Surround yourself with the best people you can find, delegate

Host: The office stood high above the sleeping city, its windows glowing faintly against the darkness. The view stretched for miles — a grid of light and movement, endless and unknowable. Inside, the air was still, thick with the quiet weight of decisions long delayed.

It was late. The kind of late when even the printers stop humming and ambition turns into reflection. On the glass conference table lay files, empty coffee cups, and the soft flicker of a laptop screen showing the last slide of a long-forgotten presentation.

Jack leaned against the window, his jacket off, sleeves rolled, eyes hollow but alert. Jeeny sat at the table, barefoot now, spinning a pen between her fingers, the rhythm oddly soothing. The only sound was the low buzz of the city below — like a thousand hearts beating in unison for someone else’s dream.

On the whiteboard behind them, someone had written earlier, in clean, black marker:

“Surround yourself with the best people you can find, delegate authority, and don't interfere as long as the policy you've decided upon is being carried out.”
— Ronald Reagan

Jeeny: “You ever notice how that quote sounds easier than it is?”

Jack: “Leadership always does. Until you try it.”

Jeeny: “I don’t think he was talking about politics, though. I think he was talking about control.”

Jack: “Same thing. Politics is just control with nicer stationery.”

Host: The city lights reflected across the glass, cutting through the fatigue in their faces. They were two people at the edge of burnout, holding the kind of conversation that only happens when sleep is no longer the goal, only understanding.

Jeeny: “You think you’re good at delegation?”

Jack (smirking): “I used to be. Until people started disappointing me.”

Jeeny: “That’s not delegation. That’s possession. You trusted them to follow orders, not to think.”

Jack: “Thinking’s dangerous in most companies.”

Jeeny: “So is silence.”

Host: The clock on the wall ticked past midnight, indifferent. Papers rustled in the faint breeze from the air conditioner. Jeeny leaned forward, resting her chin on her hand.

Jeeny: “Reagan’s advice is simple: find good people, trust them, and get out of the way. But most leaders can’t do the last part.”

Jack: “Because they confuse involvement with importance.”

Jeeny: “And control with leadership.”

Jack: “And micromanagement with accountability.”

Jeeny: “Exactly.”

Host: A quiet laugh slipped between them — dry, tired, but real. The kind of laugh born from recognition.

Jack: “You know, it’s funny. Everyone wants to build teams, but no one wants to surrender ego.”

Jeeny: “That’s because delegation means admitting someone else might be better than you at something.”

Jack: “And that’s terrifying.”

Jeeny: “It’s also liberating.”

Jack: “Only if you believe in people.”

Jeeny: “And if you don’t?”

Jack: “Then you drown in your own competence.”

Host: The city outside flickered — a plane taking off, a light blinking on a tower. The world moved on, uncaring of their existential debrief.

Jeeny: “You ever work for someone who actually followed Reagan’s rule?”

Jack: “Once. Old mentor of mine. He’d hire people smarter than him, give them full control, and then disappear for weeks.”

Jeeny: “And?”

Jack: “Company thrived. Until he retired. Then everyone started fighting for approval that didn’t exist anymore.”

Jeeny: “So he built a kingdom of trust — but not succession.”

Jack: “Exactly. Turns out even freedom needs maintenance.”

Host: She smiled — the kind of smile that hides a lesson behind empathy.

Jeeny: “Maybe that’s the real test of leadership — not just delegating authority, but cultivating belief in shared purpose. Otherwise delegation’s just abdication.”

Jack: “You should write that down.”

Jeeny: “You won’t let me forget it.”

Jack: “No. Because you’re right.”

Host: The light above them flickered, briefly turning everything sepia, like an old photograph. Jack moved to the table, picking up a file and closing it softly.

Jack: “You know what bothers me most about Reagan’s quote?”

Jeeny: “What?”

Jack: “The ‘don’t interfere’ part. I’ve seen people use that as an excuse for neglect. You can’t disappear completely and call it trust.”

Jeeny: “True. Real delegation isn’t absence — it’s awareness without intrusion.”

Jack: “Like parenting.”

Jeeny: “Exactly. You teach, you trust, and you watch quietly — ready, but not controlling.”

Jack: “It’s harder than it sounds.”

Jeeny: “All good leadership is.”

Host: The air hummed again — faintly, a reminder of systems that never stop working. Jeeny stood, walking toward the window, looking out at the infinite sprawl of lights below.

Jeeny: “Do you ever think we’ve complicated leadership? All the books, seminars, TED Talks… and yet everything we need to know fits in that one sentence.”

Jack: “Because the hardest truths are short. Trust. Empower. Step back.”

Jeeny: “And we fail at them because they demand humility.”

Jack: “And patience.”

Jeeny: “And faith in people who don’t owe you perfection.”

Jack: “Now that’s terrifying.”

Host: They both laughed again — this time lighter. Outside, the city began to pale toward dawn, the faint suggestion of sunlight creeping along the horizon.

Jeeny: “You ever think leadership’s just a mirror? It shows you who you are when power stops protecting you.”

Jack: “Then I hope I like what I see.”

Jeeny: “You will. You’re learning to let go.”

Jack: “And you?”

Jeeny: “Learning to take up space without apology.”

Jack: “Sounds like balance.”

Jeeny: “Sounds like trust.”

Host: The first light of morning slipped through the glass, spilling gold over the cold steel of the table, softening it — turning it human again.

The quote on the whiteboard caught the glow, the ink shimmering faintly as if awakened by understanding:

“Surround yourself with the best people you can find, delegate authority, and don't interfere as long as the policy you've decided upon is being carried out.”
— Ronald Reagan

Because leadership is not about control,
but confidence in the capable,
not about presence,
but faith in purpose,
and not about power,
but the humility to trust.

Host: As the sun finally broke over the skyline,
Jack and Jeeny stood side by side at the glass,
watching the city begin again —
proof that the world keeps running
not because of those who command,
but because of those trusted to act.