Why We're Hiring an Executive Director

How co-leadership served City Bureau, and why we’re evolving to meet the moment

By Bettina Chang and Harry Backlund, Co-founders and co-executive directors

Four years ago, in the summer of 2019, the four co-founders of City Bureau — the two of us, Darryl Holliday and Andrea Hart — were at a crossroads in our leadership practices. Since City Bureau launched our first participatory media programs in 2015, we practiced a form of co-leadership. Instead of one person in charge, each of us made decisions in a particular area, and we made the biggest long-term decisions by consensus. After four years of leading together, we’d grown from a volunteer team of four to a full time staff of 10, Andrea was preparing to depart for divinity school, and we were looking ahead to another period of rapid growth in our team and programming.

As we thought about leadership in our next phase, we sought coaching from Hilesh Patel, a friend and adviser to all four of us, and to many others in Chicago. Hilesh listened to our reflections about co-leadership and City Bureau’s future, and then he gave us some simple but powerful advice. (We’re paraphrasing roughly.)

“Write the words ‘City Bureau’ on a piece of paper and tape it to the wall. And when you’re talking about City Bureau, look at the paper and ask yourselves whether you’re talking about the four of you as co-founders, the people around the table who are making the thing, or whether you mean the City Bureau on the wall, the organization in the world, which you are working to grow so it exists separately from you. Both are important — but you need to cultivate an awareness of which one you mean.”

That advice really hit us, and the image of the City Bureau on the wall — not our relationships to one another but the sum total of all the relationships that make City Bureau what it is — never left our conversations. We kept talking over the next four years about the changing dynamics between our own creativity as a team and the evolving needs of City Bureau the organization, which was growing to include more and more talented and committed staff.

This week, we’re entering another moment of transition. Drawing on years of reflection and planning, we’re posting the job description for our first singular Executive Director, a new role that will collaborate with our staff, board and community to define the next era of City Bureau. We’re making this decision as part of broader shifts in how we work together, as our programs expand in scale and complexity and as our team evolves to support them.

Honesty and transparency about what we’re learning is core to City Bureau’s mission, so we wanted to take a moment to share what we’ve learned from eight years of co-leadership, what this transition means for our work and why we’re so, so excited to start interviewing folks to be City Bureau’s first Executive Director.

Co-leadership is a beautiful way to operate, and the only way City Bureau could have come to exist. 

Our brand of co-leadership emerged organically when we founded City Bureau. The four of us are all friends, and in its earliest days “City Bureau” was more of a collective than an organization — sharing leadership responsibilities delivered clear and direct benefits for our work. We each owned areas related to our complementary strengths, and we would hash out the truly critical big-picture decisions together. Co-leadership was also efficient: It let us be in many places at once, building relationships and learning from our communities. 

There was also something about co-leadership that cut right to the core of our mission: City Bureau started not to solve a singular discrete problem, but to address root causes of the structural crisis in local journalism. Structural crises require structural solutions, and true structural work is always collective. In a sense, there wasn’t really a choice: Our mission was something no one could take on alone. Leading together also — we can’t overstate this — kept us going on a personal level. Over eight years leading together we’ve often been exhausted, but leadership for us has never been lonely. The joy of working and learning together gave us the resilience to build.

Co-founders from left to right, Andrea Hart, Harry Backlund, Darryl Holliday and Bettina Chang (Photo: Laurie Fanelli/Chicagoly magazine)

Great leadership means evolving our structure to fit this moment.

Of course, City Bureau grew and evolved immensely over our years of leading together, and so has what we need from leadership. When we first designed our co-leadership practices City Bureau was an all-volunteer collective leading workshops out of a Woodlawn coffee shop; today we’re a nonprofit with 23 full-time employees running four programs and supporting organizations in 11 cities across the country. Our incredibly talented, committed and multi-disciplinary staff is now organized in multiple layers of management, working together on big, complex and cross-functional projects. 

An organization like this has fundamentally different needs than a tight-knit group of like-minded friends. It’s beautiful to have a work-family of four collaborators who can finish your sentences. It can also be — and our team let us know it — thoroughly confusing to have three or four bosses with overlapping roles. As our team grew, we realized that the same co-leadership model that had shaped our collaborative approach was starting to get in the way of actually sharing power effectively. We made a lot of adjustments to mitigate those challenges, but we eventually realized that small fixes weren’t enough. We needed bold new structures.

The biggest lesson for us is that to keep your values consistent, you sometimes have to change your practices. For us, co-leadership was a way of structuring roles that — during a period of intense experimentation and change — allowed us to create a collaborative, supportive and exciting way of working together. The transition to an Executive Director is about exactly the same thing. 

Now more than ever, we’re committed to furthering a culture of shared leadership.

City Bureau’s mission remains the same, and it’s still something no one can do alone. Hiring an Executive Director is only one piece of how we’re evolving to keep building a culture of creativity and collaboration. As we start the hiring process for our new ED, we’re shifting our own roles as founders to focus on the work we do best: expanding our leadership table to a broader group of senior staff and building new mechanisms to involve staff at every level of organizational development and planning. The process of thinking deeply about what we need from leadership has already unlocked so much potential in how we — our team and the whole community around our work — can work collectively to reimagine local media. Even the process of creating the job description for the Executive Director drew on input from our whole team.

The search for our first Executive Director will be a collective effort — and you can help!

The Executive Director role is an incredible opportunity that comes with both huge responsibilities and a deep and wide network of support and accountability from our team and our community. Please help us find the right person!

We’re looking for an experienced, accountable leader with a gift for communication and a personal connection to the mission. If that’s you, please apply. And if you know leaders who you would be excited to see run City Bureau, share the job description. It’s our greatest hope that leadership in City Bureau’s next phase will continue to be a collective practice, and that starts now with the search. Thank you for helping us find our next Executive Director, and we can’t wait to introduce them here in a few months.