Developing Humility

*This article was first written in August 2018 and further developed in April 2026.

Humility seems underrated in corporate leadership. Yet, it is arguably the single, most important determinant of how power and authority will be used by a leader. There have been several articles written on the importance of humility in leadership. This article is written as an extension of the existing discussion(s), and in particular, to explore how to cultivate humility. I approach this topic not as an expert; far from it. In fact, I have broken trust and lost employees because of the lack of humility on my part.

Humility has been defined in several ways. For the purpose of this article, humility will be taken as "not thinking that we are better than we really are in terms of our importance and our ability; but having sound judgement."

In the same vein, someone said "people with humility do not think less of themselves; they just think about themselves less." I fully agree.

Why Humility Cannot Be Studied Like a Subject

Developing humility can be challenging because character formation works differently from the conventional knowledge-based approach to learning. In my previous vocation as a church pastor, one of my primary responsibilities was to help individuals grow in character. The process was baffling. I discovered that one's knowledge of a character trait does not necessarily translate into one's practice of the same trait. Take my life for instance. Though I may cognitively know a lot about humility, my personal failings remain because of a lack of self-awareness.

This is where I feel many leaders get caught off guard. We treat character the same way we treat technical skill. Read the right book, attend the right workshop, take notes, apply. But humility does not work that way. Knowledge sits in the head. Humility lives somewhere else, in how we see ourselves and others when no one is watching.

Developing humility requires a great level of self-awareness, which is not easily acquired. And self-awareness is not really about knowing more facts about yourself. It is about who you become as the one observing yourself.A leader who only sees the world through the lens of his own importance keeps arriving at the same conclusions about every situation. Until that lens shifts, no amount of feedback will land.

The Direct Path Does Not Work

Suppose a student requires two magic bullets to ace an exam:

• knowledge of the subject matter

• time management skills.

Most will agree that knowledge of the subject matter will directly affect the grades while time management affects the end outcome indirectly. Knowledge of the subject matter directly impacts a student's ability to answer the exam questions. Time management is also required for effectiveness. Unless we apportion time to study, time to rest, time to relax, we will not be effective.

I would like to suggest that character traits are best cultivated through indirect means. Trying to be more humble in a direct way can only lead a person to be prideful. It is like making a statement "I'm so proud that I can become humble." It simply does not work. Instead, allowing people to come to their own realizations of their pride may work better. This is the practice of self-awareness.

The reason the direct approach fails is subtle. When I aim straight at humility, the “I” doing the aiming is the very thing in the way. Pride does not disappear because I declare war on it. It just finds a new costume to wear, often the costume of the humble leader.

Two Indirect Practices: Service and Listening

How, then, does an indirect approach look like?

One possibility is through acts of service. Through acts of service, one may discover their prideful areas. Are there tasks I deem too menial to act upon? Am I upset when I am not recognized for the things I have done? Why am I reacting negatively to feedback given to me?

Service has a way of showing us what we would rather not admit. The leader who enjoys running a strategy meeting but quietly resents clearing the cups afterwards has just learned something about himself. That quick flash of irritation when asked to do something small, like clearing the cups, is not a weakness to hide. It is a signal worth paying attention to. A leader who can notice these moments without rushing to defend or explain has already started the work of humility.

Another example of an indirect approach is to practice listening. Intentionally listening to others and paraphrasing what they say is a way to realize if we are more interested in others or in ourselves. Leaders who are more interested to tell others what to do usually end up causing more hurt because of a lack of empathy. Listening is one of the hardest things for leaders with big egos. I regret to say this is one of my most painful realizations.

There is a kind of listening many leaders practise. While the other person is talking, the leader is already preparing his reply, lining up his counter-point, steering the conversation back to what he wants to say. He looks like he is listening, but nothing in him actually shifts. True listening is different. Something in us has to soften. We have to be open to being changed, even a little, by what the other person is sharing. For a leader who is used to having the answers, this can feel like losing ground. I like to think it is actually the start of being trusted.

Other Quiet Disciplines

In essence, humility is a realization of how proud we are. Engaging in good disciplines such as listening and intentionally serving others are powerful ways of gaining self-awareness. Other approaches include journaling and giving thanks. Journaling slows down the rush of the day long enough for patterns to surface. Giving thanks shifts the centre of gravity. A leader who is genuinely thankful, is in that moment, no longer the protagonist of the story.

When a Good Principle Becomes a Weapon

Let me share a personal story.

One of my core beliefs is that it takes two hands to clap. I do not believe marriages or relationships break down because of one party alone. The power of such a belief should empower me to reflect, take ownership of my mistakes, and adjust my behavior. Unfortunately, a lack of humility meant I ended up focusing on where the other party had failed. In short, I like to blame others rather than search my heart.

This was the trap I fell into. A good principle, in the hands of pride, becomes a weapon. It takes two hands to clap was meant to lead me inward. Instead, it gave me a sophisticated way to keep score. Yes, I made a mistake, but so did they. The principle was sound. The observer applying it was not.

I increasingly realized how much pain I have caused my family, close friends, and my work team. My pride caused me to reject feedback. I even rationalized that I was less at fault and more humble since I was constantly adjusting my behavior. Sadly, behavioral change can be superficial. In thinking I had grown in humility, I had ironically become more prideful.

You can change the surface and leave the root untouched. You can adjust your tone, your phrasing, the way you run your meetings, and still be the same leader underneath, just better at hiding. The work is not at the level of behaviour. It is at the level of who you are being when the behaviour happens.

The Freedom on the Other Side

The truth hurts. But there is a freedom on the other side of it that the prideful leader never gets to taste. When you no longer have to defend the version of yourself that has to be right, has to be impressive, has to be ahead, something settles. The meetings get lighter. Feedback gets easier to receive. The team starts telling you the things they used to keep to themselves. If we believe that humility is thinking of ourselves less, it is extremely freeing to focus on the beauty and joy of growing our character and perhaps, the people around us. I hope I can be steadfast in seeing this beauty and joy.

Written by Victor Seet
Activator • Communication • Strategic • Self-Assurance • Command

As a Gallup and Newfield Certified Leadership Coach in Singapore, Victor is passionate about helping people be better observer of themselves to achieve the results they want, especially in the area of well-being and performance. Victor intentionally integrates the strengths-based and ontological approach into his leadership coaching and workshops.