“Well Done — and Not Done Yet”: An Interview with Doreen Kelly, Part 2

When Doreen Kelly steps down as Head of School in June, she will have been the school community’s leader for 21 years, an extraordinary tenure that has allowed her to guide and shape the institution through critical years of growth and challenge.

In December 2023, she sat down with her former Ravenscroft colleague (and good friend) Dave Monaco to discuss her years of service here through the lens of the school’s citizen leader framework, Lead From Here. Several of Kelly’s longtime colleagues spoke with Monaco as well, sharing their insights on topics including her approach to leadership, her tenacity and resilience, and her willingness to mentor aspiring school leaders.

What follows is the second half of a two-part feature, with Kelly reflecting on Leading With Others and Changing Your World.

Kelly greets former Lower School teacher Betsy Beals and other guests attending the on-campus celebration of the release of “Young Travelers on the Path of Knowledge,” a book commemorating the school’s 150th anniversary; Kelly congratulates Sienna Gilbert ’23 at her closing ceremony for fifth grade in 2016.

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Leading With Others

Lead From Here identifies several critical components for effectively leading with others, and I’d like to explore three with you: empathy, cultural inclusivity and collaboration.

What insights can you share about empathetic leadership and the pastoral nature of your vocation as Head of School?
I remember earlier in my tenure sitting down with a priest, a rabbi and an imam and having an awareness how important pastoral care would be in this role. I knew I’d have the skill set based on my upbringing. But nothing prepares you for when a mom walks into your office, before she even tells her husband that she’s got three months to live, and asks you to keep an eye on her girls — and how proud I was to hand both those incredible young women their diploma. There is no particular training for this, but I’ve always held it as part of the sacred work we do as leaders.

What have you learned as you’ve led the school community’s effort to be more culturally inclusive as it prepares students for the “complex and interdependent world” to which Ravenscroft’s mission statement refers?
I’ve taken the belief that I stand in advocacy for every child at Ravenscroft, so I don’t lead from a place of high activism. There are certainly other schools that require a leader who leads from an activist perspective, but I’ve always had great clarity that is not where Ravenscroft lives.

Kelly joins Athletic Director Ned Gonet and RAC president-elect Cathleen Peety in congratulating parent volunteer Martha Funston for her RAC Service Award during a January 2017 event; Kelly chats with trustee and benefactor Kevin Keim, center, and board chair Kevin Anderson ’82 prior to the ribbon-cutting ceremony for the Keim Center for Innovation and Research in 2018.

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I’d like to think that Ravenscroft has been, historically, a warm and welcoming community. I inherited that. And I’d also like to think that over time this beautiful table that has been set has had more leaves added to it, and more understanding around who is sitting around the table and what they may offer in their gifting to this place called Ravenscroft.

How do you articulate the rewards that have resulted from this effort?
The students have challenged us, and I have welcomed hearing and understanding their lived experiences, that we are not a community built on sameness — and isn’t that beautiful? And in our lack of sameness we are actually fulfilling the school’s mission.

We are going to differ in places of our conscience, our commitments and our commandments.

We’re allowed to hold those “three c’s” that are dear to us. And, if we can expand our ability to be more curious and less threatened by those who hold different cultural and lived experiences than us, then — in the words of one of our students — “well done, Ravenscroft … and not done yet.”

When I think about Doreen’s leadership style, what comes to mind is one that is inclusive, trusting and steady. She always remained calm, clear-headed and steadfast even during the most tumultuous times during her headship. I think she also received little credit in how open and transparent she was with her team in how she made decisions and processed information.

— Colleen Ramsden, Head of School, Derby Academy; Assistant Head of School for Academic Affairs, Ravenscroft (2011-2021)

Kelly shares a hug with Libby ’30 and Weezie ’30 Gibbons, at front, Simone Hobbs ’27 and Kat Higginson ’17 during the 2018 Pink Out game; in 2018, Kelly partners with Assistant Head of School for Student Affairs Susan Perry and Assistant Head of School for Academic Affairs Colleen Ramsden in presenting at the NCAIS Women in Leadership Conference on “Moving Beyond Thinking It’s a ‘Pipeline Problem.’”

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The renovated Keim Center for Innovation and Research, the Olander Center for Student Life at the A.E. Finley Activity Center and the upgrades to the campus entryways are highlights of the facility enhancements that have occurred over the last two decades. What makes you most proud when you think about these projects and what they will mean to future generations of Ravenscroft students?
I think I built off the legacy of those who came before me. Mrs. Pugh’s philosophy of “what’s best for the kids” has had a lot to do with how we have evolved the campus. We’ve asked, “What does contemporary research tell us that students need?” I’m, at core, not overly nostalgic. That’s why I think I’ve stayed here so long, is that I felt like I am an embodiment of the mission statement. I’m curious about legacy and honoring of that, and humbled by it, and not beholden to it. So, what do kids need in our spaces to foster their intellectual curiosity? If it means a facility’s use has to change, then let’s do it. Even to the exterior of the campus, we want to feel good about the community that we come into each day — to feel that pride — and our perimeter improvements sought to instill that sense of pride in Ravenscroft.

So many professionals you’ve mentored have gone on to lead departments, divisions or schools of their own. Describe the rewards you’ve derived from serving as a promoter for and mentor to so many in our industry.
I’m proud of the fact that at Ravenscroft we adopted a mindset of attracting talent, retaining talent and launching talent. And that comes from the board. It’s easy for a board to say, “What are you doing with so much turnover?” But I never heard that.

When you adopt the Lead From Here citizen framework with a commitment to develop leaders throughout the organization, not just students, it is employees, too. And to have five associate or assistant heads that have become heads, and eight or nine overall — it is deeply gratifying to know that we attracted, we retained and we launched, and that Ravenscroft, through its mission, is making an impact on the broader educational landscape. We should be super-proud to have developed a mindset that makes room for that.

Her track record for growing future heads of school was second to none. ... As it pertains to women, Doreen’s role at the Institute for New Heads, her work with SAIS and The Heads Network alone showed women leaders what is possible. Add to that her unselfishness in giving her time to any woman interested in leadership — from classroom teacher to department chair to division head and beyond — and it speaks volumes about what she has done for the independent school community.

— Colleen Ramsden, Head of School, Derby Academy; Assistant Head of School for Academic Affairs, Ravenscroft (2011-2021)

Kelly and Upper School student leaders Shaurik Deshpande ’20 and Claire Ziperski ’20 celebrate the opening ceremonies of the 2019-20 school year; Kelly and Assistant Head of School for Student Affairs Kendra Varnell play elf and reindeer, respectively, to Associate Head of School Justin Brandon’s Santa during the 2022 holiday season.

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Changing Your World

The third element of Lead From Here orients one’s focus outward, asking the citizen leader to consider how their leadership will change the world. What do you expect the chapters of Ravenscroft’s history to say about your legacy?
I guess I hope what’ll be said is that I stewarded it well. I feel like I’ve been the chief storyteller. And that the Kelly family lived the mission. We personified the mission because it really hasn’t been a Doreen Kelly thing, it’s been the Kelly family. Every member of this family has embodied and lived out and modeled the mission of this school.

I also hope people will see that as the world’s characteristics changed, our school changed, too, through a period of deep reflection and growth and strategy.

I also think part of her legacy will be that we are a much more diverse community, and that is 100% attributable to her leadership and what she wanted for us. … Our geographic reach is larger than it was before. We are more diverse, socioeconomically, with the families that we have here. We are more diverse racially, ethnically. We are a better reflection of the broader community than we were 20 years ago.

— Margaret Mills ’76, Director of Enrollment Management (2013-present)

If you could assure one aspect of your headship endures, which one aspect would that be?
I had someone ask me whether I would be disappointed if things that had been developed during my time went away, and my answer was, “Heck, no!” I mean, I’ve got grandkids here, and if they go a dozen years and are doing the same things, I think my prevailing feeling would be one of disappointment.

And again, it’s “well done and not done yet.”

I took the baton and just said, “OK, I’m next up!” I’m really excited for [incoming Head of School] Derrick Willard to pick up the baton. I have hope for whatever is meant to be for the future, and actually don’t have a doubt about this, that Derrick is the right person to take us forward, that there will be an ongoing balance of the EQ and the IQ at the school— “What does it mean to educate the whole child at this point in history?” I hope the legacy of that question will always be front and center, be the guiding one. However it lives out, it will be really cool and fun to see.

How do you summarize 21 years as a head of school? If I had to guess, I would say that Doreen’s enduring legacy at Ravenscroft would be her focus on people and programs. The sheer magnitude of people she has mentored and the programs started under her leadership would be her legacy.

— Colleen Ramsden, Head of School, Derby Academy; Assistant Head of School for Academic Affairs, Ravenscroft (2011-2021)

Kelly, in keeping with her long tradition of greeting students during carpool on the first day of school, walks a Lower School student to class on Aug. 16, 2023; Kelly (with grandson Declan ’37) joins speakers Nikki Gupta ’26, Ethan Silverman ’25, Sebastian Barroso ’29, Michael Owens ’24, Ethan Axler ’26, Shakira Qian ’24 and Grace Axler ’26 following the 2023 All-School Holiday Gathering in Warner Arena.

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New experiences lie ahead for you and your family. How do you envision your world will change once you leave behind the responsibilities of school headship?
I had the gift with the support of the board 10 years ago to have just an exquisite leadership coach who really challenges me. And I think I became a better leader in the last 10 years in a lot of ways, through the Lead From Here work. Both experiences have been a benefit to me in that I’ve been thinking about my life after Ravenscroft for a decade. I’ve evaluated what energizes me and know that working in leadership development will do that for me. I’m really excited about the future of Ravenscroft and the leadership of Ravenscroft — and super-excited for what’s ahead for Doreen, and that is a great, great place to be.

I have a fill-in-the-blank question for you as we conclude: Given that so much of your life has centered here at Ravenscroft over the last quarter-century, the thought of leaving it behind in June is ______.
Peaceful.

Like a parent, I have guided Ravenscroft, and under my watch this baby that has been a part of my family system is ready to grow into its next stage of development.

And this peace has enabled me to hold a place of curiosity for my own journey and, with what my coach calls “loving detachment,” to be so hopeful and excited for the future of Ravenscroft.

Kelly poses with executive vice president Lori Spear, at left, and fellow award recipients at the Southern Association of Independent Schools’ annual conference in October 2023, where she received the Distinguished Service Award.

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Read More: In Part 1 of this feature story, Kelly reflects on Leading Self. Enjoy as well our Ravens Rewind feature Interactive Timeline Traces Key Moments of Kelly’s Legacy.

Doreen Kelly reacts with delight to colleagues’ comments during a Leadership Team meeting in the 2023-24 school year.