Chief Story Officer

12 Episodes
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By: Rob D. Willis

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 takeaway...

How Great Leaders Inspire with Stories, Not Slides, Featuring Paul Smith
#11
Last Friday at 4:00 AM

Paul Smith, bestselling author and business storytelling consultant, joins the show to share how surprise turns stories into unforgettable leadership tools and why the best business lessons don’t always fit on a slide.

In this episode, we unpack why adrenaline-fuelled surprises make stories unforgettable, how dialogue trumps data in executive communications, and the simple shift from presenting slides to sharing moments that matter. We explore why even data-driven leaders can use storytelling to move teams, clarify strategy, and tackle scepticism head-on.

Paul Smith reveals how a CEO's refusal to look at slides sparked his st...


Why Every Leader Needs Story Discovery Not Just Storytelling with Esther Choy
#10
05/08/2026

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...


Rethinking Storytelling: Folklore, Collaboration, and Decolonising the Business Narrative with Annette Simmons
#9
04/24/2026

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 re...


The Magic of Metaphors: Simon Lancaster’s Guide to Transforming Boring Corporate Speeches
#8
04/10/2026

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 practi...


Turning Small Stories into Big Strategy: Insights from Shawn Callahan
#7
03/27/2026

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.


The Red Thread of Relevance: Strategic Storytelling Lessons from Kendra Valentine
#6
03/13/2026

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...


Clear Communication Drives Change: Matt Armstrong-Barnes on Leadership, Stories, and AI
#5
02/27/2026

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.


Why Executives Lose Deals: The Left Brain Trap
#4
01/09/2026

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, ed...


Why Personal Stories Sell Better Than Features
#3
12/26/2025

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 → mean...


What "Be More Strategic" Actually Means (And How to Do It)
#2
12/12/2025

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 pe...


The Chief Storytelling Officer: Why Every Company Needs a Story Guardian
#1
11/28/2025

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 fo...


Trailer: Welcome to Chief Story Officer
11/14/2025

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.