Craig Lynch started his job as CEO of Youth & Opportunity United, or Y.O.U., in July 2020, less than four months into the pandemic. The nonprofit organization was working hard to continue providing services virtually to children and families throughout Evanston and Skokie. The RoundTable interviewed him in person at Y.O.U.’s modern and spacious headquarters at 1911 Church Street on November 18.

Lynch exudes calmness. When asked about what it was like starting a new job remotely, he was both candid and reflective about the experience. Here’s what he had to say about that and a variety of other topics (responses have been edited for length and clarity):

Challenges presented by COVID-19

“I think one of the things that surprised me was just how difficult it is to both lead an organization, but also start at a new organization and in a new community, when everything is virtual. When I walked in the door in July 2020, no one was in the building. So when we think about building relationships, just getting to know people, and getting to create those bonds that help you build camaraderie … it’s really difficult to do. The remote tools are great, but they don’t quite meet the mark in terms of building relationships. We just missed those informal interactions of popping in somebody’s office or seeing them in the hallway. So relationship-building was really tough.

Craig Lynch in the Y.O.U. lobby. (Photo by Wendi Kromash)

“Another thing that I think was really challenging was trying to strike this balance between helping and supporting young people and families, but also making sure that our staff felt safe and supported. The [COVID-19] guidance was all over the place. The schools were trying to figure out how to [open safely]. So their plans were changing, and because we are a partner with the schools, some of their changes affected our plans. That was really difficult as a partner that’s dependent on access to the school buildings to deliver our program.”

Evanston as a community of nonprofits

 “I was really encouraged by how passionate and committed every organization was and how the leaders of the organizations made sure that they can meet families where they are and support them through really difficult and challenging times. I found the overall nonprofit community to be welcoming, really supportive. I was encouraged to have our organization participate and be engaged in the work of supporting Evanston in ways that matter.”

Learning to see across an organization

 “I started out as much more of a technical leader. [Lynch’s background is in computer science and information systems, with a bachelor’s degree from Illinois Wesleyan University and an MBA from the University of Illinois at Chicago.] I think with those skills, if you’re doing that work well, you develop the ability to see across the organization. You see where there are similar challenges in different parts of the organization and how to bring together solutions. Sometimes it’s technology, sometimes it’s people and sometimes it’s process.

“That ability to connect the dots on challenges that are happening across the organization and bringing creative solutions to address them is a big part of why I thought that I could add value here.”

Importance of mentors

 “I think I’ve worked with some really good people. I’ve received inspiration from some great leaders in particular. During my time at CPS [as Deputy Chief Information Officer at Chicago Public Schools before working nine years at the City Colleges of Chicago], I had a boss who took an organizational lens and approach to the solutions that we were trying to implement. I observed that and I saw how effective it was and how it resonated with people outside of the technical group. The more that I was able to observe and learn, and then start to develop my own experiences partnering with groups outside of the technical group, it became obvious that this was a way to be successful leading and collaborating for the benefit of the organization and people we were serving.”

Theory of change

“One example that comes to mind is we recently completed a theory of change for our organization. Theories of change are logic models to create the framework for the services that nonprofits provide. You look at an organization and ask, ‘Well, why do you do that? There are lots of things you could do. Why do you do that?’ It’s often rooted in this belief that we’re trying to solve this fundamental problem: If we do these things, these things will happen, and we will make progress towards that problem. So coming into the organization, there are lots of questions about our impact. But before you can really get to that, you’ve got to understand what are you doing, why are you doing those things and see what the through line is for that work.

“That’s the foundational piece. It’s not glamorous. But it’s critically important, because once you understand what you’re doing, then you’re able to ask yourself, ‘How do I measure that?’ Then you’re able to evaluate and figure out if you’re doing what you think you’re doing, and if you’re doing it well. At the end of the day, we do this work to make a difference in youth development. The only way to know that is to understand who you are and why you do the work that you do.”

Three-year strategic plan

“We just recently completed a strategic plan, which is actually really exciting, to help chart the path ahead for the next three years. So I think doing the theory of change and a strategic plan has allowed us to reflect on who we are, and update our language on what we believe, what our core values are, our mission. We have an updated set of priorities now to help guide that work forward. We’re still an organization that’s committed to helping young people succeed in whatever way they want to define success.

“[Strategic planning is] tough to do. There’s never a great time to take a look inward and reflect, but it’s so important that every organization has to do it. Communities are dynamic. The things that were priorities before the pandemic, some of them have changed. If you’re not taking a look at what you do as an organization and what the needs are in the community, there’s a greater chance that you could be misaligned. It is tough because it’s an investment in time and resources. As great as you think you are, there’s always more you can do as an organization.”

Creativity role at Museum of Science and Industry

“[Y.O.U. is] already doing work with the museum [where Lynch has been a Black creativity adviser for more than five years]. We use some of their science curriculum. The museum has really good professional development around science. It’s great to see that we are leveraging resources that exist and particularly partnering with the museum. I think it’s a great organization.

“The other thing that I think is a possibility, and one of the things that the Black creativity program at the museum does, it takes a look at the intersection of art and science. At Y.O.U., we often use art to help support our young people to express themselves and tackle tough issues around race and class and social justice through the arts. So I think there are some real opportunities to partner.”

Working (mostly) post-pandemic

“I think like many organizations, we are trying to navigate what has been termed ‘the great resignation.’ We’re trying to stabilize our teams. We’ve had a significant amount of turnover in the late fall. People are thinking about their careers differently. Work-life balance means something different now. Compensation is a big part of the discussion. And often the challenge to nonprofits is, typically [their pay is] not as competitive in the marketplace.”

Long-term goals

“I think longer-term, now that we have our strategic plan, we are starting to do the work to make the plan come alive. The initiatives and priorities that we’re going to do as an organization are going to be a big focus. I think taking more steps to understand our impact, as I talked about our theory of change, and starting to look at the indicators of our impact. So continuing to move that work forward so that we get ourselves ready for some type of evaluation is going to be a big focus. Strengthening our partnerships to support our programming for young people is important.

“I think on the mental health side, continuing to strengthen the support we provide to young people and families. Organizationally, trying to become more efficient is important. There is no shortage of work that’s out there for us to do all in the spirit of continuing to get better and have more of an impact on families.

“And we should never forget this is continuing to strengthen our own culture and climate. I want to make sure that we are doing what we can to make Y.O.U. a great place to work. It’s going to be a big area of focus. I mean, our staff have done an amazing job [in some] really scary, stressful times, especially for Black and brown community members. They’ve done an amazing job continuing to work with young people in the pandemic. I think it’s the right thing to do, for us to figure out how do we make sure that we’re continuing to support our team as we’re doing really challenging work.

“I think we’ve got a really committed and passionate team to do the work and a great, supportive board. I want to make sure that as an organization, we are also stepping up fulfilling our role as a community partner, as a school partner, and being a thought leader around youth development services. We’ve been doing this work for a long time. We definitely have a perspective that we think works. I want to make sure that as an organization, we are engaged. I think that’s really important because we’re a nonprofit focused on youth development, but we’re also a community-based organization. It’s important that we’re playing leadership roles in all of those different spaces to the extent possible.”

Wendi Kromash

Wendi Kromash is curious about everything and will write about anything. She tends to focus on one-on-one interviews with community leaders, recaps and reviews of cultural events, feature stories about...