What 35 Kindergartners Taught Me About Training Afterschool Staff
Many years ago, during the summer after I graduated from college, I took a job with a Milwaukee area recreation department. One of my responsibilities was running a t-ball program for 5- and 6-year-olds.
On the first day, I remember looking out at about 35 children who were ready to play. The problem was that I had received exactly zero training on how to manage that many young kids at once. Sure, I had completed a high school teacher education program, but managing a group of energetic kindergartners with plastic bats and balls turned out to be a learning experience of its own. I’ll admit, I was a little terrified. Fortunately, I had a high school assistant who knew a lot more than I did. If she hadn’t been there, I’m not sure I would have come back for day two.
Looking back, the experience was a reminder of something many people in the out-of-school time (OST) field understand very well: working with young people requires knowledge, preparation, skills, and support.
Today’s afterschool and summer programs are doing far more than organizing games and activities. Staff build relationships with young people, create engaging learning opportunities, and often help students navigate social and emotional challenges.
That’s why training and professional development are so important.
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Recently, I spoke with Leighton Cooper, Coordinator of Before and After School Programs for Milwaukee Recreation, about how his organization approaches staff training and why investing in the OST workforce is essential for strong programs. Milwaukee Recreation serves thousands of young people across the city each year, making staff preparation a critical part of ensuring programs are safe, engaging, and supportive. |
Making Training a Priority
For Milwaukee Recreation, training isn’t an afterthought. It’s built into how the program operates.
“We really have an understanding that we have to invest in our staff,” Cooper said. “We hire a large number of people who may not have prior early childhood or afterschool experience, so we’ve had to build a system around how we bring individuals up to speed and really invest in them.”
Milwaukee Recreation offers multiple training opportunities throughout the year, along with two large professional development events that often bring together more than 300 staff members at a time.
The goal is to meet staff where they are.
“There are staff who are brand new to the field,” Cooper explained. “But we’re also seeing staff who have moved beyond that stage and are looking for additional opportunities—college credit, increasing their registry levels, and building their skills so they can better support young people.”
Training Helps Youth Thrive
Training does more than teach strategies. It helps staff feel confident in their roles.
“When we create opportunities to invest in staff training, it builds confidence in them to do the work,” Cooper said. “And there’s nothing like having an employee who is confident and knowledgeable.”
That confidence has a direct impact on young people.
“Young people can spot weaknesses right away,” Cooper said. “But when staff are equipped with strategies and knowledge, they’re better able to engage youth, build relationships, and recognize when a young person might need additional support.”
In the OST field, those relationships are often the foundation of successful programs.
“One of the things we talk about in the afterschool space is that it’s about relationships,” Cooper said. “Young people come to trust us. We become an extension of their support system.”
Building a Stronger Youth Workforce
Milwaukee Recreation has also seen staff grow professionally after receiving training and support.
“We’ve had staff start in entry-level positions and then move into roles within the school district- becoming paraprofessionals or pursuing careers in education,” Cooper said. “Training helps build that confidence and opens doors."
To encourage continued learning, Milwaukee Recreation links professional development to compensation. As staff increase their professional registry levels through training, their pay can increase as well.
“That’s been a very successful strategy for us,” Cooper said.
The Cost of Not Investing
For OST leaders working with limited budgets, professional development can sometimes feel like something that has to wait. But Cooper says the cost of not investing in staff can be even greater.
“There’s a real cost to not investing in training,” he said. “If staff aren’t prepared, you may face higher turnover or situations where staff don’t have the knowledge they need to respond to young people’s needs.”
Today’s young people often face complex challenges—from social-emotional stress to trauma and uncertainty. Staff who work with youth after school need the skills to recognize those challenges and respond appropriately.
“We don’t really have the latitude to not be prepared,” Cooper said.
Finding Creative Ways to Provide Training
While some professional development opportunities require funding, Cooper encourages OST leaders to think creatively about how training can happen.
“Some of the best trainings I’ve had were small, informal opportunities where you could ask questions and learn from someone with experience,” he said.
Community experts, volunteers, experienced staff, and local partners can all play a role in building staff skills. Even simple peer learning opportunities can help strengthen a program.
Partnerships can also make a difference. Organizations like the Wisconsin Out of School Time Alliance (WOSTA) provide professional development opportunities and connect programs with training resources across the state. Cooper noted that these kinds of partnerships help expand what individual programs can offer their staff.
“It’s about being intentional,” Cooper said. “You don’t always need a big budget to create meaningful learning opportunities.”
An Investment in Young People
Across Wisconsin and around the country, OST programs are being asked to support young people in increasingly complex ways. Staff are mentors, teachers, and trusted adults who help students grow academically, socially, and emotionally.
That work requires preparation.
When programs invest in staff training and professional development, they are investing directly in the quality of the experiences young people have after school.
As Cooper put it:
“The better equipped we are, the better experience young people are going to have.”
Thinking back to that summer running a t-ball class, I’m reminded how much more effective I would have been if I had received appropriate training before stepping in front of those kids. Fortunately, today many OST programs recognize that preparation matters.
By investing in the people who work with young people every day, OST leaders can build more confident youth workers who, in turn, create meaningful experiences for young people and help strengthen communities for everyone.

