When an NBA team selects a 19-year-old rookie in the first round of the amateur draft, the rookie usually feels confident and proud—not to mention flush with millions in cash. This confidence can be threatened when, soon after the player is picked, the team’s shooting coach tells the player that they need to change their shot—the very thing that got them drafted in the first place. It leads to serious questions, such as: Does the team think I’m not good enough after all? Or even: What if messing with my shot makes my shot worse—causing me to get benched or cut from the team? The answers to these questions have huge implications, ranging from public humiliation to going broke.
NBA coaches, therefore, face a version of something called the mentor’s dilemma. The mentor’s dilemma is the difficult choice that many managers and leaders face between being highly critical (but crushing a young person’s spirit) on the one hand, or reducing standards to boost self-esteem (but risk poor performance) on the other. If an NBA coach critiques a player’s shot, it could cause the player to get defensive and refuse to change. If they don’t critique the shot, the player may not live up to their potential—possibly causing both the player and the coach to get fired.
I was surprised at first when I discovered that a professional sports coach, of all people, had a satisfying solution to this mentor’s dilemma. Many people think that the stereotype of a high-performing coach is a yelling, foaming-at-the-mouth chair thrower who enforces impossibly high standards, scares the daylights out of players, and breaks their wills, only to build them back up to be more obedient. After all, in the cutthroat world of the NBA, with enormous sums of money on the line, professional coaches don’t have time to suffer fools.
The NBA coach with perhaps the strongest reputation for being “heart-stopping” and “terrifying” is the legendary Gregg Popovich of the San Antonio Spurs. But did you know that Coach Popovich’s Spurs organization is nothing like that stereotype? Although it’s true that the Spurs maintain exceptionally high expectations, Popovich’s coaching staff also supports players. They’re like a family that quarrels but never doubts their mutual love. Over the decade and a half when the Spurs dominated the NBA, one of Popovich’s assistant coaches was the walking, talking embodiment of the wise-feedback note. His name is Chip Engelland.
Chip Engelland just might be the best coach you’ve never heard of. Players and beat writers have described him as a “genius,” a “master at what he does,” a “guru,” a “shot doctor,” and a “legend” who’s “recognizable by first name alone.” Chip was the captain of Duke University coach Mike Krzyzewski’s first conference-championship-winning team. At the end of his international professional career, Chip broke into coaching by hosting popular—but demanding—youth shooting camps. By the late 1990s and early 2000s, word of mouth got him gigs working with NBA stars Grant Hill, Steve Kerr, and Shane Battier. After two years on staff at a few NBA teams, Chip was hired by Gregg Popovich and the San Antonio Spurs as their full-time shooting coach.
During his 17-year tenure with the Spurs, Chip improved dozens of players’ shots, including those of NBA legends Tony Parker and Kawhi Leonard, and helped them win two NBA championships. Before Parker worked with Chip, Popovich used to think That’s a turnover every time Parker shot. Now, with years of Chip’s coaching, Parker is a Hall of Famer. “He’s the best,” Grant Hill said of Chip. “And that’s why the best team has him on their bench.”
These days, Chip works for a rival team, the Oklahoma City Thunder, who, after two years under Chip, have boosted three-point shooting by 20% and doubled their win total. Chip is a one-man Moneyball strategy. General managers can acquire undervalued players with mediocre jump shots, and after a year or so with Chip, they become all-stars or trade assets. Wherever Chip goes, team success follows.
Does Chip only ruthlessly focus on shooters’ flaws? Does he try to break down a player’s shot and rebuild it from the ground up? Is he all business, impossible to please? Not in the slightest. Here’s how one Thunder player, whose free-throw percentage jumped from the mid-60% range to the lower-80% range, described him:
“Chip’s hard to explain. He’s a wizard with what he does. It’s not unorthodox, but it’s different to every other coach that I’ve had, who’s said, ‘Shoot this way.’ . . . He’s not trying to change my whole shot or make one big difference. It’s just little things.”
In the late 1990s, Steve Kerr was the sharpshooting veteran on Michael Jordan’s Bulls, but his accuracy was falling. Chip helped him realize that he was releasing the ball off his middle finger, not his pointer finger. That was causing a wobble that made his shot unreliable. Soon, Kerr was back to his three-point-splashing ways.
When Chip turned Kawhi Leonard into a superstar by fixing his shot’s release point, Chip said, “I felt his shot didn’t need a full makeover. With just a tune-up, he could become a very good shooter, if not great shooter.” When Leonard was drafted, nobody thought he needed a tune-up. They thought he needed a whole new shot (or a spot on the bench). But Chip saw it differently. Although he was demanding—forcing Leonard to stop slinging the ball over his shoulder—he was careful to support Leonard psychologically by never disrespecting him. Leonard is now a future Hall of Famer.
Shane Battier, former NBA and NCAA champion and Duke basketball player, explained to me what it’s like to be on the receiving end of Chip’s wise feedback. One summer Battier was working at Duke’s youth basketball camp and Chip was in town. Chip offered to put Battier through a workout. At the end, Chip said, “Your shot is good. You’re a great shooter.” That made an impression because at the time NBA draft experts were doubting whether Battier’s shot would translate to the NBA. Although Chip saw Battier’s potential, he also thought Battier could be better with a few tweaks. An instant bond was formed.
“He made me believe I could become an all-NBA shooter. That gave me the confidence to work on my shot,” he told me. How so? Chip didn’t puff up Battier with a compliment sandwich. Chip did it with high standards. He crafted sessions that gradually increased the level of challenge while requiring Battier to maintain the exact same form, whether he was coming off a pick or receiving a pass or shooting off the dribble.
Chip’s main goal was to strip away unnecessary motions that made Battier’s shot unpredictable from one opportunity to the next. He was ruthless in changing small details, such as the position of the pointer finger on the ball or the spread of the thumb to control the ball throughout the shot. He was unrelenting in the need to practice new mechanics in increasingly difficult gamelike situations. While doing so, Chip was exceedingly supportive. After Battier took a shot that Chip knew wasn’t great, he didn’t yell, “Stop, what are you doing? Do it this way!” Instead he asked, “How did that feel?”
Chip respected his players’ autonomy and wanted them to do the thinking because they would compete in the game, not him. Often, Chip says to his players, “Hey, it’s your script, not mine; you write it. I’m just helping you see how you want to tweak it.”
Sometimes, changing a shot was a stressful, nonlinear, frustrating process. Chip didn’t let players quit. He assured them of his support. When Chip first started working with the Spurs’ Tony Parker, he said, “I’m with you for the ups, downs, and all-arounds. I won’t ditch you if it doesn’t work right away.” Then he critiqued Parker’s shot for the next decade, and it got better. Chip takes his players seriously by expecting a lot, but he’s there to support them through the process. That’s why his players trust him enough to take the terrifying leap of faith needed to change their shots.
In the end, Battier developed his shot and carved out a decade-long career in the NBA, capped by a transcendent performance in the decisive game seven of the 2013 NBA finals, during which Battier made six three-pointers, handing the Miami Heat an NBA championship—against Chip’s Spurs. (The Spurs got revenge the next year.) “He’s much more than a shooting coach,” Battier told me. “He’s a basketball psychologist.”
After meeting Chip, I had to agree. “The mentor’s dilemma resonated with me,” Chip told me. “As a coach, I’m constantly trying to get young players to take feedback without feeling threatened.” Ultimately, here’s how Chip resolved the mentor’s dilemma. He explained to me that “it’s fundamentally about the balance between challenge and safety.” Challenge (higher standards) helps players grow in their areas of weakness, while safety (support) helps them trust that they won’t be harmed, emotionally or physically, by stretching out of their comfort zones. That is, you don’t solve the mentor’s dilemma by maintaining impossible standards and crushing someone’s spirit. Nor do you lower standards to the point and give them a self-esteem puff up. Instead, you maintain both high standards and high support, and greater motivation and performance soon follow.
Chip even took the same approach—high standards, high support—with youth players. This reveals the similarities in optimal strategies from kids just starting puberty at age 10 to 25-year-olds just starting their careers. At his youth summer basketball camp, Chip didn’t just expect kids to do the drills. He expected them to lead the drills. By Tuesday of the second week of Chip’s youth camp, the players led the drills, not the coaches. They upheld the camp standards for precision and timeliness, they provided critical feedback, and they held each other accountable. Chip did this because he was trying to give them more than a jump shot. He wanted them to have their own “coaches in their heads” that could keep helping them improve long after they left the camp.
Chip showed me that practices that resolve the mentor’s dilemma can work even in high-pressure situations with serious constraints on our time. Of course, it took a bit of planning for Chip to teach the players how to run the camp, but the second week was a lot easier on Chip and his co-leaders. In fact, when reporting for my book 10 to 25, I repeatedly saw that expert managers, educators, and parents tended to have independent, resilient, proactive young people who didn’t need constant redirection to stay on task. That saved the adults’ time (and frustration) in the long run.
When leaders used the science and art of motivating the next generation, by maintaining high standards and accompanying them with sufficient support, they felt effective and they got the satisfaction of helping others, making their lives both easier and more fulfilling. Furthermore, they could look back on a lifetime of personal success and meaningful contributions to others. It’s a win-win proposition.
From 10 to 25: The Science of Motivating Young People by David Yeager. Used with permission of the publisher, Avid Reader Press/Simon & Schuster. Copyright © 2024 by David Yeager.