When you experience a failure as a leader, don't hide it - talk

Host: The office was nearly empty — a glass tower above a sleeping city, its corridors echoing with the faint hum of distant air vents and the occasional click of a forgotten light. Outside, the rain painted slow streaks across the windows, blurring the skyline into a watercolor of regret and reflection.

The boardroom lights were still on. Papers, laptops, and empty coffee cups littered the long mahogany table like the remains of a battle fought in silence.

Jack sat at the head, his tie loosened, his eyes shadowed with exhaustion. Jeeny stood by the window, her hands folded in front of her, her reflection hovering like a ghost over the dark glass.

The projector screen behind them still glowed faintly with the title of the day’s presentation:
Q3 Product Launch – Postmortem Review.

Jeeny: “Naveen Jain once said, ‘When you experience a failure as a leader, don’t hide it — talk about it. Your missed opportunity will encourage others to take risks.’”

Host: Her voice was soft, but the words seemed to cut through the stale air like fresh wind. Jack didn’t look up. He ran a hand through his hair, stared at the faint stain of coffee on his sleeve.

Jack: “Talk about it? In this business, you don’t talk about failure — you bury it. Preferably under the next shiny success story.”

Jeeny: “That’s the problem, Jack. We bury it so deep we forget what we could’ve learned from it. And then we repeat it — only louder, costlier.”

Jack: “Easy for you to say. You didn’t spend six months promising investors a miracle. You didn’t look them in the eye while the numbers died on the screen.”

Host: The city lights outside blinked in slow rhythm, reflected in Jack’s weary eyes. His voice carried that mix of anger and sorrow — the sound of a man trying to fight the silence his own pride built.

Jeeny: “You’re not the only one who feels it. Everyone in that meeting saw how much it mattered to you. They didn’t lose faith because you failed — they lost faith because you disappeared.”

Jack: (snapping) “What did you want me to do? Give them a TED Talk about falling short? Tell them failure’s just another word for innovation? That kind of optimism only works in books.”

Jeeny: “No, Jack. It works in leadership. Because leadership isn’t about never falling — it’s about showing people that falling isn’t fatal.”

Host: A low rumble of thunder rolled through the distance, and the flicker of lightning briefly illuminated the entire boardroom — stark, sterile, and painfully honest.

Jack: “You really think anyone wants to see weakness in a leader?”

Jeeny: “They don’t want perfection. They want truth. There’s a difference.”

Host: The rain grew heavier, tapping against the windows like a thousand fingers demanding attention. Jeeny turned, facing him now — her eyes steady, bright with conviction.

Jeeny: “Do you remember the story about NASA’s first Mars probe? In 1999, they lost a $125 million spacecraft — because one team used metric units and the other used imperial. It was humiliating. But they didn’t bury it. They published everything — every line of code, every miscommunication. And because they did, they never made that mistake again.”

Jack: “You’re comparing me to NASA?”

Jeeny: “No. I’m comparing your silence to their honesty.”

Host: Jack leaned back in his chair, exhaling slowly, watching the ceiling as if the answers were written in invisible ink. The rain’s rhythm softened, as though even the storm was listening.

Jack: “You ever notice how the higher you climb, the less you can admit you’re wrong? People don’t follow vulnerability — they follow confidence.”

Jeeny: “That’s the illusion. They don’t follow confidence — they follow courage. Confidence says, ‘I can do no wrong.’ Courage says, ‘I’ll face it even when I do.’”

Host: Her words landed quietly, but they carried the weight of truth. Jack’s hands tightened around his coffee cup until it cracked slightly under the pressure. He stared at it — the jagged line running through the porcelain like a mirror of his own control.

Jack: “You think they’d respect me if I walked in tomorrow and said, ‘Hey, I screwed up. Sorry about the millions lost.’?”

Jeeny: “They’d respect you more than if you pretended nothing happened. Because when you talk about failure, you give everyone else permission to stop being afraid of it.”

Host: Jack looked up at her, something flickering in his expression — not surrender, not quite belief, but the start of both.

Jack: “Permission. That’s a dangerous thing to give.”

Jeeny: “So is silence.”

Host: The clock on the wall ticked quietly, marking the slow march of midnight. The storm outside had gentled into a steady drizzle — soft, constant, cleansing.

Jack: “You know, I used to admire leaders who never flinched. The ones who always had an answer. Now I think they were just better liars.”

Jeeny: “Maybe. Or maybe they were just lonely. When you hide your failures, you don’t just lose honesty — you lose connection.”

Host: She walked toward him, placing her notebook on the table. The cover read, in faded ink: “Ideas worth failing for.”

Jack stared at it, a slow, reluctant smile tugging at the edge of his lips.

Jack: “You really believe failure inspires people?”

Jeeny: “Only when it’s shared. When you say, ‘I fell, but here’s how I got up,’ you turn pain into mapmaking.”

Host: He looked at her then — really looked — the hardness fading from his features. The light above them buzzed faintly, its flicker softer now, as though the room itself was beginning to exhale.

Jack: “You know what scares me, Jeeny? Not failing. But failing in front of them.”

Jeeny: “Then you’ve already done the bravest thing possible — you tried. The second bravest is talking about it.”

Host: Silence again — the heavy, thoughtful kind that lingers right before confession. Then Jack pushed his chair back and stood, his shadow long against the wall.

Jack: “Maybe tomorrow, I’ll tell them. The truth. Not the numbers, not the excuses — just the story. What we thought we’d build, what we missed, and what it taught us.”

Jeeny: “They’ll listen. Not because they have to, but because they’ll finally recognize themselves in you.”

Host: She smiled — a small, knowing thing that carried both hope and weariness. The rain outside had stopped completely now, leaving only the faint glisten of wet glass reflecting the city lights below.

Jack walked toward the window, his reflection standing beside hers — two figures framed in the glow of a city that had seen its own share of failure and resilience.

Jack: “You think they’ll forgive it?”

Jeeny: “You don’t need forgiveness for being human, Jack. Just the courage to stay that way.”

Host: He nodded slowly, watching the city breathe beneath him. Somewhere far below, headlights traced quiet paths through the wet streets — motion, life, persistence.

Jack turned, his voice softer now, stripped of its armor.

Jack: “Then maybe failure isn’t the opposite of leadership. Maybe it’s the proof of it.”

Jeeny: “Exactly. Because every scar you show becomes someone else’s permission slip to begin.”

Host: The lights in the room dimmed automatically — the building reminding them it was time to leave. Jack picked up his cracked coffee cup, holding it carefully, as if it were something worth keeping.

As they stepped toward the elevator, the faint reflection of dawn began to touch the clouds outside — a subtle gold threading through gray.

And as the doors slid closed, the world seemed to whisper the quiet truth Naveen Jain had once known —

that leadership isn’t the art of appearing strong,
but the courage to let your failures teach someone else how to begin again.