50 Gentle Questions to Ask Your Characters

Do you know people who have a difficult time accepting a compliment? Who may even be more comfortable with constructive criticism? There are story characters that are like that, too. They have no problem exploring their faults and flaws, often seeing past bad behavior as learning experiences. Or they see current cravings not as “just who they are,” but as targets for improvement.

This is not to say that the characters (or real people) are saints. They can be as human as the rest of us, but they are comfortable recognizing and (often) admitting their shortcomings. With them, getting answers to my 50 Rude Questions is easy. Maybe too easy.

One of my most important writing practices is interviewing my follow-up questions. How they evade the truth tells me as much about who they are as their actual answers. Now, a straight arrow can be a hypocrite (or worse), but someone who is less egocentric and more self aware may welcome rude questions and answer them as best as he/she can. Think of most characters Tom Hanks has played.

I ran into such a goodhearted character while working on a recent story, and I came out of the interview with useful questions, but less of a sense of who he was. So I tried something new. I went after him with some gentler questions, and he got (wonderfully) uncomfortable. He had a lot of trouble talking about and owning some good traits and behaviors. That led to the kind of hesitations, equivocations, and telling responses that mean so much to my style of storytelling.

I’m eager to do more of this sort of questions, so I’ve used the experience to create this list of 50:

    1.    What kindness did you do for someone with no expectation of a return?
    2.    What lesson do you hope someone learned from you example?
    3.    What’s the most embarrassing compliment you’ve ever received?
    4.    What achievement are you most proud of?
    5.    When did you not get credit you expected?
    6.    Can you tell me about any friends or family who helped you get through adolescence?
    7.    How has a teacher inspired you?
    8.    Tell me about a time when it was awkward or difficult to do the right thing.
    9.    When someone suffered a loss, how were you able to comfort them?
    10.    What break or advice or example made you understand what your vocation was?
    11.    What challenging day of hard work ended best?
    12.    If you had a slogan on how to live your life well, what would it be?
    13.    What example or experience deepened your understanding of a value you treasure?
    14.    If you received a million dollars to make life better for others, how would you spend it?
    15.    What advice or story have you come to appreciate more with each passing year?
    16.    If you could spend an hour with one person from history, who would it be?
    17.    What’s the most important gift you’ve given or received?
    18.    What’s the greatest act of friendship you have personal knowledge of?
    19.    Which obstacle that you’ve faced taught you the most about life?
    20.    What moment would you like to relive?
    21.    On a regular basis, what’s the best use of time for you?
    22.    Which relative would you be most proud of being “just like”?
    23.    Tell me about someone you only came to respect and appreciate over time.
    24.    What advice led wisdom when you learned to ignore or reverse it?
    25.    What’s the biggest blind spot you moved past?
    26.    What’s the most important thing you learned accidentally?
    27.    What act of kindness (by you or to benefit you) led to the biggest payoff in terms of understanding?
    28.    What advice continues to challenge you to be better?
    29.    What incident caused you to seek out help that changed your life?
    30.    Tell me about a relationship that taught you the most about yourself.
    31.    Has someone ever rescued you?
    32.    What strength of yours is most needed by your family or community?
    33.    How did you respond successfully to a setback or blow that seemed impossible to overcome?
    34.    What’s the greatest gift your family or community ever gave you?
    35.    At this point it your life, who do you depend on most?
    36.    What was the most difficult choice for you between two apparent goods? Two apparent bads?
    37.    If you were drafted to provide a year of service to your community, what would you hope that service would be?
    38.    What for you are the values that are most difficult to put live out?
    39.    How do you express loyalty, affection, and commitment to others?
    40.    Is there anything that gets in the way of your doing the right thing?
    41.    Tell me about a time when you were surprised you had the strength to do something that mattered.
    42.    Tell me about a time when you were surprised by the positive impact of a choice you made.
    43.    What historical event would you have been delighted to witness firsthand?
    44.    What question would you have liked to have asked a contemporary who is dead now?
    45.    If you had one person you could partner with to get an important job done, who would that be?
    46.    Name a work of genius you admire that was created by a horribly flawed person.
    47.    Is there a chronic injustice in this world that you believe could be remedied in your lifetime?
    48.    Is there anything others see as nonsense that you see as wise?
    49.    If you could pass on just one fable, parable, or experience to the next generation, what would it be?
    50.    What do you hope your personal legacy will be?

For many of these, the follow-up questions are invaluable. While I often conceive of some questions in the moment and make them specific to the character, “Why?” almost always pays off.