What was it like to Coach Steve Jobs? Or, was it the other way around?

He was arguably the greatest visionary genius of the modern era globally, his vision magically transformed four industries - personal computer, music, movies and mobile. A legend by the age of 30, tons of pages have been written about his creativity, innovation, intensity and focus. Sometimes called a tough manager and unforgiving, but always non-negotiable and single-minded about his vision.

A lot can be learned from Steve Jobs' two stints at Apple and his style that turned around a faltering computer maker bordering on closure into the creative powerhouse that became the planet's most valuable company.

It was indeed humbling to coach a strong personality and a legend like Steve Jobs.

In moments of deep reflection and personal discovery late in his life as he tried to grapple with his impending death and secure his legacy, Steve Jobs read my first book, "Success Yourself" (1997). It was indeed ironic that he even had the inclination to pick up my book as the book was a massive failure--honestly selling very few copies back then! Perhaps it was even more ironic that he took the 1st version Mattone Leadership Enneagram Inventory (MLEI) that was in the back of the book. Yes, Steve Jobs actually took a paper and pencil test. Call it luck or call it fate (I'll go with the latter), these "fateful" steps led to our coaching work together.

Here is what I learned about Steve Jobs and from Steve Jobs:

1. He was a visionary genius, incredibly creative and a change-agent--but, he could have been a better leader.

Having worked with him as his executive coach, I am 99% confident that if somehow he was able to come back and talk with us, he would admit to the world that he was not the leader he could have been. As we worked together and trust grew, he would reveal to me that he wasn't comfortable with his legacy as he knew he could have been a better leader in his personal and professional life. He shared deep regrets that the "inner-core" work that we did (which in many ways ignited how I work as a CEO coach today--see below) he should have done in his 30's as it would have matured him and his views of leadership. When Steve Jobs died, he accepted that leadership was not about him and it was very much about touching the hearts, minds and souls of the people around him. Deep down in the quietness of his mind I think he always knew this as I came to realize that Steve Jobs did have a huge heart. He very much cared about people but no question he struggled showing this side of himself. I believe his greatest gift--his ability to Think Different and Think Big and incite this same thinking in others--which led to creative thinking, change and positive disruption at Apple, if more positively counterbalanced by his greatest leadership weakness--his discomfort and inability with being vulnerable (I call it "The Vulnerability Decision")--would have ignited his growth as a leader and would have made him (believe it or not) even more creative and innovative. So yes, he was a legend. But his biggest regret was that he could have done more and been remembered for more. As an aside, in my work as a CEO coach, there are many CEO's and government leaders I have worked with who, like Steve Jobs, have never connected with their inner-core--their "soul" (self-concept, character, values, thinking patterns, emotions) to discover the massive gifts and gaps that hide deep within and when they discover these hidden "gems" and we work together to help them translate these discoveries into driving greatness in their outer-core (leadership skills that drive operating success), they become forever changed and better as leaders.

2. He believed in talent, leadership and culture

Go back to Cupertino speech in 1997 when Steve Jobs came back to Apple. He talked about leadership, talent and creating a culture that would sustain Apple well into the future. He put together an amazing A-team of leaders - perhaps a team of incredibly talented and diverse leaders that only he could have led. In each functional area - design, marketing, sales, operations, software, hardware engineering - he brought together people with game changing vision and talent. He served as the glue who brought them together and kept them focused on larger vision, moving ahead relentlessly. Unlike many other leaders, his choices were not compromised by personality, personal preferences or other considerations. He brought together people like Jonathan Ive, Ron Johnson, Tim Cook, Avie Tevanian ... indisputably the hottest talent and in turn they delivered.

3. He built a self-sustaining and winning institution

For the longest time, it seemed as if Apple was Steve Jobs. Articles and analysis were written about how the company could not survive without the vision of its famous co-founder. But Steve proved skeptics wrong by building an enduring institution that bears his innovation DNA and continues to make strides as the world's premier technology company. He did this by: (1) Building a unique culture; (2) Institutionalizing a process of hiring and rewarding the best talent; and (3) Growing their very own product development process.

What Did I Learn From Steve Jobs?

A Private and Courageous Man. Here is a man who suffered from pancreatic cancer for years but he showed up at work early and left late, never taking anything for granted and working his tail off. Everyday. When we worked together, he never once complained about being in pain, about having cancer. I was very deeply moved by the courage and strength he displayed. I was also moved by his sheer diligence and resilience. Yet another irony, my beautiful wife of 40 years, Gayle, in 1997 was first diagnosed with breast cancer (yes the same year Success Yourself was released and failed quickly and the same year Steve Jobs came back to Apple) and after hundreds of radiation treatments and surgery thinking she was now fine, she was diagnosed again in 1999 and went through the same series of treatments again. She never complained though because she was busy raising our 4 children and didn't want them to know. So you can see, in my life, when I see courageous people it impacts me greatly. We need more courageous leaders in the world!

My Intelligent Leadership (IL) Executive Coaching Process. I have created and evolved a philosophy and process of executive coaching that is results-oriented and guarantees that the CEO's I work with do in fact get better. I believe that greatness in a leaders outer-core comes from greatness on their inner-core. I believe that "prescription before diagnosis is malpractice" in medicine and coaching. I don't see enough coaches doing their due diligence in accurately measuring and calibrating both a leaders inner and outer-core and "mitigating risk". Inaccurate diagnosis leads to an inaccurate prescription. In many ways, my early thinking on the IL Executive Coaching Philosophy and Process, which I have evolved into what it is today and what I teach and certify coaches in all over the world, was ignited from my discussions with Steve Jobs. The very tenets of how a successful business operates literally mirrors the tenets and pillars of how leaders get better. I call it the Intelligent Leadership Code, which I am writing a book about right now and will be released in the Fall of 2019. Steve Jobs ignited my thinking on the IL Code and how the inner-core and outer-core connect to determine greatness in leaders. More on this later!