The Way, Broadly: Reflections on The Pathway with Masai Ujiri

Inspired by the first episode of The Pathway — our new series hosted by Fred Swaniker — member of The Room, Mike O’Brien, penned his reflections on Fred’s riveting conversation with Masai Ujiri, President of the Toronto Raptors. Mike is the Director of Research and Investment Strategy for AVR Asset Management in San Francisco and founded a leadership consulting firm, Independence Creek Advisors, focused on organisational dynamics and human nature. Drawing lessons from Masai’s story, he developed a powerful set of First Principles for success.

Mike O’Brien

“Listen, learn, and see where our voices are needed.” This guidance was provided to members of The Room during Fred Swaniker’s first episode of The Pathway. It was offered to our community by Masai Ujiri, a leader who knows the value of winning and has spent his life working to help others pursue their own paths. Masai’s story from Zaria, Nigeria to President of the Toronto Raptors is an inspiring one from which we all can learn.

In the words of Fred Swaniker, the goal of The Pathway is to tell stories that will “demystify the road to success by uncovering the milestones, lessons, relationships and untold serendipity that has enabled the trajectory of the world’s greatest leaders.”

Having the opportunity to hear stories like that of Masai’s is one of the most interesting aspects of The Room. This community is incredibly diverse and filled with remarkable people who are striving to disrupt the status quo and create a better future. Even more exciting is the multitude of paths everyone is taking to reach their full potential; each path is unique and comes with its own important story that needs to be heard.

Stories inspire and engage an audience. They entertain and inform. They are subtle ways of teaching, through analogy, important life lessons and conveying universal truths which bind societies (large and small) together. Whether reading a fictional story, watching a movie, or listening to a podcast, with a little effort by an audience, similarities in stories begin to emerge. It is through recognizing these common themes that we are able to “demystify the road to success.”

The question is, can we do more than listen to these inspiring stories, but also perhaps determine a set of First Principles for true leadership? Are there similar values or traits that members of The Room have developed over the course of their careers to help them achieve success? The Pathway provides us all with a unique opportunity to find out.

For the first episode, I listened to the conversation with my 11-year-old son, Jack. He is a sports fanatic who has become a huge Golden State Warriors fan (sorry Masai). Prior to the start of the conversation, I suspected Masai would use the sport of basketball to convey some important and interesting life lessons. So, while the conversation started early in the morning in San Francisco, my son eagerly woke up to listen with me.

Episode 1 of “The Pathway” with Masai Ujiri

Key Concepts of Masai’s Story

  • Masai opened by recommending young people focus on “the basics” as he called them: Kindness, Respect, and Honesty. These form the framework upon which everything else is built. His dad always told him growing up, “Treat people and treat women the same way you treat your mom.” (After hearing this, my son turned to me and said, “He sounds like our mom; always telling us how we need to be kind and honest.”)
  • He then turned to his love for the game of basketball and the importance of curiosity in life. Multiple times while discussing his playing career for the Nigerian National Team and for various teams in Europe, he used the phrase “I wondered…” Even though he was a young player on the National Team, he wondered why other players would come to him for advice? When playing in Europe, he wondered why he loved the game so much? He wondered where else the game could take him off the court and how he could transfer his love of basketball to a new path?
  • At this point, he decided to make a course correction, shifting his path into the front office, which was neither easy nor straightforward. He had to work hard and stay disciplined. He slept on friend’s couches and worked unpaid internships, starting over at the bottom of a new organisation, and working his way up the ladder.

First Principles in a Pyramid for Success

So many layers to Masai’s story emerged in the first 20 minutes that I wanted to unpack with my son. Some teaching moments include:

  • Masai’s story started with Kindness, through which he was able to develop lifelong friendships with people who would help him along his journey. It also enabled him to attract other talented individuals who wanted to work with him. Through Kindness, positive feedback loops emerge, bringing like-minded people together to build a better future.
  • Beyond Kindness, he never stopped pursuing his Curiosity, always wondering about his current situation, learning about new opportunities, and following up on them. Growth happens when we actively pursue our unique curiosities and explore our imaginations.
  • While vitally important, Kindness and Curiosity are not enough. Successful leaders still face challenges and adversity, but they possess the Discipline to keep pushing forward through the obstacles that inevitably arise.
Mike O’Brien’s First Principles for Success Pyramid

Masai openly admitted that much of his life has been impacted by luck, but as the saying goes, luck comes about when preparation meets opportunity. The combination of Discipline and Curiosity are the preparation, while Kindness helps build relationships and leads to opportunities. With these core concepts as the basics, we are then able to chart our own path towards contributing to society.

What Game Are We Playing?

The conversation then shifted to: What is next? What is Masai Ujiri’s life mission? He talked about wanting to elevate youth, to teach them life skills, and to give them an opportunity through sports. He “found” this calling because he was willing to evolve every day. Even as a successful NBA Executive, he continued to “learn, listen and see where [his] voice is needed.”

Masai’s phrase reminds me of a quote by the British-Ghanaian philosopher, Keane Anthony Appiah: “In life the challenge is not so much to figure out how best to play the game; the challenge is to figure out what game you’re playing.” Initially, Masai focused on how best to play the game of basketball. He then took the skills and values he learned as an elite basketball player and applied them to the front office as a scout, and later, an executive. Now, while continuing to be an executive, he is exploring ways to use his unique skill set to provide the next generation of leaders with opportunities to learn and grow.

For Masai Ujiri, his story is still being written. He continues to learn from those around him while also bringing his voice and perspective to the conversation. His story is one we can all learn from as we search for our own unique paths. First Principles, like being Kind, Curious and Disciplined, help guide us in the direction we aspire to travel. We then need to create our own stories on top of “the basics” with the goal of embarking on a journey that can inspire and uplift others.

A global community of trailblazers on a mission to change the world