Why One-on-Ones Aren't Broken: Manager as Multiplier
leadership
financial services
October 17, 2025· 2 min read

Why One-on-Ones Aren't Broken: Manager as Multiplier

Discover how strategic one-on-ones compound human capital through coaching and connection, transforming managers into multipliers rather than problem solvers.

Brian Chesky says one-on-ones are broken. "You become like their therapist," he told Fortune.

I couldn't disagree more.

Chesky believes "almost no great CEO in history has ever done them." When employees own the agenda, they bring up topics managers don't want to discuss. Important insights get trapped in private conversations instead of benefiting the whole team.

Here's what he's missing:

The goal isn't therapy. It's transformation.

Every one-on-one is a chance to compound human capital. Not by solving their problems. By unlocking their potential.

Think about the math:

Make someone 1% better each day? That's 37x growth in a year. Not through motivational speeches. Through removing roadblocks. Through targeted coaching. Through actually listening.

The enterprises that win understand this shift:

Old model: Manager as problem solver New model: Manager as multiplier

Old model: Information hoarding in meetings New model: Wisdom sharing through coaching

Because here's what keeps me up at night:

We're optimizing meeting structures while missing the human element. We're scaling processes while shrinking connection. We're building efficient organizations filled with disengaged people.

Chesky's right that topics arise in one-on-ones that others should hear. So share the patterns. Not the problems. Extract the insights. Not the gossip. Build systems from the struggles.

But don't throw away the format because you're using it wrong.

One-on-ones aren't where you become their therapist. They're where you become their catalyst.

The compound ROI on making your people better? Infinite.

What's your take on one-on-ones?

Stay Ahead of Disruption
Join professionals navigating blockchain and AI transformation. Get weekly insights delivered to your inbox.

More Leadership Posts

October 18, 2025

Why Toxic Leadership Costs You Top Talent

Discover how outdated management practices—no WFH, banned conversations, 100-hour weeks—drive your best people to compet...

October 10, 2025

Financial Products Are Dissolving Into Everything

NYSE and CME are blurring lines between prediction markets, sports betting, and derivatives. Financial services leaders ...

October 14, 2025

AI Killed the Maker/Manager Schedule

Solo builders with AI are shipping faster than Fortune 500 teams. Discover how federated collaboration replaces traditio...