From my experience, the best advisors help in three ways:

Host: The office was nearly empty, save for the low hum of computers and the faint, rhythmic ticking of the clock. Beyond the glass walls, the city pulsed with the pale blue light of early evening — a sea of towers and windows reflecting each other endlessly. Papers lay scattered across the long wooden table, the ghosts of a long day’s work.

Jack sat at the end, his tie loosened, sleeves rolled up, the kind of weariness in his posture that didn’t come from tiredness, but from thinking too long. Jeeny leaned against the far wall, arms crossed, her dark eyes watchful, the faintest curve of a smile tugging at her lips.

Between them, written on a whiteboard in bold, uneven handwriting, were the words of Margo Georgiadis:
“From my experience, the best advisors help in three ways: encourage you to look at the problem or opportunity from multiple angles; help you balance the tug of the short-term with important long-term priorities; and ask the tough questions you need to know to reach the best solution.”

Host: The fluorescent lights buzzed overhead. The silence was the kind that follows too many hours and too much caffeine — stretched thin, delicate, expectant.

Jeeny: “She’s right, you know. The best advice isn’t supposed to make you comfortable. It’s supposed to make you see.”

Jack: (leans back, dryly) “Or make you doubt yourself so much you end up where you started — but more exhausted.”

Jeeny: (smiling) “You always equate doubt with weakness. Maybe it’s the beginning of wisdom.”

Host: Jack’s eyes flicked to the whiteboard, tracing the words as though looking for a crack in them, a flaw to dismantle. His voice carried the quiet edge of a man who’d seen too many illusions dressed up as strategy.

Jack: “Advice is easy, Jeeny. Everyone wants to play advisor — to sound wise without having to risk anything. Most of them don’t care about your outcome; they care about being right when you fail.”

Jeeny: “You’re thinking of critics, not advisors.”

Jack: “Same species, different camouflage.”

Host: A faint laugh escaped her, soft as the echo of wind against glass. She pushed off the wall, stepping closer to him, the light catching the curve of her cheek, the small shadow under her eyes — exhaustion mixed with stubborn grace.

Jeeny: “No, Jack. A real advisor isn’t there to be right — they’re there to make you think right. The ones who ask the questions you don’t want to answer. The ones who see what you’ve decided not to.”

Jack: “You mean the ones who annoy you into clarity.”

Jeeny: “Exactly. The tough ones. The ones who care enough to be inconvenient.”

Host: Jack’s hand went to his chin, fingers tracing the faint stubble there, his thoughts heavy and deliberate. Outside, the light began to shift, dipping toward dusk, turning the glass walls into mirrors.

Jack: “You ever had one of those?”

Jeeny: “An advisor?”

Jack: “A real one. Someone who asked you the questions that hurt.”

Jeeny: (after a pause) “Yes. Once.”

Jack: “What happened?”

Jeeny: “I stopped liking them. Then I realized they were right.”

Host: A small smile ghosted across Jack’s lips — not amusement, but recognition. He turned slightly, studying her reflection in the glass rather than her face.

Jack: “And you became one yourself.”

Jeeny: “Maybe. Or maybe I just learned that truth isn’t something you say; it’s something you help someone see.”

Host: The clock ticked louder in the silence that followed, as though measuring not time, but thought.

Jack: “You know what the problem is, Jeeny? Everyone wants long-term wisdom, but they live in short-term worlds. Deadlines, deliverables, quarterly reports — no one’s got time to think in decades anymore.”

Jeeny: “That’s exactly why advisors matter. They remind you that the future still exists. That the things you do today will either haunt you or hold you later.”

Jack: (quietly) “And what if the future never comes?”

Jeeny: “Then at least you acted as if it would. That’s what separates vision from vanity.”

Host: Her voice had softened, but her words landed heavy, like rain against glass. Jack looked down, his hands folded, his jaw tight — the picture of a man caught between reason and regret.

Jack: “You ever think advice can ruin someone?”

Jeeny: “Bad advice can. Or good advice given at the wrong time. But the real danger isn’t the advice — it’s when you stop seeking it.”

Jack: “Because that’s when arrogance sets in.”

Jeeny: “Exactly. Or fear. The belief that you’ve seen all there is to see. Cohen said it once — liberalism is an attitude of questioning, not dogma. Advising is the same — it’s a practice of curiosity.”

Jack: “And exhaustion.”

Jeeny: (smiling) “Sometimes both.”

Host: The light dimmed further. The city below them now shimmered like a circuit board, veins of light crossing through darkness. The faint hum of air conditioning filled the spaces between their words.

Jack: “You ever think about how lonely good advice can be?”

Jeeny: “Because people hate the truth?”

Jack: “Because people hate hearing what they already know.”

Host: She studied him — the sharp edges of his face, the tiredness behind the cynicism. Then, slowly, she sat across from him, resting her elbows on the table, her voice dropping to a quiet, almost conspiratorial tone.

Jeeny: “Maybe that’s why advisors exist — to make you face what you already know but don’t want to admit. Not to teach, but to mirror.”

Jack: “And when the reflection’s ugly?”

Jeeny: “Then it’s doing its job.”

Host: The faint hum of laughter rippled between them — not joy, but understanding. It was the kind of laugh that two people share when they realize the world’s both simpler and harder than they want to admit.

Jeeny: “The best advice I ever got wasn’t even advice. My mentor once looked at me and said, ‘You’re asking the wrong question.’ It took me years to understand what she meant.”

Jack: “And what did she mean?”

Jeeny: “That sometimes, the answer doesn’t matter. What matters is learning how to ask better.”

Jack: “That’s the whole game, isn’t it? Asking better questions. The problem is, it’s easier to give advice than to live by it.”

Jeeny: “Of course it is. That’s why the wise are rarely the richest — and the richest rarely the wisest.”

Host: A faint smile tugged at Jack’s lips again, the kind that almost became laughter but turned back into silence instead. The rain outside began to fall — soft, insistent, steady — tracing long streaks down the glass, blurring the world beyond.

Jack: “Maybe what we really need aren’t advisors, but mirrors that talk back.”

Jeeny: “Maybe that’s what we’re doing right now.”

Jack: (after a long pause) “Then I guess you’re my mirror tonight.”

Jeeny: “Only if you can handle the reflection.”

Host: The lamp flickered. The room felt smaller now — more intimate, the kind of quiet that turns from fatigue into revelation. Jack’s eyes met hers, and for once, there was no defense in them.

Jack: “Alright, Jeeny. Then ask me one of those tough questions. The kind that hurts.”

Jeeny: (softly) “Why are you still fighting battles you’ve already won?”

Host: The words landed like a slow, deep echo. Jack didn’t answer at first. His eyes dropped to the table, to the faint reflection of the whiteboard’s writing in the polished surface.

When he finally spoke, it was quieter than the rain.

Jack: “Because winning doesn’t feel like I thought it would.”

Jeeny: “Then maybe it’s time to redefine what victory means.”

Host: The two sat in silence after that, the city lights flickering around them like the heartbeat of something vast and unknowable. The whiteboard glowed faintly in the dimness — the ink of Georgiadis’s quote beginning to smudge slightly under the moisture in the air, as though time itself was erasing it gently, word by word.

Jeeny closed her eyes, and when she spoke, it was almost a whisper.

Jeeny: “Maybe the best advisors aren’t the ones who tell you what to do. They’re the ones who remind you you’re still capable of choosing.”

Jack: (nodding slowly) “And the best advice… is the kind that doesn’t end the conversation.”

Host: Outside, the rain began to fade. The city shimmered through the wet glass, blurred but alive. Jack and Jeeny sat there, surrounded by the faint hum of machines, the afterglow of hard questions, and the quiet pulse of something like clarity.

And for the first time that night, they didn’t need more advice.
Only the courage to keep asking.