Some people are born leaders. They take control of difficult situations with confidence. They inspire others naturally. And it all seems to come so easily. But leadership isn’t a natural trait for everyone. Many parents wonder how to teach your child leadership skills, especially during the middle school years when confidence and identity are still developing.
And the good news is you can. Research has shown that the leadership abilities that appear to be inborn traits can actually be developed and nurtured during childhood:
- Researcher Carl Brungardt found in 1997 that leadership skills, “like the ability to work with others, self-confidence, and assertiveness can emerge from childhood experiences.”
- Two leadership experts wrote in 2007, “Although important leadership skills develop through one’s life, many of these skills and talents begin to develop at a much earlier age than where our society tends to focus the majority of leadership development efforts.”
This research shows that parents can play a key role in teaching children leadership skills at early ages. But how can you teach your child leadership skills during middle school? Here are a few practical ways, along with how junior boarding schools and Massachusetts private schools like Fessenden support leadership development. These ideas come from Brandon Odom, Head of Middle School at Fessenden, one of the top Massachusetts private schools.
1. Help him find leadership opportunities with younger students.
Middle schoolers often feel “betwixt and between,” Brandon says. They’re not quite old enough to do the things they really want to do and yet they’re not quite young enough to be the baby of most groups. So when they have the opportunity to be the older, experienced ones, for a change, they relish it.

“You could find leadership opportunities for your child with younger siblings, cousins, neighborhood kids, or sometimes younger classes in school, in church, or in temple,” Brandon suggests. “Sometimes libraries are looking for middle schoolers to come in and read out loud to the younger kids.” These experiences give middle school students a sense of responsibility and confidence.
Brandon has seen this work well at The Fessenden School.
“Our Middle School boys have lunch with our kindergartners and read picture books with them, and they love it,” he reports. “The kindergarten students love it too. They shout, ‘Oh, there’s my reader!’ when they see them in the hall.”
2. Encourage leadership through service and initiative.
One of the most effective ways to teach your child leadership skills is by encouraging service. Leaders rarely start at the top, as you may have experienced in your own life as a professional, volunteer, or community member. Frequently, leadership begins by simply being willing to serve, to “lend a hand,” when a hand is needed.
“I’m always interested in boys who lead by volunteering or staying to help after an event and pick up. Or boys who are willing to serve on a committee that needs help, but they’re not going to be the one in charge of it,” Brandon says. “They’re not running for office, but those are the boys that are going to move the world some day. The ones who just think, ‘What needs to be done in a situation? I can do it.’” This kind of leadership builds initiative and long-term confidence.
By volunteering, kids must take initiative, make decisions, and collaborate with others, even if they're not in charge. That's why students often have opportunities to volunteer in various capacities at many junior boarding schools. Through these experiences, kids learn to navigate real-world challenges, practicing empathy, problem-solving, and communication. These are all invaluable skills that will equip them to be future leaders.
3. Choose a school that actively teaches leadership skills.
If you’re thinking about a Massachusetts private middle school, look for a school where developing leadership skills is a core part of the curriculum.
At The Fessenden School, for example, every sixth grader leads the Middle School’s morning meeting at least once, “and sometimes,” twice a year.
“I help them script it; they orchestrate it. They get up front. They hold the microphone. They make sure it runs according to schedule,” Brandon describes. “And as teachers, we just sit and watch. We don’t feel like we need to orchestrate it because we have confidence the sixth graders will be leading.”
Additional ways to teach your child leadership skills
Parents can continue to teach leadership skills at home by encouraging decision-making, setting goals, and allowing children to take ownership of responsibilities.
Simple actions like planning activities, solving problems independently, and reflecting on experiences can help with leadership development.
Here are a few online resources for helping your child develop leadership skills.
Teaching confidence at Fessenden
Helping your child develop leadership skills takes consistent practice, support, and the right environment. At Fessenden, leadership development is built into daily student life, giving boys real opportunities to lead, collaborate, and grow.
Schedule a visit to see how our junior boarding school and Massachusetts private school programs help students build confidence and leadership skills that last a lifetime.
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