Shall we play 20 Questions with your story?

20 Questions

When I was a restless kid enduring long drives in the back seat of my dad’s VW Beetle, Mom would occupy my brain with games.

We did a lot of “I’m going on a trip and taking something that starts with A,” then B, and all the way to Z. We took inventory of license plates, trying to find all 50 states. And when all else failed, we played 20 Questions.

The first question was always: “Is it animal, vegetable, or mineral.” Evidently, everything in the world can fit into one of those three buckets. Once that detail was revealed, all subsequent questions had to be closed-ended. So, I had 19 opportunities to calculate the yes-or-no questions that would solve the mystery of my mom’s mind. Was she thinking of a loaf of bread, a church pew, or the Eiffel Tower?

Today you can play this game with artificial intelligence. You come up with the thing to be guessed, and a bot has 20 tries to figure you out. In the early 2000s, my kids did this with Mattel’s Radica 20Q game, a handheld gizmo you can still buy from the likes of Amazon, eBay, and Walmart. Or you can ask Alexa or Google Home to play. Or hop on one of many websites—like this one —to see if you can stump the digital brain.

The world of work is no place for games. Or is it?

What’s all this talk about games? You have work to do. And if that work involves communicating, inspiring, teaching, training, or persuading others, then you need to engage your Storytelling Brain.

What’s that you say? You don’t have a Storytelling Brain?

Oh, but you do! We’re all wired to think and talk and relate to one another in stories. It’s part of being human.

Alas, the workplace can sap our human-ness, lulling us into behaviors that border on robotic (if not moronic). In particular, the world of work conjures a vocabulary of vague, generic words that can mean so many things, they don’t say ANYthing.

Introducing XYZ Company’s new and improved integrated solution! It’s a best-in-class game changer that will optimize your performance and transform your experience.

If that little passage moved you to take interest or action, I’d like to offer you some oceanfront property in central Illinois.

Abstractions abound in business communication.

Such business language runs rampant on websites and resumes. And for an audience of search engines and artificially intelligent screening tools, those glittery key words might make the first cut.

But what happens next? When your pitch team comes face-to-face with a prospective client? Or you land a Zoom interview with a choosy recruiter? You know, those moments when you need to connect with a human?

What draws us together as human beings?

For that, you need stories. A story puts you and your audience on common ground, where they see what you see. Woven with well-chosen details, a story can spark interest, stir emotion, and stoke the imagination. The right story can make the sale or land the job.

Just as you can win a game of 20 Questions with a few carefully chosen questions, you can craft a compelling business story by asking good questions.

And not the yes-or-no variety designed to close in on a specific answer. No, the best storytellers explore questions that open up opportunities for connection, understanding, and moments of aha!

Right about now, you might be wondering what questions to ask in your pursuit of a winning business story. Good question! The possibilities are endless, but here’s a not-so-short list of 20 Questions to get you started.

20 Questions for Better Stories

  1. What do I mean? When you sense that your story could be even stronger, start with this question. And then follow with: What do I REALLY mean?
  2. How else can I say it? In other words, how could you say the same thing in other words? Or with different images? Or via some other delivery method?
  3. What’s the big idea? If you had to convey your message in just one sentence or word or image, what’s the one thing you’d share?
  4. What compares? When you want someone to really understand, use an analogy to make things clear. Brainstorm metaphors that will make them say, “OH! I get it!”
  5. What’s the worst that could happen? Imagine a world without your idea or product or contribution. What will be lost or missing? Paint that sad picture.
  6. What’s the best that could happen? Picture your story “landing” with an audience and eliciting the desired response. What will they think, feel, or do? Describe that!
  7. How would someone else tell it? Imagine your story told by another spokesperson. Your most loyal customer, perhaps. Or a competitor. Or Morgan Freeman.
  8. What’s newsworthy? Suppose your story took off and made world or national news. What would the headlines be? What soundbites would the commentators be repeating?
  9. Where have I seen or heard this before?  Does this situation remind you of a sitcom or song? A play or podcast? What’s the connection?
  10. Who’s the unexpected hero? You may be tempted to star in your own show. Resist! Choose an unlikely character to rise above and save the day.
  11. Who’s the villain? Your antihero may be a person, organization, situation, or concept. Describe that enemy with details so graphic, the threat feels real.
  12. Who else has conquered this beast? In another land or industry, perhaps someone has fought a similar battle and won. Describe their victory and learn from it.
  13. What if you could time travel? How would your story play out in a different era? Say, the time of cave dwellers? Or the year 2074?
  14. What would the devil’s advocate say? Adopt a contrary point of view, and craft an argument against your own.  Anticipate objections so you can defuse them.
  15. What’s the happy ending? Race past the background and rationale, and jump straight into the glorious details of a satisfying conclusion.
  16. Who would star in the feature film? Create an imaginary cast for your scenario. Imagine lining up the perfect talent to make your story a box office hit.
  17. What if I had unlimited resources? If you could invest any amount of time and money in your story, what form would it take? What would Steven Spielberg do?
  18. What’s weird? Identify the most unusual feature of your idea or offer and go deep on its oddity.
  19. Why bother? What makes your message important or crucial? Find the words to explain why it matters.
  20. Why not? List the reasons someone might not believe or buy into your story, and then refute each one.

As a storytelling human, you have genuine intelligence, not the artificial kind. Questions like these are the perfect opportunity to use that Storytelling Brain of yours. Ask creative questions, and you will find answers.

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