In this conversation, Jeff Cook sits down with Milton Stewart—an Enneagram Seven, business leader, and President of the International Enneagram Association (IEA)—for a wide-ranging look at where the Enneagram stands right now and where it’s headed next. Milton shares what the IEA exists to protect: integrity, ethics, and responsible teaching, along with a growing commitment to global community and cross-cultural nuance. They talk about the rise (and fading) of Enneagram “buzz” on social media, the expanding push for scientific credibility, and the difference between trendy typing and real transformation.

Milton also tells his personal Enneagram origin story (including his early “mistype everybody I know” phase), how the tool shaped his work in under-resourced education settings, and what it’s like to learn from teachers whose presenceteaches as much as their content. The conversation lands on a core theme: the work—and Milton names two practices that keep it real no matter how much you’ve learned: humility and presence. If you’ve ever wanted a bigger-picture view of the Enneagram world—especially beyond American culture—this one will widen your lens and deepen your hope.

1. Milton’s website: https://kaizencareers.com
2. Milton’s podcast: Do It For The Gram: Enneagram Podcast
3. International Enneagram Association (IEA): https://internationalenneagram.org
4. IEA Events (“Nine Points”): https://internationalenneagram.org → Nine Points (events posted by accredited professionals)