Leadership: Where Certainty Gets Outsourced

Leadership: Where Certainty Gets Outsourced

Previously on leadership: [Leadership: Where Certainty Goes to Die]

HEART: Last time, we agreed leadership was about standing in tension. You thought it was mostly a choice between a rock and a hard place.

MIND: And you thought it was about running into the fire while everyone else stayed on the sidelines.

HEART: Now the fire has a new kind of fuel—one that never eats, never sleeps, and insists it knows better than you. Artificial Intelligence.

MIND: Finally. A colleague who doesn’t get tired, doesn’t get political, and hands you the “optimal” answer before you’ve even touched your coffee. Honestly, we should just let it run the place.

HEART: Tempting. But leadership isn’t just about having the right answer. It’s about carrying the weight that comes after. AI can’t do that.

MIND: That’s cute. Leaders stick around for one reason: when things go sideways, someone has to stand in front of the blast.

HEART: That’s not the whole job. There’s the moment when a leader sees a team frozen at the edge of a risky decision and says, “Go. I’ll take the heat if it fails.” That’s not just shielding them; that’s giving them the nerve to move.

MIND: No. That’s just making it safe enough to move. Without safety, nobody moves, no matter how inspirational your pep talk is. You can dress it up as courage if you want, but cover is what actually tips the balance.

HEART: Cover doesn’t spark action on its own. Otherwise, the safest companies in the world would also be the boldest. We both know they’re not. Think about a crisis, a supply chain collapse, data contradicting itself every hour, and everyone paralyzed by noise. A leader cuts through it and says, “Here’s where we are, here’s what matters, and here’s what we do next.” The fog lifts. People act.

MIND: And when they act and it backfires? That speech won’t save them. The smart leader pairs it with legal shields, political backing, and a paper trail so no one gets hanged in the debrief.

HEART: Without that clarity, no one acts fast enough for your paper trail to mean anything.

MIND: Without that paper trail, your clarity is just theatre. That’s why those big consultancies still make billions even with AI spitting out better decks in seconds. It’s not the ideas leaders are paying for. It’s the letterhead they can wave in front of a hostile board and say, “This wasn’t just me.” AI can’t give you that kind of cover. It’s not about insight. It’s about insulation.

HEART: That’s such a narrow definition of leadership. You make it sound like leadership is just about optics.

MIND: It’s the definition that keeps you in the seat… assuming the seat still exists after the reorg. People love to romanticize leadership, but when the stakes are high, no one cares how “visionary” you are if you can’t survive the fallout. When the knives are out, optics decide whether you keep your head. People don’t want a leader who’s always right; they want one who can survive being wrong.

HEART: Survival isn’t enough. Sometimes you have to make a choice that doesn’t add up to a model but keeps the soul of the company alive. Like refusing to launch a product because you sense the market isn’t ready, even when every number says “green light.”

MIND: Or maybe that’s just fear of being wrong. Maybe the numbers are right, and your precious “sense” is a relic from the pre-data age.

HEART: Or maybe it’s the kind of instinct that built every breakthrough worth remembering.

MIND: And buried every company whose leaders thought they were special enough to outsmart reality. But sure, let’s romanticize it; we’re in a leadership article after all. At least AI will tell you the odds before you leap.

HEART: Odds never stirred anyone to follow you into the unknown.

MIND: That’s debatable. Regardless, speeches don’t pay salaries when you miss.

HEART: So you’d reduce leadership to risk management with better calculators?

MIND: I’d strip it of the self-flattering myths. The job isn’t just making calls; it’s knowing how to survive them.

HEART: And I’d strip it of the cynicism. The job is moving people toward something better, even when the map is incomplete.

MIND: People will follow the human… right up until the human chooses the wrong door. Then they’ll follow the machine.

HEART: People will follow the machine… right up until the machine asks them to do something they can’t explain to their children. Then they’ll look for a human to blame or to believe.

MIND: Exactly. That’s why the leader stays. To be the target when belief fails.

HEART: Or the spark when belief is all that’s left.

MIND: Which is why AI won’t replace leadership; it will expose it. Strip it bare. Show how much of it was never about brilliance and how much was about the ugly, necessary work of taking hits so others could move.

HEART: And how much of it was about seeing past the hits to what might be possible, and those spaces might matter more than ever. Because as AI takes more of what can be calculated, predicted, and automated, the value of what it can’t touch will only grow. Those spaces, the ones thick with hesitation, contradiction, and human mess, are where trust is built, where meaning is made, and where the future is decided in ways no model can replicate.

MIND: You really think that survives the machine?

HEART: I think it’s the only part worth keeping.

MIND: We’ll see….

Leadership isn’t about outthinking AI, it’s about standing where it won’t go. In the rooms where hesitation hangs in the air. In the moments where the numbers are certain but the people aren’t. AI can narrow the odds, streamline the path, even forecast the storm. But storms aren’t weather; they’re human. And they still need someone willing to stand in the middle of them, where the data ends and the mess begins.

Maina Kimani

Software Engineer | Designer

1mo

This …“People don’t want a leader who’s always right; they want one who can survive being wrong.” That flips a lot of conventional leadership wisdom on its head. Instead of glorifying flawless decision-making, it focuses on resilience under fire. Kind of like chess or any other game, it’s not the perfect opening move that makes you win, it’s surviving the mid-game blunders without losing the board.

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