58: You’re Not Leading If You’re Not Listening – Wesley Eugene on Empathy and Influence

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What if your most important leadership skill had nothing to do with technology, and everything to do with how people feel?



In this episode, I’m joined by Wesley Eugene, SVP at HIT Global and former CIO at IDEO. Wesley’s career has taken him from building computers in college to leading technology and transformation for some of the world’s most innovative companies. At HIT Global, he’s helping usher in a new way of thinking about tech leadership with a framework built entirely around human-first principles.

We talk about the moments in his career that drove home the power of trust, relationships, and empathy in technology. Wesley shares how human-centered design, storytelling, and a focus on real-world experiences can transform how leaders guide their teams and serve their customers. This is a conversation about leading people, not just managing processes.

You’ll Learn:

• The leadership shift that happens when you treat experience as your North Star
• Why telling better stories with data wins more than just arguments
• The surprising power of empathy as a competitive edge in tech leadership
• How radical candor transforms the way feedback is given and received
• The quiet damage of outsourcing critical customer experiences
• What it feels like to lead through a global crisis with trust as your main currency
• The link between human-centered design and faster, smoother transformations
• Why going analog can unlock your most creative and strategic thinking
• How to anchor digital transformation in moments that truly matter to people

Timestamps:

[00:00] Introduction

[05:58] Starting in tech through service desk work and early career moves

[08:56] Driving digital transformation and workforce reskilling at Aflac

[09:58] Leading secure remote transitions during the pandemic through trust and relationships

[12:57] Frameworks that shaped leadership including TBM and radical candor

[17:49] Immersion in human-centered design at Aflac and IDEO

[21:01] Realizing the importance of designing for real-world user experiences

[25:02] Breaking down the Human First playbook principles

[34:09] The role of unplugging and analog thinking in creativity and leadership

Resources Mentioned:

Technology Business Management Council | Website

Radical Candor by Kim Scott | Book or Audiobook

Radical Respect by Kim Scott | Book or Audiobook

Want to learn how to lead with empathy, design, and story at the core? You can connect with Wesley on LinkedIn, where he is building the Humanising IT™ movement; training, certifying, and coaching the next generation of human-first tech leaders.

Find more from Adam on LinkedIn and YouTube, and check out Adam's CTO coaching company Synova Tech.