Boardroom: How to Promote Meaningful Trustee Engagement and More Giving

Summer 2024

By Walt Edwards, Michelle Robinson, Sara Rubinstein

This article appeared as "Performance Boost" in the Summer 2024 issue of Independent School.

Have you ever wondered if you have an engagement problem on your board? Maybe attendance at board meetings and school events starts to drop off. Or maybe board members aren’t as active in fundraising activities as they once were. Or maybe they just don’t know what really motivates them in their service to the school. It’s not unusual. In our collective work—as a consultant, head of school, and director of advancement—these are some of the most common challenges we’ve encountered with boards.

Oftentimes trustees are choosing other activities over board participation—and they might be asking themselves if being on the board, attending the meetings and events, and performing the requested tasks is meaningful to them. Their quick answer might be yes, yet their actions say otherwise.

In addition to keeping tabs on how trustees are fulfilling their duties—from strategic planning to supporting school fundraising events—the head of school and board chair need to notice, address, and reinvigorate board participation when they see that it’s waning. They likely first turn to best practice resources for help, like NAIS’s Trustee Handbook or maybe the NAIS Principles of Good Practice for Independent School Trustees. And while these resources can serve as good reminders and provide a common perspective on trustee responsibilities, they don’t get to the root of the problem. 

To identify and overcome board disengagement, leaders must focus on how board members define engagement and what types of engagement they believe are meaningful to them. Regular and ongoing conversations with trustees about why they want to serve on the board and coaching throughout their term are essential.

Defining Engagement

“Engaged” can mean different things to different people. Definitions can range from being occupied or busy to being committed and invested. And when organizations don’t put forth a shared definition of what engagement means and looks like in their specific context, they lose an opportunity to create strong engagement at the outset.

It’s also important to acknowledge that engagement can look different at different points in the life cycle of a school and when organizational priorities shift. For example, the type of engagement needed during COVID-19 or another crisis is different from the kind of engagement needed during strategic planning, which is also different from the engagement needed during a capital campaign.

To better align what the school wants and needs and how board members want to contribute, it is important to define and discuss board engagement as part of the onboarding process. This is an opportunity for heads of school and board chairs to partner and establish clearly defined expectations for board members, including the responsibilities and commitments required. It’s also a time to share that there will be evaluations and check-ins during board service to ensure alignment throughout the school year. 

As trustees begin their term, board chairs and heads should inquire about what aspects of board service hold personal significance for each individual. Apart from enhancing the board experience—and to avoid unintentionally assigning board members duties and committee roles they don’t want or that don’t align with their interests or strengths—there’s another compelling reason to engage board members in these conversations. Engaged trustees often lead to stronger giving and fundraising. 

By exploring what is meaningful to new trustees, you can delve into the experiences that drive their motivations, potentially revealing passions that align with new philanthropic opportunities within your institution. In conversation, you can ask how their values align with the school’s mission. What aspects of the school’s strategic priorities interest them most? What impact has the school had on them and their family? For parent trustees, what growth or educational impressions have they seen in their own child that have inspired them?

A Conversation Framework

Among trustees’ crucial responsibilities is sharing the compelling stories of the school with others. But often, trustees don’t know how to be a cheerleader and connector for the school. Offering group trainings and coaching opportunities is a great way for the head and the board chair to provide trustees with the tools they need to be an engaged member of the board. 

To that end, we’ve developed a framework to facilitate meaningful conversations that deepen board members’ connection with their school while affirming their values and contributions. Sharing the school’s vision is an integral part of this framework and a key responsibility for board members. As part of this framework, which allows each board member to find their voice and be flexible in different situations, a script can deliver the information trustees need to confidently speak on behalf of the school. A formal training session with a facilitator can align trustees on the same priorities and talking points. As part of this training session, trustees individually can begin to articulate and practice how they’d talk about the school to others in the community. They can use parts of the script and make the dialogue their own.

Introduce role: Trustees can explain their role within the organization to community members in everyday conversations, whether with a parent at the school or a member of another organization for which they volunteer.

Highlight importance: Trustees can express why serving as a trustee is important to them personally, emphasizing their commitment to the school’s mission and values.

Invite their story: Board members can share their personal experiences with the school or any relevant connections they may have. This could include anecdotes, memories, or insights that illustrate their relationship with the organization.

Share vision: Trustees can share a compelling story about the school, outlining its goals, achievements, and impact. Alternatively, they can offer to connect community members more deeply with the school’s work or initiatives.

Offer connection: Trustees can extend an invitation for further involvement or engagement with the school, whether through volunteer opportunities, events, or additional discussions with key stakeholders.

Express gratitude: Regardless of the outcome of the conversation, trustees can express sincere gratitude for community members’ time and participation in the discussion.

Group training sessions can provide a foundational understanding of the importance of engagement, and we believe that individual coaching sessions can reinforce the work. Board members will develop and refine their communication skills, and this practice will help them better articulate their reasons for serving on the board and confidently convey the vision for the school. It also allows them to discover their distinct voice, which fosters authenticity in their interactions. This not only improves their performance in their roles but also enriches the overall board experience. Time these sessions to overlap with occasions when you anticipate heightened community involvement among board members, such as during the holiday party season or leading up to significant community events, to amplify impact.

Ongoing Conversations

Sometimes, school leaders need to take a different approach to board reengagement. It sometimes needs to happen one-on-one. A longstanding board member, known for unwavering support across various capital campaigns and philanthropic endeavors, began to show signs of donor fatigue. Through the partnership of the head and director of advancement, strategic stewardship opportunities developed, leading to an outreach—not to talk about why the trustee hadn’t given lately but to discuss the tangible impact of their prior campaign donation (the addition of a new space on campus). This evolved into a dialogue that reignited the board member and their spouse’s enthusiasm and led to a new initiative: The trustee created a club that offered students unparalleled opportunities to engage with global leaders. 

By emphasizing the significance of consistent communication and collaborative partnership, schools can sustain board members’ involvement in the institution’s mission and translate their passions into meaningful impact. Fostering deeper connections with board members, through initial onboarding and ongoing conversations, enables the institution to cultivate a high-performing board. 


Read More

Summertime is prime time for trustee training. Set your board up for success from the start with these articles:

Walt Edwards

Walt Edwards is president of Graham-Pelton Health, a fundraising consulting firm.

Michelle Robinson

Michelle Robinson is director of advancement at Carrollwood Day School in Tampa, Florida.

Sara Rubinstein

Sara Rubinstein is head of school at Carrollwood Day School.