Through CLA, Adrian Esquivel learned that being a leader can have multiple meanings.
Adrian Esquivel
Adrian Esquivel (CLA'19)

Adrian Esquivel (CLA'19) never saw himself as a leader. While he has a background in community organizing and serves as the Deputy Director of the Chicagoland Workforce Funder Alliance, he always saw himself as more of an instructor or coordinator. After completing the Civic Leadership Academy, though, the meaning of leadership changed for Esquivel; it became a title he was much more comfortable having.

The Chicagoland Workforce Funder Alliance is housed under The Chicago Community Trust. As Deputy Director, Esquivel works to collaborate with businesses and increase employment, earnings and racial equality for underserved workers in the Chicago region. Esquivel and the other members of the funder collaborative do this work through grant-making and employer engagement. Esquivel’s involvement in community organizing helped him succeed in this position: it gave him the opportunity to learn directly from the people about the issues those seeking good jobs face.

“I think we often put the pressure on the individual to change, saying they need to be doing x, y, and z, but I think what we really need to try to do is look at the systemic structures that are creating the issues and barriers in the first place,” Esquivel said. “That’s where my mind tends to go – it tends to go toward what’s the larger scale thing we need to do to turn the ship around or to move mountains around.”

The foundation seeks to motivate employers to change their behaviors and improve the systems in place that disenfranchise workers. It tries to dismantle the widespread problems people face in the workforce. However, Esquivel acknowledges that philanthropy has played its own part in creating barriers for employees.

Chicagoland Workforce Funders Alliance Logo
The Chicagoland Workforce Funders Alliance

“Some of the expectations philanthropy has put on community organizations can be frankly unrealistic at times,” he said. Esquivel said he takes it upon himself to alter these detrimental expectations. “I see myself as an anchor within philanthropy, while trying to change the face of how we do this work in the first place.”

Doing this work led to Esquivel’s interest in CLA. He spoke with CLA alumni who shared the valuable experience they had. They talked about the meaningful relationships they developed with other members of the cohort, as well as some of the technical skills they learned along the way.

Still, Esquivel remained skeptical of the idea of being a “leader.” It was also his mentality of being an outsider that made him doubtful if this was the right place for him. Going to the Harris School of Public Policy at UChicago for leadership training, he did not know how he would fit in or what it would mean for him. The desire to challenge himself, however, pushed him to apply and pursue it. 

Throughout the six months with CLA, Esquivel worked with public defenders, government workers, nonprofit founders, people from the arts, and members of the police department. He spent months learning and engaging with these individuals. Not only did they broaden the way Esquivel thought, but he said they also broadened the tangible connections he had. Esquivel said now after spending so much time with them, he can call somebody from any of these institutions and have a thought partner in the issues he works on. While he said you can still make these calls without CLA, it’s different after everyone has gone through the program together. 

Civic leadership academy logo
The Civic Leadership Academy

“There’s something really special about spending six months with people across the nonprofit and government space, and we sat with these challenges together thinking about ways  all their work could be connected,” Esquivel said. 

This strong communication and productive conversation is important to Esquivel when working across sectors. It also helped him reshape his idea of what it means to be a leader. 

Esquivel said one of his greatest takeaways from CLA was separating from the perception that a leader always has x, y, and z characteristics. Leaders have a variety of strengths they focus on. He said that different characteristics within his personality can be brought out at different times, and assessing which one to bring out when is the point of being a strong leader. In summary, he said, “ a leader is contextual to who you’re trying to lead in the moment.”

With his newfound understanding of leadership, Esquivel  looks to his work with a critical eye. While he appreciates his work, he says he has a hard time not being critical of philanthropic institutions and pushes them to work harder and fulfill their promises. Already Esquivel is planning to work with another member of his CLA cohort, Tovah McCord (CLA ‘19), Director of the Chicago Blackhawks Foundation, and Hilesh Patel (CLA'18), Leadership Investment Program Officer of the Field Foundation of Illinois, as a sub-group within CLA to drive change in the world of philanthropy.

Applications for the Civic Leadership Academy are now open. Apply by October 1st for a January 2020 start. For more information, go to