Guide + Release

Letting mentees practice and struggle.

Jason + Melissa

Jason’s life has been defined by sports, first as the son of a coach, and later as a collegiate and semi-professional athlete. But he came to work in high school athletics almost by accident. His plan had been to use the principles of sports to impact lives at a higher level. A former college athlete, he was well into the college baseball coaching career he always wanted, serving as an assistant at the US Naval Academy, when his life changed. 

A family member’s illness prompted him to reconsider his career path, and he put the transient life of a college coach aside for a more conventional work-life balance. He became a coach and later the director of athletics for a network of charter schools in Chicago. 

When his life took this unexpected turn, he planned to use the principles of sport to impact other people: “My model was my father. He coached college and high school basketball for over 30 years. I grew up watching his presence, command, intelligence, and ability to change the limits of his players. I saw the trust he built in players while also maintaining incredibly high expectations of them. I read letters they wrote to him as they became men and fathers. When I saw that impact, I knew I wanted to be a coach and be a leader who could potentially create the same impact. I learned from my father that it was possible to make people believe in themselves [to] a degree they never thought possible.”

It was in his new role in Chicago that Jason met Melissa, a young college graduate in her first job as an athletic administrator in the network. Melissa is a former athlete, and she dove into coaching as well as administrative duties in the network. 

But she was overwhelmed. She was coordinating scheduling, referees, compliance, and budgeting for a growing network of schools. She lead meetings and discuss limitations on budgets and other resources, often as the youngest person in the room, and one of few women. She was learning to juggle these duties while navigating the transition from college to the workplace.  

Jason understood that putting his coaching principles into practice as a mentor meant as much listening as telling, and as much observing as doing.

Their supervisory relationship began to develop into mentorship in their weekly, one-on-one meetings. Jason said these served both to help Melissa understand the demands of the role, and to get to know her. Both of them described the importance of a mentor seeing their mentee as a whole and complete person, and believing in their potential both in and beyond their current role.

Melissa recalled she not only felt overwhelmed by the role, but also “stuck” at this point in her life and career. Jason described simultaneously seeing Melissa’s needs for support, but also her potential. “She had to grow to a place where she believed in herself as much as I believed in her,” Jason told me.

He began attending the coaches’ meetings Melissa was leading, and letting her facilitate—and at time struggle. Jason said he sometimes stepped in to offer guiding principles, or nudge the conversation to a more productive place when coaches complained about a lack of certain resources. He intervened in one particularly contentious budget discussion, for example. But, as Melissa recalled, he largely “gave me a lot of freedom to do things by myself.” In their weekly meetings, they spent time talking about work, but also Melissa’s personal well-being and her long-term goals beyond her current position.

“He listened and challenged me,” Melissa remembers, noting that he clearly saw significant potential in her and conveyed that he wanted more for her long term in her life and career than her current job.

Jason encouraged Melissa to practice her remarks to build her confidence speaking in front of the group. He helped her attend conferences to support her learning and growth. Mostly, she recalled, he encouraged her to define her own goals, her potential for growth, and not just her limitations: “We talked about how what I’m intimated by doesn’t define me.” 

Jason was also learning and reflecting throughout this process, working on a graduate degree in leadership.

In time, their conversations about her growth turned to graduate school. It was Jason who ultimately encouraged Melissa to pursue her dream program out of state, and far from the work he was helping her to do in Chicago.

Photo by jesse orrico on Unsplash

Jason was an athlete who grew into a coach and later a mentor. This transition is an important one to understand. Athletes do the tasks on the court, the field, or the track. Coaches, on the other hand, need to understand enough about how various other people come to understand and to do those same tasks and can support others in multiple ways to perform. Mentors support this development within and beyond a task, looking at a whole person.

The late early childhood educator and scholar of early childhood education, Ruby Takanishi, called this being an “articulate practitioner” or someone who is skilled at both their trade and who can talk about it in a clear way with less experienced colleagues¹. They do not just model, but they are explicit in articulating and instructing in the key principles that have been the keys to their success. 

Great mentors are articulate practitioners. But, like great coaches, they also understand that people can take many paths to a golf swing or a jump shot, and what the common challenges are that people experience along the way. Beyond teaching, they know how to step back, observe, and have enough belief in their mentees to let them implement what they have talked about in their own way.

This notion has gained traction in teaching—especially in math classrooms—where teachers are exploring ways to get students to do more of the cognitive heavy lifting with more challenging mathematics. Math teachers call this idea “productive struggle,” or getting students to work hard individually or in groups on challenging questions while a teacher offers support, but not direct instruction². The assumption is students are more ready for more complex math if they have the learn to grapple with problems and not have the teacher come and help solve their frustrations right away. Beyond explaining, a mentor needs to be able to let a mentee get on the court and miss some shots as part of their learning process.

While Jason tried to teach and model for Melissa, he also listened to her and let her try things in meetings and communications with their coaches. In Melissa's words, “he never felt like he was my supervisor. He was there to support and invest in me.” Great mentors support and give feedback, Melissa said, but like Jason they are there to help you not only do your job, but also to help you grow into, and then out of, that role.

Jason put this philosophy into practice with Melissa as a skilled basketball coach: He offered principles, but also had to step back and let her play.

1.  Takanishi, R. (1981). Early Childhood Education and Research: The Changing Relationship. Theory Into Practice, 20(2), 86–92. http://www.jstor.org/stable/1476295

2.  Warshauer, H. K. (2015). Productive struggle in middle school mathematics classrooms. Journal of Mathematics Teacher Education, 18, 375-400.