Chris Wilson is a leadership keynote speaker with over 14 years of experience navigating high-stakes, high-pressure environments. As a former Commercial Helicopter Pilot, Aircraft Maintenance Engineer, and creator of the Dare to Fly framework, Chris brings powerful real-world insights into how individuals and teams can lead through uncertainty, embrace change, and create forward momentum.
His motivational keynotes and leadership development sessions equip companies, associations, schools, conferences, and organizations with practical strategies to: reignite employee engagement, build leadership confidence, navigate change with clarity, strengthen team connection and communication, be resilient, and turn setbacks into opportunities for growth. Whether you’re planning a corporate event, leadership retreat, or professional development conference, Chris delivers inspiring, actionable content that moves audiences to think differently, act boldly, and lead with purpose.
Every time, he brings nothing short of powerful, practical, and inspiring insight. Chris has a way of taking big, sometimes intimidating topics like risk, fear, and growth and breaking them down in a way that truly connects with people at all levels. Whether you're an emerging leader or a seasoned exec, there's always a lesson to take from his talks.
-Jessica (Fiesta) George, Head of Talent, Atlantic Street Capital Advisors Inc.
Keynote Topics
A LEADERSHIP FRAMEWORK TO ENGAGE TOGETHER, PERSEVERE FORWARD, AND SEIZE NEW OPPORTUNITIES IN CHANGING ENVIRONMENTS
The world is changing at record speed. People feel more disconnected, disengaged, and uncertain about the future. Today’s leaders and teams are navigating constant turbulence — and need practical tools to be resilient and move forward with clarity and confidence.
In this high-impact motivational and inspirational keynote, 14-year aviator, entrepreneur, and leadership expert Chris Wilson introduces Dare to Fly — a 3-step leadership framework designed to help people reconnect, re-engage, and navigate what’s next.
With real-life lessons from aviation and business, Chris shares how to: make smart, confident decisions under pressure, stay focused on what matters most — even in chaos, take action and build momentum, one step at a time. Audiences leave this session equipped with practical tools and renewed motivation to lead through uncertainty and pursue meaningful progress. Dare to Fly isn’t about waiting for the storm to pass — it’s about learning how to rise above it.
Ideal for: Leadership development events, company-wide team meetings, association conferences, professional development days, managers, leaders, associations, non-profits, schools, higher education, colleges, universities, high-performing teams, annual meetings, and corporate events.
CREATE UNSTOPPABLE MOMENTUM THROUGH PROBLEM-SOLVING, CONSISTENT ACTION AND PURPOSE-DRIVEN LEADERSHIP
In today’s fast-moving world, it’s easy to feel stuck, stalled, or overwhelmed. But lasting momentum isn’t something we wait for — it’s something we build. In this energizing keynote, aviator, entrepreneur, and leadership expert Chris Wilson shares how to shift from stalled to soaring using his practical approach to momentum-based leadership.
Through powerful stories and actionable strategies, Chris shows how to turn real-world challenges into growth opportunities, build consistency in the face of chaos, and lead with clarity — no matter your role or starting point.
This keynote delivers the tools and mindset needed to generate forward movement, take ownership, and drive results both personally and professionally.
Ideal for: Leadership development events, company-wide team meetings, association conferences, professional development days, managers, leaders, associations, non-profits, schools, higher education, colleges, universities, high-performing teams, annual meetings, and corporate events.
LEARN HOW CALCULATED RISKS AND DECISIVE ACTION CAN PROPEL YOU TO NEW HEIGHTS
Avoiding risk often feels like the safest option — but it’s rarely the most rewarding. In this bold and thought-provoking keynote, aviator, entrepreneur, and leadership expert Chris Wilson reveals how embracing calculated risk is essential for growth, change, and peak performance.
Drawing from high-stakes experiences in aviation and entrepreneurship, Chris unpacks the powerful leadership metaphor of the “Dead Man’s Curve” — a real flight principle where timing, altitude, and decisive action determine the outcome. It’s not about being reckless — it’s about being ready.
Through compelling stories, real-world insights, and a proven risk-taking framework, Chris empowers audiences to move past fear, make confident decisions under pressure, and stretch the limits of what they believe is possible.
Ideal for: Leadership development events, company-wide team meetings, association conferences, professional development days, managers, leaders, associations, non-profits, schools, higher education, colleges, universities, high-performing teams, annual meetings, and corporate events.
Chris delivered genuinely inspiring and engaging talks that resonated deeply with our students. He skillfully addressed key themes of leadership, the importance of pursuing dreams, the valuable lessons learned from failure, and the multifaceted nature of success.
Chris is a dynamic and insightful speaker, and I highly recommend him to any organization looking to inspire and motivate their audience, offering valuable guidance for personal and professional growth.
-Jana Remisova, School of Business, Capilano University