Uptown United
Chicago, IL
Challenge
Uptown United is an umbrella organization of three community economic development entities that serve one of the most ethnically diverse neighborhoods in Chicago. Uptown has a strong history of community service and organization and a population built through over a century of immigration, with substantial numbers of Black, Latino, and Asian/Asian-American residents. The executive director of Uptown United reached out to Community Allies following a major organizational restructuring and an almost-complete staff turnover. The new staff members were remarkably skilled and enthusiastic, but they had not yet figured out how their individual skills and working styles would meld into a powerful team. The boards of the three different organizations, meanwhile, were struggling to understand the distinct roles of each entity and how they would work together towards a common purpose. To feel empowered to drive the organization’s future, both board and staff needed to align around a shared vision, with clarity about their individual roles and a plan to amplify their impact through collaboration.
Approach
Between 2017 and 2020, Community Allies designed and led a series of retreats that allowed the Uptown United board and staff to step away from their day-to-day tasks, identify short- and long-term goals, and come together as dedicated and highly-functioning teams. The retreats balanced reflection, strategy, and celebration, with different themes each year as the work progressed. Each year, our work began with a research phase during which we reviewed documents and metrics from prior years; conducted interviews with the director, board members, and community members; and surveyed board members/staff members to surface any concerns and assess consensus around goals. We then developed a retreat design, balancing strategic planning with exercises for connectivity and visioning. In the first years, the groups worked on identifying the community’s values and the organizations’ roles in preserving the character of a neighborhood that was changing quickly. Later years took a deep dive into programming priorities and financial realities, with board and staff working together to weed out or revise programs that were no longer effective and identify areas where new initiatives were needed. Throughout, the groups considered their roles in leading positive change for Uptown and how to promote the Uptown community and their work in it.
Results
Bringing the three entities together for joint retreats increased the connectivity between the boards and caused them to collaborate both formally and informally. The staff reported higher productivity and less stress because of agreement about their roles and support from the boards. When the pandemic hit in 2020, Uptown United was among the best- positioned neighborhood development organizations in Chicago. While others were laying off employees, Uptown United maintained a full staff throughout, thanks to its diversified revenue stream, committed board, and clear goals. The themes the board developed during the 2018 retreat–Thoughtful Planning, Bring People Together, and Tell Uptown’s Story–remain guiding principles for the organization to this day.
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