Your EA Shouldn't Have to Guess Whether to Interrupt You on Holiday

Half term has arrived, and many founders are about to be “off”. It is also when many Executive Assistants are left guessing: is this urgent enough to message, or can it wait until Monday? A good EA will make a sensible judgement. But they should not have to guess your rules.

The guessing game

When a founder steps away without clear guidance, their EA is left to weigh up every incoming issue on their own:

• Is this urgent enough to message them about?
• Would they want to hear about it now, or on their return?
• If I make the wrong call, which way will it land?

That uncertainty tends to produce one of two outcomes. Either the EA interrupts the founder for things that could have waited, because they are not sure. Or they hold back on something important, because they did not want to disturb a break. Neither is a failure of judgement. It is a gap in the brief.

Ten minutes before you go

The fix is simple and takes very little time. Before you step away, agree five things with your EA.

1. What is worth interrupting you for

Do not leave it at “anything urgent”. Name real examples: a client issue, a board or investor request, a travel disruption, a decision that cannot wait. Concrete examples teach more than a definition.

2. How to reach you

Choose one channel for genuinely urgent matters, whether that is a call, a text or a message, and say what “urgent” looks like in that channel. Everything else goes somewhere that does not interrupt your time off.

3. What your EA can decide without you

Rescheduling, declining, holding a slot, approving spend up to an agreed limit. The more your EA is empowered to decide, the fewer decisions need to reach you at all.

4. What can wait for a summary

A short end-of-day or end-of-week note often works better than a stream of messages. It keeps you informed without breaking your focus on whatever you are away for.

5. Who covers if neither of you is reachable

Name a backup, whether a co-founder, a leader on your team or another trusted contact, so nothing important is left without an owner.

Then trust them to use it

Once the rules are set, the important part is to let them work within them. An EA who has to second-guess every decision, or who is made to feel they got it wrong for using their judgement, will start to over-escalate or under-report. Neither helps you.

If something does come through that you would rather have handled differently, treat it as a chance to refine the rules, not as a mistake to be corrected.

This is not only about holidays

Half term is a useful prompt, but the same principle applies to travel, back-to-back meeting days, board weeks and any time you are hard to reach. The clearer the rules about when to interrupt you, the better your EA can protect your time and still keep things moving.

The bottom line

The founders who get the most from their EA are not the ones who are always available. They are the ones who make it clear when they need to be. A few minutes of clarity before you go lets your EA make good decisions with confidence, and lets you take a proper break.