In theory, there should be no limit to what we can learn from mentors who have wide experience. But in practice, this is rarely the case. No better can this be seen than in Freddie Roach’s growth as a mentor.

By 2012, Freddie Roach had compiled an unprecedented winning percentage and had been awarded Boxing Trainer of the Year an astounding 5 times. But in 1978, Roach was just a promising lightweight boxer in search of a trainer that could elevate him to the next level. Freddie quickly settled on Eddie Futch, one of the most legendary boxing coaches in the field.

Futch had a magnificent résumé. As a young man he had sparred with Joe Louis. Barred from turning professional because of a heart murmur, he became a trainer, working later with some of the most illustrious heavyweights, including Joe Frazier. He was a quiet, patient man who knew how to give precise instructions; he was a master at improving a fighter’s technique. Under his guidance, Roach advanced quickly, winning his first ten bouts.

Soon, however, Roach began to notice a problem: in training he listened intently to what Futch had to say, and put it into practice with relative ease. But in actual bouts, the moment he exchanged blows with his opponent, he would suddenly throw out all the technique he had learned and fight on pure emotion. Sometimes this worked, but he took a lot of blows, and his career started to sputter. What surprised him several years into the process was that Futch did not really seem to notice this problem of his. With so many fighters in his stable, he tended to keep his distance; he did not give much personalized attention.

Finally, in 1986, Roach retired. Living in Vegas and moving from one bad job to another, in his off-hours he began to frequent the gym where he had trained. Soon he was giving advice to fighters and helping out. Without getting paid, he became a de facto assistant to Futch, even directly training a few of the fighters himself. He knew Futch’s system well and had internalized many of the techniques he taught. He added his own wrinkle to the training sessions. He took the mitt work—the large padded gloves that a trainer uses in the ring to practice various punches— to a higher level, creating a longer and more fluid practice session. It also gave Roach a chance to be more involved in the action, something he missed. After several years he realized he was good at this and left Futch to begin his own career as a trainer.

To Roach, the sport was changing. Fighters had become faster, but trainers such as Futch still promoted a rather static style of boxing that did not exploit these changes. Slowly, Roach began to experiment with the whole training dynamic. He expanded the mitt work into something larger, a simulation of a fight that could go on for several rounds. This allowed him to get closer to his fighters, to literally feel their full arsenal of punches over time, to see how they moved in the ring. He began to study tapes of opponents, looking for any kind of pattern or weakness in their style. He would devise a strategy around this weakness and go over it with his boxers in the mitt work. Interacting so closely with his fighters, he would develop a different kind of rapport than what he had with Futch—more visceral and connected. But no matter the boxer, these moments of connection would inevitably fade in and out. As they improved, the fighters would begin to tune him out, feeling like they already knew enough. Their egos would get in the way and they would stop learning.

Then, in 2001, an entirely different kind of fighter came through the doors of Roach’s gym in Hollywood, California. His name was Manny Pacquiao, a 122-pound left-handed featherweight fighter, who had had some success in his native Philippines but was looking for a trainer in the States, someone who could elevate his game to another level. Many trainers had already passed on Pacquiao—they watched him work out and spar, and he was impressive, but there was no money to be made from someone in such a lightweight division.

Roach, however, was a different breed of trainer. He immediately went to mitt work with Pacquiao, and from the first punch he knew something was different about this fighter. It had an explosive, intense quality, a snap unlike any other fighter’s. The other trainers had only watched and could not feel what he now felt. After one round Roach was certain he had found the boxer he had always been looking to train, one who could help initiate the new style of boxing he wanted to introduce. Pacquiao was equally impressed.

To Roach, Pacquiao had the material to be an unbeatable fighter, but he was somewhat one-dimensional: he had a great left hand and not much else. He was constantly looking for the knockout blow, to the exclusion of everything else. Roach’s goal was to transform Pacquiao into a multi-dimensional beast in the ring. He began with heavy mitt practice, trying to develop a powerful right hand and more fluid footwork. What immediately struck him was the intensity with which Pacquiao focused on his instructions and how quickly he caught on. He was eminently teachable, and so the progress was more rapid than it had ever been with any other fighter. Pacquiao seemed to never tire of training or to worry about overdoing it. Roach kept waiting for the inevitable dynamic in which the fighter would begin to tune him out, but this never came. This was a boxer he could work harder and harder. Soon, Pacquiao had developed a devastating right hand, and his footwork could match the speed of his hands. He began to win fight after fight, in impressive fashion.

As the years went by, the relationship began to evolve. In their mitt work, Pacquiao would adjust or improve upon the maneuvers Roach had been developing for the next bout. He gave input on Roach’s strategy, altering it on occasion. Pacquiao had gained a sixth sense for what Roach was getting at and could take his thinking further. On one occasion Roach watched Pacquiao improvise a maneuver on the ropes in which he ducked out and attacked a fighter from an angle instead of head-on. To Roach, this was a move that made instant sense. He wanted to develop this further into a whole new possible style of fighting. He was now learning almost as much from Pacquiao. The previous trainer-fighter relationship had now morphed into something interactive and alive. To Roach, this meant that they could move past the seemingly inevitable plateau for fighters in which it all became stale and opponents would catch on to their weaknesses.

In the mentor-mentee dynamic, there are several reasons that the relationship can become flat; it is difficult for us to maintain the same level of attention that we had in the beginning. We might come to resent their authority a little, especially as we gain in skill and the difference between us becomes somewhat less. Also, they come from a different generation, with a different worldview. At a certain point, some of their cherished principles might seem a bit out of touch or irrelevant, and we unconsciously tune them out. The only solution is to evolve a more interactive dynamic with the mentor. If they can adapt to some of your ideas, the relationship becomes more animated. Feeling a growing openness on their part to your input, you are less resentful. You are revealing to them your own experiences and ideas, perhaps loosening them up so their principles don’t harden into dogma.

Such a style of interaction is more in tune with our democratic times and can serve as something of an ideal. But it should not go along with a rebellious attitude or a lessening in respect. The dynamic sketched out earlier in this chapter remains the same. Like Pacquiao, you bring to the relationship the utmost in admiration and your total attention. You are completely open to their instruction. Gaining their respect for how teachable you are, they will fall a bit under your spell, as Roach did with Pacquiao. With your intense focus, you improve in your skill levels, giving you the power to introduce more of yourself and your needs. You give them feedback to their instruction, perhaps adjust some of their ideas. This must begin with you, as you set the tone with your hunger to learn. Once a back-and-forth dynamic is sparked, the relationship has almost limitless potential for learning and absorbing power.

Working together in this way, Roach was able to transform this one-dimensional, relatively unknown fighter into perhaps the greatest boxer of his generation.

What you’ve just read comes from the #1 New York Times Bestseller, Mastery by Robert Greene, now out in paperback. In it, Robert Greene studies the lives of current and historical masters—from Napoleon to entrepreneur Paul Graham, Temple Grandin to Charles Darwin—and reveals their secrets. Will you follow the path to mastery?