What do you do in the first thirty seconds with someone who does not want to be there?

A craft question rather than a fame question, which is the way in with anyone who has interviewed people for a living. The answer is usually a small physical habit, where she sits or what she does with her hands, and those details are the ones nobody thinks to ask about.

How do you know when to stop talking?

Silence is the technique most interviewers cannot manage, and she is being asked here to describe her own timing. Follow up on how long she will let a pause run before rescuing it, because the number is shorter than most people can bear.

How much do you prepare, and how much of it do you throw out once you sit down?

The ratio is the whole job. Someone who plans forty questions and uses six is doing something different from someone who plans six, and the discarded questions are where the interesting decisions happen.

What question have you asked most often, and does it still work?

Every interviewer has a house question they reach for when a conversation stalls. Asking whether it still works invites her to talk about the ones that have worn out, which is a more revealing answer than naming a favourite.

When someone starts crying, do you keep going or stop?

This is the ethical centre of the job put as a practical question. There is no comfortable answer, and whichever way she goes, the follow up is what she does with the footage afterwards.

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Questions to Ask Oprah Winfrey

Questions for the interview you will probably never get: how a conversation gets steered, when to stay silent, what gets cut, what she has stopped saying yes to, and what it is like to be read by someone who reads people for a living.

20 questions, each with the reason to ask it · includes a conversation guide

Open any question to see why it works.

1
What do you do in the first thirty seconds with someone who does not want to be there?
A craft question rather than a fame question, which is the way in with anyone who has interviewed people for a living. The answer is usually a small physical habit, where she sits or what she does with her hands, and those details are the ones nobody thinks to ask about.
2
How do you know when to stop talking?
Silence is the technique most interviewers cannot manage, and she is being asked here to describe her own timing. Follow up on how long she will let a pause run before rescuing it, because the number is shorter than most people can bear.
3
How much do you prepare, and how much of it do you throw out once you sit down?
The ratio is the whole job. Someone who plans forty questions and uses six is doing something different from someone who plans six, and the discarded questions are where the interesting decisions happen.
4
What question have you asked most often, and does it still work?
Every interviewer has a house question they reach for when a conversation stalls. Asking whether it still works invites her to talk about the ones that have worn out, which is a more revealing answer than naming a favourite.
5
When someone starts crying, do you keep going or stop?
This is the ethical centre of the job put as a practical question. There is no comfortable answer, and whichever way she goes, the follow up is what she does with the footage afterwards.
6
Has anyone ever refused to answer and been right to?
Invites her to take the side of the person across from her, which interviewers rarely do in public. It also gets at where she thinks the line is between a hard question and an intrusive one.
7
What is the difference between an interview and a conversation?
A question about the form itself, and one she is unusually placed to answer, having spent decades blurring the two on purpose. Press on whether the guest always knows which one they are in.
8
How do you decide what to leave out?
Editing is where the power sits and it is almost never discussed. Ask who else is in the room for that decision, because the honest answer involves producers and time slots as much as judgement.
9
What have you got wrong about someone in the first five minutes?
First impressions are an interviewer's working tool and she has had more chances than almost anyone to see them fail. Ask for the specific tell that misled her rather than the name of the person.
10
Have you ever recommended a book you later changed your mind about?
Recommending things in public means living with the ones that aged badly. The interest is in what changed, whether it was the book, the author, or her, and which of those is hardest to say out loud.
11
Who do you go to for advice?
People who become everyone's advisor stop being asked this. Ask for the role rather than a name, since knowing whether it is a friend from before all of this, a professional, or nobody at all is the actual answer.
12
What do you say no to now that you would have said yes to at thirty?
A better version of asking what she has learned, because it demands a concrete category rather than a reflection. The best follow up is what it cost her the first few times she started declining.
13
What did money change that you did not expect?
Everyone assumes they know the obvious answers, so ask specifically for the unexpected one. Answers here tend to be about who talks to you differently and what stops being told to you, not about houses.
14
Do you still get nervous, and before what exactly?
The word exactly does the work. Long careers do not remove nerves, they relocate them, and hearing what still produces them after all this time is far more interesting than whether they exist.
15
What do interviewers always get wrong about you?
Turns the format around on someone who has sat on both sides of it more than almost anyone. It is also a fair trade for every time she has asked a version of it, and she will recognise the move immediately.
16
What is a decision you defended at the time that you would not make now?
Asks for a change of mind without asking for regret, which is the version people can actually answer. Regret questions get a rehearsed line about having no regrets, while a specific defended decision gets a story.
17
How do you tell whether someone wants to be understood or wants to be believed?
The discrimination problem at the heart of interviewing anyone with something at stake. Ask what the tells are, because after enough years there is a list and she will not have been asked for it before.
18
What happens to the things people tell you that never go out?
Anyone who has interviewed at scale is carrying a large amount of unaired material. The question is what that does to a person, and it is one of the few places a very practised subject has to think before answering.
19
Who has interviewed you well, and what did they do differently?
She has been on the receiving end thousands of times and will have noticed the technique. This is the closest you can get to a professional review of your own craft while you are still in the room.
20
If you had to interview yourself, what would you open with?
The last question, and worth saving for last. Anyone can deflect a question about themselves, but almost nobody can resist designing one, and the question she chooses is more revealing than any answer she would give to yours.

Interviewing an interviewer

Practical guidance for the conversation itself.

If you somehow get the room

Ask about the craft, not the life

Someone who has spent a career answering questions about inspiration and success has a polished paragraph for each. Questions about how a conversation is steered, edited, or ended are the ones without a prepared answer attached.

Assume she is reading you as you ask

You are asking questions of a person whose job was watching how people ask questions. Short questions delivered plainly land better than long ones with a preamble, and she will notice which you are doing.

Do not open with what she means to you

It is sincere and it is also the beginning of most interviews she has ever done. Save it for the end if you must say it at all, and let the first thing out of your mouth be a question.

Follow up rather than moving on

The list is not the point. If she says something surprising about silence or editing, drop the next four questions and stay there, because that is where an interview stops being a form and starts being a conversation.

Questions that will get you nothing

Who was your favourite guest. It has one polite answer and no second question.
What advice do you have for young people. This is a request for a speech, and she has several ready.
Anything about a rumour, a feud, or someone else's private life. It ends the goodwill in the room and produces a headline instead of an answer.
What is your secret to success. The word secret guarantees a general answer.
Long questions that arrive at the point after ninety seconds. She will answer the first half and you will lose the rest.

Using these on someone you can actually reach

Most of these work on anyone who listens for a living: teachers, journalists, nurses, bartenders, chaplains, and recruiters.
The question about silence is the best one to ask a friend who is good at conversation, because they usually have no idea they do it.
The question about what people tell you that never goes further is worth asking anyone who holds confidences at work.
At a table, ask people what they would open with if they interviewed themselves. It runs longer than any other question on this page.
Keep the last one last there too. It only works when nobody has had time to prepare it.

The questions

What do you do in the first thirty seconds with someone who does not want to be there?

How do you know when to stop talking?

How much do you prepare, and how much of it do you throw out once you sit down?

What question have you asked most often, and does it still work?

When someone starts crying, do you keep going or stop?

Has anyone ever refused to answer and been right to?

What is the difference between an interview and a conversation?

How do you decide what to leave out?

What have you got wrong about someone in the first five minutes?

Have you ever recommended a book you later changed your mind about?

Who do you go to for advice?

What do you say no to now that you would have said yes to at thirty?

What did money change that you did not expect?

Do you still get nervous, and before what exactly?

What do interviewers always get wrong about you?

What is a decision you defended at the time that you would not make now?

How do you tell whether someone wants to be understood or wants to be believed?

What happens to the things people tell you that never go out?

Who has interviewed you well, and what did they do differently?

If you had to interview yourself, what would you open with?