These leadership takeaways are part of a new primetime series, CNBC Leaders Playbook, premiering January 7 at 10 p.m. ET/PT. Hosted by Julia Boorstin, the series goes inside the minds of the world’s top business leaders to reveal how lasting success is built.
1) Fake it, then earn it
Media mogul Barry Diller admits that even the most powerful executives start out with no idea what they’re doing.
His philosophy: fake competence until you’ve actually earned it — because overthinking or waiting until you “know enough” can lead to missed opportunities and potentially even failure.
You do fake it as you go. And then…you’re figuring it out as you go. And eventually, there it is. No more faking.
Barry Diller
IAC/Expedia Chairman & Senior Executive
2) Embrace creative conflict
For Diller, the best way to vet an idea is to get a group of people around a table and let them argue passionately about their idea. He calls it “creative conflict.”
Those differing voices and perspectives create what he calls a “brew” – and if you’re truly listening, he says, that brew can lead you to the right decision.
But he warns cynicism poisons creative conflict, shutting down insight before it can emerge – which is why he insists on leaving it out of the room and, instead, listening with an open mind.
You cannot be cynical. Cynicism kills everything.
Barry Diller
IAC/Expedia Chairman & Senior Executive
3) The secret to executing ideas
For Diller, great ideas die on the vine because leaders don’t push them hard enough.
After ideas are debated through creative conflict and filtered by instinct, Diller credits “blind willfulness” as the secret to making ideas come to fruition.
That doesn’t mean ignoring feedback or being stubborn.
For him, it means committing fully to the direction and having the force of will to make it happen even when obstacles and doubt show up.
Without that final push, he says, even the best ideas stall. Diller posits that ideas are nothing without the sheer force of will to push them into reality — a line that captures his relentless drive to bring novel ideas to fruition across six decades of leadership.
Unless you are willful, which means you will impose your will on whatever it is, nothing is ever going to happen.
Barry Diller
IAC/Expedia Chairman & Senior Executive
4) Bet on long-term truth over short-term fear
Right after 9/11, when air travel collapsed overnight, many people thought Diller’s decision to move forward with a deal to buy Expedia made no sense.
Despite that sentiment, in 2001 Diller pressed ahead and bought the platform for $1.4 billion.
That decision, he says, was anchored in the belief that the crisis in the travel business was temporary and the long-term opportunity would remain.
It was a simple, existential truth — as long as people live, they will travel.
Someone in the room — when we were talking about this at the height of the argument — said, ‘If there’s life, there’s travel.’ And as soon as I heard it, I said, ‘close [the deal]… I’m betting on that.’
Barry Diller
IAC/Expedia Chairman & Senior Executive
Watch Barry Diller’s interview on CNBC Leaders Playbook — a new prime-time series hosted by Julia Boorstin, featuring candid conversations with the world’s top business leaders on how lasting success is built.
Episode premiere (Barry Diller): Jan. 14 at 10:30 p.m. ET/PT on CNBC.
All new episodes Wednesdays.






