Jill Bradley is the Chief Operating Officer of BUILD Chicago, Inc. BUILD Chicago’s mission is to engage at-risk youth in schools and on the streets to help them realize their potential and contribute to our communities. Recently I had the opportunity to interview Jill, who started her new role at Build about six months ago.

Steve: What does it mean to be a transformational leader?

Jill: It is about knowing the people and building a relationship with them and inspiring them to drive through change. It’s about focusing on the positive as we transform and supporting people when obstacles to change seem insurmountable. It’s also about learning from failure and not calling people out for taking a risk and failing.

Steve: You just started at BUILD a few months ago. Your role as COO is new to you and new to BUILD. How has this been going?

Jill: Bringing this role into BUILD was a big change for the organization. This role was not clearly defined when I started. It was a challenge to define it and set boundaries regarding the scope of the job. This required that I ask lots of questions of the CEO, my peers and my team.

Steve: How did you clarify the role?

Jill: I clarified the role of the team I’m on – the CEO’s team and then our individual roles. I set out that my role was to steer the organization, not slow it down with operational bureaucracy. I was clear that I may not have all the answers to technical questions that surfaced; I had the leadership say to determine how deep to question the progress of various activities.

Steve: In what ways did you experience cross-functional dysfunction, and how did you address this?

Jill: First let me say that cross functional dysfunction does not need to be fatal. At BUILD I discovered that we are more cross functional than we are dysfunctional. Also, being cross-functional is messy. You must tolerate why some individuals are in the room. Not every person makes sense in every meeting, but that’s ok. Part of my role is to allow people to be messy in their pursuit of cross functional health.

Steve: How did you enroll others in the transformation to having a COO at BUILD?

Jill: One, I asked many questions. I espoused the idea of inquiry not advocacy. Second, I made my office a safe place. People can come to me with concerns without fear of reprisal. Third, understanding the sources of resistance, and using resistance to clarify the purpose and outcomes.

Steve: Please comment on organizational challenges you faced.

Jill: People here are all amazing. We do great work for the community. My role is to support the team, help them do great things for the kids in the community. My role is not to protect employees from themselves. Helping employees enroll in the mission of the organization is my number one goal.

Steve: How did you become more of a coach?

Jill: I had an amazing example earlier in my career. A man I worked for was a brilliant leader who did not promote himself. He supported us to be our best. He walked the talk. From him, I learned how to coach my employees. I also learned about coaching up, but this is more of a challenge and takes more courage.

Steve: If you could give one piece of advice, what would it be?

Jill: Live in the moment with an eye toward the future. I may not in the organization when the vision is fully realized, and that’s okay. Keeping this in front of me and the team is crucial, and celebrating the incremental progress is important.

Dedicated to your profitable transformation,




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