“Carolyn has seen it all in school leadership, connected with the most important leaders and ideas of our time, and supported an extraordinary network of colleagues and rising leaders.”
Upon graduating from Vanderbilt University, Carolyn took her first job teaching English and French at a public school outside of Chattanooga, Tennessee. After teaching for four years, she took time to immerse herself into full-time motherhood and involvement in community volunteer work.
Carolyn returned to the workforce and entered the world of independent schools as a teacher of upper school mathematics at Girls Preparatory School in Chattanooga, Tennessee. Fourteen years of teaching brought local and regional awards as Carolyn rediscovered the great joys of teaching. Under protest and only on the condition that she could continue to teach three upper school math classes, Carolyn joined the school’s administration in the newly designed position of Director of Studies.
Having quickly learned that she enjoyed the creativity afforded by administrative work, Carolyn left GPS after 19 years at the school to assume the position of Assistant Head of School at Metairie Park Country Day School in New Orleans, Louisiana, in 2003. In the fall of 2005, shortly after Katrina made landfall devastating the Country Day campus, Carolyn was named Associate Head of School, charged with managing all day-to-day school operations, restoring the ruined campus, effecting painful but necessary faculty layoffs, and reworking school finances after the sudden loss of 25% of the student body. Maintaining the character and spirit of the school became paramount. Months later, in the spring of 2006, Carolyn was appointed Head of School, stabilizing the school and returning it to a path of growth. She chronicled the lessons she learned in the article “Katrina and Disruptive Innovation” in Independent School, the NAIS magazine.
In the growth years that followed for Country Day, Carolyn participated in local, regional, and national associations culminating in leadership positions; among these were service as Vice-Chair of the ISAS board, service on The Heads’ Network faculty and Council, and election to the NAIS Board where she chaired the Engagement Committee and served on the Executive Committee, the Equity and Justice Committee, and the Presidential Search Committee. Involved with the Klingenstein Center at Columbia University since 2010, she has participated in their Heads’ Program, acted as a Klingenstein Field Instructor, and currently serves on the Center’s Advisory Committee. Carolyn’s involvement with five New Orleans charter schools has also been extremely meaningful for her, including serving as short-term Interim CEO for one of these schools, Bricolage Academy. She is on the boards of Madison Country Day School, in Madison, Wisconsin, and Girls Preparatory School in Chattanooga, Tennessee. In November of 2023, Carolyn was invited to join the board of the Edward E. Ford Foundation.
Carolyn was drawn to Strategic School Leadership by the firm’s emphasis on character-based leadership and by the founding partners’ reputation for excellence. Since joining the firm in 2021, Carolyn has earned certification as a Return on Character® Provider from KRW International, as a Team Management Profile Practitioner from TMS Americas, and as a Leadership Forecast Series Practitioner and Provider for both individuals and teams from Hogan Assessment Systems.
Carolyn has enjoyed serving as the thought partner and executive coach for heads and upper-level administrators in a variety of schools. A partial list of clients includes the Oak Hill School (TN), Jewish Community Day School (LA), Deerfield Academy (MA), St. Michael’s Catholic Academy (TX), St. Luke’s School (CT), Girls Preparatory School (TN), and the Episcopal School of Baton Rouge (LA).
Carolyn offers her extensive leadership experience to groups as well as to individuals by leading board retreats and conducting team-building workshops. It has been Carolyn’s particular privilege to lead five school leaders through the Return on Character® leadership assessment.
Since 2022, Carolyn has presented at NAIS, SAIS, ISAS, and NWAIS conferences.
- Dodging Potholes: An Open Letter to New Heads of School in an SAIS newsletter
- Working Toward Better Head-Board Alignment in Independent School
“Carolyn Chandler was and still remains one of my leadership role models. I had the incredible fortune of working with her during one of the most turbulent and extraordinarily challenging times of our careers, when she had to bring a school community back after Hurricane Katrina, and I served as a division Head under her. She showed courage, compassion, strength, and optimism in the wake of the disaster. Her resilience, grace, and perseverance steered us away from devastation and towards a better, more vibrant, and inclusive school. Carolyn is one of the best leaders to have worked in independent schools, and I’m thrilled that she’s sharing her talents and wisdom with others at this stage in her professional life.”Katherine Dinh
Head of School, Marin Country Day School, Corte Madera, CA
Past-Chair, NAIS Board of Trustees
“It is hard to express how very much Carolyn Chandler has meant to me as mentor, advisor, and friend in my headship. Her wisdom, experience, and insight into the fundamentals and nuances of effective leadership, communication, and decision-making have been invaluable for my success. In particular, our work together with the Return on Character instrument has provided a window into my strengths and areas for growth as a leader that has served me more than any other single professional development experience in my career. Any school leader would be fortunate indeed to have Carolyn’s guidance and collaboration.”The Reverend E. Gary Taylor
Head of School, Trinity Episcopal School, New Orleans, LA
“As a first-time Head of School, what a gift it was to have Carolyn Chandler in my corner! Carolyn’s experience as a Head of School and her connections to other educational leaders around the country make her an invaluable mentor and advisor.
Her role as executive coach involved a school visit to interview my Administrative Cabinet and Chair of the Board of Trustees to assess the school’s current challenges and help guide leadership goals for the future. The skill with which she listened, asked probing questions and made thoughtful recommendations impressed my team instantly. With a strong moral compass as her guide, Carolyn also provided wise, expert counsel for me in our confidential, bimonthly meetings.
Additionally, Carolyn conducted a visual, interactive Team Management Profile workshop with the leaders of my school. It was fascinating to explore how individuals approach work-related aspects such as relationships, information, and decisions, but the most informative part of the workshop was considering how the work preferences of each individual complement the work of others, thus identifying the strengths and weaknesses of our team as a whole.
I cannot say enough about my respect for Carolyn Chandler and the work she does to guide educational leaders. Her experience, compassion, and grace made her an exceptional mentor, and my school was blessed to have her work alongside us.”Carrie Steakley
Head of School, Episcopal School of Baton Rouge, Baton Rouge, LA
“Over the past two years, I’ve had the honor of collaborating with Carolyn and the outstanding team at Strategic School Leadership. Whether administering the Return on Character leadership assessment, engaging in executive coaching, or leading board and administrative retreats, each service has been exceptional, warm, and thorough – a testament to the character, experience, and reputation of Carolyn and her colleagues.
SSL’s approach is meticulous and data-driven, utilizing tools that offer a robust framework for reflection and assessment. What sets Carolyn apart is her coaching style which not only addresses immediate challenges but also cultivates the capacity for strategic growth in the long term. I’ve experienced significant personal and professional development under Carolyn’s guidance.”Hart Roper
Head of School, The Oak Hill School, Nashville, TN
“Carolyn Chandler is an expert in school leadership and well respected throughout the independent school community. She understands schools and school culture and possesses a broad range of knowledge in advancement, finance, leadership, personnel, and crisis management. She models lifelong learning, which she regularly and generously shares with her colleagues and clients. Intelligent, thoughtful, curious, and bold, she has never stopped learning and growing in any role she has held—as an educator, school leader, board member, or consultant.
Carolyn listens carefully, questions thoughtfully, and offers sound advice with a wealth of knowledge to share. Her passion for fostering the next generation of school leaders and helping schools be their absolute best makes her a true thought partner who is discrete, nonjudgmental, and unconditionally supportive. Her warmth, kindness, and wonderful sense of humor are an added bonus!
I highly recommend Carolyn for anyone seeking a brilliant executive coach, board member, or a facilitator for an administrative team or board retreat. I am grateful for our work together and am a better leader because of Carolyn’s expertise, encouragement, and guidance.”Megan Cover
Head of School, Girls Preparatory School, Chattanooga, TN
“I had the distinct pleasure and privilege of being coached by Carolyn, as her first non-Head of School client, thanks in large part to my former Head of School’s encouragement and commitment to my professional growth. As a woman of color with career aspirations beyond my current senior leadership role as Director of Equity and Inclusion, not only did I benefit from Carolyn’s deep well of knowledge and wisdom as a former Head, but also her active and ongoing sponsorship and mentoring.
Early on in our executive coaching sessions, she introduced me to the Hogan Assessment as a tool for uncovering my professional strengths, values, working style, behavioral tendencies, and potential saboteurs. The personal and professional insights gained from the assessment, and more importantly from Carolyn’s focused coaching have been invaluable as I focus my career advancement vision.
During and after her school visit, my students and colleagues who met with her couldn’t stop talking about how present, professionally curious, and encouraging Carolyn was during her small group interviews and community conversations. When Carolyn extended an invitation to dinner with my husband and two young children I came to fully appreciate the thoughtful and comprehensive nature of her coaching style, knowing that she saw my family as essential elements to consider in my professional journey.
Over my 13-year career in education I have participated in a broad range of professional development experiences and I can confidently say that the year I spent working with and being coached by Carolyn has been one of the most impactful and invaluable opportunities to date.”Jacqueline Nelson
Anti-Bias Educator, Facilitator, and DEI Practitioner, St. Luke’s School, New Canaan, CT
“In the two years since Carolyn led our board retreat, the trustees and leadership of Jewish Community Day School have continually referred back to her recommendations and the work she inspired in us. Her experience, insight, and warmth bring out the best in every with whom she works. She is kind and nurturing when she needs to be and tough and no-nonsense when that is what is required. Her humility creates a safe environment for others to be more courageous in engaging with difficult ideas, and her experiences in schools, on non-profit boards, and as a national thought leader in education are all brought to bear in her work.
As an institution, we consider ourselves very lucky to have been her client; as an individual, I am incredibly proud to have earned her friendship. Her imprint on our school after a relatively brief engagement will last a very long time, and we look forward to working with her again.”Brad Philipson
Head of School, Jewish Community Day School, New Orleans, LA