Storytelling is more than the accumulation of writing tactics.

Most people wanna know how to write:

The “perfect” hook.
A structure that keeps things moving, while allowing the message to sink in.
An ending that is thought-provoking and meaningful without being internet guru preachy.

New storytellers especially agonize over word choice and formatting.

And while that’s certainly important as you practice the craft, it’s not where good storytelling begins.

“If I had an hour to solve a problem, and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask… for once I know the proper question, I could solve the problem in less than five minutes.”

— Albert Einstein

As any good journalist, and Albert Einstein, will tell you, the good stuff rarely materializes without good questions.

This is unfortunate because most professionals are never asked good questions about their expertise — so it stays in their head.

Vocalists often lament that when someone finds out they’re musically inclined, and inevitably asks them to “sing a little something,” their mind goes blank, as if they’ve never heard a song lyric in their entire life.

When I was a business reporter, this happened all the time to CEOs too.

We’d lineup an interview.

They'd be excited to talk about their mission, their cause, or new project, but when we sat down to get into the nuts and bolts, they’d blank.

Then go full corporate speak with a PR spin to compensate.

I’d walk away with word vomit, I would have to spend the next six to eight hours un-gunk-ifying in time for press.

The subject matter was never the issue.

What was missing was interesting dots to connect. The details, thought process, and emotional resonance that make certain stories stand out.

To unearth the right dots, you need the right questions for your most compelling personal brand storytelling to come to light.

Better Questions, Better Stories

To this day, I have to tell clients, your story can do so much more than answer “why did you start your business?” In fact, they should.

Or you’ll end up with the same story as every other business owner.

Something predictable like: “I had a job, but I was called to do something more, and now I have a business doing something I love.”

But “why did you start your business?” is often the only question business owners know to ask when they’re telling their stories, leaving the interesting pieces unexplored, disconnected, and unsaid. Their audience misses out on the piece they need to hear to take action when the business owner loses the plot.

Your best stories are the ones no one knows to ask you about.

What Makes A Good Question

To solve for the word vomit problem, I committed myself to asking better questions. To find the things no one else was bringing to light.

Not only to give my readers something special, but to make the person I was interviewing come off on the page as interesting and smart as they were in real life. It worked, and not only were the articles more exciting to read, they earned arm-fulls of journalism awards too.

This week’s StoryCraft practice is about asking yourself better questions so you can tell stories from a fresh and interesting angle.

1. Unexpected Framing

→ “If you were a tree, what kind of tree would you be?”
Barbara Walters (in)famously asked this to Katharine Hepburn, who had just said she felt like a very strong tree in her old age. Barbara followed that thread—seizing on metaphor—and turned it into a deeper question. It became iconic because it seemed strange at first, but it tapped into an original perspective people couldn't stop talking about back then. When you use metaphor to describe your experience (e.g., “what kind of weather was that year in your life?” or “what role were you playing back then?”), you bypass the logical, polished version of your story. You start tapping into texture—the feelings, visuals, and inner narrative that make a story memorable. Use it when you’re trying to get beneath surface identity or give emotional shape to a moment.

2. Cognitive Disruption

→ “What were you thinking?”
Barbara once asked Monica Lewinsky this in the now-famous 1999 interview. The line was sharp—not accusatory, but direct. At a time when the story had been sensationalized, spun, and dissected by the media, this question just asked what everyone was wondering. In essence: What was happening inside you while the world saw something else?
We often recount events in hindsight, but gloss over our actual thinking at the time. Asking “What was I thinking at that moment?” gives you more than a summary to work with. It puts you and your audience back in the room—with the emotion, fear, thrill, or fog that was present then. That detail is story gold. Use it when you want to add emotional depth, reveal the thought process (like experts must do in stories).

3. Get The Second Answer

Barbara’s strength wasn’t just in the bold questions—but the simple follow-ups. When someone answered vulnerably, she wouldn’t jump to the next cue card. She’d latch on with:

“Why is that?”

“Was that hard to admit?”

“Did something change for you then?”

Most stop at the first insight. But when you follow your own answer with another question, you go deeper.

The most compelling nuance always lives in the second answer. Use it when you want to add depth and insight, find the real meaning, or give your audience an aha-moment.

Moral Of The Story

The most compelling stories don’t start with perfect wording.

They start with better questions—
and turn into stories no one else can tell.

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Happy Storytelling!

Cyndi