How Executives Lead with Storytelling
Making better decisions, aligning people, and maintaining credibility under pressure
I work with CEOs and senior leaders to turn strategy into shared understanding and coordinated action. Storytelling is the mechanism leadership uses to make intent, trade-offs, and risk travel through organisations, boards, and capital markets without distortion.
This work treats storytelling as leadership infrastructure, not communication or performance.
→ Storytelling for Executives
→ Work with Simon
As organisations grow, strategy degrades.
Not because leaders stop thinking clearly, but because context is lost, decisions are reinterpreted, and intent fractures as it moves through layers. Alignment weakens. Execution slows. Credibility erodes under pressure.
Storytelling is how leaders solve this problem, whether deliberately or by accident.
When used poorly, it creates confusion and spin.
When used well, it becomes infrastructure.
Storytelling is upstream of communication.
It shapes how leaders:
make decisions under uncertainty
explain trade-offs and risk
coordinate action across complexity
sustain belief over time
This is not the same thing as presentation skill or messaging - it is a disciplined leadership capability.
I am formalising this work as Storytelling for Executives, grounded in leadership practice, organisational sensemaking, and real operating experience.
→ The Discipline: Storytelling for Executives
Bio.
Co-founder of WumDrop, acquired by Walmart
Led scale and post-acquisition integration
Advisor to executives navigating growth, capital, and change
Media: Forbes, CNBC, Quartz, Bloomberg
Co-founder of Thorndale, where this work is stress-tested in the field
Ways to work with me
Executive Narrative Advisory
Retained advisory for CEOs and Chairs working through complexity, scale, or transition.
This is hands-on work shaping the narratives that affect:
board and investor confidence
leadership alignment
execution under uncertainty
Capped at a small number of clients.
→ Executive Narrative Advisory (Retainer)
Keynotes & Executive Workshops
High-substance interventions for senior audiences.
Keynotes reframe how leaders think about storytelling, decision-making, and credibility. Workshops move from reframing into applied alignment.
→ Executive Keynotes & Workshops
Thorndale Executive Storytelling Retreats
Multi-day retreats in complex natural environments where this work is integrated, embodied, and pressure-tested.
Thorndale is the field lab for this discipline.
→ Thorndale Storytelling Retreats
If you’re leading through complexity and your strategy isn’t travelling the way it should, we should talk.
“Simon is a true leader in entrepreneurship, new business development, business strategy, and organizational development.”
Paris Philippou - Vice President in eCommerce, Walmart Africa