Funny Questions to Ask Your Principal
For the student with a microphone, a camera or a yearbook deadline and ten minutes of the principal's time, whether that is the school news show, an assembly or a spirit week video. The 54 questions run in the order a good interview does: Warm-up, Back in school, On the job and Food, then a fast This or that round and a set of What if questions to finish on. All of them are built to get a laugh with the principal and never at their expense.
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The questions
Each question, and why to ask it
Warm-up
How many cups of coffee does it take to run this school?
Why ask it
A safe opener, because it is quick and it works even on a principal who goes stiff in front of a camera. If the answer is tea, soda or nothing at all, ask what keeps them upright through the last period on a Friday.
What sentence do you say more than any other during a school day?
Why ask it
Expect 'walk, please' or 'where are you supposed to be?', and expect the audience to say it along with them. Have them deliver it in the exact voice they use in the hallway.
Do you live at school, or is that only a rumor?
Why ask it
The youngest students half believe it, and an older student can ask it with a straight face, which is funnier. If they play along, ask where the bed is; if they deny it, ask who locks up at night and how late that gets.
What is in your desk drawer right now that students would never guess?
Why ask it
The item is funnier seen than described, so invite them to open the drawer on camera. A spare tie, a stress ball or a pile of sticky notes would all be ordinary; hope for something stranger and find out how it got there.
What time does your alarm go off on a school day, and how many times do you hit snooze?
Why ask it
The time is usually earlier than students expect, and the snooze count is the confession. Follow with who is already in the building when they arrive, since somebody, often a custodian or a coach, tends to beat them in.
Where do you go all summer, and do you miss us even a little?
Why ask it
Plenty of students assume the office goes dark the day they leave. How much of the summer a principal works depends on the school, so let them describe an ordinary July morning, then enjoy the pause before they answer the second half.
What is the best joke you know that is clean enough for the morning announcements?
Why ask it
Give warning of this one, because almost nobody can produce a joke on demand. A groan from the room counts as a win, and if it lands you can propose a joke of the week on the announcements and get an answer on the spot.
If you had walk-up music for every assembly, what song would it be?
Why ask it
Take the answer seriously and play the song the next time they walk into the gym. Check the lyrics before you promise anything, because only a clean version is going to get past the office.
Which spirit week dress-up day do you look forward to, and which one do you quietly dread?
Why ask it
Handy if the video goes out during spirit week, because you can cut straight to a photo of their best costume. The dreaded day is the funnier half, so wait for it and do not let them skip it.
Back in school
What kind of student were you at our age: front row, back row, or staring out the window?
Why ask it
Three choices make it quick to answer, and people tend to pick one and then confess to another. Ask what a teacher most often had to tell them to stop doing.
Were you ever sent to the principal's office yourself, and what for?
Why ask it
This is the one the audience most wants answered, so do not bury it at the end. A flat no gets a groan from the room; rescue it by asking for the closest call.
Which subject gave you the most trouble, and what is the worst grade you ever brought home?
Why ask it
Students who are fighting the same subject hear this differently from everyone else, so let the answer run. Then ask what was said at the dinner table that night.
Did you ever pass notes in class, and did a teacher ever catch one and read it out loud?
Why ask it
A principal who grew up folding paper notes will usually have a story about one being intercepted; a younger one can answer for texting under the desk. Either way, ask whether they can spot today's version from the doorway.
What was everybody at your school obsessed with that students today would not recognize?
Why ask it
You are fishing for a fad: a toy, a band, a haircut, a brand of sneaker. If the students watching have never heard of it, have the principal explain it as if it were a lesson.
What did your worst school photo look like, and may we show it?
Why ask it
Request the photo days ahead, since nobody carries one and the picture is the whole joke. Show it only if they hand it over gladly, and let them tell the story of the haircut themselves.
What was your signature move at school dances, and is it still in working order?
Why ask it
Say out loud that the demonstration is optional, which oddly makes people more willing to do it. Keep a song cued up in case the answer is yes.
What did you want to be when you were our age, and was 'principal' anywhere on the list?
Why ask it
Few people will claim they planned on this job at ten, so the route from the first dream to the office is the story. It gives you one sincere minute among the jokes, and that keeps the interview from turning into a roast.
Which teacher from your own school days would be most surprised to see you running a school?
Why ask it
Have them imagine that teacher walking through the door right now and what would be said. It often turns into a thank-you, which is worth keeping in the edit.
On the job
What is the funniest thing a student has ever said to you?
Why ask it
The youngest students tend to supply the best of these: a blunt guess at the principal's age, or family news nobody was meant to hear. Ask for the line word for word, with the name left out.
What is the strangest thing you have ever had to take away from a student?
Why ask it
Every audience is waiting for this. You want the object and not the owner, and if they will not say, settle for the category: animal, vegetable or battery-powered. Whether there is a drawer of these things, and when they go back, differs from school to school, so ask how it works at yours.
What is the most creative excuse a student has given you for being late?
Why ask it
Get a score out of ten for originality. The student stays anonymous, even if half the school already knows who it was.
Do teachers ever get sent to your office?
Why ask it
Students love the idea that adults can be in trouble too. Expect a diplomatic answer, then steer it somewhere harmless: which staff room rule gets broken most, the copier, the microwave or the last cup of coffee.
What is the funniest thing that has ever gone wrong during the morning announcements?
Why ask it
A mangled name, a microphone left on, Tuesday's lunch menu read on a Thursday: that is the kind of story you are after. If your school has a news show instead of an intercom, ask for their worst moment on it.
What is the most embarrassing thing that has happened to you in front of the whole school?
Why ask it
A slip on the gym floor, a squealing microphone, a name read wrong on awards night. Let them choose the story, and do not offer one you witnessed unless they bring it up first.
Have you ever been called 'Mom' or 'Dad' by a student by accident?
Why ask it
Adults who work with children tend to collect these, and the slip embarrasses the student far more than the grown-up. Find out how they answered, and whether they ever did it to a teacher of their own.
What is the funniest thing you have seen in a hallway when students thought no adult was looking?
Why ask it
Tell them up front that you want the scene and not the names. A principal who laughs before answering has a good one, so give them a moment to decide how much of it to tell.
Has an animal ever gotten loose in the building?
Why ask it
A bird in the gym, a squirrel in the cafeteria, a class hamster on the run: if there is a story, the staff have been telling it for years. The detail to get is who finally caught it, and with what.
What is the oddest thing that has ever ended up in the lost and found?
Why ask it
Good for a filmed segment because the pile itself is the picture. Finish by having them hold up three items and plead with the owners to come and collect them.
When you spot a student at the grocery store, do you wave or hide behind the cereal?
Why ask it
Students are amazed that staff exist outside the building, and that is the whole joke. The follow-up is the most awkward place they have ever run into one of us.
Be honest: on a snow day, are you as happy as we are?
Why ask it
Who decides to close school varies by district, so find out how it works where you are before you blame them for the last one. Where it never snows, swap in whatever does shut your school: heat, storms or a burst pipe.
Food
What is the best thing on the cafeteria menu, and what do you quietly avoid?
Why ask it
The first half is safe and the second takes nerve, with the kitchen staff likely to see the video. Let them dodge it kindly, then take the clip to the cafeteria manager for a reply.
When did you last eat a full school lunch, on a tray, at a table with students?
Why ask it
A dare dressed up as a question. If the answer is 'not lately', invite them to your table on a named day and film it as the sequel.
If you could add one item to the lunch menu with no budget and no rules, what would it be?
Why ask it
Taking away the budget and the rules frees them to say something silly: a taco bar, a grandmother's recipe, breakfast all day. Menus are often decided above the principal, so do not report the answer as a promise.
What did you eat for lunch when you were a student, and who packed it?
Why ask it
A gentle one that brings out a parent, a lunchbox and usually a trade they still regret. Ask what the most valuable thing to trade was at their school.
What snack is hidden in your office, and who else knows where it is?
Why ask it
Warn them before they answer that whatever they admit to will be requested by every visitor to the office for a month. The second half tends to give up an accomplice at the front desk.
What do you bring when the staff has a potluck, and does anybody eat it?
Why ask it
Students rarely get a look at staff room food politics, which is why this works. If there are no potlucks at your school, ask what happens to leftovers in the staff room on a Friday and who gets there first.
Is a hot dog a sandwich? We need an official ruling from the office.
Why ask it
Treat it as a formal decision: the ruling, the reasoning, and whether it will be read on the announcements. It splits a room cleanly, so at an assembly take a show of hands first.
This or that
Pizza day or taco day?
Why ask it
Start the round here because nobody needs time to think. Push for one answer, since 'both' is how a this-or-that round dies.
Bus duty or lunch duty?
Why ask it
Both are jobs many adults would trade away, so you are really asking which kind of chaos they prefer. Some principals do neither, in which case ask which one they are glad to have escaped.
Covering a gym class or covering a music class?
Why ask it
In some schools the principal steps in when a teacher is out and in others never does, so start by asking whether it has happened. The pick tells you whether they would rather face a bag of dodgeballs or thirty recorders.
Walkie-talkie or email?
Why ask it
Many principals spend the day with a radio on their belt, and it is where the odd messages come from. Ask for the strangest call they have had over it that is fit to repeat; where nobody carries one, make it intercom or email.
A fire drill in the rain or a full week of indoor recess?
Why ask it
Elementary principals feel this one in their bones. In a middle or high school, change the second half to a full week with the wifi down.
Field day or pep rally?
Why ask it
Their pick shows whether they would rather be outdoors with a whistle or indoors with a microphone. Then find out which event they have been talked into competing in.
Kickball or four square?
Why ask it
Turn the answer into a challenge: a match at recess or lunch against the winners of a student tournament. Get the date on camera before they can think it over.
Would you rather teach kindergarten for a day or drive the school bus for a day?
Why ask it
Make them explain the choice, because the reasons are the funny part. Whichever they pick, go and ask the people who do that job for real whether the principal would last until lunch.
What if
What dare would you agree to if the school hit a big goal: a pie in the face, a dunk tank, or a day in the mascot suit?
Why ask it
Have a real goal in mind before you ask, such as a reading total or a fundraiser, because a yes on camera is hard to take back. Clear the idea with the office first so the dare can actually happen.
If you could be a student here for one day, which class would you go to first, and which would you try to get out of?
Why ask it
The first pick is a compliment to whoever teaches that class, so expect it to be chosen with care. The joke is in the second half; if they will not name a class, ask which lunch table they would head for.
If you had to enter the talent show tomorrow, what would your act be?
Why ask it
This is how you find the hidden skill: juggling, a card trick, an instrument left over from middle school band. If they name something real, request ten seconds of it on the spot.
If you could make one silly rule that everyone had to follow for a single day, what would it be?
Why ask it
Walking backwards, talking in rhyme, hats required: the sillier the answer, the more you learn about what makes them laugh. A good-natured principal can be asked to declare it for a Friday.
Which superpower would make your job easiest: reading minds, being in two places at once, or silencing a cafeteria with one look?
Why ask it
Offering three keeps it from stalling, and principals often claim they already have the third. Ask for a demonstration of the look, then ask which power they are glad students do not have.
If a student got your job for one day, what is the first thing you think they would do?
Why ask it
They will guess longer recess or no homework, and that sets up your reply: tell them what students would really pick. Some schools run a principal-for-a-day prize, so ask whether yours could.
If this school were a movie, which actor would play you?
Why ask it
Keep a suggestion of your own ready in case they freeze, and make sure it is a flattering one. Casting the assistant principal is the second laugh.
If the students wrote your report card this year, what would the comment say?
Why ask it
It lets them poke fun at themselves, which is the safest kind of joke in the whole interview. Follow up with the grade they expect for hallway behavior.
If you could turn the microphone around and ask the students one question, what would it be?
Why ask it
Save this for last, and have an answer of your own ready, because a good principal will make you give one. At an assembly, let them put the question to the whole gym and hold the microphone out for the reply.
How to interview your principal and get the laugh
Practical guidance for the conversation itself
Before the interview
Ask the office, and say where it will be shown
Book the time through the front office and say whether this is for the news show, an assembly, the yearbook or a video that goes online. A principal answers differently for a gym full of students than for a page in a book, and a clip that leaves the building may need a permission you do not know about. Ask what the rule is at your school.
Share the topics, keep two surprises
Send the general topics a day or two ahead: your school days, the cafeteria, a this-or-that round. People are funnier when they have had time to remember a story. Hold back two questions as surprises so that some of the reactions are fresh.
Request the props early
The old school photo, the walk-up song, the joke and the open desk drawer all need notice. Bring them up when you book the time, and take a no without making a face.
Cut the list to the time you have
Three minutes of airtime is room for five or six questions, not the whole list. Choose one or two from each group, mark your two favorites, and get to those early in case a bell or a radio call ends the interview.
Getting a funny answer
Ask for the story behind the yes
A lot of these can be answered in one word. When that happens, say 'tell us about the time' and wait. The laugh is in the details: what the confiscated thing was, who caught the squirrel, what the note said.
Leave the silence alone
When a principal pauses and grins, a story is on the way. New interviewers fill the gap with the next question and lose it. Count to three in your head first.
Run this-or-that at speed, then stop on one
Read the pairs quickly and accept one-word answers for the first few. Then stop on a single pick and make the principal defend it. The change of pace is what makes the round work on video.
Laugh, but do not top the answer
React the way the audience would, then move on. An interviewer who answers every story with a better one of their own turns the segment into a show about the interviewer.
Keeping it school-appropriate
Tease the job, never the person
Coffee, bus duty and the intercom are fair game. Age, weight, hair, clothes, salary and family are not, even if the principal jokes about them first. If you would not want it asked of you in front of the whole school, cut it.
Keep classmates' names out of the stories
Confiscated items and late excuses belong to real students. Say before you start that you want the story with the names left out, and edit out any that slip through.
Offer a pass at the start
Tell the principal before the first question that 'next question' is always allowed. Knowing the exit is there relaxes people, and you may never hear it used.
Show the final cut before it airs
Whatever you edit should be seen by the principal, or by whoever approves the show, before anyone else sees it. It is their face and their school, and it is how you get invited back for a sequel.
Four ways to use the list
News show segment
Open with one Warm-up question, take two from On the job, run five This or that pairs and close on a What if. Film in the office if you can, so the desk drawer and the lost and found are within reach.
Live at an assembly
Pick questions the whole gym can react to: the hot dog ruling, the dare for a school goal, the sentence they say most. Take a show of hands before the principal answers, and finish by letting them turn the microphone on the students.
Yearbook sidebar
Print favors short answers. Set the This or that round as a two-column list, pull one Back in school answer out as a quote, and run the old school photo beside the new one if the principal agrees to it.
Spirit week video
Put the same three questions to the principal, the assistant principal and a couple of teachers, then cut the answers together. The dress-up day question and the dance move are the two to build it around.