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 TOPICS

1. Why story listening, not storytelling, is the foundation for culture change in business [00:01:56]
2. The genius of group “anecdote circles” for unlocking reluctant stories in teams [00:04:33]
3. How co-creating the strategy story forces leaders to clarify real choices and avoid business-as-usual clichés [00:09:18]
4. Scaling strategy through progress stories and “overwhelming the system” with examples at every level [00:17:12]
5. The pitfalls of story banks and why oral, not written, stories drive authenticity and connection [00:23:01]

GUEST BIO & LINKS

Shawn 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=en

ABOUT THE SHOW

Chief 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 ROB

Want frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"

→ subscribepage.io/robdwillis

Connect with Rob:

Website: robdwillis.com LinkedIn: linkedin.com/in/robdwillis Instagram: @robdwillis TikTok: @robdwillis

Subscribe to Chief Story Officer wherever you listen to podcasts.

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 TOPICS

1. How to explain what you do (even to your mum) with story strategy [00:01:15]
2. The difference between strategic storytelling and just telling stories [00:02:09]
3. Why most people focus on features, not outcomes and why that’s a problem [00:03:34]
4. Imposter syndrome versus structural gaps in pitching [00:05:11]
5. The “mercenary in Stockholm” story and learning to articulate your value [00:08:42]
6. The Pocket Pitch: a modern, simple framework for introducing yourself [00:13:49]
7. Why leading with transformation gets more buy-in than describing tasks [00:15:48]
8. Having multiple “pocket pitches” and why you might need more than one [00:17:38]
9. The one exercise you can do tomorrow: lead with how you help [00:28:24]

GUEST BIO & LINKS

Kendra 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 SHOW

Chief 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 ROB

Want frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"

→ subscribepage.io/robdwillis

Connect with Rob:

Website: robdwillis.com LinkedIn: linkedin.com/in/robdwillis Instagram: @robdwillis TikTok: @robdwillis

Subscribe to Chief Story Officer wherever you listen to podcasts.

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 TOPICS

1. The meeting where only two out of thirty technologists understood the technical problem and what happened next [01:07]
2. Imposter syndrome and why tech leaders are afraid to ask “obvious” questions in meetings [04:04]
3. How leadership behaviour around jargon shapes organisational culture and communication habits [05:07]
4. The hidden ambiguity of terms like “artificial intelligence” across academics, technologists, and business leaders [06:15]
5. The exercise of having multiple leaders articulate strategy and why it always reveals misalignment [07:37]
6. Using stories, metaphors, and writing to structure and clarify your message as a leader [08:43]
7. Why ownership of your message and regularly testing team understanding makes strategies stick [11:08]
8. The real stories companies tell themselves about AI and how these myths either paralyse or mislead [17:14]
9. The “coffee machine test”: how to check if your team can explain your vision in 30 seconds or less [27:12]

GUEST BIO & LINKS

Matt 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.html

LinkedIn: https://www.linkedin.com/in/mattarmstrongbarnes/

ABOUT THE SHOW

Chief 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 ROB

Want frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"

→ subscribepage.io/robdwillis

Connect with Rob:

Website: robdwillis.com LinkedIn: linkedin.com/in/robdwillis Instagram: @robdwillis TikTok: @robdwillis

Subscribe to Chief Story Officer wherever you listen to podcasts.

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 & LINKS

Jeremy 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:

1. LinkedIn: www.linkedin.com/in/jeremypaulwaite
2. Website: betterstories.org (400+ free storytelling resources)
3. Book: "The 109 Rules of Storytelling"
4. Podcast: "The Truth in Ten"
5. Blog: jeremy.earth

BOOKS MENTIONED:

1. "Emotional Intelligence" by Daniel Goleman
2. "Neuroscience for Leadership" by Tara Swart
3. "Emotional Ignorance" by Dr. Dean Burnett
4. Harvard Business Review Emotional Intelligence Box Set
5. "Save the Cat" by Blake Snyde
6. "The Creative Act" by Rick Rubin

ABOUT THE SHOW

Chief 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 ROB

Want frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"

→ subscribepage.io/robdwillis

Connect with Rob:

1. Website: robdwillis.com
2. LinkedIn: linkedin.com/in/robdwillis
3. Instagram: @robdwillis
4. TikTok: @robdwillis

Subscribe to Chief Story Officer wherever you listen to podcasts.

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 TOPICS

1. Why "I don't have any stories" usually means you're the keeper of everyone else's stories [00:07]
2. The financial advisor who turned family tragedy into his opening pitch [11:00]
3. How a "naked in the closet moment" became a real estate coach's signature story [18:00]
4. The three-part framework: Moment → Shift → Meaning [15:00]
5. The dinner party test: which stories make everyone stop scrolling? [24:00]
6. Why starting with a story beats starting with your resume [15:25]
7. The Justin Timberlake letter: how embarrassment creates connection [22:00]
8. From journal to Instagram to podcast: repurposing one story across platforms [27:00]
9. The Google test: does your online presence match who you want to be? [31:00]

GUEST BIO & LINKS

Lauren 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:

1. Website: laurendaviscreative.com
2. LinkedIn: linkedin.com/in/ldaviscreative
3. Instagram: @ldaviscreative
4. Podcast: The Real Personal Branding Podcast

ABOUT THE SHOW

Chief 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 ROB

Want frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"

→ subscribepage.io/robdwillis

Connect with Rob:

1. Website: robdwillis.com
2. LinkedIn: linkedin.com/in/robdwillis
3. Instagram: @robdwillis
4. TikTok: @robdwillis

Subscribe to Chief Story Officer wherever you listen to podcasts.

Charlie Curson, strategist and leadership coach with 25+ years advising companies like VISA, McDonald's, and Unilever, joins the show to break down what "being strategic" actually means.

In this conversation, we explore why executives can't define the very thing they demand from their teams. Charlie shares the story of a 20-year operational veteran told he needed to "be more strategic"—but when Charlie asked the boss what that meant, he couldn't explain it either. This gap inspired Charlie's book and his approach to making strategy accessible beyond boardrooms and MBA programs.

You'll walk away with Charlie's "12 people exercise" using post-it notes to surface strategic misalignment, a stakeholder mapping framework that reveals who you're wasting time on, and the discipline high-performing teams use to over-communicate (hint: Olympic teams, rugby squads, and military units do this naturally—corporate teams don't).

GUEST BIO & LINKS

Charlie Curson is a strategist, leadership coach, author, investor, facilitator, and OKR expert. He's the founder of Mandarin Associates, with 25+ years helping 250+ organizations across 30+ industries, from global giants like VISA and McDonald's to ambitious start-ups.

Connect with Charlie:

• LinkedIn: www.linkedin.com/in/charliecurson
• Website: www.teammandarin.com
• Book: "Be More Strategic: 12 Essential Practices to Build the Life and Career You Want" (Available November 6th) - Join the waitlist: https://www.teammandarin.com/be-more-strategic-book
• Future Agenda: www.futureagenda.org

ABOUT THE SHOW

Chief 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 ROB

Want frameworks for strategic storytelling? Download the free guide: "5 Ways to Make People Care About Your Strategy"

→ subscribepage.io/robdwillis

Connect with Rob:

• Website: robdwillis.com
• LinkedIn: linkedin.com/in/robdwillis
• Instagram: @robdwillis
• TikTok: @robdwillis

Subscribe to Chief Story Officer wherever you listen to podcasts.

Rain Bennett, award-winning filmmaker and fractional Chief Storytelling Officer, joins the show to discuss why storytelling isn't just marketing—it's strategy.

In this conversation, we explore what a Chief Storytelling Officer actually does, how Nike used story listening to beat Adidas in the 1970s, and why misalignment kills trust faster than bad products. Rain shares his framework for building a brand narrative that guides every decision from product development to sales pitches.

You'll walk away with a vision story exercise (resilient, inclusive, service-oriented), an understanding of how storytelling creates virality through community, and one framework for making sure every department tells the same story.

KEY TOPICS

• What is a Chief Storytelling Officer and why companies need one [01:00]
• How Nike's Nelson Ferris built shoes by listening to high school track athletes [14:00]
• The ROI of storytelling: long-term growth vs. short-term metrics [08:00]
• Why misalignment between departments destroys trust [11:30]
• The three tests every vision story must pass [30:00]

GUEST BIO & LINKS

Rain Bennett is an award-winning filmmaker, author of "Chief Storytelling Officer," and host of the Storytelling Lab podcast. He's conducted over 1,000 interviews in 20 years and now embeds himself in companies as a fractional Chief Storytelling Officer.

Connect with Rain:

• Website: rainbennett.com
• Book: "Chief Storytelling Officer" [coming soon]
• Podcast: The Storytelling Lab

ABOUT THE SHOW

Chief 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 ROB

• Website: robdwillis.com
• LinkedIn: https://www.linkedin.com/in/robdwillis/
• Instagram: @robdwillis

Subscribe to Chief Story Officer on Apple Podcasts, Spotify, or wherever you listen to podcasts

Welcome to Chief Story Officer.

In this quick trailer, host Rob D. Willis introduces the show: conversations with executives and thought leaders about how storytelling shifts strategy, wins buy-in, and drives results.

Every episode delivers tactical frameworks, real examples, and specific moves you can apply immediately in your leadership communication.

New episodes drop every two weeks. Subscribe now and never miss a conversation that could change how you communicate strategy.