How Sharing Stories Can Build Rapport in Unpredictable Situations
Release Date: 02/19/2025
How Storytelling Can Turn Crowd Chaos into Connection
Storytelling School
It’s my very first time at Comic-Con. I’m with my dear friend Denise, and it’s her first time, too. The second we arrive in downtown San Diego, we’re hit with a wave of everything - cosplayers everywhere, camera crews darting around, and volunteers all over the place. There are 135,000 people moving in every direction at once. It’s buzzing, massive, and honestly thrilling! Since it’s Day One, we find our way to the convention center and step onto this long escalator. We’re heading up to the top, and I’m trying to act calm - for Denise, sure, but really for myself, too. Inside,...
info_outline
200 Episodes In: Your Storytelling Masterclass in 50 Moments
Storytelling School
It’s a Tuesday morning. I am sitting in front of my computer, matcha tea in hand, staring at my podcast dashboard. A little number in the top corner catches my eye. 200 episodes, 200! Part of me can’t even believe it. I think back to those first recordings; I was so nervous, wondering if people would care about storytelling the way I do, yet week after week, I kept going. I didn’t always know if I’d have the time, the stories, or the right guests to keep it fresh. But every single conversation, every solo episode, every moment behind the mic has taught me something. And at each...
info_outline
Why Storytelling Mastery Lives in the Middle
Storytelling School
I am standing on a court in Santa Barbara, and it's my very first pickleball lesson. I arrived early and I’m already warmed up, focused and ready to do everything exactly right. In fact, even before booking this lesson, I researched every single coach in town. I landed on Richard Pastoria because he's the real deal: a professional coach for over 25 years, the resident pickleball pro at the Valley Club of Montecito, and - not only that - he also has a military background. That combination of structure and discipline and high standards speaks to me because I've been an athlete my entire life,...
info_outline
How Great Speakers Rehearse (It’s Not What You Think)
Storytelling School
I'm on a Zoom call with one of my private clients. She is a powerhouse executive and is preparing for a TED-style keynote. Her ideas are solid, and her story is incredible; it's emotional, has high stakes and everything you would want in an opening story. And the rest of her Talk? That’s epic as well. Plus, she's done the work and is ready to go. We start rehearsing and everything… falls flat. Her delivery is kind of robotic, and there's no energy in her voice. Even the transitions between her story and her insights kind of feel like speed bumps. She is reciting her script but isn't...
info_outline
The Callback Strategy Every Speaker Should Know
Storytelling School
I’m working with my client on a TEDx Talk. In her opening story, she shares a vivid moment from her childhood: She is standing on a stranger's doorstep, completely nervous and uncertain if anyone is going to answer at all. It's a small detail yet it’s emotionally powerful and completely gripping. After the story, we go ahead and develop the rest of the Talk. And as a whole, her Talk is strong. It's structured and meaningful… except when we get to the end. Something is missing. Her idea and her content are clear, but there isn't really an emotional lift at the end. I suggest going...
info_outline
What Knife Fighting Taught Me About Storytelling
Storytelling School
I am standing in the dojo, drenched in sweat. We’re in the middle of a dynamic circle knife drill, and I’m surrounded by fellow black belts, each armed with metal training knives and ready to attack in a simulation of real-life danger - fast, chaotic, and unrelenting. At first, I hold my own, fueled by adrenaline and a strong desire to prove that I can hang with the best. I move quickly, using flashy moves and relying on sheer speed, but as the drill speeds up, my technique falls apart. I'm rushing transitions, missing critical details, and losing confidence. My partners sense the...
info_outline
Why Sharing Difficult Stories Can Change Lives
Storytelling School
I'm a freshman at the University of Hawaii, living the dream on a full-ride softball scholarship. One night during finals week, my roommate and I decide to take a break from studying and grab a bite to eat. On our way back to the dorms, riding our mopeds, the unthinkable happens and I get hit… by a cement truck. I wake up five days later in the hospital with massive head injuries and indescribable pain. The doctor tells me that my sense of taste and smell is gone, permanently. For years, I don’t talk about the accident. I think, who wants to hear a story like that? It feels too...
info_outline
How Embracing Imperfection Can Transform Your Storytelling
Storytelling School
It's the early 2000s, and I get invited to speak in New York to a room full of tech heavyweights - people and thought leaders I dreamed of being in front of. I am determined to crush it, so I do what any overachiever would: I obsess. I write, rewrite, and practice endlessly. No improvising. No mistakes. I even buy a stiff, serious outfit that doesn’t feel like me but seems like something a “real” speaker would wear. On the day of the event I deliver my Talk flawlessly, every word in place. The audience claps, though I leave feeling like something is off. It was perfect, yes, but...
info_outline
How to Make Numbers Unforgettable Through Story
Storytelling School
It’s 2006. I am sitting in the audience at TED surrounded by visionaries, innovators, and thought leaders. The energy in the room is electric and everyone is buzzing with anticipation about who’s going to take the stage next and what new insight we’ll walk away with. When the next speaker, a Swedish professor specializing in global health and data, is introduced, I brace myself for a dry, academic talk full of statistics and charts. Instead, the speaker starts moving across the stage with visible, infectious enthusiasm, pointing at animated visuals and telling a story through data....
info_outline
Why Many Stories Fall Flat in the Final 10 Seconds
Storytelling School
I am coaching a speaker as she prepares for one of the biggest keynotes of her career. Her story is powerful, full of resilience and triumph. As she runs through her story, I am captivated... until it just... stops. She smiles, says thank you, and that’s it. There is no call to action and no invitation. I deliver the news, gently: her ending isn’t serving her or the audience. She pushes back because she doesn’t want to sound salesy. And while I do definitely understand her concerns, I explain that, while her story hits hard, her ending needs to hit home. So we roll up the sleeves...
info_outlineIt’s the end of 2002 and I am fully immersed in the world of technology, running a bicoastal tech event. Over lunch with a new connection, we start unraveling a really wild idea - what if we were to build a software application using technology that has never been combined before? Just for fun, we scribble our ideas onto a napkin.
A few days later, something truly incredible happens. We get invited to build this software for the TED Conference. I think to myself, This is way out of my league. We have no team. No roadmap. Just a napkin. And only eight weeks to somehow make this happen.
However, the chance to create something that the world has never seen before is way too thrilling to ignore, so within a weekend, we pull together a team from all over the U.S. and Canada. Eight weeks go by, and we barely sleep. There are moments where I wonder, Is this a huge mistake? Day after day, though, fueled by adrenaline and sheer audacity, we keep pushing forward.
When TED arrives, we hold our breath as we unveil our creation. Guess what? Not only does it work, but people engage with the software in ways we never even imagined. In that moment – watching as people interact and seeing our vision come to life – it truly hits me that we did it. And that moment changes everything.
As it turns out, a little innovation and audacity can rewrite the rules in a life-altering way. Someone who knows all about that is today's guest, Gina Osborn. After nearly three decades in law enforcement chasing Cold War spies, foiling terrorist plots, and tracking down cybercriminals, this is just another day on the job for her. In this episode of the Storytelling School Podcast, you’ll learn about the best way to build rapport, whether the glass ceiling is just a state of mind, and the consequences of choosing a hill to die on. You’ll also get answers to questions like:
How do real-life experiences shape the way we tell and also interpret stories? How can unexpected challenges or turning points redefine the course of a story - or of a life? And how do you get wary people to trust you?
What you will learn in this episode:
- How being innovative and audacious can lead to unexpected success
- How role models can help shape our beliefs about what’s possible
- How careers can be redefined by both adversity and opportunities
- The importance of collaboration and persistence when taking on a challenge
- Why preparation and resilience are important in any career - especially a dangerous one
Who is Gina?
Gina Osborn spent 28 years in law enforcement where she took on espionage, terrorism, and cybercrime. Initially beginning her career in 1986 as a Counterintelligence Special Agent in the U.S. Army handling high-profile Cold War espionage cases in Europe, she transitioned in 1996 by joining the FBI, where she investigated Asian Organized Crime, supervised counterterrorism operations in Southeast Asia, and led major cybercrime cases.
After her retirement in 2018, Gina became a sought-after keynote speaker, using her real-life experiences to educate and inspire audiences. She is also the host of the upcoming podcast Making Maverick Moves which will feature trailblazers who challenge norms and redefine success!
Links and Resources