Kym & Diane – Class of 2025
Kym Watson and Diane Headley – Class of 2025 – bonded in Greater NY over shared management and leadership styles that center integrity and care. When the Partnership began, Watson was two years in to being President and CEO of Graham Windham, a 200-year-old child welfare organization. Headley was Chief People Officer at Ford Foundation. Both leaders brought decades of experience to the partnership and through two years of Greater NY conversations refined a leadership approach that supported Watson’s personal and professional development.
Graham Windham serves more than 8,000 children and families annually. The organization works with children, young adults, and families involved in the child welfare and foster care systems, providing foster care, prevention services, mental health support, and programs that help young people transition to adulthood. Graham Windham collaborates with families, communities, and public systems to ensure that children can grow up safe, supported, and connected to opportunity.
“I don’t know what the chemistry formula is that you use to bring us together, but it was on point,” says Watson. “We’re both very intense and intentional about the work that we do. Our commitment to excellence and high standards was a real place of connection.”
A recurring theme of their conversations was leadership as a human experience. “Leadership opportunities I’ve had always focused on skill development and management style,” Watson says. “Very rarely—very rarely—on me as a person.”
She describes how Headley helped her see situations differently: “There were times when I had a fixed perception. Diane would offer an alternative view, and in many cases, she was right. I would have headed down the wrong path if I hadn’t had her perspective.”
One example of this was in Watson’s development of her own Board leadership style. “I talked to Diane a lot about my board,” Watson says. “Her counseling, based on her own experiences, was so valuable.”
Headley says that her role in supporting Diane’s Board leadership was to reframe the challenge in terms of human experience: “The Board is not one big organism. It’s made up of individual people, and you have to take the time to get to know them one by one,” she says.
Headley encouraged Watson to use leadership as human experience to think beyond the role she held. “This isn’t just about you being the CEO of Graham,” she told Watson. “You’re leading the field.” That reframing unlocked new leadership priorities for Watson, who says the ideas for Graham Windham’s ‘Reckoning Conversations’ addressing issues of race and equity came directly from her conversations with Diane. “She understood how important this was for me as a person,” Watson says. “She asked some very pointed questions, and bam… it led right to what has been a transformative approach to our work at Graham.”
The Partners’ shared commitment to leadership as human experience included focusing on Watson’s self-care. “There was a point,” Headley recalls, “when we were talking about the work and bringing care to the work, and I said, ‘What about your care? What about self-care?’ I told Kym, ‘If it’s okay with you, I’m going to hold you accountable for that too.”
For Watson, that shift was profound. “Her advice was lifesaving,” she says. “I don’t mean that figuratively. I mean literally.” She adds, “Some of the things we talked about required vulnerability. But there was safety. And once there’s safety, you can have real conversations.
The Partnership also resulted in tangible organizational change. “Diane told me I had too many direct reports,” Watson says. The Partners’ conversations led Watson to secure the Board’s approval to restructure and limit her number of direct reports.
Greater NY connects leaders in strategic service to the people of New York City. For Watson and Headley, this meant an opportunity to reinforce shared values of intensity, integrity and care and coalesce them into a leadership approach that centers human experience. Headley says: “At first, I didn’t know how Greater NY was supposed to work. But it’s not coincidental it’s set up that way. Greater NY is very intentional in the freedom and agency it gives partners, so you can establish the relationship you need. It was magical.”