Head of School Transitions: How the Development Team Can Help Onboard the New Leader

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Ladder-UpHead of School transitions can happen for any number of reasons—from retirement to a new opportunity arising. Planned or unplanned, the transition presents both an opportunity and a challenge for independent school communities. Whether an internal candidate is becoming the new Head or an outside candidate is taking over the role, you need to create a sound plan to ensure a smooth onboarding for the new leader.

Download a checklist of materials to share with the new Head of School and a guide to setting introductory meetings.

The development team plays a large role in making sure the new Head of School is able to integrate into the community seamlessly. Fundraisers should take the following steps when formulating a transition plan:

Identify families for introductory 1:1 meetings. The development team should select 20 families for the Head of School to meet with upon arrival. These families should have the following characteristics:

  • Long-term families (potentially with multiple children)
  • Families who have been involved with fundraising at the school
  • Top cumulative lifetime donors
  • Board chair and leaders of Board committees
  • If the school is in a capital campaign, the Head of School should meet 1:1 with campaign leadership

After the initial meetings, the development team should prioritize additional 1:1 meetings from the following groups of people:

  • Top 10 percent of donors (cumulative giving)
  • All donors who have made a gift of $5,000 or more in the last three years (If the school is in a campaign, the threshold will likely be higher)
  • Board roster
  • Former Trustees
  • Engaged parents or alumni volunteers
  • Previous campaign donors
  • New families with high wealth screening scores

Head-of-School-CalloutThe Director of Development should facilitate these meetings, calling each of the individuals/families and scheduling a time. Prepping the Head of School is key. Prepare the following information for each meeting:

  • A comprehensive bio for the individual/family including:
    • Background and relationship to school
    • Volunteer information
    • Giving history
    • Children’s names
    • Graduation year and involvement (sports, academic teams, etc.)
    • Relationships to other volunteers/staff members or faculty
  • Talking points describing:
    • The purpose of the meeting
    • Pertinent/recent information that you think they should be aware of (for example, if the individual/family made a recent gift or just finished a season of coaching, the HOS should be prepared to show gratitude)

In these initial meetings, there may be occasions for the Board chair or other key volunteer leaders to join the Head of School. For instance, if a top lifetime giver has been less engaged recently but is close with a parent/volunteer, it may be advantageous to bring them along to facilitate the new relationship. 

After the meetings, it will be important for the Head of School to follow-up with the individuals and families. They should draft handwritten notes, with the development team playing a coordination role to ensure they’re sent in a timely manner. Additionally, the Director of Development should meet with the Head of School to review the next steps for each of the individuals/families they met with. Developing a cultivation plan will be critical to further relationship building.


Laying a solid foundation at the outset of the Head of School’s tenure will help them to fully integrate into the community—and strengthen relationships with your most important supporters.