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    4. May - June 2022

    Talking Shop: Acting Out the Ask

    How role-playing can help volunteers gain fundraising confidence
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    By Holly Leber Simmons
    May 1, 2022

    Incorporating role-playing into board training can help trustees and volunteers gain confidence and be able to anticipate roadblocks when fundraising for institutions. Laura Grams, Director of Institutional Advancement at Berkeley Preparatory School, knows that role-play can be a powerful tool to engage trustees. During a workshop, one trustee veered off script and declared that he was making a $1 million endowment to the school. Grams said she asked if he was still role-playing. “No,” replied the trustee, to a collective gasp. 

    Grams discussed how her school is applying the practice of role-playing to make for better advancement opportunities.

    Laura Grams

    Laura Grams
    Director of Institutional Advancement
    Berkeley Preparatory School, Tampa, Florida, U.S.

    Credit: Berkeley Preparatory School

    How did this practice of incorporating role-play into fundraising come about?
    We want our volunteers to feel prepared for anything. Fundraising is not their profession. Role-playing allows them to become more comfortable. In one scenario, we had the role of a current parent talking with a friend who is an alumnus. It may not be comfortable for a volunteer to ask for a gift supporting our school. So we scripted that natural flow of conversation they might have as they’re playing golf or having dinner. We scripted questions from the alumnus that would be encouraging for the volunteer but also inserted objections so the volunteer was prepared to handle those. 

    What do you hope volunteers learn?
    Our purpose was to take away the anxiety and the fears. We always want to send volunteers out teed up for success. We are not going to send them to someone [if] we have no idea whether or not they love our organization. This is never a cold call; this would be a conversation where a no may not mean no, it might just mean not right now. So we’re preparing them more for those. We prepare the volunteers just to thank the person for having the conversation and for their interest in the organization. Then ask if there’s a good time to follow up. [We encourage them to be] just be really good stewards of that person’s time.

    Do you plan to continue the role-playing trainings with new trustees and volunteers?
    We do. It’s a great practice for anyone new to a development or advancement team to do some role-playing activities. You never know when you might be in a conversation where someone asks: What are the priorities? What do you need? How can I be helpful to your organization? And the more people who have this training and could be comfortable having that conversation, the better. 

    What advice would you give a fellow advancement professional who wanted to launch a similar training program?
    Talk to your colleagues. Those who are closest to your mission can help you come up with some of the scenarios. There are so many people in an organization who have had these conversations, whether they know they’re fundraising conversations or not. 

    We worked with consultant Bob Carter, who presented with me about this at the 2021 CASE-NAIS Independent Schools Conference. He gave us the framework, and then we made [it] more personal to our mission and our trustees.

    Who are the best people to participate in role-play exercises?
    Something we stressed in training is that there’s a role for everyone. We had some trustees who said, “I’m just not comfortable,” so we gave them stewardship roles. This training provides the tools, but you want people who are comfortable. One thing we know is that people give to people. We have to build trust, and that takes time and effort. 

    What makes for a great fundraising volunteer?
    You want volunteers who believe in your mission and a particular project. We want them to have invested in the organization themselves. When a volunteer is asking a peer or friend to invest, and the friend says, “What did you do?” we want to make sure the volunteer is ready to answer that question enthusiastically and is truly inviting their friends to join them. 

    We want the volunteers to tell our story and be good listeners. They should be sharing the mission of the organization, then inviting the people they’re talking with to share their stories, so they know exactly how to make donors feel that they’re able to have the greatest impact. 

    About the author(s)

    Holly Leber Simmons

    Holly Leber Simmons is a writer and editor based in Silver Spring, Maryland, U.S. 

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    US/Canada Independent Schools Fundraising Donors Currents Magazine Department

    Article appears in:

    Cover of the May-June 2022 issue of Currents
    • May 1, 2022

    May - June 2022

    Diversity and inclusion, engagement, leadership: Inside the challenges and opportunities for senior diversity leaders in higher education; integrating alumni relations and development; and resetting in-person, online, and hybrid events. 

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