Eleven Questions to Ask About Your Story Premise

The deeper I get into writing, the more I appreciate the value of making careful choices about the material I choose to write about. Though I still get value out of doing quick drafts (five pages or so) to explore story ideas and characters, I’m much more selective about projects that will likely take more than a week to reach “the end.”

This is not to say my radar is still up for what might be interesting to audiences. For me, both capturing notions (real or imagined) and brainstorming are processes done without filters. The strangest ideas smash together (sometimes years later), and weird, inappropriate stuff will often lead me to treasure.

Which brings up a Washington Post story that popped up today. A climber reached the site of a 1966 airline crash and found a box full of emeralds and sapphires. What a story prompt! The box was found in France and headed to India. I’ve visited both countries! This is perfect for me!

No. No. No. My connection is not exactly strong since I have not climbed in the Alps and I have no expertise in jewels. This is a front page story internationally, meaning writers worldwide will take this as a prompt (no doubt, one with a deal with the climber). And I’ve just suggested this to you and anyone else who reads this post. (Or blog, possibly books, of those who regularly harvest my blog posts for non-English-speaking audiences.)

No. (Probably not.)

On the basis of analysis and instinct, I’ve been cutting back on my to-be-written and to-be-rewrtten lists. I’m happy with the results, so I’m sharing some questions I use to qualify premises. (For an earlier view on this, see A Story Premise You Can Love and Cherish: 10 questions. For analysis of premises, see my series on the topic.)

• After noting the idea, developing a premise, and exploring with a few pages, am I still excited? Even after letting the premise cool for a month? Does the excitement rise to a sustainable passion to tell the story?
• Am I the best one to tell this story? Can I really get into the world (either because I know it or I can do enough research)? Can I authentically present the characters? Does this resonate with an experience or issue that matters to me?
• Is the character compelling? Already whispering in my ear? Insistent? Popping back into my head even after I say no to the story?
• Are there already intriguing answers by a character to some of the 50 Rude Questions?
• Are more than one ideas connected in a fresh way that implies specific scenes?
• Does this premise fill me with anticipation and expectations? Does it fit into a genre I’m comfortable with?
• Is the setting one I know well or could learn about through friends, lesser known research materials, or my processes for speculation?
• Do I have one big scene or three small scenes of interest already running through my brain?
  

Not necessary, but supporting my commitment, are these questions:

• Do I see a connection with an emerging social issue?
• Can I already see an appealing ending? Beginning?
• Do I have a terrific title?

Work still needs to be done. Research may show necessary information is inaccessible. The character in mind may be a bad fit as a protagonist. Development may reveal reasons not to proceed. A shorter work that includes most of what I love may be a better choice.

The main advantage for me of making questioning and ranking premises part of my process is focus. The stuff that’s set aside isn’t distracting or tempting me. In addition, the questions suggest pathways for further exploration and development. Overall, my commitment to projects (and eagerness to stay engaged) goes beyond completing a draft (a problem for some, but not for me) to doing all the rewrites that make the story as good as it can be (often my worst problem).

Though I hope some of these questions are useful, one size does not fit all. I’d encourage you to develop your own. The more they are yours, the higher the possibility that you’ll get full value from this step.

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.

Five Ways to Make Your Story Stand Out - Premise, character, deep knowledge, language, and perspective

Clichés are killers. They are stale and unpalatable and pull down everything good about your story. They are also the perfect excuse for an editor or producer or contest judge to move on to the next submission.

Nowadays, you can use an automated program to pull out cliché language, but you need more than a program to discover situations, characters, and ideas that are dead-on-arrival dull. That's lazy writing that comes from being inundated with second-rate stories. Sadly, I've seen pale reflections of mediocre work show up in manuscripts I'm excited about. But rather than rant about these failings, I'll focus here on doing things the right way. Since even good writers seem to slip, paying attention to opportunities to be fresh and innovative will make your work noticed.

Premise. I think high concept took hold when scripts started to be sold based on single statements. Outland apparently got the green light when it was described as High Noon in space. I cringe when I read similar combinations that suggest much but promised little. Rather than smashing together two concepts that sound like writing prompts, it's better to find something you're passionate about, I concept you can't let go of that also needs to be written by you. I like the questions often asked during pitches:

Why you?

Why now?

I get lots of cool ideas that make great stories… for other writers. I'll admit that sometimes my first reaction — that the premise is better for someone else — turns out to be wrong. But in all those cases, the rejected idea refuses to let me go. That insistence is a clue, and perhaps the best one for developing a good premise. Ultimately, the “why me” and emerges from discovering a connection with an idea that resonates with areas I want to explore (most of my work is about outsiders with gifts to share with a larger community that rejects them) and/or knowledge and experience I have that would make the work specific.

To get to a good premise, begin to develop a list of your own areas of curiosity and theme. Also make a list of experiences, education, and knowledge that most writers would not have.

The “why now” piece is about considering the audience for your premise and what they might be interested in. "Now" is really the future. What's knocking around today may be stale tomorrow. So work for a “why now” that is deeply relevant to your audience’s lives without being a current area of investigation (except for, perhaps, in forward-looking communities).

Character. The easy part of this is coming up with an interesting character. If you look closely at the people you know or have known, you're likely to see potential for characters based on them. This is far from the only way to find good characters, but I always keep a list around to consider as I approach new stories. (My alternative is to take small observations and exaggerate them or to springboard off a dream.)

Wherever you discover a possible character, the next step is development. I'm not a big fan of lists of traits, although these are invaluable to some writers. I usually interview my characters, often using some of my 50 rude questions. I have another trick, inversion. I may, for instance, make an introvert into an extrovert or an angry person into a mellow person. I may even turn someone I think of as villainous into a hero.

Dialogue says so much about the character, it's really good to try it out with two characters discussing something that would make you lean in and want to listen. Just as an exercise, this becomes an opportunity to hear the character’s manner of speaking and to understand how the character evades certain subjects.

I also pay a lot of attention to flaws, especially for my protagonists. For a lot of writers, this is difficult and painful work. Many identify too closely with their characters and can't imagine their dark sides. Others worry that flawed characters will be unlikable. That's not fatal for some stories, but choosing to have goody-goody characters (or irredeemable villains) throws away a wonderful opportunity for the story to stand out.

Ultimately, the goal is to arrive at a character who is distinctive and interesting.

Deep knowledge. Some of us have had notable experiences. They may be instances. (I once foolishly walked through a crowd of helmeted, baton-swatting cops). Or they may be jobs or other long-term experiences. (I was a speechwriter for senior executives in a large corporation.) Education (I'm a scientist) may also provide a lot of potential for delving deeply into subjects with great authenticity. Audiences and readers are always hungry for authenticity if it's about subjects that matter to them and are made accessible. I'm currently working on a play where all the action happens within the critical early days of genetic engineering, and I'm drawing on my experience both in working in the field and in having met and interviewed many of the pioneers.

Language. Charm makes many people irresistible. They can walk into a room and have everyone present fascinated within moments. Mastery of language — the right word, the sounds, the rhythms, and the implications — can make writing charming. And the best part is that it can start out shabby and unpredictable. You can always rework your prose for as long as you want to make it lyrical and evocative. So, this is one of the areas for getting noticed that is in almost everyone's control. Minimally, reading the work out loud until it's smooth and clear and musical is within the capabilities of most people. It may require delving into great poetry (even trying to write some). It may require hearing other people read the work (including actors). But it's within reach. And it amazes me how many writers never read their work out loud.

Perspective. This is a wonderful time for people who belong to communities kept silent too long. Whether gender or ethnicity or race or education or class has held them back, more doors (not enough) are open now. And because these points of view have been restricted for so long, many people are eager to hear the untold stories. I believe we need to hear the stories. These are human stories that put all of our lives into different perspectives and engender empathy. This is not to say that there is only room for "identity" stories or that there are writers who should "sit down and shut up" (as I heard one pundit state). 

Everyone has a perspective that could be fresh or new or deeper or unrecognized. I often will use my scientific training to analyze traditional stories that I like for unnoticed potential, digging out nuggets in well mined material. That comes from what Theodore Sturgeon called "asking the next question." So no matter who you are be curious and persistent, and you can find a perspective that's truly different.

Do not expect to create a manuscript that stands out in all ways in a first draft. It's also possible that many revisions will still leave scenes or characters or ideas that are familiar. But, if you want to stand out, raise the bar. Demand more that commands attention in everything you submit.

Courageous Writing - Eight ways to get out of your comfort zone

The new things, the interesting things, the surprising things all wait for us just past the familiar and safe. The only path to fresh knowledge and understanding is on the other side of what’s expected and accepted.

But it’s a lot easier to fall back on cliches. Language is rich in similes and metaphors that get a head nod, but never touch our hearts. The same for all the characters (some offensively stereotypical) who have popped up in stories with no effort at reimagining. Throw in (or better throw out) all the car chases, first kisses, explosions, and pies in the face that could have been grabbed from 100 other stories and substituted in without calling attention to themselves.

Besides, the price the writer pays for cliches is low, and short cuts can be very tempting to writers who are discouraged, lost, or under pressure.

Resolve to pay the price. Don’t ruin your stories because you lack the commitment or courage to make them your own. Reach beyond exhaustion and fear and discomfort to create something wonderful.

How?

Write what you don’t want anyone else to read. - Some of the most disturbing stuff we have access to is deep within ourselves. If you don’t want to share it, it will take courage to do so. But it will probably provide fodder for a story that has more to offer. Many writers who journal have access to lots of thoughts and experiences that fit here. If you don’t my 50 Rude Questions post might prompt answers that fit this category. Especially if you are good at follow-up questions.

Set high standards. - I tend to alternate between classics and contemporary works when I read. This helps me to recognize quality writing. Not surprisingly, much of the impact of fine stories comes from making insights and deep truths clear and emotionally resonant. It is not unusual for me to read such work and to conclude the author had (or has) courage that is rare. (They certainly cover issues that would take me out of my own comfort zone.) Such examples both become references (did I go far enough?) and models for my own work.

Know what you avoid. - This may be the most difficult. Dodging truth can become a habit. Facing truth can be painful. Armor can get so comfortable, you forget you’re wearing it. Reading the work of others critically, imagining scenes pursued further, can help create questions and checklists to analyze your own work. I’ve actually found that I am more alert to dodging when I read the work of peers, so I collect questions and comments aimed at helping them bring more meaning to their works, and I bring those to my own drafts.

Write until you get an aha. -  My usual practice is to get three to five beats per scene. Since I’m looking for conflict in the scene and a shift in power for each beat, this often pushes one of the characters into something unexpected. I call those surprises ahas, and they frequently take me into subjects that challenge me be being taboo or beyond what I assess to be my normal skill set. But sometimes the scene has no ahas and nothing very courageous. So… I may continue writing the scene. Often I do this in revision, keeping the tension high and making the characters more demanding until one of them blurts something out.

Go there. - Sometimes, you stumble upon a possibility that is absurd, unbelievable, naughty, uncouth, or politically incorrect. These are easy to dismiss. Blink and they’re gone. Don’t blink. Don’t give yourself reasons not to explore them. Don’t put off the journey. Jump in, make mistakes, scramble, respond — to these gifts from your muse — with full commitment and no holds barred. You may end up with useless pages. You may end up with something special. You’ll always finish your writing session with more power and capability as a writer.

Give the story its dignity. - Important subjects find their ways into stories. These can touch on the issues of the day, on critical life decisions, on tragic mistakes, and life-changing experiences. Never trivialize them (what Gardner calls the sin of frigidity). Traumas that have wounded fellow humans deserve time, space, thought, perspective and emotion. They should not be mentioned as a way to justify a character’s behavior. They must be more than plot devices. Do them justice. It is likely to lead to challenging, difficult work and, perhaps, memorable scenes. But taking care of these elements also shows respect for those who suffer misfortunes.

Take a stand. - If you’re a people pleaser, this is tough. Creating conflict and inviting arguments probably are not your thing, so there’s a tendency to always add, “on the other hand.” This is the rhetorical version of adding junk words (somewhat, nearly, about). Limiters don’t add clarity, they just hide strong words. Not taking a position hides strong, well-argued opinions. Sadly, readers react to evenhandedness with “meh.” But a clear statement that is backed up, is apt to be found engaging and received with respect, even by those who disagree.

Write in a different voice. - This is my fall back position. It never fails me. I have a collection of very different writers whom I respect, and I can step right into their styles and perspectives and take no issues that terrify and dismay me. If you can do this, it’s provides something marvelous in terms of getting past your inner censors to dig into subjects that are difficult. (After all, it’s not YOU writing it.)

It’s fine to wait until a draft is done to make it fresh. There is value to be found in inserting placeholders to maintain momentum all the way to “the end.”

I believe in stage fright. I believe in wincing. Getting too close. Being so emotional, it’s frightening. The minimum for any scene I write is that I get so jumpy writing it that I have to abandon the keyboard and walk around. Tears and laughter are better, but if I don’t a least have a moment where I’m overwhelmed, the pages need revision or deletion.

There must be danger.

Discovering Your Characters’s Secrets - Interviews that probe deeply

The more complex my characters, the more difficult it is to get the best answers from them. Even 50 rude questions only give me some of what I want. Their evasions can be revealing, but I’ve found with my current characters — who are all smarter than I am — there’s a glibness that hides the truth.

In my non-fiction life, I’ve interviewed a range of people, from Linus Pauling to Steve Allen to Nora Roberts. I’ve had to bring my A game to them. Why not characters, too?

So this week, I’m sharing some questions that provided more of the inner lives for me. Some questions worked for some characters. Some worked for others. I hope you find some useful ones. And if these don’t fit yours? I have some approaches to forming your own questions that might work.

The first approach is providing a prompt rather than a question. “Tell me about…” has given me more wonderful responses than any other approaches, so here’s a sampling of them.

Tell me about the worst advice you ever got.
Tell me about the best advice you ever got.
Tell me about a gift that was important to you, why, and what happened to it.
Tell me about a difficult choice you’re proud of making.
Tell me how you expect you’ll be remembered and why.
Tell me about an interesting pet you’ve had (or why you’ve chosen not to have pets).
Tell me about your most life-changing experience with nature.

Note that the only answer here that would be likely to get a quick answer is the first. The others probably will develop in the process of responding. They invite exploration and most of them don’t prompt for good/bad values.

The second approach is active and focused on preparation. This reveals awareness, planning, and sometimes fight or flight responses that are surprising. It is good to set these up with limits. For instance:

You have two hours. What do you pack for a camping vacation?
or
You have a thousand dollars. How do you spend it for a wedding?

Limits for the following may vary:

How would you prepare for two weeks with no phone or Internet?
How would you prepare for a days-long dust storm?
How would you prepare for a final conversation with a loved one?
How would you prepare for police questioning after you’ve witnessed a murder?
How would you prepare when a bully from your childhood calls and says he’s coming to your house?

The third approach is “either/or.” Sometimes these are dilemmas.

Would you rather spend the rest of your life homeless or homebound?
Would your rather wake up with empathy intact but logic lost or the reverse?
Would you look at the genetic test data answering whether the child you’ve been raising is really yours?
Do you rescue the only copy of a lost Dickens novel or the ninety-year-old serial child abuser?

But these can also explore dreams.
Would you rather win a Grammy or a Nobel Prize and why?
Would you rather have a happy child or the ability to fly and why?
Would you rather have a  billion dollars or create a song that people will still love and sing 1,000 years from now, and why?
Would you rather get sole credit for an app the blocks online bullying 100% or be part of a mostly anonymous team that ends world hunger?

Again, these are example questions, mostly tied to understanding the values, fears, needs, and wants of characters. You can use them as is, but making up your own versions is what will probably reveal the most about your characters.

One final suggestion. Listen to the answers (even though they come from fictional characters). This is something real-life interviewers often don’t do. It’s starkly evident when I hear questions asked that have already been answered. That is unlikely with your characters, but, when you get a “wow” response, it’s easy to be impressed and declare success. Don’t. Ask a follow-up question. Why stop digging when you strike gold?

Casting Your Stories 1: Three questions to qualify your heroes (and other characters)

Did you ever notice how often the characters you remember are the villains? I don't think this implies anything sinister about humanity. The popularity of Hannibal Lecter is not evidence that many of us long to be cannibals.

Instead, I think it plays on our curiosity, fascination with limits (freak shows and disasters), and a rejection of the safe and the mundane in fiction. The last of these is intimately related to how many writers approach their stories. They create main characters who are comfortably close to who they are. These characters often hide or minimize their flaws, do unsurprising things, and provide justifications for anything that edges toward being antisocial.

Authors protect themselves when they protect their protagonists. They let their guard down when they're dealing with villains and often can be more authentic with these characters. One trick a writer shared with me was grabbing some of the best lines from villains and seeing if they might be easily adapted to (or stolen for) the heroes. It's surprising how often and exercise like that can open up a story in later drafts. I've seen this both with my students and with my own work.

We often look to ourselves when we create viewpoint characters, but it can be more powerful to take on a bigger challenge. For important characters, especially the protagonists, I look to answer three things:

Does the character make me feel uncomfortable? One thing my sister used to do to me what I was very small was provide tours of the terrifying. It might be an abandoned house where ghosts were supposed to be or a place in the words where a murder (according to her) had taken place, or a ditch where a ravenous animal was known to slice off the limbs of little boys. While ghosts, murderers, and predators all create visceral responses, they never has the power over my imagination my sister did. Or created indelible memories. It was difficult for me then (and now) to understand who this creepy tour guide was. Those experiences created a puzzle about my sister’s identity that could not be solved. So characters that create questions that are difficult to answer but important tend to be memorable. And these characters can be the heroes of our stories if we dare to make that choice.

Does the character surprise me? In an earlier post, 50 Rude Questions, I provided examples on how to challenge and interrogate characters. Even though the questions are probing, the answers are not always revealing. Often this means that the character will never do something unexpected. Unless I have some means to take more deeply, the right tool for character vivisection, these characters do not belong my stories. At least not in major roles. But some characters give answers that suggest new questions, intrigued me, or even shock me. The more my interviews of characters make me curious or takes me in fresh directions, the more likely it is that these characters will find their ways into my stories. And, more more, it's the protagonists who speak and act in unexpected ways.

Does the character know things or experience life in ways I don't? I get excited when I learn new things. As much as "write what you know" is good and tested advice, it's valuable to create characters that require research. By definition, a story can't be predictable if there are a lot of open questions. So I tried to include characters whose histories and professions are different from my own. This is scary when those characters are protagonists or antagonists or viewpoint characters. Sometimes I have a premise that falls apart because new information proves my initial assumptions were wrong. (And the real danger is not having to put a story aside, but twisting the facts to allow the story to proceed.)

A safer route is to make these characters who are strange to me secondary within the story. That way they can liven things up without tearing things down.

Of course, these three questions assume you've found characters that could fit your premise and that are defined enough to take a closer look at. It takes a lot of preparation to build characters that lead to clear answers to these three questions. Unless… You lean on your own experiences in terms of people who interest and intrigue you… Or you are a history buff who digs into quirky people who existed in the past… Or you've heard gossip about someone you never met, where the stories hook you, but there are blanks that need to be filled in. Each of these may provide just enough to supply starting points for characters without "from scratch" work required.

Ultimately, I want to be thrilled by all my characters, including those who are the heroes. If I start out contented with a character as opposed to uneasy and excited, I'm suspicious. I want to be challenged, confused, and uncertain at times. If I'm happy with all the choices my characters make, I can’t learn anything new or experience the joy of discovery as I write. And neither can my readers.

50 Rude Questions to Ask Your Characters

One of the best ways to engage your readers is to discover deep, unexpected dimensions in your characters. For me, these tend to emerge organically as the story develops, but some of the characters that intrigue me most hide their true selves.

A few years ago, I came up with tricks to get to know my characters better. I also have had some success finding aspects of character by referring to Susan Shapiro’s Make Me Worry You’re Not O.K.

In a current work, a key character is unusually taciturn, and I’ve had to move to a tough approach — interrogation. I came up with 50 questions even I would be reluctant to answer because they are rude, invasive, and suggestive of negative characteristics. In other words, they probe the areas that most interest readers.

It’s a brutal “getting to know you” exercise, made more excruciating by my tendency to ask follow-up questions. (My poor characters.) I would not recommend methodically working through all of these questions. Instead, print out the list and check off ten to which you respond viscerally. For me, that means either I would never want to answer the question or I’d really like to hear my character’s answer.

Once you have a solid ten questions, interview your character. I’ve done this both by typing questions and answers and by using dictation. It depends on the character I’m interrogating.

I tend to press for specific answers. Also, I often convert the questions to “Tell me about…” For instance, instead of “What’s the sneakiest thing you’ve ever done?” I’m apt to say, “Tell me about the sneakiest thing you’ve ever done.” Occasionally, when the answer seems superficial, I’ll dig by saying, “Tell me about the three (or ten) sneakiest things you’ve ever done.” Or I’ll just say, “Tell me more.”

On a scale of one to ten in intensity and story value, see if you can get five answers that are eight or higher, even if it means choosing more questions to ask. Feeling generous? Try to turn some questions to the positive. Instead of “When did you first have contempt for an adult?” try “When were you first inspired by someone a lot younger than you?”

If you want to practice before you interview your character, you can take on someone else’s (perhaps from a favorite book or movie). I had some success interrogating a mentor of mine that I know well (in my imagination since he is deceased). Not only did I come out of the exercise with a better sense of the questions, but I had great answers that are likely to be applied to a character some day. If you are really eager, try the questions on yourself.

Ready? Here are the questions I came up with:

    1.    What’s the sneakiest thing you’ve ever done?
    2.    What did you think you’d get away with, but didn’t?
    3.    Why are you so mean?
    4.    What was you most embarrassing moment?
    5.    How did you escape someone who wanted to tag along with you or loved you?
    6.    How were you humiliated?
    7.    What’s the ugliest thing you ever wore?
    8.    What’s the most disgusting job you ever had?
    9.    What’s your guilty pleasure?
    10.    What’s your worst trauma?
    11.    What should no one ever ask you to do?
    12.    What caused you to laugh at someone?
    13.    What did you do as part of a group that you never would have done by yourself?
    14.    What’s your biggest secret?
    15.    What’s your biggest fear?
    16.    What did you witness that was most discouraging?
    17.    What did you witness that most upset you?
    18.    When were you most shaken by the possibility of death?
    19.    When did you first have contempt for an adult?
    20.    What’s the most horrendous secret you know about someone?
    21.    Which lie caused you the most anxiety?
    22.    What do you wish you could forget?
    23.    How did you hurt someone you loved in an unforgivable way?
    24.    What’s the most reckless thing you ever did?
    25.    How did you endanger an innocent person?
    26.    Where have you visited hoping you wouldn’t meet anyone you know?
    27.    What compliment or honor did you receive you didn’t deserve?
    28.    Who thinks well of you who shouldn’t?
    29.    Who would you cross the street to avoid talking to?
    30.    What’s the worst thing you did accidentally?
    31.    What did you break and never tell anyone about?
    32.    What’s the worst thing you did where the victim never found out it was you?
    33.    What did you see that you want to unsee?
    34.    What did you ask for one too many times?
    35.    What did you wrongly assume that caused the worst consequences?
    36.    Who did you treat like crap?
    37.    What’s the most significant promise you’ve broken?
    38.    Who do you owe an apology who’ll never get one?
    39.    Where are you most vulnerable?
    40.    What task would you avoid at all cost?
    41.    What’s the dearest thing you’ve lost and will never recover?
    42.    Which temptation would be irresistible to you?
    43.    What’s the most extreme thing you’ve ever done?
    44.    What belief did you hold onto for years that turned out to be false?
    45.    What torture would make you betray everything?
    46.    What’s your most loathsome desire?
    47.    How would you NOT want to be remembered?
    48.    What do you find most disgusting or perverse that is generally considered acceptable?
    49.    What was your most unsettling experience?
    50.    What’s your biggest regret?