I don’t know of a single organization that has not spent the past year reevaluating its priorities and assessing the continued relevance of its mission. A year of existential upheaval seems to have given all of us a new sense of permission to explore our most daunting problems—particularly the question of how to address systemic racism in our organizations and in the development field.

Systemic racism may play out differently in each of our sectors. But as development professionals we all face the same conundrum: our work is inextricably bound up with issues of class, privilege, inequity, and the notion that the most prized features of a civilized society must be paid for by wealthy benefactors. How do we even begin to address this? (Those FY22 revenue goals aren’t going to take care of themselves.)

Mission-based organizations are used to grappling with deeply complex problems, but we can be overly focused on answers. That’s our big mistake.

One of the most transformative ideas I have encountered over the course of my career is to let go of answers and instead focus on getting to the right question—the question that will guide continued exploration, honest reflection, and rigorous assessment.

When I joined the Hanover Theatre and Conservatory in Worcester, I found an organization deeply committed to creating a 360-degree culture of diversity, equity, inclusion and belonging, where each department was asked to set goals and institute practices that actively promote these values. Like many of us, I was tasked with leading my team in this effort with no particular expertise or experience.

A turning point for me was a conversation with Michael Bobbitt, ED of the Mass. Cultural Council, about his tenure as Artistic Director of the New Repertory Theatre in Watertown. New Rep had essentially dismantled every aspect of traditional fundraising that did not support a culture of equity and inclusion—tiered donor benefits, dynamic ticket pricing, hierarchical donor recognition, etc. I could see how this would be possible at New Rep, but I was at a 2,300-seat theatre presenting hundreds of shows and events each year, with donors that are deeply invested in the benefits they receive, and a department that was immersed in maintaining that system.

That’s when I found my very simple guiding question: “What if?”

We didn’t have to blow up this whole system. We just had to take a fresh look with a critical eye and start asking ourselves, “What if we did this differently?” Some changes were relatively straightforward—replacing language like “VIP” and “exclusive” that felt antithetical to the values of equity and inclusivity. Here’s a more complicated example.

Our major donors have access to a private salon in the theatre before performances and during intermission. It is a prized benefit that gives us terrific access to our most generous supporters and it feels absolutely fundamental to our culture. It also means that there is literally a guarded door between us and, on any given night, more than 1,500 other people who may just be waiting for an invitation to get more involved.

What if we used the salon a different way? What if we used it to cultivate donors rather than to reward them? What if we used it to be welcoming rather than exclusive? As we dug into these questions, we realized that currently we don’t even gather enough data to know how effectively we’re leveraging this tremendous asset. So this season, we will implement a new system to track salon attendance and to test models for a more inviting and cultivation-focused strategy. It will be an extended process and we don’t know what the outcome will be, but a simple “what if?” inspired an effort that will significantly increase our understanding of donor behavior (with valuable data to back it up) and promote a more welcoming and inclusive culture of philanthropy.

This is a long game, and along the way we will likely have to contend with resistance, skepticism, and our own uncertainty. But in the process of engaging in this work, I have been completely energized by the generosity and good will of donors, board members, co-workers, and development colleagues. I invite you to sit down with your colleagues and just start asking “What if?” I would love to hear what happens.