“Well Done — and Not Done Yet”: An Interview with Doreen Kelly, Part 1

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 first part of a two-part feature, with Kelly reflecting on Leading Self.

Kelly, then the Director of Lower School, joins several students in performing Irish dance for students in the first-grade center.

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Doreen, a phase of transition has begun both for you and for the school community, accompanied, I suspect, by a range of emotions. How are you experiencing the start of your transition phase?
What I am experiencing is a lot like a heart transplant, where we are taking my heart out of the Ravenscroft body and preparing the body for [incoming Head of School] Derrick Willard’s heart. I feel like I am going, “Where are some of the rejection points?,” so that this organization is ready to put his heart in it and move forward.

Personally, I would say I’m very much like a senior mom now, running around, making sure everything’s in the bins ready to go. And with enthusiasm and curiosity, and like, an “Oh, is everything going to be OK?” feeling. It’s Ecclesiastes: There is a season at a time, and it’s time for Ravenscroft to launch. So, there’s a sense of excitement, anticipation, longing and missing, but, like a senior mom, I also have great conviction of how well things are going to be in the future.

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Leading Self

You were raised by two educators, and two of your three brothers are long-tenured heads of school as well. At what point in your career, either with their urging or the support of other mentors, did you first consider becoming a school head?
I think I had an awareness since fifth grade that I was a storyteller — I remember being affirmed by a fifth-grade teacher. So I carried that knowing with me, [but] whatever role I’ve occupied I’ve had mentors and allies who have encouraged me, including my parents. The mindset was getting in the game. It wasn’t what game. It was just a game. So, if you have this particular role and you want to be flexed and stretched into another role, go and take that next step.

You arrived in Raleigh in 1999 to become Director of Lower School. All of your previous school experience had been in middle and upper school positions — and at a boarding school for boys. Which experiences in your first years at Ravenscroft gave you confidence that you could be a head of school one day?
When we went to receive the Blue Ribbon Award (2003), that was a really defining time… I knew the culture of the Lower School deserved to be acknowledged for their excellence, and it was the idea that we moved an idea forward to great success and great celebration that gave me confidence.

Later, I attended a conference on moral leadership that [then-Headmaster] Jim Ledyard had approved me to go to, and I didn’t really understand that it was really for heads of school. So I was sitting in a room thinking it was for division heads, and once I revealed that I didn’t think I was supposed to be at the conference, that group of leaders poured into me and were like, “No, no, no, you belong… you have some chops!”

Kelly and Director of Middle School Dave Monaco accept Ravenscroft’s 2003 award as a Blue Ribbon School; Kelly congratulates graduating senior Mallory Deutsch ’04 during her first commencement exercises as Head of School.

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You were 39, a wife, mom of three young children and still relatively new to North Carolina and Ravenscroft when you began your tenure as Head of School. In which of your competencies and skills were you most confident?
My strength was in the area of leading self, if you’re going by the citizen leadership framework, in that I had aspects of self-awareness. I also had some strengths in what we would call leading with others. I felt like there were good relationships to build upon on our team. I didn’t come at it from a place of hubris — that I had all of the answers.

Doreen, at the time, as a young Head of School, had an eagerness and an energy about her that I think really benefited her transition. She was all in.

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

What most worried you as you prepared to assume the role?
I have a very clear memory: [My son] Sean Kelly ’11 was in fourth grade, Ryan ’09 was going into sixth grade and Erin ’15 would have been four years younger than that. When we sat the kids down, Sean asked me a really cool question. He said, “Mom, if you don’t like the job or they don’t like you doing the job, do you get to go back to your old job?” I had to explain to him using the metaphor of a college coach: You just move on to the next team. And I’ll never forget him looking me square in the eye and saying, “Well, then you better do a good job, because we like it here!”

So part of my internal motivation was that freckle-faced little boy and for other kids like him. The point of anxiety was not a fear of the board or leading employees, it was “Would I do enough for them?” And, “Can the organization measure up to what Sean and students like him deserve?”

Kelly and board chair Vic Bell ’74 pose with Winston Holloway ’12 during the 2012 commencement exercises; Upper School students and teacher Mark Laskowski, at left, engage in a Lead From Here activity in 2013, as the school prepares to roll out the groundbreaking framework.

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Did your status as a female head of school — Ravenscroft’s first female school leader in the modern era — inform your leadership style in any way?
I was aware of being first. I was aware that representation mattered. If I look at a blind spot from that time, it was me thinking I needed to show up making sure that whatever bias you had about me as a female leader, I would shore that up and probably over-prepare — be aware that I needed to be sure that I’ve got this because maybe, given my age and my gender, there might be question marks around whether I could really handle the hard stuff.

She’s very driven. And in a way that has benefited everyone here, and it’s ambition in the very best way. A lot of people don’t like that word associated with a female leader and it makes them uncomfortable, but I think she had just a tremendous vision for really what this place could be — and a belief that she could take it there.

— Caryn McNeill, Ravenscroft Board Chair (2015-2017)

The board hired you to “connect the school’s head and heart.” What did this charge mean to you then, and how much do you see it as part of your role now, some two decades later?
Almost more so, given the conditions of the current landscape. You know, the level of anxiety in parents today can force, unintentionally, a lot of pressure on kids to be worried about aspirations and [college matriculation] lists rather than who their child is and who he or she is becoming.

The concept [of head and heart] predated me. It was in the ethos of the school, the notion of “the whole child.” While we don’t use that language as much, we continue to balance care with accountability for high expectations in our work with students. I advocate for the “head and the heart” balance, and that does not diminish my belief in the gift of high expectations. I leave unapologetic that the inside of kids should be equally balanced with what is going on in their brains.

As I finish, I’m as energized by that charge and believe I have run that good race being focused on it.

I think the best leaders, male or female, lead with their heads and their hearts, and for Doreen that’s just a natural thing. I think she was “authentic” before anyone would have used that word as a key to being an impactful leader.

— Caryn McNeill, Ravenscroft Board Chair (2015-2017)

Kelly and members of the Class of 2029 — who are now in ninth grade — smile in Holding Garden in this photo from 2015; Kelly offers a celebratory hug to Abbie Green ’16 during the Class of 2016’s Alumni Association Welcome Dinner.

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Your ability to sustain yourself over such a long period of time has been remarkable. What have been the secrets to your lengthy tenure? From where did you source the energy to persist?
Having that strong family system, one in which we have always been in it together. My family would say that Ravenscroft’s been the other child, has been the baby of the family. They have beautifully understood that when the baby needed attention, Mama needed to go to the baby. So for the whole family to adopt the mindset that the organization is a member of the family just gave room to work through points of grace.

I would also say that sustainability included an awareness that a couple of times throughout my career, I fired myself. Those exercises have been deeply helpful to step away from the work for a couple of days and decide, “If I were to start the job again on Monday, where would my points of curiosity be?” To ask myself, “Who or what am I taking for granted?” And I might then show up in a colleague’s office to say thank you for their loyalty and make sure we maintained our humanity at work. Or, when you get to those understandable low points, you go to the kids. You go back to finding the joy of the work.

I come from a family system where there’s no whining. If you chose to be on the team, to be in the game, to be tapped as captain, then you accept the big responsibilities that come with it. Learning to recharge, then, probably meant showing myself some grace from time to time.

Today, I see a woman who has tremendous energy and passion for the school, is a confident leader and is looked to as a mentor to other heads of school.

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

Kelly shares a smile with board chair Caryn McNeill in 2017 as the school wraps up its five-year, $15M Embrace Possibility campaign; Kelly, at center, officially opens the Olander Center for Student Life at the A.E. Finley Activity Center in 2022 with members of the Olander family and current and former trustees.

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Tell me about one of the many high points you will cherish in the years to come when you reflect on your time as Head of School.
I will always cherish at the board level the development of the Educational Stewardship Committee to be informed advocates of the school. When we began this committee in 2004, we were going against the grain in the industry, which felt that boards should deal with the elephants of running a school and not the amoebas. But our committee created synergy and raised hypotheses. We didn’t want to raise selfish children, and we asked what our public purpose as a school was. And this led to the unique partnership with the Center for Creative Leadership which, through Lead From Here, has allowed us to really live out the head-heart piece of our mission. The birth of that committee and its work was really invigorating.

Lead From Here was such a great connection at so many levels with Doreen and who she is and her focus on leadership ... [when] judgment and the ability to lead other people are the skill sets that people will need in every kind of setting.

— Caryn McNeill, Ravenscroft Board Chair (2015-2017)

Lead From Here tells us that the self-aware leader is also resilient. In reflection, is there a low-point moment in your tenure that most demanded your resilience?
I think there are always shadow sides to great forward progress.

So today, we would use the language of D-A-C: do we have direction, do we have alignment and do we have commitment to one another? I think there are understandable times in any organization where you think you have alignment and there are tension points when you don’t. And there were a lot of learnings for me as a leader making sure that I didn’t run out ahead of my skis with ideas,  making sure that when engaging in change initiatives that I was bringing people along.

Also, when my dad died in 2007. Probably my worst year as a leader. I did not take the time to heal. And that goes back to gender. Feeling like I had to be there. It was a vulnerable time. And I would say to my younger self now, “Oh, my gosh, take a few weeks off. Heal.” I think, particularly as a female leader, you don’t want to come across as being needy, so you buck up until you don’t have anything to give. And I used to have belief that I had the ability to know when I had a lower tank. But now I have a real heart for leaders around that self-care. I have no recollection of Ryan’s junior season of basketball, and looking back I am sad about that. But it was also beautiful at the end of that year, where I had to grow as a leader to give language to the board, because I think as a head, you don’t want to come across as needy. But they actually needed to hear it.

Was there a critical turning point or two during your tenure, a juncture when you felt the momentum gather and thrust the school forward?
I would offer getting to a place with a governing board to say we are going to come out of [the challenges of] COVID with the Olander Center for Student Life at the A.E. Finley Activity Center coming out of the ground … that we cared enough about the student voice and perspective to have meaningful spaces for connection and collaboration. It was yet another synergistic moment when we were living into [trustee emeritus] Fran Pugh’s reminder that it’s all about the kids!

The resilience I saw in those two big, challenging times [the 2008 recession and COVID-19], I saw someone who was calm, clear-headed and reassuring.

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

Kelly and Director of Enrollment Management Margaret Mahood Mills ’76 (at right) join board chair Laura Helton Kalorin ’92 and longtime trustee Fran Pugh at the New Parent Barbeque in 2023; Kelly speaks at the Southern Association of Independent Schools’ annual conference in October 2023; Kelly hosts Amory Martin ’30 as Head of School for a Day in the fall of 2023.

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Read More: Kelly reflects on Leading With Others and Changing Your World in Part 2 of this feature story. Enjoy as well our Ravens Rewind feature Interactive Timeline Traces Key Moments of Kelly’s Legacy.

In this photo from the cover of the Winter 2003 Ravenscroft Magazine, Kelly walks with interim Headmaster Ned Fox as they prepare for the leadership transition.