Managing unclear requests is part of every EA’s job. Remember the scene in The Devil Wears Prada where Miranda Priestly reels off a string of requests to Andy, one after another, with no context or explanation, and expects her to know what she means? It’s an extreme example, but we’ve all been on the receiving end of a vague request. “Can you set something up with the Edinburgh team next week?” comes in between meetings, and you’re left to figure out who should be there, for how long, whether it’s in person or online, and what the meeting is actually for.
Most EAs are brilliant at filling those gaps because we know our Executive and the people they work with, so we often get it right the first time. But with that being said, managing unclear requests on instinct alone can mean the occasional wrong guess, and that usually means redoing the work and asking your Executive to explain it twice.
A practical tool to help EAs manage daily, weekly, and monthly responsibilities.
This template is a resource to help you manage responsibilities effectively, improve alignment with your executive, and maintain organized, consistent support.
Why Requests Arrive Unclear
So why do these unclear requests keep happening? Most of the time, it comes down to the person asking you for something knowing exactly what they mean; it just happens to be in their head, and they struggle to articulate it. The request feels complete to them but not to you.
In 1990, Elizabeth Newton, a graduate student at Stanford, asked people to tap out the rhythm of well-known songs while a listener tried to name the tune. The tappers expected listeners to get it right about half the time, but they actually got it right about 3%. Psychologists call this the curse of knowledge: once you know something, it’s very hard to imagine what it’s like not to know it. When your Executive types “set something up with Edinburgh”, they know all the background, so it feels like a complete instruction to them, even though most of the detail isn’t in the message.
Writing the request down makes it harder still. In a 2005 study by Justin Kruger and Nicholas Epley, people sending emails expected about 78% of readers to understand their intended tone, but only about 56% did. A request quickly typed on a phone probably loses even more of what the person meant.
Working Out What Is Missing
The first step in managing unclear requests is to work out what’s actually missing before you start. Most unclear requests are missing one or more of the same few things:
- What the request is actually for. For example, organizing a meeting to make a decision needs different people and a different approach from a catch-up.
- The real deadline, which might be much later or much earlier than “ASAP” suggests.
- Who else needs to be involved, so you don’t end up rebooking because someone important was left off the invite.
- What level of detail or budget your Executive expects. Again, a quick summary and a board-ready paper take very different amounts of time.
Once you work out what details are missing from the request, you can decide what to do about it.

Deciding Whether to Ask For More Detail
This part of managing unclear requests requires the most discernment, because asking about everything has a cost, too. Every question is another interruption for your Executive, and if you ask too many, it can make it look like you can’t work things out on your own.
A good rule of thumb is to think about what happens if you get it wrong. If the request is low-risk and easy to undo, like booking an internal meeting or drafting a first version of a document, make a sensible assumption, get on with it, and tell your Executive what you assumed. If it involves someone outside the business, or it would be awkward or expensive to undo, ask first.
The more often your assumptions turn out to be right, the more your Executive will trust you to make the call yourself, and the fewer questions you’ll need to ask them.
How to Ask Without Slowing Your Executive Down
When you do need to ask, make it as quick as possible for your Executive to answer. Keep a running list rather than sending each question as it comes up, and write questions that can be answered with a yes, a no or a name.
Playing the request back to them is one of the most useful habits for managing unclear requests. Instead of asking:
“What do you want me to set up with the Edinburgh team?”
Try:
“Just to check, I’m setting up an hour on Zoom with Sarah and James next week to agree the Q1 budget. Is that right, or do you need anyone else there?”
Can you see the difference? The first question makes your Executive explain the whole thing again. The second one does the thinking for them so that they can reply with a yes or a no. This approach will really help with managing unclear requests.
Getting Fewer Unclear Requests in the First Place
Managing unclear requests gets much easier once you start noticing patterns. Keep a note of your Executive’s defaults, such as how long their meetings usually run, how they like to travel, which meeting rooms they prefer, and who always needs copying in, so you have fewer gaps to fill each time. And if the same kind of request always arrives half-formed, it’s worth agreeing a simple format for it, either with your Executive or with the colleagues who send it. Our posts on creating communication principles and improving information quality go into this in more detail.
So, where to start with managing unclear requests? Keep a quick note each time a request needs a follow-up question, noting what was missing. By Friday, you’ll probably see the same few gaps coming up again, and those are the ones to fix first.


