Questions to Ask an Executive Assistant
For an executive starting with a new assistant, or resetting an arrangement that is not working: twenty questions that settle how you reach each other, what they can decide alone, how the calendar gets defended, and what you are expecting that has never been said out loud.
The questions
Open any question for the note
How do you want to be reached when something is genuinely urgent, and what counts as urgent?
Why ask it
Agreeing the channel matters less than agreeing the threshold, because most friction comes from an executive marking everything urgent. Settle both now and you will avoid the pattern where they stop trusting the word.
What does the first hour of your day look like, and when do you want my priorities?
Why ask it
Assistants usually triage early, and a list arriving at four in the afternoon lands after the day has been arranged. The answer gives you the one deadline in the relationship that actually matters.
Looking at my week, what should I stop doing myself?
Why ask it
Ask this in the first fortnight and again a month later, when they can see the waste. Expect scheduling threads, expenses, document formatting and follow-ups, all of which cost you more time than you think.
What can you decide without asking me, and where would you rather check first?
Why ask it
The boundary should be theirs to propose, because they know which decisions come back to bite them. If everything sits on your side of the line, you have built a queue and made yourself the bottleneck.
How much of my inbox do you want access to, and what would you like to answer for me?
Why ask it
Full access with no rules is how assistants end up guessing on things they should not. Agree categories they answer, categories they draft for you, and categories they never touch.
When people come to me directly instead of you, how do you want me to handle it?
Why ask it
Usually the answer is to send them back with a short line naming the assistant as the person who holds the calendar. Every time you book something yourself, you undo a rule you asked them to enforce.
What is your rule for a double booking, and how do you break the tie?
Why ask it
Look for a stated hierarchy rather than a promise to ask you: customers before internal, external commitments before recurring meetings, anything with travel attached first. This is the single most common source of avoidable irritation between the two of you.
How much buffer do I need between meetings, and where should protected time sit?
Why ask it
A back-to-back calendar looks efficient and produces late starts all afternoon. Agree the gap and one or two protected blocks, and agree what is allowed to break them.
If I agree to something without telling you, how do you want to find out?
Why ask it
You will do this. The useful part is agreeing that you send them the thread immediately and without apology, so it enters the system rather than surfacing as a conflict a week later.
Which of my recurring meetings would you cancel for a month to see whether anyone notices?
Why ask it
Assistants can see the whole grid and often know which standing meeting has stopped earning its slot. Their answer is usually right, and giving them permission to raise it makes them an editor of your time rather than a clerk.
What do you need from me before a trip, and once, so you never have to ask again?
Why ask it
Passport details and expiry, loyalty numbers, seat and hotel preferences, dietary needs, approval limits, who books the ground transport. Handing it over in one go is faster than answering the same questions each time.
How do you want to handle expenses and receipts so it is not a monthly scramble?
Why ask it
This is the task most often done badly by executives and then blamed on the assistant. Agree a weekly rhythm, one place for receipts, and what they are authorised to submit without asking.
What information about me is off limits, and what should you say when someone pushes?
Why ask it
They will be asked where you are, why a decision is delayed, and whether someone is being let go. Give them wording they can use so they are not improvising under pressure or accidentally revealing something.
What is the most awkward thing you have had to decline on an executive's behalf, and how did you word it?
Why ask it
It is a practical test of how they say no, which is most of the job. Listen for language that protects the relationship rather than blaming your diary, and steal the good phrasings for yourself.
When you think I have my priorities wrong, how would you like to tell me?
Why ask it
Assistants see the gap between what you say matters and what you spend hours on. Agreeing the form of that message now, a note, a standing slot, a direct sentence, is what makes it possible for them to say it at all.
When three people all want something from you today, how should we sort it out?
Why ask it
If they support more than one person or the team routes work through them, you need to know how your requests rank and who arbitrates. Assuming you are always first is how good assistants get quietly overloaded.
What did a previous executive do that made your job harder?
Why ask it
You will hear the mistakes you are about to make: late decisions, changing plans without telling them, undermining them in front of others, work handed over with no context. It is the most useful answer in this list.
Who covers your work when you are away, and what usually breaks?
Why ask it
Coverage is rarely arranged until the week before a holiday, and then badly. Ask what they would want documented, and treat building that handover as a shared task rather than theirs alone.
What do you want to be doing in two years, and is there anything in my work that would help you get there?
Why ask it
Some assistants want to run operations, some want to stay and be excellent at this, and treating either as the obvious answer is a mistake. If they want to move, agree what you will teach them and what you will put their name on.
What have I not told you that you need to know about how I work?
Why ask it
It hands them the last question, and the answers tend to be practical: how you like to be prepared for meetings, what makes you late, which people you avoid, what you never want to hear about after seven in the evening.
Setting the Arrangement Up
Practical guidance for the conversation itself
Write the standing decisions down in the first fortnight
- Which meetings you always take, whatever else is happening, and which you never take.
- Who gets fifteen minutes on request, who gets a slot next month, and who gets a polite no.
- Your hard stops: school pickup, a standing commitment, the time after which nothing gets booked.
- What can be moved without asking you, and what can never be moved.
- Travel preferences in one place: airlines, seats, hotels, how early you want to arrive, whether you work on planes.
- Where documents live, what naming you want, and who else has access.
- How you want to be prepared for a meeting: a one-page brief, the thread, the names and roles, or nothing at all.
- Keep it as a single page you both edit. It answers most of the questions they would otherwise have to interrupt you with.
Give context, not just tasks
Say the outcome, not the action
I need thirty minutes with the three of them before Friday because the contract expires lets them solve it. Book a meeting with them makes them come back to you twice.
Forward the thread, not your summary
Your two-line version leaves out the history they need to judge the request. Sending the whole thread takes less of your time anyway.
Tell them what changed as soon as it changes
Most assistant work is spoiled by finding out late. If a plan shifts on a call, send one line immediately, before you have thought it through.
Name the deadline behind the deadline
Say when something is actually needed rather than asking for everything today. Inflated urgency destroys their ability to sequence work.
Backing them where other people can see it
- When someone routes around them to reach you, reply saying to ask your assistant, who holds your calendar. In writing, so it is on record.
- Do not overrule a no they gave on your instruction. If you want to change it, change the rule with them rather than the answer in public.
- Give them the authority in the words you use: they can approve this, they speak for me on scheduling, treat their reply as mine.
- Never let them absorb blame for a decision you delayed. Say plainly that the hold-up was yours.
- Include them where the information is: the pre-read, the team channel, the leadership calendar. An assistant working from fragments will make errors that look like theirs.
Reviewing the arrangement
- Twenty minutes a month on what is working and what is annoying both of you, separate from any task list.
- Ask what they have raised more than once that you have not acted on. There is usually something.
- Check what has quietly accumulated: personal admin, family scheduling, errands. Some of that may be fine and some of it should be agreed and paid for rather than assumed.
- Watch your own habits: sending requests at midnight, deciding at the last minute, changing plans after they have been arranged.
- Say thank you in a form that counts. Pay, title, scope and being named in the room outrank a gift at Christmas.
Common pitfalls
- Keeping all approval to yourself, so everything waits on you and the assistant becomes a queue.
- Giving inbox access without agreeing rules, then being surprised by how something was answered.
- Treating them as a scheduling tool while expecting them to anticipate your priorities.
- Letting a colleague treat them rudely and not addressing it.
- Asking them to hold information from people they work with daily, which puts them in an impossible position.
- Never explaining the business, then wondering why their judgement about priorities does not match yours.