Trust Me When You Don’t Understand Yet

The deepest leadership moments are not when people applaud you. They are when someone you love looks at you with disbelief and asks, “Why did you do that?” And you have to stay long enough, close enough, consistently enough, that one day they understand without needing your explanation.

I keep returning to that hospital memory because it refuses to stay in the past. It keeps showing up in new clothing, in new rooms, with new faces, but the same emotional shape.

Many years ago, one of my sons fell sick in a way that did not resolve quickly. We went to a clinic, and antibiotics were given. Week one, no real improvement. Week two, the dose got heavier. Week three, heavier again, until my son began vomiting. That was the part that broke something in me, not only because he was suffering, but because I could feel how easily care can turn into harm when the situation drags on and you keep trying the same lever harder.

Eventually, the doctor said what he should have said earlier, maybe we should admit him to the hospital.

My son was young, but he was unusually good at articulating fear. When the hospital explained that he needed a drip, he understood only one thing, his hand would be poked. To him it was not medicine, it was punishment. He begged, he promised, he negotiated like a small human trying to bargain his way out of death. He cried as if he would be killed.

That night taught me something I did not have language for then, children do not always process pain as “necessary”. They often process it as “someone is doing something to me.” Even well-meant reassurance can land the wrong way, there is research showing that when adults repeat “don’t worry” during a painful procedure, children can read that as a signal that something really is worth worrying about, because the adult’s anxiety leaks through the words. So even comfort can become fuel for fear if it is not backed by calm presence.

In that moment, I did what every father hopes he never has to do. I held him down. I distracted him with his favourite cartoon, I spoke gently, I waited for a small window where he was calm enough to be caught, and then I nodded to the nurse. The needle went in. He screamed like we were slaughtering him. And then he looked at me, furious, disbelieving, betrayed.

“Daddy, why did you do that?”

I tried to explain. I told him it was necessary. I told him it would help him heal. But he was not at an age where logic could outvote fear. The gap was too wide. So I said the only thing left.

“Trust me.”

I remember repeating it like a prayer, not because it sounded wise, but because there was nothing else to offer him that he could hold. He fought a little longer, then exhaustion took him. He fell asleep.

And then something quietly important happened over the days that followed. I stayed. I did not leave him alone with the needle and the pain and the confusion. At night, I squeezed onto the bed beside him and hugged him, patting him in a steady rhythm until his breathing slowed. When he woke, I was there. When he cried again, I was there. Over time, as his body recovered, he began to sense what he could not understand earlier, that the pain was not proof of cruelty, it was part of care.

That is the first time I learned that explanation is not always the bridge. Presence is.

When I Thought My Boss Was Using Me

Years later, in my first corporate job, I found myself reacting to leadership the way my son reacted to the needle.

Every conversation felt like it carried a hidden agenda.

My bosses could be kind, even encouraging, but there was always direction, performance, alignment. And because I grew up knowing only one kind of love that asked nothing from me except my well-being, I judged corporate leadership through the wrong lens. I assumed that if someone had a plan, they must be using me.

So I did what I thought was intelligent, I tried to “hack” people. I studied what they wanted. I learned how to deliver outcomes while keeping my heart guarded. I told myself I could see through the plot.

The older I get, the more I realise that what I called a “plot” was sometimes simply stewardship. A good leader cannot pretend the organisation does not exist. A good leader cannot spend resources, including human resources, without responsibility. They may care for you, genuinely, and still have to carry direction. Both can be true. The problem is not that there is an agenda. The problem is when the agenda is detached from care.

At that age, I did not know how to separate those two.

When I Became the One With the Agenda

When I started Stellar, reality had no interest in my ideals.

Johor Bahru sits beside Singapore. Talent moves. Money moves. People compare. You can call it “opportunity” if you want, but when you are trying to build an organisation and you watch your people disappear across the Causeway, it does not feel like a theory, it feels like a leak.

There is a reason the Causeway is one of the busiest land crossings in this region. Channel NewsAsia has reported that more than 300,000 Malaysians travel across the Johor–Singapore Causeway each day, many of them drawn by currency strength and pay differentials.

And when you read Malaysian government-linked findings reported in early 2024, you see how practical the pull is, the majority of Malaysians living and working in Singapore fall into working salary bands that, once converted, reshape what “reasonable pay” looks like back home, even before you add the exchange rate effect.

We could not compete on salary. Sometimes we could not even pay market rate consistently. So we did what many purpose-driven organisations do when money is not their strongest lever.

We sold a vision.

We spoke about meaning, growth, contribution, building something that matters. People stayed. Some stayed longer than they would have if we had only talked about money.

And then the uncomfortable mirror appeared.

I had an agenda too.

I was plotting for people to stay. Not because I wanted to exploit them, but because the organisation needed stability to survive and to serve. And when my “plot” worked, it forced a second realisation that landed heavier, if you convince people to stay through vision, your life has to back up the vision. If it does not, the same words that inspire can become manipulation.

This is where leadership becomes very exposing.

Because the difference between manipulation and stewardship is not whether you have a plan. It is whether your plan is willing to absorb cost for the people you are asking to carry it with you.

When Trust Breaks Before Understanding Arrives

Recently, we were strategising with directors. A sensitive conversation took place. Through what I experienced as negligence, part of that conversation leaked. The information reached someone who shared it with me as if it was purely friendship, purely personal, purely relational.

But that information mattered. It affected our next strategic steps. So it was discussed further, including with people who needed to know for responsibility and direction.

When the original source realised it had travelled, the reaction was fury. Betrayal. “I can’t take this anymore.” That kind of pain that does not want explanation, it wants justice.

Watching that person’s face, I suddenly saw my son again.

The same disbelief.

The same anger.

The same sense of, “How could you do this to me?”

I apologised. I nodded. And I moved on.

Not because the pain was small, but because I knew what happens when you try to explain something to someone who is not ready to understand it. Words can become salt. Explanations can feel like excuses. Logic can feel like gaslighting, even when you think you are being fair.

Sometimes the only responsible thing is to stay calm, acknowledge the wound, and remain present long enough for the person to see your posture over time.

That is not a technique. That is a cost.

Seeing My Old Boss Clearly, At Last

Some time ago, that old boss I once resented visited my school. We spoke. And I found myself apologising to her, not as a social courtesy, but as a correction of my younger self.

I told her I was naive.

I used to think she was using me. But now I see something else. She may have cared about me personally, and still had to steward the organisation. A leader is not allowed to be only “nice”. A leader has to be accountable. That accountability is not cruelty. It is responsibility.

When I look back, I realise I was hungry for unconditional love in a place that was never designed to give it. Work is not family. But work can still be human. Work can still be caring. Work can still be dignifying. It just cannot pretend it has no direction.

That is the difference I could not hold when I was younger.

Levels Shape Perception

Here is the pattern I keep seeing.

People at different levels see the same action differently, not because one side is evil, but because perception is shaped by position, capacity, and fear.

My son saw punishment. I saw healing.

I saw manipulation. My boss saw stewardship.

A colleague saw betrayal. Leadership saw responsibility.

What resolved the gap with my son was not my explanation. It was my consistency after the pain. He watched me suffer too. He watched me stay. He watched that I did not abandon him once the needle went in.

This is why a quote like Maya Angelou’s continues to hold weight across generations, people may forget what you said and did, but they rarely forget how you made them feel.

In a strange way, that is both comforting and terrifying for leadership. Because it means your strategy can be perfect, and still fail if your presence is absent. And it means your words can be imperfect, and still work if your posture is trustworthy.

Why We Raise Leaders

This morning we talked about why we raise leaders.

Some joked that it is so we can have holidays. I understand the humour, but that is not empowerment. That is escape. That is not why we build people.

We started as a small preschool. I cleaned toilets. I drove. I did everything. It is not that I cannot do those things now. It is that time does not work the same way anymore.

The older I get, the more I feel how every hour becomes more expensive, not in money, but in closeness to the end. In my twenties, I could burn hours and recover. In my forties, every hour feels more precious. And I can already imagine how it will feel in my seventies, when an hour is not just an hour, it is a visible step toward the grave.

So output must change. Not output as money, but output as impact.

That is why we raise leaders, because you cannot scale impact by doing everything yourself. You scale impact by multiplying capable people who can carry responsibility with integrity.

And yes, an organisation has a “plot” when it raises leaders. It wants continuity. It wants sustainability. It wants growth that outlives one person. That is normal stewardship.

But the test is always the same.

Does the agenda serve the people, or does it consume them?

The best leaders disappoint people sometimes. Not because they enjoy it, but because reality and direction require hard choices. Ronald Heifetz captures that tension in a line that feels almost rude until you live it, leadership is disappointing your own people at a rate they can absorb.

I do not love that quote because it sounds tough. I love it because it names what every leader eventually learns the hard way, leadership includes moments where people will not understand you, and you still have to carry what you believe is necessary.

The Quiet Line Between Love and Leadership

Leadership always carries a plan.

Parents plan for healing.

Organisations plan for sustainability.

Stewards plan for multiplication.

The question is not whether there is a plan. The question is whether the plan is held with integrity, empathy, and excellence, and whether the person holding the plan is willing to stay close enough to absorb the emotional cost of it.

Sometimes people will misunderstand you and call your care betrayal.

Sometimes they will not be ready for the explanation you are eager to give.

Sometimes all you can offer is a steady posture over time, and the willingness to remain present long after the moment that made them angry.

That is the line I keep watching in my own life.

Cross it, and leadership becomes manipulation, even if you use beautiful words.

Stay on it, and leadership becomes stewardship, even when people do not yet understand your reasons.

And maybe that is why that hospital memory keeps returning.

Because the deepest leadership moments are not when people applaud you.

They are when someone you love looks at you with disbelief and says, “Why did you do that?”

And you have to live long enough, close enough, consistently enough, that one day they can finally see the answer without needing you to say it.