No joke: serious questions for smart storytellers

Good questions

Ann, Barb, and Chuck walk into a meeting room.

Sounds like the start of a joke, right? Actually, it’s the start of a storytelling project. These three managers have been designated “storytellers” for an event their company is hosting next month. A crowd of their peers will come from around the world, pour into a massive ballroom, occupy round tables, and fix their eyes on stage. Leaders will present visions. Experts will share insights. Facilitators will lead discussions.

And the three storytellers? Well, their job is to inspire. To say something that will compel the crowd to walk out of that ballroom with more than newfound knowledge: the genuine desire to use it.

It’s a good addition to the agenda—and an increasingly popular one. Looking to spice up meetings, conferences, and training programs, more and more business leaders are adding “storytelling” to the docket. The smartest leaders are giving their storytellers a useful balance of clear direction and creative latitude.

Smart storytellers invite early input.

And the smartest storytellers? They’re taking time to road-test their material, not just because practicing is a good idea (though it is, as I’ve said here and here), but because they crave the kind of feedback that will make their stories stronger. Rather than waiting for dress rehearsal to ask, “How’d I do?” they’re inviting feedback while their stories are in the formative stage.

That’s why Ann, Barb, and Chuck have gathered in a meeting room. They’ve been thinking about the stories they will tell. The key points and themes are taking shape in the space between their ears. Now, they want to know how those ideas will play in the hearts and minds of other human beings.

These three managers aren’t just good at crafting stories; they’re brilliant at asking questions. You’re about to eavesdrop as they “workshop” their stories-in-progress. Notice what they ask. By digging deeper than the generic, “What do you think?” each one of these storytellers is about to get some truly useful feedback.

Here’s how their story swapping goes …

What did you see?

Ann shares her story idea first. She describes a personal experience learning to use a new technology. She admits to some humorous mistakes, revealing that she needed time and practice to get comfortable with a new, digital way of working.

“As I was talking, what were you seeing in your mind?” Ann asks. “Any specific images? People? Places? Things?”

Barb smiles and says she had flashes of Fred Flintstone and Dora the Explorer. Chuck laughs out loud and says, “No way! I kept thinking of Jimmy Neutron and the Jetsons!”

Ann’s story had nothing to do with cartoon animation, and she didn’t bring any illustrations, videos, or PowerPoint slides to the conversation. Yet, something about Ann’s words—probably the self-deprecating details she shared—gave her colleagues a playful view. That’s good to know! If Ann was hoping to strike a solemn tone, she’d need to make some serious adjustments. But since she wants people to feel hopeful, optimistic, and at ease, she’s on the right track.

When I said X, what was your Y?

Barb is up next. She describes tackling a project she didn’t feel entirely prepared to handle. Even though she was tempted to give up, she struggled through the process. Eventually, she completed the work. More important, she learned a valuable lesson she wants to share about what she calls “empowerment.”

“When I say that,” asks Barb, “Where does your brain go? What words or ideas are moving through your mind now?”

Chuck says his first thought is actually a question: “What do you mean by empowerment?” Barb answers that she wants their teammates to know it’s okay to not have all the answers, as long as you’re willing to go after the answers.

Those are good details, says Chuck. They make him think of trust—as in, “The company trusted your intelligence enough to hire you for this job. We need you to trust yourself to do the hard stuff.” Ann nods, but says she’s churning a different word: permission. “It feels like you’re offering me a license to try,” she says.

“Oh, I love that!” says Barb. She adds the words “trust” and “permission” and “license to try” to her notes. She’ll look for ways to weave them into her story, so the audience will know exactly what she’s encouraging them to do.

What has you saying “yeah, but”?

Now it’s Chuck’s turn. Talking from some notes he’s scribbled on a printed PowerPoint deck, he rattles off a few key points: something about how the team needs to align on a change management strategy to leverage best practices, enable peak performance, and optimize their collective impact.

After he’s covered the list, he looks up at Ann and Barb. “Those are the big ideas,” he says. “What might get in the way of people really hearing my story? Where will they struggle or object or get distracted?”

Ann and Barb look at each other, both reluctant to bear the bad news. Finally, Barb clears her throat and says, “Chuck, I don’t know what you mean.” Words like “alignment” and “enable” and “impact” may be familiar, but they’re too vague to tell a story. Stories need specifics.

Ann suggests that Chuck turn his notes over and just talk, from the heart, about his idea. “Tell us about the moment you realized you had a story worth telling. What happened? Forget that we work together and talk to us like we know nothing about what you do.”

Chuck leans back and sighs. “You’ll never believe it, but it all started when I installed our kitchen faucet the wrong way, so the hot and cold levers were on the wrong sides.” Wow! That’s relatable. Chuck is on his way to translating a big business message into a relatable, human experience—raising the odds that people will find their way into his story and take the action he intends.

Even natural storytellers need feedback.

Every day, Jill and I remind people that storytelling is an innate skill. We all have it. We all think and talk in stories. Still, taking this natural ability into the workplace can feel like an act of bravery. It is! It’s in your best interest to be a smart storyteller: one who invites useful feedback while your story is taking shape.

Like Ann, Barb, and Chuck, find at least one early audience for your story-in-progress. Share your ideas, ask good questions, then listen carefully to the responses. The input you receive will help you craft a story that paints a clear picture, stirs the right emotion, and generates the kind of action you have in mind.

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