22. The moments I most need humility

A bold experiment in feedback

I facilitated a group coaching session where I introduced a format I had learned from No Rules Rules, the book about Netflix’s culture. Each person was asked to give one positive and one developmental feedback to every other person. We went one by one: the first person received feedback from everyone, then the second, and so on.

This kind of semi-open feedback exchange is unusual. But when it is done with a high-trust group, it can be powerful. People learn on several levels: receiving feedback about themselves, noticing how others give feedback, and seeing one colleague through many perspectives. I had used this approach with other teams before, and it often led to remarkable growth.

But this time, one participant told me afterward that it didn’t land with her. I could sense her genuine discomfort. That moment taught me two lessons, one practical and one deeper.

What the feedback taught me

Practical lesson: In my push for growth, I hadn’t checked whether everyone was ready for such a vulnerable process. I assumed their trust level was high enough, but I hadn’t asked. A simple check-in beforehand could have helped me design the practice with more care. I felt embarrassed for not being considerate and empathetic. 

Deeper lesson: When I am passionate about something, especially regarding growth, feedback, learning, deeper connections, I can lose sight of others. In my mind I’m saying: “This will be so good for everyone.” “How could anyone not want this opportunity to grow?” And in that conviction, I forget to see where people actually are. 

I’ve seen this pattern at home too. With my wife and children, I’ve encouraged them to share their feelings during conflicts, believing it would bring us closer. My intention was connection. But later I realized I had pushed too hard. They weren’t ready, and I wasn’t listening from their side. 

Woman Holding a Balance, Johannes Vermeer

Being bold with humility

Most of the time, the feedback I get is that I am too modest, too quiet, not promoting me enough. That kind of feedback, while sometimes uncomfortable, is easier for me to hear. But when I do step forward boldly, when I try something I believe in, and someone says I went too far, that feedback stings much more. It feels like the courage I worked to build is being knocked back down. I wonder why this type of feedback stings me more. Perhaps it is connected to Asian cultural values that I still hold, being modest and not sticking out. Because acting boldly can feel like going against those influences, the pushback carries a sharper sting. And maybe, precisely for that reason, it holds a bigger lesson for me.

This resonates with the concept of overcorrection, a hidden stage in the leadership journey. Often after years of cultural conditioning toward not sticking out and being modest, the swing into boldness can feel jarring  both to ourselves and to others. We find ourselves oversteering from our familiar default, and the discomfort it creates can teach us more than any gentle correction.

The feedback helped me see a pattern that I didn’t realize clearly. I am generally reflective and try to see others clearly and objectively. But sometimes, I don’t. This experience taught me that my passion for learning and growth becomes more powerful when I pair it with humility: checking in with others, appreciating their comfort level, and tailoring the experiment with care while not losing the direction. The moments I feel most passionate are also the moments I most need to be humble.

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23. Why self-authoring matters to me as an Asian American

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21. Leaving a little earlier