Executive assistant CV guides · by Lily Shippen, EA recruiter

Executive assistant interview questions: what's really being asked

Written by Lily Shippen, founder of the Lily Shippen EA, PA and chief of staff recruitment agency. Thirteen years of shortlisting, tens of thousands of CVs read, and every rule on this page is one I use at my own desk. Who I am

I've interviewed executive assistants for thirteen years, first for my own clients and now for the CVs Margot writes, and the pattern is remarkably consistent, because candidates prepare for the questions about diary systems and software, which almost never decide anything, and then get caught out by the questions about judgement, which always do. I've watched brilliant EAs go quiet on "tell me about a decision you made without asking" simply because nobody had warned them it was coming, so consider this the warning, with the questions that matter, what each one is testing and how a good answer sounds.

The questions about judgement

"Tell me about a decision you made without asking your executive."

This is the single most important question in an EA interview, and the answer sorts candidates faster than anything on the CV, because I want to hear that you have authority, that you know its edges and that you can describe a specific occasion when you used it. A weak answer talks about being proactive, whereas a strong answer names the decision, along the lines of "The CEO was on a flight and a board member asked to move Thursday's meeting. I moved it, reshuffled two other meetings to protect the focus day, and told the CEO on landing. He would have made the same call and he had asked me to make those calls without waiting."

"How do you decide what reaches your executive and what doesn't?"

Here I'm asking whether you have a method, so describe it, meaning what you resolve yourself, what you batch for a daily conversation and what interrupts anything, and give a proportion if you know it, because "Roughly 60% of what comes in, I resolve or redirect without the CEO seeing it" is the kind of line that gets remembered and written down.

"When did you get it wrong?"

Every experienced EA has a story here and I want to hear it told plainly, covering what happened, what you did in the next hour and what you changed afterwards, because the candidates who worry me are the ones who can't think of anything, given that nobody who's run an office for five years has got everything right and I'd rather hear the story than the silence.

The disaster question

"Tell me about a day when everything went wrong."

Cancelled flights, a board pack with an error discovered at 11pm, an executive stuck in the wrong city or a family emergency on results day, and what I'm testing is whether you stayed calm, whether you had a sequence and whether you fixed the cause afterwards. Structure the answer as what happened, what you did first, what you did next and what changed so it couldn't happen again, because "Rebuilt the US roadshow overnight after a cancelled flight, and the CEO was in front of every investor on the original schedule. We now book a backup on any route with one daily flight" is a complete answer in two sentences.

The confidentiality question

"How do you handle confidential information?"

I'd ask you not to say you're discreet, because everyone says it, and instead to describe the mechanics, meaning where things live, who can see them, what you do when someone senior asks for something they aren't entitled to and an occasion when that happened. "A partner asked me for the succession paper. I told him I would check with the chair, and I did, and the answer was no. He respected it" is an answer in a way that "I am extremely discreet" never will be.

"Have you ever been asked to do something you weren't comfortable with?"

This is a judgement question dressed as an ethics question, because I want to know you have a line and that you can hold it politely, so give a short, real example and what you did.

The questions about the executive

"Describe the most difficult executive you've supported."

This is never a character assassination and never a claim that nobody was difficult, so describe the pattern, what you learned about how they worked and what you changed to make the office run, as in "She changed her mind about travel late and often. I stopped booking non-refundable fares and built a standing brief with her chief of staff each Monday, and cancellations fell from two a week to two a month", because then I hear adaptability and a result rather than a complaint.

"How would your executive describe you?"

Answer with what they actually rely on you for and, if you can, with something they've said, because your referees will be asked the same question and the answers should match.

"What would you do in the first 90 days?"

Learn how the executive works before changing anything, map the people who matter, find the two or three processes causing the most friction and fix those first, and say so in that order, because candidates who arrive with a plan to change everything are a risk to a functioning office and the interviewer knows it.

The questions about your CV

"Talk me through this achievement."

Every figure on your CV will be tested, and I mean every one, so if your CV says you saved £38,000 on travel, be ready to explain how the saving was measured, over what period and what you did to get it. This is why a CV should never carry a figure you can't defend across a table, and it's why Margot checks every figure with you before she finishes a CV, because a number you can explain in detail is the strongest thing you can bring into the room and a number you can't is the fastest way out of it.

"Why are you leaving?"

Keep it short, true and forward-looking, because the reason you moved between every role on the CV should already be there in a sentence, stated positively, and the interview answer should match it.

"What do you want to be doing in five years?"

Some EAs want to be the best EA in the building and some want to be chief of staff, and both are good answers if they're honest, because I've placed plenty of each, and the chief of staff guide covers what the second path looks like on the page.

The questions that rarely decide anything

Which diary software you use, whether you can take minutes, your typing speed and how you prioritise in the abstract all get asked, and they should be answered briefly and specifically, but I've never seen an EA lose a role on them and I've seen many lose one on the judgement questions above, so spend your preparation time in proportion.

Questions to ask them

An EA interview is also your assessment of the executive and the questions you ask show it, so ask how the executive likes to receive information, what the last assistant did that they valued most, what authority the role carries in practice and what a bad week in this office looks like, because the answers tell you whether you want the job and the questions tell them you know what the job is.

How to prepare

I'd rehearse examples rather than answers, which means taking your CV and, for every achievement and every substantial bullet, writing down the story behind it in four lines covering the situation, what you decided, what you did and what changed, because eight to ten of those give you an answer to almost every question above in your own words and with figures. A tip I give to everyone I coach is to record yourself telling each story on a voice note and listen back, because it builds belief far faster than reading. The Search Kit includes an interview preparation sheet built from your own CV in exactly this way, with the six questions a hiring manager is most likely to ask off the back of it, and the section by section guide covers getting the CV to a standard that earns the interview in the first place. Then walk in, back yourself and tell the stories, because you've earned your place in that room.

Lily Shippen

FOUNDER, LILY SHIPPEN, EA, PA AND CHIEF OF STAFF RECRUITMENT · THIRTEEN YEARS PLACING EAS

Lily has read tens of thousands of EA CVs and shortlisted the ones that worked. Margot is her screening interview, written down. About Lily and this site