What if becoming a better leader meant letting go of being the expert? In this Unlearn episode, I’m joined by David Tuck, Chief Executive of Waracle, for a thoughtful and human-centered conversation on the mindset shifts required to lead high-performing teams in complex, fast-changing environments.

David’s leadership journey spans over 15 years of agile transformation, commercial growth, and organizational design. He’s held executive roles at Kin + Carta, The App Business, ThoughtWorks, and Scott Logic, and now leads Waracle, a strategic design and technology consultancy that builds trusted digital products for enterprise clients.

Known for his calm conviction and people-first approach, David shares how curiosity, craft, and long-term client intimacy have shaped his leadership philosophy. From stepping back in his career to hone his sales skills, to becoming a CEO who leads experts by asking better questions, David reflects on what it means to grow companies—and yourself—by design.

This episode explores how to lead through inquiry, build trust at scale, and why today’s leaders must become “Chief Unlearn Officers” to stay relevant in an AI-powered world.

Key Takeaways

Craft First, Climb Later: David shares why stepping back from leadership to deepen his sales craft at Waracle gave him the clarity and credibility to lead more effectively.
Lead Without Knowing Everything: CEOs don't need all the answers—they need to ask better questions and create space for their teams to excel.
AI Starts with Literacy: Leaders must understand AI fundamentals to steer transformation and avoid becoming disconnected from how value is created.
From Specialist to Generalist: The CEO role is about orchestration—shifting from doing to enabling across functions and disciplines.
Human Connection Still Wins: At Waracle and beyond, trust, empathy, and meaningful relationships still drive long-term business success in an AI-powered world.

Additional Insights

Redefine Leadership as Service: A CEO’s job is to help others succeed, not to control every decision or be the expert in the room.
Ask Better Questions: Using frameworks like the probing pyramid can unlock better thinking and faster alignment across teams.
Don’t Automate the Human: AI can accelerate delivery, but it can’t replace the emotional intelligence and trust that drive real impact.
Create Space for Reflection: Strategic pauses and structured dialogue lead to more thoughtful, inclusive decisions—especially in hybrid teams.
Unlearn to Move Forward: Leaders need to let go of outdated habits and create the conditions for new thinking to thrive.

Useful Resources

Follow the Host:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Stress and Overwhelm Hacks - Feel Amazing About Your Day