As part of Chicago Latino Network’s 2026 vision, we’re proud to continue 5 Questions — a written leadership series featuring a curated group of leaders whose perspectives help shape Chicago’s business, civic, and cultural landscape.
Each installment invites a respected leader to respond to five thoughtful questions, creating space for insight, reflection, and meaningful dialogue with our network of professionals, entrepreneurs, and decision-makers.
Rather than soundbites, 5 Questions is designed to be thoughtful, accessible, and enduring — spotlighting leadership philosophy, decision-making, and lessons learned that resonate beyond a single moment.
Our Featured Leader Susanna Wickham
President & CEO, Boys & Girls Clubs of Chicago
Susanna leads one of the city’s most impactful youth-serving organizations at a moment of growing need and opportunity. Her career spans media, nonprofit leadership, and large-scale organizational transformation — from serving as Editor-in-Chief and Publisher of Chicago Magazine to leading PAWS Chicago through a period of growth and national recognition. Across every chapter, Susanna has built a reputation for thoughtful leadership, strong culture-building, and an ability to align mission with measurable impact.
At Boys & Girls Clubs of Chicago, Susanna brings a people-first approach grounded in purpose, accountability, and belief in what’s possible when communities invest in young people. In this 5 Questions conversation, she reflects on leadership transitions, earning trust in new roles, and how listening — to staff, partners, and the communities served — shapes better decisions and stronger organizations.
1. You stepped into this role at a moment when expectations for youth-serving institutions are higher than ever. What’s one truth about leading a citywide organization that you didn’t fully appreciate until you were in the seat?
Something I didn’t fully appreciate until stepping into this role is just how deeply woven the Boys & Girls Clubs of Chicago are into the everyday fabric of the city. In my day-to-day life, I have been delighted by how often I bump into kids and families we serve.
What’s also been powerful is realizing how many connections this role creates across communities and sectors, through our young people, our partners, and the shared commitment we all have to Chicago’s future. From sports organizations to financial institutions and neighborhood leaders, there’s a remarkable breadth of support. I love seeing how many people are joining around the common goal of showing up for Chicago’s youth in need.
2. Boys & Girls Clubs of Chicago serves young people at vastly different starting lines. How do you balance scale with depth, ensuring impact isn’t diluted as the organization grows?
One of our most significant points of differentiation is the time spent consistently, every day, with Club members. During the summer, our kids are with us eight hours a day, and for about four hours after school during the school year. That sustained presence allows us to go deep, not just wide.
We provide character and leadership development, academic support, engaging activities and balanced nutrition, including daily meals. This isn’t a once-a-week touchpoint, and it’s a continuous, safe, and dependable environment. Our Clubs become our kids’ second home, a second family, and it’s a privilege to play that role.
Our Club staff reinforces that depth. Club Directors are trusted extensions of families, and quite a few of our staff have their own children enrolled. We see generations come through our doors, a mother or father was a Club kid during their youth, and they want that support system for their children as well. Many young people start with us at five or six years old and stay until they’re 18. That continuity is how we ensure impact isn’t diluted as we grow. It’s been built into the culture throughout the last 120 years.
3. You’ve led successful turnarounds in both mission-driven and media organizations. When change is necessary but uncomfortable, how do you decide what must be preserved versus what must be disrupted?
The first place I always start is with respect for what already exists. It’s easy to come into a new role and immediately point out things you want to change, but authentic leadership begins with listening and learning, and understanding why people love the organization and what has sustained it over time. At Boys & Girls Clubs of Chicago, that includes a deeply committed team, with many employees having average tenures of 10-15 years or more. Some were former Club kids themselves. That kind of longevity tells you something is working, and our people are passionate about their work.
When change is needed, I believe it has to be thoughtful and strategic, not disruptive to the long-term mission. New ideas and evolution are necessary parts of leadership, but they’re most effective when they build on an organization's strengths. I focus on amplifying the incredible stories within our Clubs, bringing more attention to our dynamic Club youth, strengthening the organization, and inviting new partners into our Club community.
4. What role do you believe Chicago’s business leaders should play in youth development — not as donors, but as partners — and where do you think many still fall short?
Financial support is critically important, but partnership also means time, visibility, advocacy, and genuine engagement. One of the best examples is Boys & Girls Clubs of Chicago’s Board Chairperson, Bill Huffman. No matter how busy he is serving as CEO of Nuveen, a giant company that has him traveling all over the world, he makes time.He checks in, texts back, congratulates the team on great work, and shows up for our kids and our events. He uses his voice to open doors, makes calls on our behalf, and invites others into the mission. He’s a thoughtful leader and tremendous sounding board, and I’m so fortunate to have him as a partner in charting the organization’s future.
There’s a reason someone like Bill has been elevated within his company. He understands that people and community matter. I’m continually impressed by the caliber of leaders on our board who lead this way.
We are excited to engage with more of Chicago’s corporate leaders at this deeper level. We love to work with partners to create special moments for our kids, to share their expertise, and truly make a unique and lasting impact in the city for generations to come.
5. When you think about the young people walking into Clubs today, what skills or mindsets do you believe will matter most for their futures, even if the world doesn’t yet reward them?
Adaptability is at the top of the list. The pace of change over the next 20 years in technology, industries, and the nature of work will be extraordinary. Being open to continuous learning and new possibilities will be essential, not just for our young people but for all of us.
Club environments are uniquely designed to build that mindset. While our programming is consistent and reliable, we’re constantly introducing new opportunities through evolving programs and partnerships. Kids are learning how to try new things, adjust, and stay curious. As an example, our CC’s Little Village Club partnered with the University of Chicago last summer on a quantum computing course.
Just as important are the soft skills that don’t always get enough credit. How to interact with people, make eye contact, smile, engage, and show confidence. Every time I walk into a Club, the young people greet me warmly and openly. That doesn’t happen by accident; it’s the result of being surrounded by caring adults in a safe, nurturing environment. They’re building comfort with adults, beyond their parents or teachers, and that sense of ease and true engagement will serve them well throughout their lives. We also create opportunities for them to practice public speaking, such as through our Youth of the Year program. By the time they’re 18, many of them are mature and confident public speakers. This is great training for their future lives.
