a dark-skinned boy with very short hair and a navy blue vest over a white short-sleeved shirt and tie sits at a desk in a classroom, writing with a pencil on paper. there are four other young people and a green chalkboard in the background.
Supporting families in the transition to high school
with Big Shoulders Fund

Big Shoulders Fund provides support to inner-city schools which provide a quality, values-based education for Chicago’s children.


Chicago, IL

Topic Area


Project Type

Digital & Physical Tools

Transitioning from middle school to high school can be confusing; it’s hard to keep track of events and deadlines, learn about options and requirements, find the best fit, and do all of this within a limited time period. Big Shoulders Fund saw an opportunity to make the process more transparent.

We engaged with students and academic stakeholders to understand the barriers to accessing high school. We then designed a website using an iterative process that allowed us to build it alongside users and specifically address the challenges they faced.

Our Process

Kicking off the process, we interviewed students, administrators, teachers, and counselors on their experiences of navigating the transition from 8th to 9th grade. After synthesizing insights and sharing them at a workshop, we generated ideas with the learning community and distilled them into two concepts: Timeline and Match.

We then addressed both ideas with one tool: a website that allows users to enter personalized search criteria and matches them to schools that best fits their needs, while also tracking important dates in the enrollment process.

Our research led us to include a range of factors that can determine a family’s decision to apply, from practical considerations such as transportation and scholarships to academic and extracurricular programs. We tested with parents and teachers to gather feedback on the site’s effectiveness and usability, and launched in 2018 with those improvements.

Working with Greater Good helped us engage stakeholders in ways that we would not have been able to do. Through their focus groups and workshops, we were able to hear more voices and glean more perspectives that we needed to hear.

Dan Bennett Big Shoulders Fund

Client & Community Outcomes

Schools are actively using the site CatholicHighSchoolChicago.org and sharing information on it. As of the start of the 2018-2019 school year, 28 Catholic schools had submitted their information to the site. This tool helps Big Shoulders Fund achieve their mission of supporting children’s access to quality, values-based education in Chicago. The website allows families to directly access information to help them make informed choices about their children’s education.