Executive Assistant Questions to Ask New Boss
Questions to put to an executive in your first weeks supporting them: how they want to be reached, how the calendar should be defended, what to do with the inbox, and what you can decide without asking.
The questions
Open any question for the note
How do you want me to reach you when something can't wait?
Why ask it
Get one channel agreed on the first day. If they say email, watch whether they actually read it, because many executives say email and answer only to text. Establishing the urgent channel early prevents the failure where you did tell them and they never saw it.
If I get one thing right in my first month, what should it be?
Why ask it
Forcing a single answer surfaces the thing that has been irritating them, which is usually not what the job description led with. Whatever they name, do it visibly and early, because their view of you sets faster than it should.
Talk me through a good week. What has to be in it?
Why ask it
You learn what to protect: a standing block for writing, Friday afternoons clear, one day without travel. Without knowing this you will fill the gaps efficiently and be told you have wrecked their week.
Which meetings would you drop tomorrow if you could?
Why ask it
This gives you an explicit mandate to start pruning, and it is far safer than trimming on instinct. If they say none, the calendar problem is theirs, not the schedule's, and you should ask instead how they decide what to accept.
How much unbooked time do you want in a day, and where should it sit?
Why ask it
Vague answers like as much as possible are unusable. Push for a number and a location: an hour before the first external meeting, or thirty minutes after each interview. That is something you can actually enforce against other people's requests.
When two commitments collide, what wins by default?
Why ask it
You need a rule you can apply at 8am without waking them. Customers over internal, board over everything, anything with their own team can move. If they will not give you a default, every collision becomes an interruption for them.
When and how do you want the next day's schedule?
Why ask it
The useful detail is the format and the hour: a message the night before, a printed page at 8am, nothing at all because they check their phone. Getting this wrong is a small daily friction that quietly shapes their view of you.
Do you want briefing notes in writing, or a two-minute rundown before you walk in?
Why ask it
Some executives read everything and resent being talked at. Others never open the document and want the names and the ask spoken aloud in the corridor. Preparing the wrong format wastes real hours every week.
Who can put time on your calendar without going through me?
Why ask it
There is almost always a short list: a co-founder, a spouse, one direct report. Knowing it stops you from unpicking bookings that were meant to stay. It also tells you where your gatekeeping does not apply.
Who should I be slow to schedule, or push out a few weeks?
Why ask it
Executives rarely volunteer this but will answer if asked plainly, and it saves you from booking the person they have been avoiding for a month. Ask for the reason too, because avoiding a vendor and avoiding a colleague need different handling.
For travel, what do you actually prefer, and what have you learned to avoid?
Why ask it
The avoid half is the valuable one: no red-eyes, no connections through a particular airport, never the hotel by the station. These are specific habits you cannot infer from a policy document, and getting one wrong is remembered.
How much time do you want between landing and a first meeting?
Why ask it
This is where itineraries fall apart. Some people will take a meeting from the airport, others need a night. Ask once and you can build every future trip without checking.
What do you want me to do with your inbox: sort it, answer it, or leave it?
Why ask it
These are three different jobs with three different levels of trust, and executives often have not decided. If the answer is start with sorting and we'll see, agree a review point so the question gets settled rather than drifting.
If I write something in your voice, what would make you wince?
Why ask it
Easier to answer than asking how they write. You will get concrete rules: no exclamation marks, never says circle back, always signs off with just their initial. Those details are what make a drafted reply pass as theirs.
What can I decide without asking you?
Why ask it
The answer sets how useful you can be. Look for real boundaries: decline anything under thirty minutes, approve spend to a limit, move internal meetings freely. If nothing comes back, ask again in a month once they have seen your judgment.
When I get something wrong, how do you want to raise it?
Why ask it
Agreeing the mechanism while nothing is wrong makes the first mistake far less costly. It also tells you whether they are the kind of person who says nothing for three months and then mentions everything at once.
If something urgent lands while you're in a meeting, how should I interrupt?
Why ask it
You need the threshold as well as the method. What counts as urgent to them, and does urgent mean a note on the table or a message they will see afterwards? Guessing this wrong in either direction is remembered.
What should I treat as confidential even from your own team?
Why ask it
Compensation, hiring plans, a deal in progress, and sometimes just where they are today. Ask for the categories rather than the cases, so you can apply the rule to something new without checking.
When is contacting you in the evening or at the weekend genuinely fine?
Why ask it
Most executives have a real answer, call me for anything about my family or a customer outage, nothing else, but will only give it if asked. Otherwise you either over-contact or sit on something they wanted to know at once.
What did the person before me do that you'd like me to keep doing?
Why ask it
This uncovers habits nobody documented: the Monday summary, the standing coffee order, the reminder before their mother's birthday. It also lets them praise a predecessor, which often loosens them up to say what did not work.
Setting up a new working relationship
Practical guidance for the conversation itself
Timing and pacing
Do not ask all of this at once
Twenty questions in one sitting reads as an interrogation and gets you rushed answers. Take the four or five that block your work this week, then bring more as the situations arise. A question asked at the moment it matters gets a much better answer.
Ask for one standing slot
Fifteen minutes at the same time each week, even in a busy diary, is worth more than ad hoc grabs in corridors. Bring a short list of decisions rather than open questions, and the meeting will survive.
Watch before you ask
Some answers are visible from the calendar and the sent folder: how late they work, whether they reply on Sundays, how they sign off. Asking about something you could have observed spends credibility you will want later.
Keep a preferences document
Keep one private page and add to it every time you learn something. It shortens the ramp and, if you ever go on leave, it is what makes cover possible.
- Contact rules: which channel for urgent, which for routine, what counts as urgent.
- Calendar defaults: buffers, protected blocks, who can book directly, what wins in a clash.
- Travel: airlines, seats, hotels, minimum connection time, what they always ask you to check.
- Meeting prep: format, how far ahead, what they want on one page.
- People: who never gets declined, who to route elsewhere, correct names and titles.
- Personal logistics they have asked you to track, and nothing they have not.
Early mistakes
Taking stated preferences as fact
People describe the working habits they aspire to. If they said they read briefing notes and three go unopened, switch to a verbal summary without making a point of it. Adjust to what you observe, not what you were told.
Asking for permission on everything
Constant checking reads as caution at first and as helplessness by week six. Once you have a decision rule, use it, and report what you did rather than asking what to do.
Rebuilding their systems in week one
New assistants often arrive with a better folder structure and a preferred tool. Wait until you understand why the current mess exists. Some of it is deliberate, and some of it is a person's memory.
Never asking about the harder subjects
Confidentiality, after-hours contact, and how mistakes get raised are all easier to discuss in the calm of week one than in the middle of the first incident. Bring them up before you need them.
What to listen for
The way an executive answers these questions predicts the working relationship as clearly as the answers themselves.
- Precise answers about buffers and formats mean someone who has been well supported before and knows how to delegate.
- Repeated use of whatever works or you'll figure it out means you are setting the rules, so write them down and confirm them in writing.
- Reluctance to name anyone you should decline means gatekeeping will not be backed, so expect to route rather than refuse.
- An answer that turns into a list of past frustrations is useful. Note each one, they are your first month's work.