Gabrielle Dolan Blind-Tested Her Stories Against AI's

Gabrielle Dolan writes stories for a living and teaches other people to tell them, so she ran an experiment to test her own advice: she wrote a story for each of six subjects, gave the same six subjects to ChatGPT and a second AI tool, then had readers blind-rate all eighteen stories without knowing which were hers. Her stories beat the AI's in four of six match-ups. One came out even. AI won once. The scoreboard wasn't the interesting part of the results — where the points landed was.

That experiment sits at the center of Dolan's latest book, Story Intelligence: The Craft of Authentic Storytelling Made Smarter with AI, and of a conversation she had with Students Incorporated co-host Josiah Ann Proud about what more than two decades of teaching storytelling has taught her that AI still hasn't caught up to.

Eighteen Stories, One Missing Ingredient

Dolan had readers score every story on categories like clarity — did the story make sense — and authenticity — did it feel real. For her own stories, the two scores landed close together; a story that made sense also felt true. For the AI-written stories, clarity consistently scored well above authenticity. The stories tracked logically. They just didn't land as real, and readers kept reaching for the same word to explain why, even before they knew which stories were AI-generated. "It just felt cliché," one told her. Another said it "didn't seem real." When Dolan later revealed which stories had been written by AI, one reader admitted rating a story generously because "I didn't want to be mean to the person" — not realizing there wasn't one.

"It's a human connection. It's the energy."

That's how Dolan describes the quality the AI stories kept losing points on. She's clear that this isn't an anti-AI position. She used AI as a creative partner while writing the book itself, including to brainstorm the title. But the test convinced her that AI can produce a story that reads fine and still be missing the one thing a story is supposed to do.

Twenty-One Years Making a Business Out of It

Dolan spent years in corporate Australia in senior leadership and change-management roles before she noticed something: when she explained the reasoning behind organizational change through stories instead of logic, people actually understood the message. The best leaders, teachers, and presenters she watched all did the same thing. Twenty-one years ago — with two children, ages two and five, at home — she left to teach storytelling full time, telling herself she could always go back to a regular job if it didn't work out. She's since published eight books on the subject, a fact she finds funny given that she failed English in her final year of school. She also co-hosts a podcast called Keeping It Real.

The Story That Got a Risk Team to Listen

To show what she means by a story doing real work, Dolan told the one she considers her best example: a client named Rosemary, head of a corporate risk team, had spent months failing to convince business units that managing risk was their job, not just hers. Case studies didn't work. Business examples didn't work. So Rosemary tried something else — she told her audience about growing up on a farm, about the hot day her mother called her to grab her bike from the front gate, and she froze because a massive copperhead snake was lying in front of it. She remembered exactly what her mother had taught her: freeze, stay still, back away slowly. She made it back to the house safely. Then she connected it to the point: "All I can do is give you the skills, knowledge, and advice, so when you come across your own copperhead snake — regardless of what that looks like — you will know what to do."

Dolan tests every story against three questions, and she ran them live on air: did it help you understand the message? Yes. Will you remember it? Yes. Could you retell it to someone else without losing the meaning? Yes. That, she says, is the whole case for storytelling in one exchange — a good story doesn't just explain a message, it makes the message sticky enough to repeat.

The Mechanics: Short, Named, Felt

Dolan's tactical rules are specific. Keep a story to 60, maybe 90 seconds — beyond two minutes, an audience starts silently thinking "get to the point." Skip the throat-clearing: don't announce "let me tell you a story," because the phrase itself makes people brace to disengage. Open with time and place instead — "when I was a kid, I grew up on a farm," or "in my early twenties, I went on an African safari" — which signals a story is coming without the warning label, because humans are wired to lean into a story once they recognize one starting. Name every character the first time they appear (her daughters are "Alex and Jess," not "my daughters"), with one exception: parents and grandparents keep their family titles. And say how you felt, not just what happened — the difference, she says, between a flat sequence of events and a story that actually taps into emotion.

Four Kinds of Stories, and a Starfish on a Beach

Dolan's framework sorts usable stories into four types: personal stories (pulling a non-work moment into a business message, which she considers the most underused and most powerful), professional stories (the classic work anecdotes people reach for in interviews), public stories (borrowed case studies — the Steve Jobs example everyone already half-knows), and parables, the Aesop's-fables category that can carry a message without any of it being personally true.

She offered one of her own: walking on a beach with her daughter Alex, then in her early twenties and adrift about not having found her "purpose" yet, Dolan retold the parable of a man throwing stranded starfish back into the ocean while a fisherman tells him it's pointless — there are too many to save. He picks up one more and answers, "I made a difference to that one." Her advice to Alex distilled the same idea: figure out, every day, how to make a difference to one person. It doesn't have to be bigger than offering to grab someone a coffee.

Using AI as a Coach, Not a Ghostwriter

Dolan's guidance for using AI in storytelling is narrower than "use it to write." She recommends prompting it to act as a storytelling coach — asking it to interview you with questions, the way a person across a coffee table would, rather than asking it to generate a finished story from a few bullet points. If AI does hand back a full story, she says the job is to fact-check it against your own memory ("the story that AI comes back could be like, I was really excited... and you could go, I wasn't excited, I was really scared") and then read it out loud, because a story can look right on the page and still not sound like you.

Structurally, she teaches a simple shape: get clear on one single message before anything else, since trying to carry more than one message is one of the most common mistakes she sees. Open with time and place. Use the middle to decide, deliberately, what stays and what gets cut — everything has to serve the message. And avoid ending on "the moral of the story is..." which she considers too directive; better to close with something like "imagine what we could achieve if..." and let the audience arrive at the point themselves.

Her closing advice to anyone who wants to get better at this: treat it like a skill, because it is one. People who try storytelling once, without preparing, and have it fall flat often conclude storytelling "doesn't work" for them — when the real lesson, she says, is closer to learning golf. You don't get better by taking lessons forever; you have to go out and actually play.

Headlines: Likeness, Trust, and the Human Core

The episode's news roundup circled the same tension from three directions. YouTube's 2026 creator-likeness tools now let creators authorize AI to re-render their videos in other languages using their own face and voice, paired with mandatory "altered content" labels and new detection tools to flag unauthorized use. CEO Neil Mohan framed the feature as a "creative accelerator" rather than a replacement for human imagination. Thai news director Dr. Natha Kamolwatin, of The Standard, was cited describing a shift in local newsrooms away from speed and toward deep, ethical reporting and niche communities AI can't replicate — what the report dubbed "signature storytelling" — as more than 43 percent of Thai audiences move toward video-first news. And marketing executive Matt Salvedo, CEO of Amplify, argued that even law, one of the most traditional professions, is being reshaped by the same principle: AI can draft a brief, but it can't replicate the human core that persuades a courtroom.

Part 7: "The Crime"

The show's ten-part serial, The Mystery of St. Augustine, kept pace alongside the interview. Part 7 opens on Chief Sullivan arriving at a basilica where lead archivist Sarah Ferguson has been found dead inside a hidden vault beneath the altar — burn marks under her arm, markings on her neck, and no sign of her phone or SIM card. Lieutenant Walsh walks him through the caretaker's account: the victim had come in after hours to research the vault and never came back out. Outside, Lieutenant Walsh breaks the news to Tom and Cece, who'd been at dinner with the rest of the El Dorado team twenty minutes earlier; Cece, who considered Sarah a mentor, walks away in shock.

The story then cuts to the people responsible: a crew of operatives — Chair 4, Chair 5, Chair 6, and a handler named Midnight, reporting to a boss known only as Chair 1 — ditch a phone in a canal but lose track of the SIM card in the process, and report back that their "simple job" has turned into two bodies in two days. What they do have is new evidence: carvings found in a lower chamber of the church, showing two broken ship masts and Latin text Chair 1 translates as "two burdens broken" — a possible sign of a second wreck. Chair 1 gives the team a choice to walk away or keep pursuing the lead off-contract; all of them, including a fifth operative identified only as Three, choose to stay in.

Meanwhile, at dinner, English aristocrat Eleanor Bennett hands Professor Hawthorne's team a portfolio of authentic late-17th-century parchment documents — engineering plans for the Castillo de San Marcos fort — as a "gesture of good faith." Amanda Chase decodes a cryptic "M1" marking on an earlier map as Italian navigational shorthand for "less than one nautical mile" from shore, which lines up with where Sir Francis Drake's smaller ships would have needed to operate. Later that night, studying the parchment further, James and Amanda realize the fort was built directly over the old inlet where ships once docked — meaning the long-sought "ghost ship" might never have left the harbor at all, but sank and was buried right where the fort now stands. Tom calls just as they're piecing it together, and James picks up eager to share the news. Instead, a long silence on the line gives way to Tom's own shaken voice — "What? How? I can't believe this" — and the episode cuts away before anyone learns what he's reacting to.

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