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Best questions

By John Brady
Published: October 1, 2004
While it's often helpful to have some off-the-rack questions on hand, it's always best to use them to make a connection to the subject's real life. Using canned questions can be likened to walking on a beach with a metal detector. When you get a hit, start digging and forget everything else--including the next canned question.

For professionals on career tracks
What do you hope to accomplish in the next three years? Five years? Ten?
What's the dumbest decision you ever made?
What lesson(s) have you learned from a mistake or error in judgment?
How do you deal with pressure?
What's the biggest issue facing your field today?
Do you ever work as a mentor to young people in the business? What do you tell them? How do you coach them? What advice would you give to someone starting out in this business?
What motivates you?
What is the biggest professional risk you've taken?
What did you learn in college or graduate school that helped you in your profession?
If you could retire and start a second career, what would you do?
What do you do to get away from work? Can you shut it off?
What is your proudest professional achievement?
Who has been a role model in your life?
How might a colleague describe your work habits?
At the end of a long day, what's your idea of a perfect evening?
To what personal traits do you attribute your success?
What traits do you admire in other people?
What professional challenges have you had to face?
As a youngster, what did you want to be when you grew up?
What adjectives might a colleague use to describe your work habits?
What challenges have you faced on the job?
What historical figures do you most admire?
What personal sacrifices have you made to stay competitive?
What have you learned that you might not know if you had not chosen this field?
Can you give me an example of an irritant you might encounter in your work, something that annoys you, distracts you, that you wish you didn't have to put up with?
In a typical day, how much of your time is spent on the phone, computer, in meetings, at your desk?
What inspires you?
What challenges you?
How would you describe yourself? What are your character traits?
What do you enjoy about your work? Dislike?
How is it you have been able to be successful in this competitive field?
How would you categorize your relationships with peers in your field?
What constitutes a safety net for you? What makes you feel safe?
What zaps your energy? What rejuvenates it? What would you like us to know about you that we haven't asked?
Did there come a time in your career where you were faced with a "fork in the road?" If so, do you ever revisit the decision you made or didn't make?

Work habits
Can you tell me about any project you had to tackle where you had to meet a hard deadline? What did you do?
Do you work best in the morning or evening?
How often do you fail at work?

For someone who has led a company to success
What role have you played in turning the company around?
What impact did you think you could have before taking your present position?
What would you be doing if you weren't in this business?
What inspired you to get into this business?
What's the most disappointing business trend that you've seen lately?
What's the smartest business decision you've made?
What advice would you give to someone starting out in the business?
What do you think you accomplished at the company?
Name one person you are dying to work with.
What's your biggest fear?
How do you turn around a big ship like this?
Is failure ever valuable?

Questions about a co-worker's job performance
Can you describe his work habits?
How reliable is he?
Does he meet deadlines consistently?
How much direction does he need?
Does he work well with others?
Is he self-motivated? Is he assertive?
What are his job strengths?
What areas does he need to work on?

Reading habits
What's the best book you've read in the last year?
What's your favorite quote?
Who is your favorite author?
Do you check the bestseller lists when buying a book?

Personal pleasures
What makes you happy?
When are you happiest?
Do you have a prized possession?
What country would you like to visit but haven't?
What three CDs would you want with you on a desert isle?
What part of the world would you like to visit but haven't yet?
Do you have a favorite band?
Do you ever memorize song lyrics?
If you could share a taxi from the airport with any celebrity, who would you choose?

Anxieties
What's your biggest fear?
Beyond death, what do you think is the biggest fear of most people?
What are your goals?
What are your aspirations?
What is your greatest wish?

Getting to the sensitive side
When you look in a mirror, what do you see?
If you could eliminate a trait of your own, what would it be?
Can you tell me the story of your growing-up years, the first 10 years of your life?
If you could go back and be a certain age again, what age would it be?
Who influenced you more, your mother or your father?
What did your father do? Your mother?
Were you ever bullied in school?

Lifestyle influences
How has California (or New York, Texas, etc.) influenced your life?
What's your favorite place in Los Angeles?
Give me three words to describe yourself.
What is your personal motto?
What is your favorite quote?

Proust questionnaire
(from the last page of Vanity Fair; Proust was a brooding sort of fellow, one who like to explore life's deep questions of ultimates and whose characters were prone to intense bouts of self-examination.)

What is your idea of perfect happiness?
What is your greatest fear?
Which historical figure do you most identify with?
What is the trait you most deplore in yourself?
What is the trait you most deplore in others?
What is your favorite journey?
What do you consider the most overrated virtue?
On what occasion do you lie?
What do you dislike most about your appearance?
Which living person do you most despise?
Which words or phrases do you most overuse?
What is your greatest regret?
Which talent would you most like to have?
If you could change one thing about yourself, what would it be?
If you could change one thing about your family, what would it be?
What do you consider your greatest achievement?
If you were to die and come back as a person or thing, what do you think it would be?
What is your most treasured possession?
What do you regard as the lowest depth of misery?
What is your most marked characteristic?
What talent would you most like to have?
What is the quality you most like in a man?
What is the quality you most like in a woman?
What do you most value in your friends?
Who are your favorite writers?
Who is your favorite hero of fiction?
Who are your heroes in real life?
If you could have dinner with three people, living or not, whom would you choose and why?
How would you like to die?
What is your motto?

What do you know for sure?
(from the last page of O, The Oprah Magazine)

Variations on that old standby, "How did you feel ...?"
What were you thinking?
What went through your mind?
How did you decide that?
Let's go through your thinking process when that happened ...

When was the last time you ...
(from last-page department, Details magazine)
Lost all composure?
Were cruel to an animal?
Had impure thoughts?
Abused your power or celebrity?
Did something reckless?
Gave in to peer pressure?
Spoke another language?
Exposed yourself?

Probing the personality
Interviews for personality profiles are all about individuality--explaining why someone lives where he lives, behaves as she does, and so forth. Your questioning should accentuate the individualistic, and the answers should explain why this individual is not quite part of the crowd.

Can you name five things you like very much?
Five things you dislike?
Did you have a happy childhood?
Describe the incident in your childhood that you think most affected you.
How do you feel about your mother? Your father?
What are your favorite hobbies?
How have your hobby interests changed over the years?
Do you pray? Do you meditate? Chant? Do yoga?
Do you consider yourself a religious person?
What are your politics?
What is your philosophy of life?
What is your attitude toward money?
If you had a million dollars, how would you spend it?
What is your idea of a perfect vacation?
How do you usually spend a workday?
Have you had any medical difficulties?
Have you had any experiences with death?
What kind of education did you have, and how do you feel about it?
How do you think other people react to you?
What are you proudest of?
What are you most ashamed of?
How do you feel about food?
What do you dream about?
What makes you feel good?
What sort of work do you try to avoid or put off?
What person do you think has influenced you the most?
Are you athletic?
How methodical are you?
What are your chief taboos?
How much traveling have you done?
Can you describe a situation in which you feel you behaved courageously?
Do you see yourself as a self-centered person?
Do you see yourself as a loving person?
Do you see yourself as a popular person?
What is your definition of power?
What do you see as the responsibilities of power?
How artistic are you?
What are your plans for the future?
How idealistic are you?
How realistic are you?
How successful are you?
What are five things that you most often object to in other people?
Name three things that you most object to in yourself.
How gullible are you?
Do you believe that the end justifies the means?
What do you worry about most?
Do you know of anything worth dying for?
For you, what makes life worth living?
How do you react to the current world situation?
Which changes now taking place in the world should be encouraged, and which resisted?
What ideas now popular in our society do you consider potentially dangerous?
What mistakes in your life have you learned from?
Ultimately, how would you like to be remembered?

Barbara Walters' questions for celebrities
(Tears not always optional.)

To actress Renée Zellweger:
How did the role in Chicago change you as an actress?
Let's go back to your childhood ...
What was the first movie you ever saw?
What did your parents teach you? Your mother? Your father?
(Zellweger mists at recollections of her mother; not quite tears. Barbara continues.)
Take me back seven years ago, before you got your big role in Jerry Maguire. What were you doing?
Is anyone in your life now?
Any sense of a biological time clock? Marriage? Children?
And what's next?
I've read that you need serenity. Tell me about that.
(After asking Zellweger if she wants to find true love, Baba closes, saying: "I hope it happens. That's my wish for you.")

To actress Julianne Moore:
Why do you prefer to play these sad, difficult women?
When you first met your [younger] husband, did the nine-year difference bother you?
What has motherhood meant to you?
(The tears flow.)
You have said, "If somebody said 'you can't be an actor anymore,' it might be a relief." What did you mean by that?
(And in closing: "You've given people a lot of pleasure," says Baba. "I hope that gives you a lot of pleasure.")

To actor Nicholas Cage:
At what age did you really know you wanted to act?
Your father was an eccentric. Tell me about him.
Let's talk about your mother, a woman you love very much, but who was difficult ... Did you ever worry that you might inherit your mother's illness? [schizophrenia]
Everything I read about you describes you as weird, eccentric, wild. What three adjectives would you use to describe yourself?
(Cage chooses shy, romantic, and emotional, saying the reports Barbara read were "part of a plan to create an image.")
Let's talk about something I read about and clear up myths. Are you obsessed with Elvis Presley?
Do you think someday you will find the perfect mate?
What's been the best time of your life?
("Right here, right now, with you," says Cage. Baba closes with: "Awwww.")

Barbara Walters & the hypotheticals
Barbara Walters once revealed to the New York Times her five "foolproof" questions for the over-interviewed:

1. If you were recuperating in a hospital, who would you want in the bed next to you, excluding relatives?
2. What was your first job?
3. When was the last time you cried?
4. Who was the first person you ever loved?
5. What has given you the most pleasure in the last year?

Walters says that question three is "an especially good one for comedians. They're hard to interview because you're always the straight man."

When the Times asked Walters how she would answer her foolproof questions, she demurred, "Uh, well ... I don't think I want to. It would take me too long to think of some good answers." (Which may confirm that the most difficult interviewees are often interviewers.)

Walters' first foolproof question, and many similar icebreaker questions, are hypothetical. And the interviewer skates at his own risk.

Walters recalls the time she asked Prince Philip of Great Britain if, in the event England elected a president, he would have enjoyed being a politician. Philip replied, without warmth, that this was a hypothetical question, which he normally didn't answer.

"I was crushed," says Walters, "but I learned a valuable lesson about talking to people in very high places: avoid the hypothetical question, of the sort that usually begins, 'What if ...' and then departs into some fanciful situation that never happened and never will. That type of question can be asked of creative people, for whom imaginary situations are intriguing, but practical, crisp people dismiss it as a waste of time."

When the subject is inventive and in the mood, however, hypothetical questions are fecund. Kenneth Tynan asked Richard Burton, "If you had your life to live over again, would you change anything?"--a question that is as worn out as vaudeville.

But Burton's reply was fresh and revealing: "I'd like to be born the son of a duke with 90,000 pounds a year, or an enormous estate. ...

"And I'd like to have the most enormous library, and I'd like to think that I could read those books forever and forever, and die unlamented, unknown, unsung, unhonored--and packed with information."

Avoid clichés
How does it feel to ask cliché questions? One of the most incessant cliché queries is, of course: How do [or did] you feel?

"When you interview all the time, people keep asking you about your feelings," said tennis queen Billie Jean King. "How did it feel to do this? How did it feel to do that? I want to get away from it. I want to get out of myself."

The question is not only a cliché; it is also lazy and obvious, often saying more about the interviewer's cliché thinking than the subject's ability to respond to the "feel-gooder." Stock questions invite stock replies.

Mary Ann Madden, New York magazine's veteran quizmeister, once conducted a competition in which readers were asked for predictable replies by an interviewee from which we might infer the question asked--a litany of cliché responses to cliché questions.

Sports figure: "It was a team effort."
Politician: "I want to give this government back to the people."
Actor (on tasteful nudity): "Only if it's really essential to the plot."

Here are some of the honorable mention responses in Mary Ann Madden's competition; they are perhaps even more telling about the cliché nature of questioning in the field of entertainment reporting (you can fill in the interviewee blanks yourself).

"Living apart has strengthened our marriage and given new meaning to our relationship."
"Exploited? Certainly not! This is a scholarship competition, not a beauty pageant. I'm just proud to have been chosen to represent the women of our great state ..."
"Oh, man, like great, you know what I mean, man, like great probably's the only way to describe being on the charts."

Are dumb answers the direct result of dumb questions?

Reprinted with permission of the author from The Interviewer's Handbook: A Guerrilla Guide by John Brady (The Writer Books). (c) John Brady 2004.

--Posted Oct. 1, 2004
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