The 1 big regret Steve Jobs shared with his coach before he passed

 John Mattone had five coaching sessions with Steve Jobs before he passed. What Jobs admitted in their second session changed forever how Mattone thinks about leadership.

John Mattone didn’t go looking for Steve Jobs. Steve Jobs found him.

In 2010, about a year before he passed, Jobs picked up a copy of Mattone’s book, Success Yourself, and was intrigued enough to reach out. What followed were five coaching sessions that Mattone describes as transformative.

But it was the second session that changed everything.

“He told me that what he was learning with me, if he had applied it in his thirties and forties, he would have been a better father, better husband, better leader,” Mattone told me. “I still get chills sharing that.”

Think about that for a second. One of the most legendary founders in history, someone who literally changed how the world communicates, admitting that the missing piece wasn’t vision or drive or intelligence. It was vulnerability.

That moment became the foundation for everything Mattone has built since. He launched John Mattone Global in 2011, has written eleven books, including five bestsellers, and has now brought his coaching framework to leaders in 55 countries.

When I asked him what separates the best leaders he’s worked with from everyone else, his answer surprised me.

“We have no shortage of intellect in the world,” he said. “There are so many people with high IQs running around, yet we’ve got massive problems everywhere. The heart and soul got lost.”

He calls his approach Intelligent Leadership, and the core idea is that intellect alone creates a lopsided leader. The companies that collapsed during the pandemic were the ones that never invested in heart and soul before the crisis hit. The ones that thrived had leaders who understood that drive and compassion aren’t competing forces. They coexist. And when they do, culture gets stronger.

But here’s where it gets practical.

Mattone treats leadership development the way a business treats strategy. He starts with measurement, using 360 assessments, behavioral observation, and objective scoring to calibrate what he calls the inner core. That includes self-image, values, thinking patterns, belief systems, and character. Then he maps how that inner core drives the outer core, which is how a leader actually shows up every day.

From there, he co-creates a strategy with the leader. What are the gifts we can make stronger? What’s getting in the way? Who are the stakeholders we need to involve for accountability?

“It’s literally a parallel universe to building a business,” he told me. “If you want to become the best, you have to execute a strategy. You have to measure. You have to be held accountable.”

One question he asks every executive early on stops most of them cold: What is the vision of the essence of the leader you must become?

Not want to become. Must become.

“They look at me and say, I’ve never been asked that before,” he said. “And that’s when the real work begins.”

What struck me most is that Mattone doesn’t position himself above the people he coaches. He talks openly about his own failures. He spent ten years running a speaking business that wasn’t working. He struggled for years after the Jobs sessions to even figure out how to bring his coaching to the world. He told me he initially thought he had just gotten lucky.

“Looking back, I don’t think I was lucky,” he said. “I think it was meant to be.”

He also credits his wife, Gail, as his number one advisor across 46 years of marriage. And he told me about meeting his uncle Joseph Mattone, a famous New York attorney, at age 85. Joseph looked him in the eye and told him: you’ve accomplished a lot, but you have to give back. That conversation led Mattone and his wife to create endowed scholarships at the University of Central Florida.

“The greatest mentors believe in you more than you believe in yourself,” he said. “You’ve got to catch up.”

I asked him what Steve Jobs taught him that he carries with him every day. His answer came back to that one word.

Vulnerability.

“It took dying from pancreatic cancer for Steve Jobs to embrace being vulnerable,” Mattone said. “You don’t have to wait for that. You can make the decision right now.”

For founders reading this, that might be the most important takeaway. We celebrate drive, ambition, and toughness. We build cultures around those traits. But the leaders who sustain greatness over decades are the ones willing to slow down, go deep into their own souls, and admit where they’re falling short.

The irony is that the person who taught John Mattone that lesson was Steve Jobs, the founder we all associate with relentless, uncompromising intensity.