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Defining Aspirations

Students at whiteboard.

Salisbury School is pleased to announce that it is embarking on a strategic planning initiative we have titled: Defining Aspirations.

Below is chairman Dicky Riegel's introduction of this process to our Salisbury community, please be sure to check in regularly as we will be posting updates as we move forward:

December 3, 2019

Dear Members of the Salisbury Community,

Salisbury School is a magnificent place. The Fall of 2019 has been one of our best starts to the academic year in recent memory and, by all accounts, the Hilltop has never been more vibrant and dynamic, and is operating on all cylinders. The faculty and staff continue to be entirely focused on our character mission of inspiring boys to become their best selves, while the boys befriend classmates who will be their Salisbury Brothers for life. With such a solid foundation and strong momentum across so many areas of the community, the Board of Trustees believes it is now, in this time of strength, to focus on how we can best prepare for the opportunities and challenges of the next decade. What better time to study these strengths, to “double down” on them, but also to be open to change and to think creatively about how best to educate our boys for their future?

In partnership, the Board of Trustees and the school community recently began a strategic planning process entitled, Defining Aspirations. It is an initiative that will set the direction for the School, as we prepare to celebrate our 125th anniversary in 2026. To commence this initiative, the Board joined with the School’s senior administrative leaders and held a summer retreat, resulting in the identification of key areas of opportunity and growth. Those areas include, but are not limited to, our academic, athletic, spiritual and community aspirations; how best to adapt to changing consumer behavior by parents, families and boys; how best to ensure Salisbury has the resources and flexibility to continue to grow in the future; and how we can continue to strengthen our leadership in the area of teaching young boys to become men. To not only become men but to become Salisbury Gentlemen.

The Board and senior school leadership also identified the need for more focused attention toward external relations, how we are communicating to the larger community, and how we can continue to build our marketing efforts. Initiatives like our new website, videos and live-streaming are new ways for all of us outside the school to share the wonderful excitement, values and growth happening on the Hilltop every day. This continued external engagement, communication and outreach will be a higher priority for Salisbury going forward.

One of the great strengths of Salisbury is that we are fortunate to have such a dedicated, loyal and experienced Headmaster in Chisholm Chandler. For the last 17 years, the school has benefited from his stewardship, dedication and hard work to make Salisbury the thriving institution it is today. His leadership also affords the School some critical flexibility as we determine how best to address these strategic areas and how best to re-align responsibilities to address the immediate opportunities. Moving forward, Headmaster Chandler will work even more closely with the Board of Trustees to deploy his extensive knowledge of the school, connections with alumni, and his depth of relationships formed with our community over nearly three decades, to enhance our external focus. In this role, Chis will play an integral part in steering the strategic planning process by focusing his efforts on ensuring the financial health, development goals and resource growth for the School.

Salisbury is also fortunate to have a talented, dedicated and experienced team to drive our daily operations and mission of the institution. To that end, I am proud to announce that Bobby Wynne has been promoted to Associate Headmaster with responsibility to manage the day-to-day operations of the Salisbury community while continuing to lead the college office and lacrosse program. Bobby is a veteran member of our leadership team who has served Salisbury faithfully for the past eighteen years in a variety of roles including Assistant Headmaster, Director of College Advising, Dean of Students and varsity lacrosse coach. In each of these roles, he has achieved great success and brought Salisbury to new heights with a steady hand, wide capacity and a love of Salisbury. The Board has total confidence that he will excel in his new role.

Partnering with Bobby will be Peter Gilbert in a new role of Assistant Headmaster of Institutional Advancement. With this promotion, Peter will continue his good work in Admissions and Marketing and will now extend his responsibilities to assume full responsibility for managing the Development program. We believe there is great value in combining these disciplines and bringing them under Peter’s leadership. Peter has been the first introduction to Salisbury families for the past twenty years. We are excited for Peter to connect with legions of Salisbury Gentlemen in his expanded role and to collaborate with Chis to effect a more dedicated and strategic focus to our development efforts.

Given Bobby’s and Peter’s combined years of service to Salisbury School, we are in very good hands indeed!

The process of Defining Aspirations will continue with trustees, senior faculty and staff leaders spending the coming months working with our outside partners from Strategic School Leadership to refine our planning. We will continue to solicit feedback and to narrow the challenges and opportunities. We look forward to sharing early feedback and research associated with our identified areas of opportunity with the idea of a completed strategic plan crafted by the end of 2020. Soon we will be asking you to also provide your input via a community survey – stay tuned! Please let us know what you think, as your engagement and perspective are critical for the strategic plan’s success and making sure we get this right.

We are poised and ready to dig deeper into those areas identified as part of our strategic planning process, and we are excited to take advantage of the benefits of this re-alignment and the positive impact it will have on the future of Salisbury School.

As always, thank you for your steadfast commitment to Salisbury School.

Forever Salisbury,


Dicky Riegel III '84
Chairman, Board of Trustees