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In this milestone 50th episode, Jen is joined by her original Enneagram teacher and mentor, Diane Ring, for a full-circle conversation about the deep architecture of inner work. Diane brings three decades of experience coaching senior leaders to the discussion. They examine the Enneagram not just as a categorization tool, but as a "sense-making" GPS that can help accurately locate where someone is and provide a specific growth path to help move the "edges of a proverbial box".

The conversation also dives into the "Core Gift" bridge, a framework that helps  distinguish between defensive personality strategies and the deeper "why" for being in the world. From real-world stories on shifting leader intensity to the introduction of EnneaEdge—an AI-supported Enneagram coaching experience designed for the "moments that matter"—this episode is an invitation to get out of your own echo chamber and engage with a professional mirror.

In this episode, we explore:

• The Enneagram as a Leadership GPS: Understanding the framework as a map that points to where you currently are and provides a specific growth path to help you break out of automatic identities. 
• Shifting from Intensity to Grounded Presence: By recognizing an automatic pattern of "intensity," a leader can experiment with "downshifting" to find a calmer, more productive way of engaging with their team.
• The Distinction Between Personality and Core Gift: While personality is a strategy system for self-protection, your core gift (such as attunement) is what you are uniquely called to give to the world.
• EnneaEdge | AI-Supported Enneagram Coaching: To solve the problem of "fall off" after leadership workshops, Diane created an AI coach designed to help professionals apply Enneagram insights when they are most likely to succumb to autopilot default patterns.

The Work of You via Diane Ring:

1. Find somebody with professional capabilities, a coach, mentor, or peer-support group, that can help you recognize and reflect on your patterns, motivations, and blind spots. The goal is to intentionally step outside your own echo chamber and build self-awareness through guided reflection.

About the Guest: 

Diane Ring is an executive coach who has been bringing the Enneagram into the real work of leadership for 30 years. Through her company, Ring Results, she helps senior leaders and teams understand the deeper patterns that shape how they communicate, make decisions, handle pressure, and relate to others. Diane is known for making the Enneagram practical, relevant, and deeply useful—helping leaders see not only why they do what they do, but also the core gifts they are here to bring forward. She serves on the faculty of Integrative Enneagram Solutions and has presented several times at global Enneagram conferences. Diane is also the creator of EnneaEdge™, an AI-supported Enneagram coaching experience designed to help leaders apply insight in the moments that matter.

Resources | Links:

Download this Free Resource: Discover Your Hidden Layer of Leadership

Get Your Enneagram Report Here

Diane's Company | Ring Results

LinkedIn | Diane Ring

The Work of You on Substack

Instagram | The Work of You

Website | The Work of You

Instagram | Grow Collective

Website | Grow Collective

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