Schools LOVE to teach leadership.
And frankly, it’s probably for a good reason. We get the same message crammed into our heads, nonstop:
“Everyone can be a good leader! You’re not born with it! You can learn it!”
So we teach kids to be leaders. We teach them to nurture some mysterious “spark” even when no one can define what it is—and, god forbid, you be led. That means you lost. No one likes a loser.
And it doesn’t get better as you grow older. It gets worse. Primary → Secondary → Tertiary → Employment. The same question, over and over, endlessly:
“Are you a good leader?”
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Chasing Shadows
Throughout my education, the name “Elon Musk” came up constantly — sometimes casually, sometimes as a formal case study where we had to explain why he was a good example of an engineering leader.
I was asked to do it in the early Tesla days. Then the early SpaceX days, with the “multi-planetary species” dream. Then again, and again, as the eras shifted: the anti-vax era, the “if they don’t take my ideas they’re pedophiles” era, the chainsaw-at-TPUSA era. We kept treating him like a timeless template—like the same moral still applies to a story that has long took a deep, dark turn.
And the part that messes with me is: I used to buy it too.
For a long time I idolised what he stood for — or what I thought he represented. It was genuinely surprising, in a good way, to hear a billionaire say: fossil fuels are finite, so change has to happen now. That version of him gave younger me hope: that the people with power might actually care, and that we might solve real problems with real urgency.
Now he’s out here flirting with extremist imagery and hurling slurs at anyone who points out that — just maybe — he has a problem with minorities.
So here’s what I don’t understand: why does it feel like younger people are the only ones allowed to experience that betrayal out loud? Why are we still being told to analyse him like he’s the explanation for Tesla’s early success, instead of one highly-visible beneficiary of timing, capital, teams, and a story the market wanted to believe?
And why are we still teaching students to look at him like a checklist of traits to collect?
“See what he has. Go get that.”
Teach the opposite lesson—that there’s nothing mystical about the men in the high castle. That a lot of what we call “genius” is access, narrative control, survivorship bias, and the freedom to fail expensively. That many of us, given the same runway, could clear the same moderate bar of aptitude.
Schools keep packaging admiration as an assignment—and calling it leadership education.
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At least this trend’s better in Singapore.
Just kidding. It’s worse.
We’re a small island-state with a front-row seat to global tech power — and a weirdly muffled audio feed. We mostly encounter these figures as names: a CEO mentioned in a slide deck, a headline about another deal, a visiting leader shaking hands with the right people. We don’t really hear them, don’t watch the full arc, don’t sit with the uglier parts. Their beliefs don’t always land here immediately in a visceral way, so it’s easy to keep a clean, curated impression of who these “tech leaders” are.
That insulation saves us a lot of mental anguish. But it also makes it easier to import myths -- without examining them critically.
Because the who’s-who of tech isn’t just a QuizUp game (i know - im old) — it’s governance by other means. Altman, Zuckerberg, Musk, Nadella, Pichai: these are names with the power to shape what Singaporeans see, say, buy, build, and believe—sometimes more directly than our own leaders. And we don’t elect them. The main vote we get is our wallets, our usage, and our dependence.
So when any one of them decides to dabble in anti-humanistic beliefs — or just builds incentives that reward harm — we’ll feel it. You don’t need to be a citizen to be governed by a platform. You just need to sign up, and log in.
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Please do not idolise. And I’m looking at you, educators.
What makes a good leader? Is it the power they accumulate? The market share they capture? The revenue they rake in?
Does it depend on what MBTI they are?
You laugh, but I spent two semesters being made to “find” the MBTIs of powerful people. And the same thing always happens: personality typing becomes a way to aestheticise power, while skipping the one step that matters—interrogating accountability, challenging the premise in the first place.
Schools keep obsessing over leadership from the leader’s perspective. We get the same checklist:
1. Be a servant leader.
2. Handle crises effectively.
3. Manage disagreements.
4. Speak to diverse audiences; don’t drown people in engineering terms.
5. Be cross-functional.
But leadership isn’t historically “good” because the leader is charismatic, competent, or successful. A leader’s goodness must be validated by the people bearing the costs of their decisions — especially the led.
Success can be real and still be morally empty. “Good” is a title. It’s earned — then granted (or denied) by the people who live with the consequences.
So tell the story from their perspective instead:
1. A good leader can be held accountable for missteps and mistakes.
2. A good leader isn’t a personality type. Timing matters, but preparation and values decide what you do with timing.
3. A good leader is defined not only by what they extract from subordinates, but by the utility they create for the broader good.
4. A good leader is sensitive and compassionate to those they lead—and to those they affect.
5. A good leader builds systems that don’t require them.
6. You do not have to be a leader.
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So what should schools teach, instead?
Higher education forgets this sometimes: it shouldn’t just mirror the world as it is. Universities are supposed to shape what comes next—training people not in the image of today’s mastheads, but toward better models we’ll need for the long, long road ahead.
The trap educators keep falling into — trait worship — is no longer a usable north star. Replace it with a simple rubric for evaluating an engineering leader:
1. Incentives
2. Accountability
3. Externalities
If universities only evaluate leadership case studies on market cap, what exactly is a think tank for? Judge leadership on worker outcomes. Safety records. Retention. Whistleblower treatment. Downstream harm. Raise the standards — because we’ve all watched how low the bar can go when “results” becomes a blanket excuse.
Stop telling our kids to look at mastheads just to say:
“See what they have? That’s what you need.”
Instead, tell them — patiently, honestly:
“See what they have? You can do better.”