We’ve all been there. That tension that builds in the run-up to your exec’s annual leave. Like the run-up to a small siege, only worse.
Everyone who’s ever wanted five minutes of their time suddenly wants an hour, right now, before the window closes. Decisions that have been sitting in queues for three weeks are suddenly urgent. And somewhere in the middle of it, you’re expected to have already thought of everything that could possibly go wrong while they’re horizontal on a beach, so that nothing lands on their phone.
It’s a strange irony that the run-up to someone else’s holiday is often the least restful week in your own calendar.
The Job Nobody Actually Trained You For
Nobody sits EAs down and teaches them how to plan an executive’s absence properly. You learn it by getting burned once (or several hundred times by several hundred tiny fires). The first time something blows up while they’re away, usually something small that snowballs because nobody knew who was meant to make the call, you learn fast that “covering for annual leave” is actually a discipline in its own right, not just a lighter workload for a fortnight.
Done well, it’s mostly invisible. Things simply carry on, decisions get made by the right people, and your exec comes back to a calendar and inbox that don’t make them want to go straight back on leave. Done badly, it’s the opposite: a fortnight of firefighting, followed by a return where your exec spends day one undoing decisions other people made in their absence, and wondering why nobody flagged it to them sooner (and frankly, you’re wondering that too).
The gap between those two outcomes is almost entirely down to how much thinking happened before they left, not how well anyone reacted once they were gone.
Why This Always Feels Harder Than It Should
Part of the difficulty is that annual leave prep sits in an odd category of work. It’s not urgent until suddenly it’s very urgent. It’s not glamorous, so it rarely gets protected time on anyone’s calendar, including your own. It requires you to think several steps ahead about problems that haven’t happened yet, which is a different mental gear to the reactive, in-the-moment problem-solving most of the job runs on.
There’s also a subtler issue. Planning someone’s absence well means, implicitly, admitting that things can run without them for a bit. Some execs are entirely comfortable with that. Others, whether they’d say it out loud or not, find it slightly threatening to have a smoothly functioning fortnight happen in their absence. Some actually want something to break to make them feel important (albeit probably subconsciously). That tension can make the handover conversation more delicate than it should be, and it’s worth knowing which type you’re dealing with before you walk in with a plan.
The Real Risk Isn’t the Big Decisions
Here’s the thing that catches most EAs out: it’s rarely the big, obvious decisions that cause chaos while your exec is away. Everyone already knows those need escalating or holding. It’s the medium-sized ones, the ones that feel too small to interrupt a holiday for, but too significant for anyone else to feel confident making alone. Those are the ones that either stall for two weeks, get made badly by the wrong person, or get made fine but with nobody quite sure they had the authority to make it.
The job, in other words, isn’t just clearing the diary. It’s building a decision map for the in-between.
What Actually Needs Doing Before They Go
Build the decision map, not just the diary. Sit down, ideally a good week or two before they leave, and go through what’s likely to land while they’re out. For each one, work out: does this need to reach them anyway (genuine crisis, high-stakes external relationship), does this get held until they’re back, or does this get delegated to a named person with actual authority to decide, not just “keep an eye on it.” Write this down. A vague verbal “just use your judgement” is how well-meaning colleagues end up making decisions they shouldn’t have, or sitting on ones they should have made.
