Questions to Ask Historical Figures
Questions to ask someone from the past, for a piece of writing or the old dinner table game of choosing one person and one thing to ask them. For a school project they work as interview questions to ask a historical figure, opening with the classics (childhood, obstacles, proudest achievement, what really happened) and then going where biographies are thin: ordinary days, money, fear, unrecorded credit, and what they would make of us. The guide fits the list to two people as worked examples, Benjamin Franklin and John Locke.
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The questions
Each question, and why to ask it
Classics
What was your childhood like, and where did you grow up?
Why ask it
The usual first question in a school interview. Go past the birthplace to who raised them and what the household lived on, because the later story often starts there. For very early figures the honest reply may be that nobody wrote it down.
What first set you on the path you are remembered for?
Why ask it
Biographies like a single turning point, and the truth is often a job that came up or a door that happened to be open. Check whether the famous origin story appears in anything written at the time or only in a memoir decades later.
What was the hardest obstacle you faced, and how did you get past it?
Why ask it
Teachers set this one because it has a researchable answer: an exile, a bankruptcy, a law that kept the person out of the room. The stronger reply admits which obstacle was never beaten and only worked around.
Which of your accomplishments are you proudest of?
Why ask it
It is often not the one on the monument. Thomas Jefferson's own instructions for his gravestone listed three achievements and left out the presidency, so look for what your figure chose to stress late in life.
What really happened at the moment you are most famous for?
Why ask it
Given a single question, this is what most people would spend it on: the disappearance, the missing hours, the meeting nobody minuted. Before writing a reply, list where the witnesses agree and where they split, and keep the split in view.
What was school like for you, if you went at all?
Why ask it
Plenty of famous people had a few years of teaching at most, and many more were shut out by sex, race or rank. Follow up with how they learned what they knew, which tends to be a story about one book, one tutor or one stubborn relative.
Who were your heroes when you were young?
Why ask it
Influence leaves tracks: the books a person owned, the names they quoted, who they named a child after. An answer also puts the figure back in a line of people, which is where they usually saw themselves.
What did you most want to change about the world you lived in?
Why ask it
Put the answer in the person's terms, not ours. A reformer may have wanted one law repealed or one tax lifted, which is narrower than the cause later attached to their name, and their own speeches or petitions will say which.
If you could go back and change one thing you did, what would it be?
Why ask it
Regret is hard to source, since few people filed their second thoughts. Try late letters, wills and revised editions, where a change of heart shows up as an action. If nothing turns up, say the record is silent.
How do you want to be remembered?
Why ask it
Ask it late, then set the reply beside how the person is in fact remembered. The distance between the two makes a ready conclusion for an essay or a presentation.
Daily life
What did an ordinary day of yours actually look like?
Why ask it
Biography records the crisis and skips the Tuesday. An ordinary day would show how much of a famous life went on administration, travel, and waiting weeks for a letter to arrive.
What did the place you lived smell and sound like?
Why ask it
Coal smoke, horses, tallow candles, church bells and no engine noise anywhere: this is what a period drama leaves out. For a piece of writing, visitors' complaints about a town are a good place to find it.
What did you eat on a normal day, and who cooked it?
Why ask it
Food is one of the better documented corners of ordinary life, through account books, recipes and complaints in letters. Asking who cooked puts a second person in the scene, usually unnamed and sometimes unfree.
What did you do when there was nothing to do?
Why ask it
Before screens, an empty evening went on cards, mending, reading aloud, music made at home and long letters. If your figure kept a diary, the uneventful entries answer this one, and they are often the entries a biographer cut.
What made you laugh?
Why ask it
Jokes keep badly, yet some figures left puns, teasing letters and rude nicknames for their enemies. Put one real joke into a portrait or a presentation and the audience will remember it after the dates have gone.
When were you happiest?
Why ask it
Often not the years in the history books. Look for the stretch the person kept going back to in later letters: a first workshop, a posting abroad, the farm before public office. It gives an interview one warm answer among the obstacles and regrets.
How did you earn a living before anyone knew your name?
Why ask it
The years before fame are thin in most biographies and full of surveying, clerking, teaching and sewing. That early trade often supplied the exact skill the person later became known for, so ask what it taught them.
How did money work in your life, and were you ever short of it?
Why ask it
Heroic accounts leave money out, yet it decided who could travel, who could study and who could afford to hold a principle. Debts, patrons and inheritances can be traced, and a figure who died owing money reads differently from one who died rich.
What was the longest journey you ever made, and how long did it take?
Why ask it
Distance used to be counted in days and weeks, and every plan bent around it. Tracing the route and the travel time of one real trip is a small research job that improves any scene, timeline or class presentation.
How did you find out what was happening beyond your own city?
Why ask it
News came weeks late, second hand and often wrong. The Battle of New Orleans was fought about two weeks after the peace treaty had been signed in Europe, because word was still crossing the Atlantic, so ask what your figure knew on the day they acted.
People
Who did you talk to when you needed to think out loud?
Why ask it
Almost every documented achievement had an undocumented sounding board: a spouse, a servant, a sibling, a correspondent. Asking who lets the answer name somebody the archive never did.
What did your family think of what you were doing?
Why ask it
A public life was paid for at home in absence, debt and danger, and family letters often say so bluntly. A parent's or spouse's objection is good evidence of how the choice looked before anyone knew the ending.
Who were you afraid of?
Why ask it
For most people in the past somebody held real power over them: a monarch, a landlord, a creditor, a father, a crowd. Name that person and a cautious decision that looks like weak principle starts to look like plain sense.
Who was your greatest rival, and what did you honestly think of them?
Why ask it
Rivals wrote about each other constantly, so this one can be answered from both sides. Look for respect hiding inside the insults, since people seldom spend that much ink on someone they consider a fool.
What did the people who disliked you say, and was any of it fair?
Why ask it
Every notable figure had contemporaries who thought them a fraud, a fanatic or a bore, and admiring biographies tend to leave those voices out. Hostile pamphlets, cartoons and reviews often survive, so read one and decide which charge has something in it.
Who deserves credit for your work that history has left out?
Why ask it
Credit went to whoever could publish, employ and sign. Assistants, wives, translators, students and enslaved workers did work that carries another name, and an acknowledgement, a payroll or a workshop notebook is where they turn up.
Which person from your own time do you wish you had met?
Why ask it
The dinner party game, turned round. Famous contemporaries often knew each other only by reputation, and whoever your figure names shows which news and whose work actually reached them.
Choices and luck
Did you ever come close to giving up?
Why ask it
Long campaigns nearly always have a low point, and it tends to sit in a private letter far more candid than anything said in public. Find that letter and the eventual success stops looking like fate.
Which of your decisions came closest to going the other way?
Why ask it
Looking back, the choice seems obvious because we know how it ended. A draft, a close vote or a letter asking a friend what to do shows the moment it was still open. Find out what the other option was and who argued for it.
Did you know at the time that you were making history?
Why ask it
Mostly they did not. Letters written in the week of a famous event tend to be about weather, pay and sore feet, and the sense of occasion arrives in memoirs years later. Where both survive, put them side by side.
What did you change your mind about?
Why ask it
Later accounts press a person into one fixed position. A documented shift, with a date on either side of it, persuades better than a claim that they always knew, and the natural next question is who or what moved them.
How much of your success came down to luck?
Why ask it
An honest reply would tally timing, patrons, weather and other people's mistakes. If the answer is none, bring up the contemporary who was just as able and is now forgotten.
What were you certain of that turned out to be wrong?
Why ask it
Confident mistakes were often shared by everyone in the room, which is why nobody objected: the war that would be short, the investment that could not fail. Ask whether anyone warned them, and what became of that person.
What illness or loss shaped you most?
Why ask it
A child buried, a year lost to fever, a parent gone early: these were common enough that a biography may give them one sentence. Read what the person wrote in the months afterwards, and in a role play ask it as gently as you would of anyone.
What did you want that you never got?
Why ask it
Unmet ambitions rarely make the plaque: the post never offered, the book left unfinished, the voyage nobody would fund. They account for a good deal of late bitterness, and they make a figure easier for a class to sympathise with.
What would you have done if you had been born somewhere else?
Why ask it
Move the same person to another country, a poorer family or the other sex, and ask which doors close. It is a fair way to bring up privilege without scolding someone for the century they were born in.
Was it worth what it cost you?
Why ask it
Let the figure count the cost before answering: years in prison, a fortune spent, children who grew up without them. Some would say no, and if a late letter supports that, do not tidy it into a yes.
The record
How much of what is attributed to you did you actually say?
Why ask it
Famous lines are often polished or made up after the speaker has died. Trace your figure's best known sentence to the earliest place it appears in print, and if that is decades too late, let them deny it.
What did you write that you would take back?
Why ask it
Some authors spent years disowning or buying up their early work, which you can check. A pamphlet written in anger or a letter never meant for print lets the figure separate what they meant from what they published in a hurry.
Which of your letters or papers were destroyed, and who decided that?
Why ask it
Gaps in an archive are often deliberate. Jane Austen's sister destroyed many of her letters, and widows and executors did the same for others, so knowing who did the burning changes how you read what survived.
What do the portraits and statues of you get wrong?
Why ask it
Likenesses were flattery, propaganda or guesswork, and some famous faces were painted long after death by artists who never saw the sitter. For a project, find out when the best known image was made and who paid for it.
Who told your story first, and did they get it right?
Why ask it
The first biographer was often a relative, an admirer or an enemy, and later books copied them. The cherry tree story about George Washington comes from Mason Locke Weems, writing after Washington had died, so find out who wrote your figure's first life and why.
What do people today most misunderstand about you?
Why ask it
Here the figure gets a right of reply and a student gets a thesis. State the popular version fairly first, then let the person answer it with only what the sources support.
What secret did you keep that you would tell us now?
Why ask it
A favourite when the dinner table game allows only one question. Distrust any confident reply, since a secret that was kept left no document. For a project, name the gap instead (the missing months, the unsigned pamphlet, the unnamed parent) and say what historians have guessed.
Today
What did you assume the future would look like?
Why ask it
Old predictions miss in telling ways: flying machines but the same servants, new empires but the same borders. Whatever your figure left out of the forecast is what they took to be permanent.
What do you wish you had lived to see?
Why ask it
Many figures died before the outcome: the vote, the treaty, the proof, the first printing. Naming what they missed by a year or a decade shows how unfinished everything looked from inside the life.
If you were alive today, what would you be doing?
Why ask it
Match the trade to its modern descendant and ignore the fame: a pamphleteer might post online, a court painter might shoot advertisements, a ship's surgeon might work in an emergency room. It suits a group because everyone can argue with the casting.
What in our world would horrify you, and what would delight you?
Why ask it
Asking for one of each stops the reply turning into a lecture on modern morals. Clean tap water, a message that crosses an ocean in a second and most children living to grow up would astonish nearly anyone born before 1900, so start with the delight.
Which modern invention would you want explained first?
Why ask it
A lighter one that suits younger classes. The best answers follow the person's own trade: a navigator asks about satellites, a physician about vaccines, a printer about the phone in your hand.
Which problem of your time did you expect us to have solved by now?
Why ask it
For once the figure does the judging. War, hunger, plague and debt would head most lists, and going through which of them are actually solved is a sobering exercise for any group.
What did your time have that we should have kept?
Why ask it
It questions the assumption that the present improves on the past in every respect. Expect quiet, dark nights and knowing the neighbours, then weigh each one against what it cost the people who lived with it.
What advice would you give young people today?
Why ask it
Nearly every school interview includes it, and it is the easiest to answer badly, with a modern slogan in an old voice. Keep the advice to something the person demonstrably lived by, even where it sounds stern or strange now.
If you could ask us one question, what would it be?
Why ask it
The interview changes hands here. Whether they would ask if the cause won, if the family line lasted or if the house still stands tells you what they cared about more directly than any answer about themselves.
Using these questions well
Practical guidance for the conversation itself
For a classroom or a book club
Pick the person first, then discard half the list
Questions about money, fear and ordinary days work for almost anybody. The ones under The record only work for someone who left papers or had a biographer. Choose before you start; do not grind through in order.
Use the groups as a running order
For an interview assignment, the Classics give you the spine: beginnings, the famous moment, the hard part, the legacy. Add two or three from Daily life or People so the person sounds alive, and close with one from Today.
Answer from evidence, not atmosphere
If you are role-playing, require every answer to be traceable to something: a letter, a household inventory, a court record, a wage book. That constraint is what turns a parlour game into an exercise in history.
Let the answer be boring
The honest reply about a famous day is often that the person was tired, cold, or waiting for somebody. Give that answer full marks: it is usually the one with a source behind it.
Fitting the list to one person
Questions to ask Benjamin Franklin
Franklin suits an interview because he wrote a great deal about himself and still left gaps. Each of these is a question from the list with his particulars filled in.
- From the Classics: you had about two years of formal schooling in Boston, so who or what taught you to write the way you did?
- From Daily life: what did the years as an apprentice in your brother James's printing shop give you, and why did you leave for Philadelphia at seventeen?
- From People: what passed between you and your son William, who stayed loyal to the Crown when you did not?
- From Choices and luck: you held people in slavery for much of your life and signed a petition to Congress against slavery in your last months. What changed your mind, and when?
- From The record: what happened on the day of the kite? Franklin's own published description is short, and the fullest account came years later in Joseph Priestley's history of electricity.
- Also from The record: how many of Poor Richard's sayings were yours to begin with? Franklin wrote that most of them were gathered from older sources, so the reply can be checked.
- From Today: which modern invention would you want explained first? For a man who spent years experimenting with electricity, a wall socket is the place to start.
Questions to ask John Locke
A philosopher is harder, because the books are well known and the life is not. The same groups still supply the questions.
- From the Classics: you trained in medicine and came into politics as physician to Lord Ashley, later Earl of Shaftesbury. Would you have written about government at all without that household?
- From People: who were you afraid of when you left England for Holland in 1683?
- From The record: why did the Two Treatises of Government go out without your name, and why did you admit to writing it only in your will?
- From Choices and luck: you wrote about liberty while helping to administer the Carolina colony and holding shares in a company that traded in enslaved people. Did anyone in your own time put that contradiction to you?
Avoiding anachronism
- Do not ask what they thought about ideas that had not been articulated yet. Ask what they noticed that they had no word for.
- Do not ask them to answer for a moral framework that postdates them. Ask who in their own time disagreed with them, and on what grounds.
- Do not assume they knew they mattered. Most people we now document had no idea anyone would be reading about them.
- Do not assume literacy, privacy, leisure or accurate clocks. Those assumptions are what give a modern question away.
If you are writing rather than discussing
- Start with the Daily life questions. Food, travel time, smells and noise supply the detail that makes a scene work, and travellers' accounts and household books are full of them.
- Find the person who appears in the record but is never named, and give them one of these questions instead.
- Where the evidence runs out, say so on the page rather than filling the gap with invention.
- Check every quotation against a primary source. The lines repeated most often are the ones to check first.
If you only get one question
- The dinner table version of this game allows one person and one question. Choose the person for the gap in their record more than for their fame: someone whose papers were burned or whose side lost has more left to tell.
- Ask about an event, not an opinion. What happened on a particular night can only come from them, while what they thought about most things is already in print.
- Skip anything with a yes or no answer unless that yes or no would settle a real dispute.
- If you are putting questions to a chatbot playing a historical figure, treat every reply as fiction until you have found it in a source. The voice is a costume, and it will supply confident detail where the record has none.