The most successful independent school campaigns have one crucial common denominator: a head of school that devotes significant time and provides exceptional leadership during the campaign.
A head of school’s role in a capital campaign cannot be overstated.
Families expect access to senior leadership—they won’t give sacrificial and transformational gifts unless they feel certain those gifts will be used well. This kind of assurance comes only after they feel an emotional connection to a school’s vision and are confident that school leadership will faithfully execute on that vision.
For this reason, a head of school should plan to devote at least 50 percent of their time to campaign efforts during specific phases of the campaign. The more time they can spend, the better the campaign results will be.
Core Responsibilities of the Head of School
Cultivating Major Donor Relationships
Building relationships with prospective donors is essential for a successful capital campaign, and if done well, will result in the quintessential achievement of creating sustainable, long-term generosity. Donor cultivation at this level requires a significant investment of time, and today we are seeing more and more campaign donors wanting direct access to school leadership.
During the height of a campaign, a head of school should spend 50%-70% of their time cultivating and stewarding major donors. While this schedule can be arduous, the time spent with donors and prospects is invaluable and pays dividends for the campaign and beyond. For some heads of schools this work comes more naturally than others.
Representing the Campaign Vision
The head of school shoulders the responsibility of being the “face” of a campaign, and whether they are sitting one-on-one with a prospective donor or giving remarks at an event, it is critical to communicate priorities and impact effectively. Furthermore, they must be able to articulate this information in a way that draws people in and inspires them to become a part of the project. This takes practice, and every head of school should have a 10- to 15-minute campaign speech that he/she knows backwards and forwards and can modify for any audience.
Leadership Time Commitment During Campaign Phases
Feasibility Study: 5 hours per week
Campaign Planning: 12 hours per week
Quiet Phase (Lead): 20+ hours per week
Quiet Phase (Major): 12 hours per week
Public Phase: 5 hours per week
Note: In a campaign, “leadership” can include heads of school, upper/lower school heads, athletic directors, artistic directors, and similar family-facing leadership positions.
Delegating and Leading Internally
A campaign highlights the importance of the head of school’s ability to delegate tasks and manage their time, highlighting his/her ability to balance campaign responsibilities while leading a staff efficiently and effectively. It is imperative that the head of school stay focused to maintain the right cadence for achieving the goals and timeline of a campaign.
At the height of a campaign, the head of school will likely spend nearly 70% of their time on fundraising. It’s therefore imperative that they pass day-to-day responsibilities and trust senior staff members with added tasks and responsibilities. And because their buy-in is critical, it is also important for the head of school to connect faculty, administration, and staff with the campaign’s goals. If communicated well, the campaign’s priorities are part of the pathway to the larger goals and vision of the school’s impact and mission. A motivated and enthusiastic team is incredibly important during a campaign, particularly those who interact regularly with school families.
Team Involvement: Supporting the Head of School
The head of school shouldn’t be the only one involved in cultivation efforts. Consider the many school leaders your families interact with: the lower, middle, and upper school heads, the athletic director, or the director of fine arts. If your campaign’s priorities include, for example, a gym or field space, a new performing arts center, faculty development, maker spaces, or classrooms, it is important for these leaders to communicate the need for improvements with families.
Coaching the Head of School as a Fundraiser
Strong organizational leadership does not always equate to strong fundraising skills, particularly if a head of school comes from the teaching side. We have worked with many heads of school who were once reluctant fundraisers. Asking for money is out of their comfort zone, and often the fear of rejection is paralyzing. Yet, with the proper coaching, practice, and dedication, these heads are pleasantly surprised by their aptitude and newfound affinity for asking for an investment in the school.
The key to the transformation is taking a donor-centric approach to the ask which allows the head to step into the shoes of the donor. Then, it’s not about the ask. It becomes a conversation centered around the educational experience.
In fact, a campaign can be one of the most effective training grounds for heads of schools to refine and hone their critical fundraising skillset, one of the most desirable skills any head of school can have. A campaign creates a unique sense of urgency and drives them to articulate a compelling and inspiring vision.
Campaign Committee and Board Engagement
A head of school should never keep the board of trustees in the dark about campaign plans. This resource illustrates the importance of preparing the board well before a campaign planning study is launched.
It’s not necessary to assemble a campaign committee prior to the launch of a feasibility study. One of the outcomes of a robust strategic plan should be a list of parents, grandparents, alumni, alumni families, or school supporters who express a desire to volunteer to make the campaign successful. Those with wide spheres of influence and the willingness to be actively involved in the campaign will be recruited for the campaign committee.
The head of school collaborates closely with the board and capital campaign committee members throughout all stages of a campaign. While the board approves the priorities for the campaign, it is the head’s responsibility to execute the campaign’s vision and strategy. In turn, the head of school will strategically utilize board and committee members to advance the campaign.
In addition to providing regular updates on progress toward the campaign’s goal, the status of donor prospects, and any challenges from the campaign, a head is expected to assist board and committee members with prospect meetings and introductions. Board and committee members heavily rely on the head of school’s leadership skills to bring these prospects along and inspire a meaningful investment in the school’s future.
Take a Deeper Dive
These resources will help ensure the success of your next campaign:
Stewardship and Sustaining Generosity
Once a campaign gift is committed, the journey does not end; donor stewardship is essential to the long-term success of the school. The head of school ensures stewardship is a top priority throughout a capital campaign, including managing a timely acknowledgment process, providing regular progress reports to donors, and demonstrating transparency in financial management.
An effective stewardship practice during a campaign is to use in-person tours or Zoom calls to connect appropriate faculty and administration with campaign donors to articulate how their investment has been spent and the impact it is having. For example, if one of the campaign’s priorities is a larger gym, have the athletic director give hard hat tours to donors that supported its construction. If a new STEM lab was one of the priorities, have donors speak with an engineering teacher who show donors what the new space will mean to students. Many donors appreciate the flexibility and convenience of a virtual meeting; others want to see the space first-hand. Why not offer both? While donors want to be thanked and acknowledged consistently, they are also grateful for the accountability, which engenders continued trust and confidence in the school.
Leading Through a Campaign: Final Thoughts
Overall, the leadership strength and time commitment needed from the head of school cannot be understated. It requires innovative, strategic thinking, the ability to connect to a range of families and supporters, and the willingness to step outside one’s comfort zone.
It is also important to note that not all heads of school are born fundraisers. A good campaign consultant can and should help coach and train the head to become more comfortable in a fundraising role. The Winkler Group, for example, spends significant time mentoring the head and other school leaders through role playing and helping leadership see solicitation as a way to connect a donor to a compelling vision.
Leading a campaign while continuing to run a school is no easy task, but efficiency and commitment are key to the success and ultimately reaping the long-term rewards of the effort.
Looking for Hands-On Campaign Training? Join Us in Sarasota.
SAIS Advancement Summit: Capital Campaigns
If your school is considering a capital campaign, or even just laying the groundwork, don’t miss our upcoming capital campaign workshop in Sarasota, Florida.
In partnership with the Southern Association of Independent Schools (SAIS), this dynamic, hands-on workshop covers everything your head of school and advancement team need to know about capital campaigns—from planning and donor recognition to campaign execution and long-term stewardship. Join a cohort of your peers for breakout sessions, dynamic discussion, and long-lasting connections.
Eligible for 11.5 CFRE credits.
June 16-18, 2025
Sarasota, FL
