This month, we sit down with Cindy Leong, coach, author, and long-time student of the Enneagram. Her recent work, Parenting and Educating with the Enneagram: Understanding Our Children in Singapore Culture, explores how the Enneagram can support healthier, more attuned family relationships. In this conversation, Cindy reflects on her personal journey with the Enneagram, the nuanced tension around “typing” children, and the lessons she’s learned from parenting as a Type Three.

Kristina Lor: To give our readers a personal sense of your journey, how did you first encounter the Enneagram? What initially drew you to it?

Cindy Leong: I first encountered the Enneagram during a period when I was hungry to understand how personalities affect relationships. I was recovering from a divorce while helping others make sense of their relationships as a coach. I wanted to be the coach I never had for myself. 

I needed to understand why all my past relationships had to fail. Why do behaviors not always make sense on the surface? What is the best advice I can give to my clients of different personality types?

As a Psychology student in university,  I tried all personality profiling tools. Unlike others, the Enneagram didn’t just give me labels; it gave me language for my inner world. My friend who read books on the Enneagram shared with me. Immediately I know this is the one!

What hooked me was brutal clarity, the kind that quietly exposes your blindspots before you can defend yourself. Instead of feeling attacked, I felt relieved. I finally saw the machinery underneath my drive, my ambition, and my fear of failure. Most importantly, it offers a growth path for me to be a better version of myself.

My lesson:

I used to treat relationships as projects with timeline, milestones and KPIs, exerting pressure on them and losing interest when it is not working out. Through the lens of the Enneagram, I learnt that a relationship is a journey, not a destination.

I flew all the way to California to learn from Dr. Claudio Naranjo, the legendary man that combined the ancient wisdom of the Enneagram with Personality Assessments, did all the healing I needed, came home with a new me and new found passion, and the rest is history.

Kristina Lor: Your book addresses one of the most nuanced questions in Enneagram-informed parenting: the paradoxical struggle of, “Don’t type your children… but also parent according to personality.” Can you expand on the ways you help parents navigate this paradox?

Cindy Leong: The famous paradox: “Don’t type your children… but also please parent them according to their personality.”

This confuses parents all the time.

Here’s the nuances of why we shouldn’t type kids prematurely:

  • Their core motivations are still forming.
  • Kids shape-shift to please parents, teachers, and authority figures, so what you see may not be who they truly are.
  • Early typing can become a self-fulfilling prophecy (“You’re a Little Type 1, so behave!”).
  • It can limit a child’s potential because adults unconsciously lock them into a box.
  • Kids deserve to grow without adults projecting their anxieties or unrealistic expectations onto them.

But here’s the reality: families already feel the energies

Whether or not you name the type, you can feel when:

One child hates being controlled

One child needs reassurance

One child wants space

One child wants significance

Parents cannot, and should not, pretend these differences don’t exist.

So how do we navigate this responsibly?

I encourage parents to stay curious instead of conclusive.

Tactical approaches I teach:

Observe behaviour across different environments, not just at home (school, playground, relatives’ houses).

Ask clarifying questions that reveal motivations, not just emotional states:

“What made you feel that way?”

“What were you hoping would happen?”

Notice stress responses, because they often reveal instinctive patterns.

Hold hypotheses lightly. Say: “I wonder if…” rather than “You are…”

Focus on nurturing all nine capacities: emotional regulation, adaptability, discipline, logical thinking, creativity, empathy, courage, boundaries, autonomy, etc.

Parents don’t need to type the child nor tell them their type.

They need to understand the child in front of them.

The Enneagram simply gives them a lens, not a verdict.

Kristina Lor: To give our readers a glimpse into how you’ve navigated your own relationship with your children, what is something meaningful or unexpected you learned through this journey with the Enneagram?

Cindy Leong: One of the biggest shifts for me as an Enneagram Type 3 parent was realising this tough truth:

I was parenting my children through the lens of performance, and how the way to connect is different.

I realised the difference between being human doing vs human being. 

A concrete example?

My Type 5 son asked me to “sit beside him” one day. So I thought he wanted to connect with me. So I used a Type 3 connection mode. I started asking him questions! 

How was school? 

Who are your best friends?

Which are your favorite subjects?

And he was completely quiet. 

It was only after I spoke to an adult Type 5 colleague, then I realised what he wanted was for me to literally SIT BESIDE HIM, without talking! 

That was when I realized I needed to learn how to be quiet while being present. Being present is me doing something without doing anything.

Cindy Leong is a coach, speaker, and author. She is also the founder of Relationship Studio and The Enneagram Academy.  Her work focuses on helping others make sense of your professional and personal relationships. Her newest book, Parenting and Educating with the Enneagram: Understanding Our Children in Singapore Culture, explores how parents and educators can better understand children through a lens of compassion, curiosity, and developmental awareness.

You can learn more about Cindy’s work, courses, and coaching at: The Enneagram Academy and Relationship Studio; and follow them on Instagram at: The Enneagram Academy and Relationship Studio.