The Virtue of Trick Questions

My maternal grandparents are sales people.  Literally.  The story of how they met and got together is an epic about travelling magazine salesmen, complete with loved-and-lost-and-found-again elements, nefarious sales managers, and buying a top of the line car with coupons they’d been trading for while on the road.  As I get older, I get more and more details, and it becomes more and more obvious how very much I’m cut from the same mold.  I’m sales-people, too.  I’ve already got enough hind-sight to look back and things and go, “Yeah, that there should have been a clue.  This is just how my brain works.”

I’m also very much a writer, but that’s not something I had to figure out.  It just was.  I have never at  any point seriously contemplated making my living off writing – I enjoy it far too much to turn it into work – but the fact that my brain is wired like a writer’s has always been something I’ve known.

What’s fascinating is looking at how the two things feed and reinforce each other.  I go about being a particular kind of sales person because it’s what appeals to my sense of narrative, to my expectations about how the series of anecdotes that collect together to form the story of my life ought to go.  And I approach writing in a certain way because it’s how my brain assesses the world.  I’m sensitive to a certain kind of problem, and prone to a particular tack for solutions.  Which details are salient to me, which questions are important, how the consequences of a thing play out, my instincts for them are all completely warped by my sales brain.

Here’s an example: I spent a lot of time in high school figuring out where I was going to go to college.  A whole lot of time.  I got serious about the search in sophomore year, and did a tour of nearly a dozen colleges the summer after.  (This was also, conveniently, a tour of hitting all my relatives flung across the coastal Southern states.)  This was great, because it meant that when I figured out that my initial assumptions about what a college I wanted to go to looked like were HORRIBLY WRONG, I had plenty of time to start over and try again.  But it also meant I got really, really good at the college interview process.

Before the Great Southern College Tour, I read up on what one should do when touring colleges and having admissions interviews.  One bit of advice was always that you should have questions specific to the school to ask.  For most of the schools I didn’t really have any specific questions – they were sorta all the same on paper and I lacked all kinds of information for establishing a baseline that I’d need to think of questions.  So instead I came up with one question I’d ask every school.  And then, in my College Spreadsheet of Doom, which I’d developed with a detailed scoring rubric (I was considering about 130 schools at one point), I had a column for recording how colleges did on that question.  It was pass or fail, and worth more points than any single other criteria other than the “Fuzzy gut instinct” column.  One college passed (University of Chicago).  One got partial credit (Queens in NC).  The rest were dismal failures.

This was the question: What do you think of Charles Dickens?

This was a malicious trick question.  “I like him,” is the wrong answer.  “I don’t like him,” equally wrong.  Responding to the question as if I care at all about Charles Dickens is the wrong answer.  The right answer was to use that as an opportunity to talk about English Professor X, or required course Y, or Program Z, or, really, in any way tie the question into an opportunity to talk about something that person liked about the school.  The wording of the question is about a verbose British hack with inconsistent quality that should have prepared us for the way Stephen Moffat likes to abuse us, but what it’s really asking is, “Tell me what’s awesome about you and why.”

You can’t, of course, just ask them that question.  They think they’ve answered it already with their brochures and their prepared spiel.  But that’s marketing.  It’s bunk.   I didn’t care about their marketing.  I wanted them to sell me their school.  I wanted to know, not just that they loved it, but that they loved it for reasons that would appeal to me, too.  I needed to know that the school had enough sincere advocates on hand to train the ones who were good at it into being their recruiters.  In short, I wanted a look at how the sausage of their sales department was made.  It’s the question you ask the customer to get the answer you really need, instead of the one you ask to have them regurgitate what they think they want.

But it’s also a question that delves into the narrative of the school.  Every school has story it tells about itself, and identify for what it thinks it is or aspires to be.  The marketing brochure is the “As you know, Bob,” exposition.  The malicious trick question is the natural point you look for to demonstrate your world-building and character development.  Give your customers the opportunity to accidentally tell you what you need to know.  Give your characters the opportunity to show the reader who they are and how the world they live in works.

Whichever brain you’re using, sales or writing, always look for opportunities to ask trick questions.  And really listen to your answers, and what the answers tell you.