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by Rob D. Willis
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- 1 weeks ago34 min
Why Every Leader Needs Story Discovery Not Just Storytelling with Esther Choy
Esther Choy, CEO and Chief Story Facilitator at Leadership Story Lab, joins the show to challenge the idea that the leader must always be the "sage on stage" and explains why real power lies in helping others uncover and share their own stories.In this episode, we dive into the art of story discovery and why the best leaders are both sage on the stage and guide on the side. Rob D. Willis and Esther Choy unpack how shifting from persuasion to genuine curiosity transforms the way leaders connect, influence, and unlock the hidden stories within their teams.Esther Choy reveals her process for surfacing untold stories, from asking crazy good questions to synthesising meaning without fixating on being “right.” She shares real-world examples, including a CEO who dissolved silos simply by introducing innocuous questions at meetings and a senior leader who learned the power of narrative over technical detail.You'll walk away with practical approaches for uncovering overlooked stories, rituals to foster team trust, and a mindset that champions wonder over certainty. Plus, learn to enter any conversation with a pocketful of questions and a readiness to see things differently.GUEST BIO & LINKSEsther Choy is CEO and Chief Story Facilitator at Leadership Story Lab, a top contributor to Forbes Leadership Strategy Channel, and the author of two leadership books published by HarperCollins, including the newly released Winning Without Persuading. With over 15 years coaching thousands of executives worldwide, Esther equips leaders to move beyond persuasion and unlock the stories that foster team trust and connection. She teaches at Northwestern’s Kellogg School of Management and the University of Zurich, drawing on decades of experience helping clients discover, synthesise, and tell the stories that make strategies stick.Connect with Esther Choy:Website: https://www.leadershipstorylab.com/LinkedIn: https://www.linkedin.com/in/estherchoy/Instagram: https://www.instagram.com/leadershipstorylab/Podcast: https://www.leadershipstorylab.com/podcast/ABOUT THE SHOWChief Story Officer is a podcast about how stories drive strategy, not just communication. Host Rob D. Willis talks with executives and thought leaders about the moments where the right message changed everything.Real stories. Real impact. Every two weeks.CONNECT WITH ROBWant frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"→ subscribepage.io/robdwillisConnect with Rob:Website: robdwillis.com LinkedIn: linkedin.com/in/robdwillis Instagram: @robdwillis TikTok: @robdwillisSubscribe to Chief Story Officer wherever you listen to podcasts.
- 3 weeks ago36 min
Rethinking Storytelling: Folklore, Collaboration, and Decolonising the Business Narrative with Annette Simmons
Annette Simmons, author of The Story Factor and Whoever Tells the Best Story Wins, joins the show to challenge the idea that business storytelling is just about heroes and conflict. She reveals why real influence comes from sharing subjective, emotionally resonant stories, and how rituals of story-sharing can repair trust, build collaboration, and shape organisational culture.In this episode, we dive into the true role of storytelling in organisations, exploring why stories are more than just narratives with conflict and how they're evolution’s way of ensuring collaboration, trust, and survival at work. With business storytelling often reduced to formulas and templates, we challenge what’s been lost, and how leaders can reclaim storytelling’s real strategic power.Annette Simmons reveals her journey from advertising to storytelling, unpacks the difference between objective and story thinking, and introduces the vital but overlooked concept of repair after betrayal stories. She shares practical rituals to surface tacit knowledge, the six stories that every leader needs, and why rituals, not rules are the key to keeping ethics and values alive in business.You’ll leave with tangible prompts to spark more vulnerability and collaboration, a new appreciation for restoring trust after setbacks, and concrete steps to make stories a lived ritual in your team, not just a communication tool.GUEST BIO & LINKSAnnette Simmons is a renowned author, keynote speaker, and storytelling expert whose books The Story Factor and Whoever Tells the Best Story Wins have influenced leaders worldwide. Over three decades, Annette has helped organisations like Microsoft, NASA, and the Brookings Institute use storytelling to resolve conflict, foster trust, and shift mindsets not merely through data, but through powerful shared experience. Drawing on early influences in psychology and marketing, Annette’s approach challenges the dominance of “objective” thinking in business. She advocates for bringing back the lost art of tacit, folk-inspired storytelling and establishing rituals that make subjective wisdom and values central to team culture. Her latest work, Drinking from a Different Well, explores how women’s stories redefine power in collaborative settings.Connect with Annette Simmons:Website: https://annettesimmons.com/LinkedIn: https://www.linkedin.com/in/annettesimmonsstory/Article: Evolution’s Lessons We've Left BehindEmail: annette@annettesimmons.comABOUT THE SHOWChief Story Officer is a podcast about how stories drive strategy, not just communication. Host Rob D. Willis talks with executives and thought leaders about the moments where the right message changed everything.Real stories. Real impact. Every two weeks.CONNECT WITH ROBWant frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"→ subscribepage.io/robdwillisConnect with Rob:Website: robdwillis.com LinkedIn: linkedin.com/in/robdwillis Instagram: @robdwillis TikTok: @robdwillisSubscribe to Chief Story Officer wherever you listen to podcasts.
- Apr 10, 202636 min
The Magic of Metaphors: Simon Lancaster’s Guide to Transforming Boring Corporate Speeches
Simon Lancaster, leading speechwriter and author of Connect! How to Inspire, Influence and Energise Anyone, Anywhere, Anytime, joins the show to break down why most corporate communication fails and what leaders can do to finally make their words stick.In this episode, we dive into why most corporate communication misses the mark, what truly captures audiences’ attention, and how leaders can transform tired presentations into memorable moments that stick. Simon Lancaster and Rob D. Willis dissect the neuroscience behind effective messaging and the pitfalls of “tin-eared” delivery in boardrooms and beyond.Simon Lancaster reveals his practical approach honed over decades writing for Tony Blair’s cabinet, CEOs, and global brands. He shares his signature “three keys” metaphor, moral appeal, and story plus his favourite questions for unlocking a leader’s deepest values and most powerful narratives.You’ll learn how to spot a dead presentation, the one-word speech technique for instant engagement, and why care, empathy, and musicality matter more than flashy slides. Expect tactics you can use straight away to bring your next speech, meeting, or message to life.KEY TOPICSWhy most corporate presentations fail to connect—and how to pass the coffee break test [00:02:34]The neuroscience-backed trio for unforgettable communication: metaphors, moral appeals, and stories [00:08:18]Extracting stories from leaders with one question and a list of 50 moral values [00:12:04]The EVA formula (Empathy, Values, Action): a speechwriter’s fix for political Q&A and crowd control [00:25:19]The “Golden Six” rhetorical devices that instantly make any speech sound powerful, breathless sentences, repetition, contrast, metaphor, exaggeration, and rhyme [00:29:12]GUEST BIO & LINKSSimon Lancaster is one of the world’s top speechwriters, trusted by CEOs at global giants including HSBC, Unilever, and InterContinental Hotels, and political heavyweights such as Alan Johnson from Tony Blair’s cabinet. Beginning his career in government communications. Simon now specialises in helping business leaders transform strategy into story, drawing from the latest neuroscience to craft messages that truly connect. He is the author of several acclaimed books on influence and communication including Connect! and is widely known for making rhetorical devices accessible through TikTok videos. Simon regularly consults for senior executives, leads masterclasses, and demystifies the art of storytelling for modern leaders.Connect with Simon Lancaster:Website: https://bespokeleadershipdevelopment.com/Website: https://bespokespeeches.com/LinkedIn: https://www.linkedin.com/in/simon-lancaster-speechwriter/YouTube: https://www.youtube.com/user/bespokespeechesABOUT THE SHOWChief Story Officer is a podcast about how stories drive strategy, not just communication. Host Rob D. Willis talks with executives and thought leaders about the moments where the right message changed everything.Real stories. Real impact. Every two weeks.CONNECT WITH ROBWant frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"→ subscribepage.io/robdwillisConnect with Rob:Website: robdwillis.co
- Mar 27, 202636 min
Turning Small Stories into Big Strategy: Insights from Shawn Callahan
Shawn Callahan, founder of Anecdote International and author of the award-winning book Putting Stories to Work, joins the show to reveal how story listening, not just storytelling can transform corporate culture and strategy, and why the best stories in business aren’t heroic sagas but small, authentic moments that drive change.In this episode, we dig into how storytelling drives strategy and culture, with practical examples from the boardroom to the frontline. You'll hear why most corporate stories skip the hero’s journey, and how the right conversation can coax stories from even the most reluctant leaders.Shawn Callahan shares behind-the-scenes insights from decades of helping Fortune 500 companies, including the real reason slide decks and town halls fail, the “Costanza manoeuvre” for sharper strategic choices, and how story listening cannily triggers change from the inside out.You’ll walk away with actionable ways to spot, craft, and scale stories in your organisation, plus a simple framework for making strategy stick. Discover why authentic, everyday anecdotes beat polished presentations and how to transform your own strategy into something your team not only hears, but owns.KEY TOPICSWhy story listening, not storytelling, is the foundation for culture change in business [00:01:56]The genius of group “anecdote circles” for unlocking reluctant stories in teams [00:04:33]How co-creating the strategy story forces leaders to clarify real choices and avoid business-as-usual clichés [00:09:18]Scaling strategy through progress stories and “overwhelming the system” with examples at every level [00:17:12]The pitfalls of story banks and why oral, not written, stories drive authenticity and connection [00:23:01]GUEST BIO & LINKSShawn Callahan is the founder of Anecdote International, author of Putting Stories to Work, and one of the world’s leading experts in story-based communication for business. With over 20 years helping Fortune 500 companies across 22 countries and 11 languages make their strategies stick, Shawn is known for his practical approach, starting with story listening and small, real-world anecdotes. From his days at IBM’s Centre for Organisational Complexity to building Anecdote into a global consultancy, Shawn has worked with executives to co-create strategic narratives, drive culture change, and scale storytelling across entire organisations. His work empowers leaders to move beyond slides and scripts, fostering genuine buy-in with stories people actually remember.Connect with Shawn Callahan:Website: https://anecdote.thinkific.com/LinkedIn: https://www.linkedin.com/in/shawncallahan/Instagram: https://www.instagram.com/shawndcallahan/?hl=enABOUT THE SHOWChief Story Officer is a podcast about how stories drive strategy, not just communication. Host Rob D. Willis talks with executives and thought leaders about the moments where the right message changed everything.Real stories. Real impact. Every two weeks.CONNECT WITH ROBWant frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"→ subscribepage.io/robdwillisConnect with Rob:Website: robdwillis.com LinkedIn: linkedin.com/in/robdwillis Instagram: @robdwillis TikTok: @robdwillis</p
- Mar 13, 202631 min
The Red Thread of Relevance: Strategic Storytelling Lessons from Kendra Valentine
Kendra Valentine, story strategist and author of How to Pitch (Almost) Anything, joins the show to unpack how leading with your value rather than your credentials transforms the way you communicate, pitch, and build confidence in any room.In this episode, we dig into the real difference between good storytelling and truly strategic storytelling and why most professionals trip up when pitching themselves, their work, or their ideas. Kendra Valentine uncovers the invisible traps of over explaining, jargon, and focusing on deliverables instead of the outcomes audiences really crave.Kendra Valentine shares her journey from being called a “mercenary” in the boardroom to developing her Strategic Story Design framework. She breaks down the “Pocket Pitch,” explains why confidence is often a structural, not psychological problem, and reveals how leading with “how you help” cuts through complexity, whether you're in a sauna or a boardroom.You’ll walk away with a simple framework for clarifying your value, a quick exercise to make your message instantly more compelling, and the one communication shift that unlocks better buy-in no matter who’s listening.KEY TOPICSHow to explain what you do (even to your mum) with story strategy [00:01:15]The difference between strategic storytelling and just telling stories [00:02:09]Why most people focus on features, not outcomes and why that’s a problem [00:03:34]Imposter syndrome versus structural gaps in pitching [00:05:11]The “mercenary in Stockholm” story and learning to articulate your value [00:08:42]The Pocket Pitch: a modern, simple framework for introducing yourself [00:13:49]Why leading with transformation gets more buy-in than describing tasks [00:15:48]Having multiple “pocket pitches” and why you might need more than one [00:17:38]The one exercise you can do tomorrow: lead with how you help [00:28:24]GUEST BIO & LINKSKendra Valentine is an internationally renowned story strategist, author, and creator of the Strategic Story Design approach. With nearly 20 years’ experience spanning film production at Warner Brothers and Universal to branding and business communications for clients like Boston Consulting Group, Nickelodeon, and Techstars, Kendra helps businesses and creatives articulate the value they provide clearly and confidently. She’s passionate about making strategic storytelling accessible, whether you’re pitching on stage, at a bar, or in a boardroom. Her framework, Pocket Pitch, turns even the most complex roles into powerful, service-led stories. Kendra is the author of How to Pitch (Almost) Anything, now available worldwide.Connect with Kendra Valentine:Website: https://www.kendravalentine.com/LinkedIn:https://www.linkedin.com/in/kendra-valentine/Instagram: https://www.instagram.com/misskendrav/ABOUT THE SHOWChief Story Officer is a podcast about how stories drive strategy, not just communication. Host Rob D. Willis talks with executives and thought leaders about the moments where the right message changed everything.Real stories. Real impact. Every two weeks.CONNECT WITH ROBWant frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"→ subscribepage.io/robdwillisConnect with Rob:Website: robdwillis.com Linked
- Feb 27, 202629 min
Clear Communication Drives Change: Matt Armstrong-Barnes on Leadership, Stories, and AI
Matt Armstrong-Barnes, Group AI Practice Director at Servita and keynote speaker, joins the show to uncover why the real challenge of AI transformation isn’t just the technology, it’s the story leaders tell about it.In this episode, we dive into the art of translating complex technical ideas into clear, actionable strategies, exploring how jargon can alienate teams and how the right story brings everyone onto the same page. Matt Armstrong-Barnes, Group AI Practice Director at Servita, reveals the moments that changed his approach to communication and why leaders must own their message to drive transformation.Matt shares practical lessons from his 25-year career, from deciphering AI hype to empowering teams to ask “obvious” questions. He unpacks the real reasons people hesitate to speak up, the value of writing things down, and his signature “coffee machine test” for strategy clarity.You’ll walk away with a toolkit for breaking through jargon, building genuine team alignment, and turning abstract strategy into bite-sized, memorable stories, even if you think you’re “not a storyteller.”KEY TOPICSThe meeting where only two out of thirty technologists understood the technical problem and what happened next [01:07]Imposter syndrome and why tech leaders are afraid to ask “obvious” questions in meetings [04:04]How leadership behaviour around jargon shapes organisational culture and communication habits [05:07]The hidden ambiguity of terms like “artificial intelligence” across academics, technologists, and business leaders [06:15]The exercise of having multiple leaders articulate strategy and why it always reveals misalignment [07:37]Using stories, metaphors, and writing to structure and clarify your message as a leader [08:43]Why ownership of your message and regularly testing team understanding makes strategies stick [11:08]The real stories companies tell themselves about AI and how these myths either paralyse or mislead [17:14]The “coffee machine test”: how to check if your team can explain your vision in 30 seconds or less [27:12]GUEST BIO & LINKSMatt Armstrong-Barnes is the Group AI Practice Director at Servita, a published thought leader, keynote speaker, and technical reviewer for the British Computer Society's International Conference on AI. With over 25 years’ experience guiding organisations through complex technology transformations, Matt specialises in making the intricacies of AI accessible and actionable for business leaders. His approach combines deep technical expertise with a passion for clear, jargon-free communication empowering teams to ask better questions, demystify strategy, and unlock AI's real value. Matt is a regular contributor on LinkedIn and a champion for mentorship, helping the next generation navigate the evolving landscape of technology with confidence and clarity.Connect with Matt Armstrong-Barnes:Website: https://www.hpe.com/us/en/home.htmlLinkedIn: https://www.linkedin.com/in/mattarmstrongbarnes/ABOUT THE SHOWChief Story Officer is a podcast about how stories drive strategy, not just communication. Host Rob D. Willis talks with executives and thought leaders about the moments where the right message changed everything.Real stories. Real impact. Every two weeks.CONNECT WITH ROBWant frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"→ subscribepage.io/robdwillisConnect with Rob:Website: <a href="http://robdwillis
- Jan 9, 202629 min
Why Executives Lose Deals: The Left Brain Trap
Jeremy Connell-Waite, Global Communications Designer at IBM and author of "The 109 Rules of Storytelling," joins the show to reveal why smart executives fail at persuasion.In this conversation, we explore the data behind failed pitches. Jeremy shares how he coached an executive who was losing 4 out of 5 deals to competitors—despite being eloquent, experienced, and well-paid. By mapping every word they used, Jeremy discovered they were trapped in left-brain communication: logic, ROI, and technical specs. Missing entirely? The emotional connection that drives decisions.You'll walk away with Jeremy's 6-part framework that balances left-brain content (inform, educate, solve) with right-brain storytelling (inspire, excite, challenge), the Jane Goodall principle of "one sermon, 52 ways to preach it," and how to structure 90-minute business presentations like blockbuster movies using Blake Snyder's Save the Cat method.GUEST BIO & LINKSJeremy Connell-Waite is a Global Communications Designer at IBM, speechwriter for executives, and author of "The 109 Rules of Storytelling." He's trained with Al Gore as a Climate Reality Leader and created IBM's Communications Thinking™ system—using AI and neuroscience to help leaders tell better stories.Connect with Jeremy:LinkedIn: www.linkedin.com/in/jeremypaulwaiteWebsite: betterstories.org (400+ free storytelling resources)Book: "The 109 Rules of Storytelling"Podcast: "The Truth in Ten"Blog: jeremy.earthBOOKS MENTIONED:"Emotional Intelligence" by Daniel Goleman"Neuroscience for Leadership" by Tara Swart"Emotional Ignorance" by Dr. Dean BurnettHarvard Business Review Emotional Intelligence Box Set"Save the Cat" by Blake Snyde"The Creative Act" by Rick RubinABOUT THE SHOWChief Story Officer is a podcast about how stories drive strategy, not just communication. Host Rob D. Willis talks with executives and thought leaders about the moments where the right message changed everything.Real stories. Real impact. Every two weeks.CONNECT WITH ROBWant frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"→ subscribepage.io/robdwillisConnect with Rob:Website: robdwillis.comLinkedIn: linkedin.com/in/robdwillisInstagram: @robdwillisTikTok: @robdwillisSubscribe to Chief Story Officer wherever you listen to podcasts.
- Dec 26, 202533 min
Why Personal Stories Sell Better Than Features
Lauren V. Davis, personal branding consultant and host of The Real Personal Branding Podcast, joins the show to reveal why the executives who say "I don't have any stories" are usually the ones holding everyone else's.In this conversation, we explore why connection beats credentials in building trust, how a financial advisor turned his mother's death into his most powerful client story, and why a real estate coach's "naked in the closet moment" converted more leads than any feature list ever could.Lauren shares her three-part framework for extracting stories from reluctant leaders (moment → shift → meaning), the dinner party test for finding your best material, and why you should Google yourself right now with the keyword you want to own.You'll walk away with a simple journaling practice that captures stories before they disappear, the empathy exercise that reveals gaps in your narrative, and one question that helps people overcome both imposter syndrome and storytelling paralysis: "What do people thank you for most often?"KEY TOPICSWhy "I don't have any stories" usually means you're the keeper of everyone else's stories [00:07]The financial advisor who turned family tragedy into his opening pitch [11:00]How a "naked in the closet moment" became a real estate coach's signature story [18:00]The three-part framework: Moment → Shift → Meaning [15:00]The dinner party test: which stories make everyone stop scrolling? [24:00]Why starting with a story beats starting with your resume [15:25]The Justin Timberlake letter: how embarrassment creates connection [22:00]From journal to Instagram to podcast: repurposing one story across platforms [27:00]The Google test: does your online presence match who you want to be? [31:00]GUEST BIO & LINKSLauren V. Davis is a personal branding consultant, speaker, podcast host, and former record store owner. She helps business owners, speakers, and entrepreneurs establish visibility through masterminds, retreats, and 1:1 consulting. Her work has been featured in Reader's Digest and Huffington Post, and she hosts The Real Personal Branding Podcast (top 2% worldwide).Connect with Lauren:Website: laurendaviscreative.comLinkedIn: linkedin.com/in/ldaviscreativeInstagram: @ldaviscreativePodcast: The Real Personal Branding PodcastABOUT THE SHOWChief Story Officer is a podcast about how stories drive strategy, not just communication. Host Rob D. Willis talks with executives and thought leaders about the moments where the right message changed everything.Real stories. Real impact. Every two weeks.CONNECT WITH ROBWant frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"→ subscribepage.io/robdwillisConnect with Rob:Website: robdwillis.comLinkedIn: linkedin.com/in/robdwillisInstagram: @robdwillisTikTok: @robdwillisSubscribe to Chief Story Officer wherever you listen to podcasts.
About Chief Story Officer
Most leaders know storytelling matters. But can stories actually be strategic?On Chief Story Officer we talk to executives and thought leaders who know that the right story at the right time can shift strategy, align teams and transform businesses.Hosted by Rob D. Willis, a strategic story producer who's helped leaders at HelloFresh, Babbel, and Raisin craft compelling stories that make strategies stick, so teams live it and clients feel it. What You'll Discover:🎯 Real world examples of stories shifting team direction, clarifying strategy or closing deals. 🧠 Strategic frameworks to think about storytelling as part of business strategy⚡ Practical takeaways you can use in your next meeting, pitch, or all-hands🎙️ Diverse perspectives from CEOs, strategists, and operators who've cracked the code on strategic storytellingThis isn't about crafting perfect presentations or learning narrative tricks. It's about understanding how stories shape decisions, drive alignment, and create meas
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