the first three things that would stop?
If you can't answer the third question, that is the reason to send them.
What To Do This Week
Pull the leave balances. Pick the person with the most leave owing and the most on their plate. Agree dates for a full block inside the next three months. Open a blank page with their role at the top and be ready to write on it.
Quick Reference
- A role that is always staffed never gets tested.
- A big leave balance on a key person is a warning. The person you suspect least is often the one who never goes away.
- Key people take their leave in a block, with no contact.
- While they are away, list everything that stalls, with the date.
- Fix the small things that week. Go through the rest with them when they return.
Reading that list with an owner, and deciding what goes back to the person and what leaves the role for good, is work I do in Mentor.