Shark Tank’s Kevin O’Leary shares the one trait every great leader needs

Shark Tank star and entrepreneur Kevin O’Leary has shared what he believes is the single most critical trait for successful leadership: the ability to manage doubt without letting it show.

O’Leary’s advice about projecting confidence in uncertainty comes at a time when many business leaders are grappling with shifting markets, inflation and employment volatility.

In a video posted to his official Instagram account on October 25, O’Leary discussed how leaders must project confidence even amid uncertainty.

Shark Tank's Kevin O'Leary on what makes a great leader

O’Leary said in the clip, 

“When you're a leader in a business, you're going to have to deal with doubt, your own doubt about whether the direction you're going is the successful one. You don’t know with certainty. You can’t know with certainty because the markets can change on you overnight.”

O’Leary, best known as one of the original investors on Shark Tank, emphasized that great leaders cannot allow internal hesitation to weaken their outward focus.

He continued,

“But you can't emulate that you don't know, you have to be 110% committed to the path you're plotting for the team. If it has to change, you'll change it, and they will trust you that you have the ability to distinguish what the signal is and you have your ear to the track.”

The investor, who has built a reputation on his sharp business instincts and direct style, underlined that leadership is largely about perception and trust.

O’Leary said,

“Part of leadership is understanding what's coming at you and not letting it run you over. If the team believes you're good at that, they will follow you even though they know there must be uncertainty—but you don't show it. Internalizing that doubt is difficult sometimes, but you can't let it show.”

The Shark Tank judge’s remarks align with his long-standing philosophy on business strategy and resilience, which he has shared throughout his career. O’Leary has previously stated,

“Vision is nothing without a plan to execute it; you may lose your wife, you may lose your dog, your mother may hate you. None of those things matter. What matters is that you achieve success and become free. Then you can do whatever you like.”

Known on Shark Tank as “Mr. Wonderful,” O’Leary built his entrepreneurial empire through strategic investments and his co-founding of the educational software company SoftKey, which later became The Learning Company.

The company was sold to Mattel for $4 billion in 1999, launching O’Leary to international prominence. On Shark Tank, he is known for his blunt assessments and high standards for business leadership. 

“I go out there, I want to kill the competitors. I want to make their lives miserable. I want to steal their market share. I want them to fear me, and I want everyone on my team thinking we’re going to win.”

His insistence on certainty in demeanor—if not in reality—reflects his ongoing message that successful founders must safeguard workplace morale by providing direction even in times of crisis. In another quote from his past appearances, O’Leary said,

“Nobody has a monopoly on good ideas. Risk represents everything you have to lose. But risk could also lead toward reward.”

Over the years, Shark Tank has provided a national platform for O’Leary’s direct leadership messages, influencing a generation of emerging entrepreneurs.

His on-show discussions often stress the importance of accountability and focus. He once said,

“Whatever you pay attention to grows.” 

His leadership message also resonates with his approach on Shark Tank, where he regularly advises contestants to operate with both conviction and adaptability. 

“If I’m going to invest in you, I want to see that you can take a punch.”

O’Leary once told a contestant, referencing his core belief that emotional resilience equals business longevity.​

According to O’Leary, effective entrepreneurs must manage both perception and change, shaping their teams’ confidence. 

Stay tuned for more updates.