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CLICK HERE TO DOWNLOAD SIMON WALLER 2026 SERVICES GUIDE
Contact Simon
CLICK HERE TO DOWNLOAD SIMON WALLER 2026 SERVICES GUIDE
contact Simon

Leading in Uncertainty

Supporting leaders to move forward in unpredictable times

Combining compelling storytelling with practical inquiry Leading in Uncertainty draws on Simon’s experience of the 2004 Sydney to Hobart Yacht Race. In a race where only half the fleet made it to the finish line, the story provides deep insights into leadership and teamwork in the face of literal headwinds and a perfect storm of uncertainty.

Leading in Uncertainty is an immersive, interactive workshop that blends Simon’s storytelling with practical leadership insights. Drawing on his experience in the 2004 Sydney to Hobart Yacht Race, Simon recounts how, under extreme conditions, true leadership and sound judgement shifted the crew’s focus from the dream of winning to the need for survival.
Through engaging stories, real-world scenarios, and interactive reflection, participants explore what leadership really means when the environment is uncertain and outcomes are unknown. This is not a story of heroic survival, it’s a blueprint for how ordinary teams can achieve the extraordinary under pressure.

Participants will walk away with practical insights to:

  • Navigate uncertainty by finding clarity and making informed judgements
  • Prioritise long-term resilience over short-term wins
  • Make reliable decisions when outcomes are unknowable
  • Earn trust and influence through clarity, confidence, and care
ENQUIRE NOW

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Who Is This For?

Ideal for extended leadership teams, especially in organisations launching a new strategy, undertaking a major transformation or facing high levels of uncertainty. This highly interactive workshop equips leaders to navigate complexity with purpose and confidence.

Ideal Timing:
Why Start Now?

Well suited to periods of strategic transition, including strategy launches, major change initiatives or moments where direction needs to be reset. It works particularly well as an opening session for leadership off-sites or strategy days, setting the tone for deeper discussion and alignment.

ENQUIRE NOW
Not just yet but I’d like to download the brochure.
From the moment we mind mashed I felt the energy and ideas coming to life. Your mentorship and experience allowed the event to land for the audience and your keynote and facilitation were both awesome. Gold plated work!
Courtney Smith
Event Owner, Forge Summit

Clients Include

casey

Other Workshops

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All your possible futures

Navigating Uncertainty is a unique participant experience. Seamlessly blending powerful storytelling with actionable insights, this session will help foster a culture that embraces the unpredictable and helps your people find joy and fulfillment on their voyage together.
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How Better Decisions Get Made shows how leaders can make better decisions in complex, uncertain environments. It explores how sound judgement, clear process, and productive disagreement each contribute to effective decision-making. Participants gain practical approaches for counteracting bias, navigating disagreement, and making confident decisions when the way forward isn’t clear.
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Looking for a
keynote instead?

Simon delivers engaging, thought-provoking keynotes on future thinking, decision-making, AI, and the human-tech relationship. His 'practical futurism' approach helps organisations sharpen strategic thinking and navigate uncertainty with confidence.

READ MORE

Work With Simon

If you’re considering engaging Simon please reach out to book a to chat. You can do this by filling out the form below, contacting Sarah at 1300 66 55 85 (within Australia), or emailing her at sa***@*************om.au. If it’s for a speaking engagement please provide the event date and any information that might be helpful.

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Enquiry Form

If you’d like to find out more about Navigating Uncertainty Workshop for in house delivery, or want to know about upcoming public workshop dates, fill out the form below or call 1300 66 55 85  (within Australia).

The Scenario Planning Guide

How scenario planning can be used to align thinking, stimulate ideas and overcome the inertia of uncertainty.

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