In my previous reflection, I wrote about fundraising as the work of creating a culture of philanthropy rather than asking for money. That mindset only becomes meaningful when it shows up in practice, especially in real conversations with donors.
Over time, I have come to think of donors not simply as supporters, but as investors in the school’s mission and future. This language matters. Investors are people who believe in where you are going and want to help you get there. When fundraising conversations are rooted in deep listening and alignment, something powerful happens.
Not long ago, I met with a generous couple who wanted to explore making annual gifts to our school through their family foundation. They had grown up with modest means, experienced significant professional success, and felt a deep desire to give back. Our conversation was not focused on a specific dollar amount. Instead, we talked about the school’s strategic priorities, where we were heading, and what they found most meaningful about our community.
In my follow-up email, I shared something that has become central to how I approach philanthropy. I told them that the most important outcome was that they felt inspired, connected, and fulfilled by their giving. I asked them to reflect on which aspects of our school's vision resonated most deeply with them so we could explore ways for them to engage in those areas.
That conversation led to a second meeting and, ultimately, to generosity that allowed us to move forward on elements of our strategic plan that had previously felt aspirational. Just as importantly, the donors felt genuinely connected to the impact of their investment.
Not every vision resonates with every donor, and that is okay. Ethical fundraising means helping people give in ways that align with their values, even if that leads them elsewhere. When leaders approach philanthropy with respect, curiosity, and integrity, it creates a powerful symmetry between donor purpose and school mission. That is how transformational work becomes possible.