Interview with James Flaherty. Teaching as the art of pointing. Next Next Generation Society supports the growth and development of young adults.
Introduction
In this episode of The Enneagram Insights Podcast, Flemming Christensen welcomes James Flaherty for a conversation that explores a deceptively simple yet profound question: How to teach the Enneagram in a way that genuinely supports learning, maturity, and human development.
The two have known each other for years, and the dialogue unfolds with trust, curiosity, and mutual respect. Rather than focusing on methods or techniques, the conversation moves toward something more profound: what teaching actually is when it works.
Flemming enters the dialogue from his experience within the Danish educational culture, where three pillars often shape learning. Education is understood as lifelong rather than finite. Teachers and students are considered equal participants rather than holders of fixed authority. And learning is rooted in community rather than individual-oriented performance.
These assumptions quietly challenge more hierarchical models of teaching and raise essential questions about how the Enneagram should be taught, especially to younger generations.
James Flaherty responds from decades of experience as a teacher, coach, and Zen practitioner. For him, teaching is not primarily about transferring knowledge. It is about pointing something out in a way that allows another person to notice what they have not yet learned to notice. From this perspective, how to teach the Enneagram is not a question of curriculum alone, but of attention, presence, and relationship.
As the conversation unfolds, Flemming and James explore lineage, transmission, maturity, and responsibility. They ask what it means to pass something on so it remains alive beyond the teacher. They question whether teaching can be good or bad. And they reflect on how educators can support younger generations without projecting their own identities, ambitions, or unfinished work onto them.
What emerges is a view of teaching that is less about authority and more about contact. Less about performance and more about presence. Less about improvement and more about awakening.
Summary
Flemming Christensen opens the conversation by situating it within a Danish educational mindset that emphasizes lifelong learning, equality between teacher and student, and collaborative learning communities. From this starting point, he asks James Flaherty what teaching actually is when it succeeds, especially in relation to how to teach the Enneagram as a living developmental framework rather than a static model.
James describes teaching as the art of pointing something out so another person can pay attention to what was previously unnoticed. Teaching can involve speaking, reading, movement, art, or silence, but it is only successful if learning actually occurs in the student. Teaching that does not lead to learning, he suggests, is merely performance.
The art of pointing
He emphasizes that meaningful learning must engage all three centers of intelligence described in the Enneagram: cognitive understanding, emotional connection, and bodily enactment. If teaching addresses only the mind, students may become knowledgeable but disconnected. If it addresses only emotion, insight may lack structure or application. If it focuses only on behavior, depth and meaning may be lost. Understanding how to teach the Enneagram, therefore, requires an integrative approach.
Flemming brings in a phrase from James’s longer programs: self-observing and self-correcting. James explains that this is not about self-criticism, but about cultivating independence. A student who can observe what happened, compare it with intention, and adjust accordingly no longer needs to rely constantly on the teacher. Good teaching, he argues, leaves the student more capable, not more dependent.
The conversation then turns to lineage. James explains how lineage in Zen practice provides orientation, humility, and protection against self-deception. He contrasts this with contemporary coaching cultures where authority is sometimes self-appointed rather than earned through practice and accountability. This has direct implications for how to teach the Enneagram responsibly.
The episode concludes with concern for younger generations facing anxiety, depression, and isolation. James suggests that kindness, presence, and genuine contact may be among the most important things teachers can offer today.
Three key topics
How to teach the Enneagram as pointing and awakening
A central theme in the conversation is that teaching is fundamentally about attention. James Flaherty frames teaching as the act of pointing something out so another person can notice what was previously invisible. This perspective has profound implications for how to teach the Enneagram.
Rather than presenting the Enneagram as a system to be memorized or categorized, teaching becomes an invitation to awareness. The Enneagram then functions as a mirror, helping students see patterns they already live inside but have not yet named. From this view, learning is not about acquiring something new, but about awakening to what is already present.
James talks about how real teaching must engage all three centers of intelligence: head, heart, and body. Teaching the Enneagram only cognitively risks producing students who can explain the types but cannot relate to them differently. Teaching only emotionally may inspire without grounding.
Teaching only behaviorally may produce techniques without depth. Understanding how to prepare the teaching of the Enneagram well therefore means designing learning that integrates insight, feeling, and lived practice.
The conversation also challenges the desire for shortcuts. Flemming recognizes the modern tendency to ask for condensed versions of deep teachings. James responds that teaching which actually transforms a person takes time, because it works on habits of attention, identity, and relationship. The Enneagram, when taught well, unfolds over years rather than minutes.
From this perspective, teaching is not about delivering content efficiently. It is about creating conditions where students can notice themselves more honestly and act with greater freedom.
Self observing and self correcting as the goal of teaching
Another key theme concerns independence. Flemming returns to James’s emphasis on self observing and self correcting, asking whether this capacity is always necessary. James clarifies that while exceptions exist, the spirit of the idea is essential to good teaching and central to how to teach the Enneagram responsibly.
Self correction does not mean harsh self judgment. It means developing an internal sense of feedback. A student learns to notice when an intention does not produce the desired outcome and to adjust accordingly. James uses the metaphor of cooking soup. At first, a student cannot tell what is missing. Over time, they learn to taste and respond with discernment.
This distinction matters deeply in Enneagram teaching. Without self observation, the Enneagram becomes another external label. Without self correction, insight does not translate into change. Teaching that cultivates these capacities allows students to continue learning long after the course or teacher is gone.
Flemming summarizes this as leaving the student independent. James agrees. Teaching that creates dependency may feel effective because the teacher remains central. Teaching that builds independence is quieter, but more honest. It prepares students to work with their patterns in real life, not just in structured learning environments.
In this sense, how to teach the Enneagram is inseparable from how to support psychological safety within the learner. When mistakes are treated as information rather than failure, growth becomes possible. Teaching then becomes a practice of empowerment rather than control.
Lineage, transmission, and teaching without ego
Lineage becomes a central topic because it addresses both ethics and effectiveness. James describes lineage in Zen practice as a lived connection across generations that provides orientation and accountability. It is not about copying the past, but about remaining honest and awake within a living tradition.
This has direct implications for how to teach the Enneagram. Without lineage or accountability, teachers risk teaching from personal bias, unexamined blind spots, or ego-driven motivation. James contrasts disciplined schools of practice with self-appointed authority, noting how easily identity can replace depth.
Flemming asks whether great teachers can exist without lineage. James responds that he has never seen it. Innovation does not arise from nowhere. Every teacher emerges within a cultural and relational context, whether acknowledged or not.
We all have a liniage of teacher who have brought us to where we are today
The discussion then turns to transmission. James rejects the idea of transmission as information being sent from teacher to student. Instead, he describes transmission as something awakening in the student when two people meet in presence. Teaching feels both new and familiar because it connects with lived experience.
Ego becomes the main obstacle. Teachers who seek legacy, recognition, or relief from speaking their truth may unintentionally block learning. James emphasizes that transmission becomes possible when attention stays with the other person rather than the teacher’s self-image.
Understanding how to teach the Enneagram, therefore, includes learning how to step aside enough for something larger than personal identity to move through the teaching.
Closing the interview with James Flaherty
By the end of the episode, teaching appears less as a role and more as a disciplined form of relationship. Flemming Christensen consistently situates the conversation within culture, education, and generational responsibility, while James Flaherty returns again to presence and contact. Together they suggest that how to teach the Enneagram cannot be separated from how the teacher shows up as a human being.
Good teaching, in this view, is not about moral superiority or technical mastery. It is about whether teaching opens or narrows life. Whether it builds independence rather than dependency. Whether it acknowledges lineage while remaining alive to the present moment.
Is your teaching opening or narrowing life?
The conversation closes with concern for younger generations facing anxiety, depression, and disconnection. James offers no formula, only an orientation: kindness, generosity, and presence. Flemming allows this to stand without adding solutions, implicitly trusting the intelligence of contact itself.
The deeper suggestion is that something life-giving happens when a teacher is present with a good heart and genuine attention. Even when outcomes cannot be measured, something is passed on. Not because the teacher is exceptional, but because contact awakens what is already alive in the learner.
Links
Learn more about coaching by James Flaherty
