The Art of Building Trust and Embracing Failure | Jill Willard

The Art of Building Trust and Embracing Failure | Jill Willard

Author: Bill December 19, 2025 Duration: 57:36
40% Better - Engineering Leadership
BusinessManagement
In this episode of the 40% Better Podcast, host Bill Lennan speaks with Jill Willard, Chief Technology Officer at IXOPAY, about her leadership journey and how she empowers software and payments teams to build trust, embrace failure, and drive innovation. Jill draws from over two decades of experience leading global software and payment platform teams, offering insights on situational leadership, accountability, effective communication, and building a thriving work culture that encourages psychological safety and experimentation in engineering environments. 
ixopay.com
Whether you’re a tech leader, engineering manager, or aspiring CTO, this episode is packed with actionable takeaways to help you become a more effective and inspiring leader.

🎯 Key Takeaways
Jill’s leadership journey began with a desire for control
Transitioning from small to larger teams requires evolving leadership skills
Building trust is essential for high-performing software teams
Failure is a natural part of engineering and growth
Leaders must give teams permission to take risks and learn
Accountability should be shared between leaders and team members
Situational leadership supports individuals at their level
Effective communication drives healthy team dynamics
Innovation thrives in environments that are engaging and fun
Self-awareness is a critical skill for leaders
🎙️ Memorable Sound Bites
“Failure is built in.”
“You can’t scale that way.”
“Confidence is contagious.”

I hope you enjoy this episode! Give it a like, share, and subscribe to not miss the content coming your way weekly. – Bill and the 40 % Better podcast team
Connect with Bill on LinkedIn: https://www.linkedin.com/in/wblennan/ 
Visit the 40 Percent Better website here: https://40pb.com/

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#40PercentBetter #BillLennan #Leadership #TeamPerformance #EmployeeEngagement #PsychologicalSafety #BusinessGrowth #Kaizen #EngineeringLeadership #Coaching The 40% Better podcast with Bill Lennan unlocks previously unheard-of performance levels in teams and leaders. Bill Lennan, founder of 40 Percent Better, interviews experts on employee engagement, psychological safety, engineering leadership, and actionable mental models. Learn how to foster high-performing teams, improve team productivity, and achieve sustainable success in business through a focus on human-centered systems.

Hosted by Bill, 40% Better-Engineering Leadership is a conversation for those who build and guide technical teams. This isn't about abstract theory; it's a practical dialogue focused on the tangible mechanics of morale, motivation, and output. Each episode features a single expert in employee engagement, and together we dissect the specific strategies that lead to measurable leaps in performance. You'll hear detailed explorations into what actually moves the needle for engineers and their managers, translating research and experience into actionable leadership techniques. The goal is straightforward: to provide the insights that can help your team operate at a significantly higher level of effectiveness and satisfaction. Tune in for a focused, deep-dive podcast that cuts through the noise of generic management advice, offering concrete ideas you can apply directly to the unique challenges of engineering leadership.
Author: Language: English Episodes: 100

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40% Better - Engineering Leadership
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