Questions to Ask When Interviewing a Secretary
For an office manager, a small business owner, a school or church administrator, or a law or medical practice hiring a secretary or administrative assistant. The 55 questions follow the order of the interview: background, phones and calendar, typing and other office skills, competing priorities, people and privacy, and a close. Each has a note on what a good or a worrying answer sounds like, and the guide sets out practical tests for typing, taking a message and sorting an in-basket.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Background
What kind of office have you worked in, and how many people did you support there?
Why ask it
One boss in a quiet practice and a front desk serving twenty teachers are different jobs with the same title. Listen for the number of people, whether the public walked in, and what was theirs alone to look after. If the scale is far from yours, say so and ask what they think would change.
Walk me through an ordinary day at your last desk, from the first thing you did to the last.
Why ask it
Someone who ran the desk gives it in order: voicemail, the mail, a look at the calendar, the mid-morning rush. 'General office duties' with no sequence usually means another person was running the day. Notice which tasks they describe with some energy, since those are the ones you will get the best of.
What do you think matters most in a good secretary?
Why ask it
Nearly every candidate says organized and good with people, so the word is only the start. Ask for a morning when that quality was tested and what they did. An answer that gets to reliability, being the one who remembers what everyone else forgot, comes from someone who knows what the desk is for.
What made you apply for this job at this office in particular?
Why ask it
A school, a church, a law firm and a clinic each put the secretary in front of very different people. The answer to hope for mentions yours: the children, the congregation, the clients, the patients, or simply the hours and the size. 'I need the work' is honest and no reason to say no, so follow it by asking what would make them want to stay.
Why are you leaving your current job, or why did you leave the last one?
Why ask it
A plain reason is enough: the hours changed, the office closed, the boss retired, the drive got too long. What to notice is how they speak of the people they worked for, because a secretary who runs down a former boss to a stranger will one day describe you the same way. If the story is vague, the reference call is where to check it.
Which parts of secretarial work do you enjoy most, and which would you hand to someone else if you could?
Why ask it
Everybody has a least favorite task, and the honest candidate names it. It only matters if the thing they would give away is the center of your job, such as the phones in a busy practice or filing in an office that lives on records.
If you had been away from your last job for a week with nobody covering, what would have gone wrong?
Why ask it
This asks about strengths without inviting a speech. You should hear particulars: the payroll sheet only they knew how to submit, the calls that would have gone unanswered, the supplier who dealt only with them. A modest candidate may go blank, so prompt once with 'what did people come to your desk for?'
What do you expect to have to learn here that your last office never asked of you?
Why ask it
The terms, the forms and the rules about who may be told what can all be taught, so no experience in your field is not a rejection. An outsider who names what they expect to study, such as the court calendar or the insurance forms, has thought about the job. From someone with the background, expect a routine particular to the field without your prompting.
Phones and calendar
How many lines were you answering in your last job, and what did you do when several rang at once?
Why ask it
The number is a fact to compare with your own desk. The method is what you are after: answer, ask to hold, wait for the yes, come back in order. A candidate who never mentions asking permission to hold has probably left callers listening to nothing.
What do you write down when you take a phone message for someone else?
Why ask it
A complete message has the name with its spelling checked, the number read back, what the call is about, when the caller can be reached and how soon it matters. Count how many of the five they list unprompted. The guide below turns this into a test: leave a rambling message and read the slip they hand you.
A caller starts in the middle of their story and you can't tell what they need. How do you find out?
Why ask it
Good answers let the caller run for a few seconds, then ask for a name and one plain question, and repeat the request back before doing anything. Passing the call on at once to get rid of it is the habit to worry about. If there is time, play the confused caller yourself and let them show you.
You are on a call and someone walks up to the desk. What do you do?
Why ask it
It sounds small and it is your office's first impression. Look for eye contact, a nod, and 'I'll be right with you' at the first pause in the call. You already have some evidence: think about how they treated whoever greeted them on the way in today.
Someone arrives without an appointment and says it will only take a minute. What happens next?
Why ask it
Every front desk gets this, from parents, patients, parishioners and sales reps alike. The candidate you want greets the person, finds out the reason, and either offers a time or checks quietly, without promising what the boss has not agreed to. Afterward tell them how you would want it handled and see how they take the rule.
Whose calendars have you kept, and could you move things on your own or only suggest it?
Why ask it
Booking appointments for a practice, keeping one person's calendar and scheduling the rooms of a building are three different skills. Find out which they have done and how much authority came with it. Then say how much you plan to give, because someone used to deciding will chafe at asking, and the reverse is true too.
Two people ask for the same room, or the same hour with the boss, and both asked properly. How do you settle it?
Why ask it
A strong answer works out which booking is harder to move, offers the other person a specific alternative, and tells both. 'First come, first served' with no further thought is weak. So is deciding on the boss's behalf without a word, unless you intend to give that authority.
What did you do to keep appointments from being missed, by the people you worked for and by the people coming in?
Why ask it
You are asking whether the calendar was managed or only recorded. A reminder call the day before, a morning rundown for the boss or a confirmation text all count. Ask what happened when someone did not show up, and who decided whether to rebook them.
A meeting for six people has to move at short notice. Take me through how you would rearrange it.
Why ask it
Order matters here. The efficient version confirms the constraint with whoever caused the change, finds two possible times, checks the hardest person to pin down first, then sends one clear notice and fixes the room. Starting with an open email asking all six when they are free tends to use up the whole day.
Have you organized an event or booked travel for someone else? Take me through one, from the first request to the day itself.
Why ask it
What you are testing is whether anything was left to chance, and a board lunch shows it as well as a conference trip. Good accounts include the list they worked from, the confirmation call the day before and the one thing that went wrong anyway. If your desk never arranges anything of the kind, skip this and spend the time on the phones.
What is your routine for the mail, the voicemail and the shared inbox first thing in the morning?
Why ask it
People who are good at this have an order and can say why, for instance voicemail first because those callers have waited longest. Follow up by asking what they do with an item that belongs to nobody. Things like that either find an owner at the secretary's desk or sit in the tray for a month.
Office skills
How fast and how accurately do you type, and when was that last measured?
Why ask it
A figure with a date beats 'pretty fast'. Take it as given, mention that finalists will do a five-minute typing exercise, and see whether the figure changes. On a desk like this a clean page usually matters more than a quick one, so ask about errors as well as speed.
Which word processing, spreadsheet and email programs do you use every week, and what do you do in each?
Why ask it
Ask for tasks, not product names: a mail merge, a letter template, a sorted and filtered list, a shared calendar invitation. 'Proficient in office software' on a resume stretches from typing a memo to building the template everyone else types into, and only the tasks tell you where on that range they sit.
How much of the writing at your last job did you compose yourself, and how much did you type from dictation or someone else's draft?
Why ask it
Typing up what the boss wrote and being told 'write to the Hendersons and say no politely' are different levels of the job. If they composed, ask about a letter they were pleased with and who signed it. Where your office still dictates, as some law and medical practices do, ask what they transcribed from and what they did with a word they could not make out.
If I handed you a page of handwritten notes for a letter, what would you need to know before you started typing?
Why ask it
The questions back are the answer: who it goes to, who signs, which letterhead, how it is sent, and by when. A candidate who would simply start typing will produce a neat letter that has to be redone. This one is easy to turn into a real exercise with a made-up note.
How do you proofread something you typed yourself?
Why ask it
It is hard, because the eye reads what the hand meant. Listen for a method: reading aloud, printing it, checking names, dates and figures as a separate pass, or coming back after a break. 'I run the spell check' on its own is the weak answer, since spell check is happy with the wrong Tuesday and the wrong Mrs. Allen.
Tell me about a mistake that went out from your desk: a wrong date, a wrong name, a wrong attachment. What did you do?
Why ask it
Anyone who has typed for a living has one. Trust the candidate who names it without a long preamble, says who they told, and describes the check they added afterward. 'I can't think of any' is the reply to be wary of.
Tell me about a spreadsheet you kept. What was in it, and who else worked in it?
Why ask it
It might be an attendance sheet, a petty cash log or a mailing list, and the subject hardly matters. The telling parts are how they kept it tidy when other people typed into it, and whether they can explain a formula if they say they wrote some. Where spreadsheets are a small part of your job, a simple answer is all you need.
Tell me about a program you had to pick up without formal training. How did you get comfortable with it?
Why ask it
Whatever you run, be it a student records system, practice software or a membership database, will be new to most candidates. So the method counts for more than the product: the help pages, a practice record, a colleague's ten minutes, a page of their own notes. Ask whether they still keep notes like that, because the next person at the desk will be glad of them.
How were the files organized at your last job, paper and electronic, and who decided what was kept?
Why ask it
A filing system is tested on the day its keeper is out sick. Good answers mention how files were named, what was kept and for how long, and who made those decisions. Try asking how long it would have taken a stranger to find a letter from two years earlier.
Have you taken minutes at meetings, and how soon afterward did they go out?
Why ask it
Good minutes record what was decided and who is doing what, not everything that was said. A candidate who sent a draft to the chair and had them out within a day or two has a routine you can use. If minutes are part of your job, ask whether they can bring a sample with the names removed.
Have you handled money at the desk, such as petty cash, deposits, invoices or supply orders?
Why ask it
Many secretary jobs include this without saying so: lunch money, copays, an offering count, the stationery order. Ask what the safeguards were, such as receipts, a log, or a second person counting. If money crosses your desk, describe how you handle it and listen to whether the checks sound normal to them or like a nuisance.
When the copier jammed or the phones went down at your last office, who did people come to, and what did you do about it?
Why ask it
In a small office the secretary is the help desk whether or not anyone planned it. The useful candidate tried the obvious fix, read the panel, and knew when to call the supplier. Lack of experience is fine as long as the idea of learning the phone system does not make them wince.
Priorities
Your boss wants a letter out by noon and a colleague needs fifty copies in ten minutes. Which goes first, and what do you say to the other person?
Why ask it
Either order can be defended, which is why it works. Listen for a question about the real deadlines, a quick word to whoever has to wait, and some sense of who sets the priorities in an office. Be wary if the loudest person wins, or if they would say nothing and hope to manage both.
How do you keep track of everything you have been asked to do, including the requests made in passing?
Why ask it
The tool can be a notebook, a running list or flagged emails, and it matters less than whether they can describe it without thinking. The hallway request is the test, so ask where it gets written down. 'I just remember' holds up until the first busy week.
You are in the middle of something that needs concentration, and the phone and the front door will not stop. How do you get it finished?
Why ask it
At most front desks the interruptions are the job, and someone who resents them will not be happy with you. Practical answers include stopping at a clean point, leaving a note of where they were, or asking for an hour of cover for the payroll run. Say plainly how often your desk is interrupted and see whether they still look interested.
What was the busiest time of year at your last office, and what changed about your days?
Why ask it
Every office has one, whether it is enrollment week, tax season or the run-up to a trial. The useful part is what they did differently: came in early, batched the calls, dropped something that could wait. Then describe your own busiest stretch and watch how they take it.
You have been left instructions you don't fully understand, and the person who wrote them is gone for the day. What do you do?
Why ask it
This sits between guessing and stalling. The sensible middle is to do the part that is clear, hold the rest with a note of the question, and ask first thing, or to prepare it both ways if time is short. Guessing and sending is the answer that should worry you, most of all for anything leaving the building.
How do you chase a signature or a form from someone senior to you without becoming a nuisance?
Why ask it
Timesheets, permission slips and a partner's sign-off take up more of a secretary's week than any job description admits. Hope for a system: one reminder with the date in it, then a word in person, then walking the paper over with a pen. Notice the tone as well, since good humor wears better than a grievance.
Tell me about something you noticed needed doing before anyone asked you.
Why ask it
A small example is the right size, because this is a job made of small things: toner running low, a license due for renewal, two events booked into one hall next month. If nothing comes to mind, ask what they do when the desk goes quiet for an afternoon. Tidying the files or writing up a procedure is a better sign than waiting to be handed something.
Have you ever written down how the jobs at your desk are done so that someone could cover for you?
Why ask it
In many offices the secretary's procedures exist only in the secretary's memory, and nobody finds out until the first sick day. A candidate who has kept a desk manual, or even one page on how the bulk mailing is run, tends to leave a desk in better order than they found it. Ask what was in theirs.
People and privacy
What kinds of confidential information have you handled, and what did you do day to day to keep it private?
Why ask it
Habits tell you more than principles here: a locked screen, nothing left on the copier, sensitive calls taken away from the counter. Whether it was student records, patient charts or payroll matters less than whether those habits come out without prompting. The rules themselves differ by field and by place, so explain yours instead of quizzing them on law.
Someone you know well asks, in a friendly way, about something you saw at work. What do you say?
Why ask it
In a school, a church or a small town this happens in the grocery store. Look for a warm refusal that does not even confirm there is anything to tell. Be careful with 'I'd only say a little', and with a candidate who illustrates the point by telling you a private story from their last job.
A caller says they are a relative of someone in your files and asks for information. How do you decide what to tell them?
Why ask it
The right instinct is not to take an identity on trust: check who is authorized on the file, or take a message and have the proper person call back. What may be released, and to whom, depends on your field and where you are, so learn your own rules before the interview. Judge the caution here, not the legal detail.
Tell me about the angriest caller or visitor you have dealt with. What did you say, and how did it end?
Why ask it
Ask for the actual words. A capable answer lets the person finish, says the problem back to them, tells them what will happen and by when, and knows the point at which to fetch someone else. Notice how they talk about that person now, with some sympathy or still irritated.
A caller insists on speaking to your boss, who has asked not to be disturbed. What do you do?
Why ask it
Gatekeeping is half of this job in some offices. You want someone who finds out what it concerns, offers a time for a call back, and asks you which people and which situations go straight through. Give them your short list afterward, since no candidate can guess it.
Someone at the desk asks what you think they should do about their case, their symptoms or their child's grades. What do you tell them?
Why ask it
People ask the person at the desk because the desk is easier to approach than the lawyer, the doctor or the principal. A good candidate is kind and firm that it isn't theirs to answer, and gets the question to whoever can. 'I've picked up enough to help them myself' is the reply that should stop you.
Someone at the front desk becomes threatening. What do you do?
Why ask it
The sound answer is about safety and not about winning: stay calm, don't argue, get help, keep a way out. Follow it by explaining the procedure your office has. If you find you have none to explain, write one before the new person starts.
You see something at work that looks wrong, such as cash handled oddly or a record changed. What do you do?
Why ask it
From the front desk a secretary sees more of what goes on than almost anyone. A steady candidate would not investigate alone or mention it in the break room, and would take it to a named person. Use the moment to say who that is in your office, including who they would go to if the concern were about you.
How do you handle it when the person you work for is short with you on a bad day?
Why ask it
A secretary and a boss work at close quarters, and it will happen. Letting it pass in the moment and raising it later if it becomes a habit is a healthy answer. Look again at a candidate who would put up with anything, or one who is still angry at a former employer, and be truthful about your own temper while you are at it.
Closing
Part of this job is stuffing envelopes, restocking the copier and setting out coffee for meetings. How do you feel about that side of it?
Why ask it
Swap in your own unglamorous tasks and name them plainly. 'That's the job', said easily, is the answer you are after. A pause, or a joke about being overqualified, deserves one more question, because resentment over small tasks rarely stays hidden once the job is no longer new.
These are the hours the desk has to be covered. Can you reliably work them?
Why ask it
State the schedule first, including any evening meetings or weekend duties, since a front desk that opens late is noticed by everyone. Ask only whether the hours work, not why they might not. What you may ask about a candidate's circumstances varies from place to place, so check with whoever advises you on hiring.
How do you like to be given work: a written list, a morning conversation, or as things come up?
Why ask it
There is no wrong preference, only a mismatch with yours. If your habit is to call out instructions on the way to the car, admit it now and ask how they would cope. Someone who says 'I'd follow you with a notepad' has just solved the problem for you.
If I called the person you last worked for, what would they tell me about how the office ran with you in it?
Why ask it
The prediction shows how they see themselves, and you can then make the call and compare. For this job the best reference sat within earshot of the desk. Ask that person about two things above all: showing up, and keeping quiet about what they saw.
Would you be willing to do a short practical exercise: type a letter, take a phone message and put a pile of desk items in order?
Why ask it
A capable candidate usually welcomes it, since it is the one part of the interview where they can show the work. Use made-up material, give every finalist the same exercise, and keep it under half an hour. If your organization or your location has rules about testing candidates or trial shifts, ask how it works there first.
What would you want to be shown on your first morning at this desk?
Why ask it
Strong candidates ask for the phone system, the calendar, who is who, where the keys and passwords are kept, and who covers lunch. That list is a preview of how they would take over the desk. It also happens to be a ready-made plan for their first day if you hire them.
What would you like to ask me about the office or the people you would support?
Why ask it
Expect questions about who they would answer to, how many people bring them work, what the phones are like and why the job is open. None at all can be nerves, so offer a topic and try once more. Answer honestly, including about the difficult colleague, because they will meet that person in the first week anyway.
How to interview for the front desk
Practical guidance for the conversation itself
Before the interview
Write down what the desk does all week
List the real work: roughly how many calls, who walks in, whose calendar is kept, what gets typed, what money passes through. The word secretary covers a quiet one-boss desk and a school front office alike, and which questions are worth asking depends on which of those you have. The list also becomes the honest job description you give the candidate.
Choose ten or twelve
An hour holds about ten questions once you allow for follow-ups. Take two from Background, then lean toward what your list showed. A phone-heavy desk draws on Phones and calendar, a records-heavy one on Office skills, and a practice full of sensitive files on People and privacy. Keep one from Closing for the end.
Ask every candidate the same core
Use the same questions in the same order for everyone you see, and jot the answers down as you go. It makes the comparison fairer, and it stops you from hiring the person who was simply the easiest to chat with.
Find out what you may not ask
Questions about age, health, family plans, religion and similar personal matters are restricted in many places, and the rules differ by country, by state and sometimes by type of employer. Before the first interview, ask whoever handles your HR or employment advice what applies to you. Then keep the conversation on the work and the schedule.
Count the first contact
How the candidate wrote the application email, confirmed the time and spoke to whoever met them at the door is a sample of the job itself. Ask the person who let them in for an impression afterward. They saw the candidate before the interview manner was switched on.
Practical tests that fit in half an hour
A letter from rough notes
Hand over a handwritten note of about 150 words and ask for a finished letter on your letterhead. You will see speed, layout, how names are spelled and whether they ask who signs it. Invent every name and detail in the note. Never use a real file.
A phone message
Play the caller from across the table or from another room. Speak quickly, give the number once, and bury the urgent point in the middle of a long story. The slip they hand you afterward is what you would be reading on a busy Monday.
An in-basket
Write eight or ten slips: a room booked twice, a visitor due in ten minutes, a supply order, a note marked urgent by someone junior, a call back for the boss, a form with a deadline tomorrow. Ask the candidate to put them in order and explain. The reasons matter more than the order, and a good candidate will ask you a question or two before sorting.
A page to proofread
Prepare a one-page letter with six or eight planted errors, including a date that falls on the wrong day of the week and a name spelled two ways. Count what is caught. The candidate to notice is the one who checks the facts as well as the spelling.
Keep it fair
Give every finalist the same exercise, the same time, and a minute to get used to the keyboard. Keep it short enough that nobody is doing unpaid work for you. Rules on testing candidates and on trial shifts vary by place and by organization, so ask how it works where you are before you set one.
Reading the answers
Listen for the order of things
People who have done the work describe it in sequence: first this, then that, then check. People who watched someone else do it describe the result. When an answer has no steps in it, ask 'what did you do first?'
Ask for the words they used
On every phone and visitor question, ask what they said, not how they handled it. 'I calmed him down' tells you nothing. 'I said, let me write this down so I get it right' tells you how your callers would be spoken to.
Weigh manner beside skill
A new program can be learned on the job. Steadiness with an upset parent or a frightened patient is harder to teach. If two candidates are close, think about which gap you could more easily close yourself.
Check what can be checked
Compare the typing figure with the exercise, the software list with a task done in front of you, and the account of the last job with the reference call. Small differences are normal. A large one is worth a direct, friendly question before you decide.
Allow for nerves
Someone who is calm with a full waiting room can still be stiff in an interview. The practical exercise gives a second look at a candidate who answered poorly, and it is often where a quiet one pulls ahead.
Mistakes to avoid
Hiring on the software list
A resume line naming every program in the suite says little about what the person can produce. Ask for one task in each program that matters to you, or watch one being done.
Making the job sound nicer than it is
If the desk is interrupted every few minutes, if one colleague is difficult, or if a third of the job is filing, say so. The candidate who hears the true description and still wants the job is the one more likely to stay.
Marking down for not knowing your systems
Few candidates will have used your particular records system or phone setup. Ask how they learned the last unfamiliar one. That predicts more than whether the product name is on their resume.
Using real files in an exercise
A candidate is still a member of the public. Never hand one a real student, patient, client or member record to type from or sort, however harmless it looks. Made-up material tests the same skills.
Skipping the reference call
This job rests on showing up and keeping confidences, and neither can be seen in an hour's conversation. Ten minutes on the phone with someone who worked near the candidate's desk is the best check you have on both.