Asking someone for a major gift can be one of the most anxiety-inducing moments in a fundraiser’s career. No matter how well you know your donor, the act of making a bold ask especially when the stakes are high, rarely feels easy. That’s why fundraising role-play isn’t just helpful; it’s essential. Practicing the conversation before the real thing allows fundraisers to feel more grounded, confident, and prepared when it matters most.
In this blog, we walk you through a team-based fundraising training exercise that uses role-play to strengthen your ask. Whether you’re managing a team of development professionals or just want to sharpen your own skills, this kind of intentional practice can dramatically improve both confidence and outcomes.
Why Role-Play Is a Game-Changer for Fundraisers
When it comes to fundraising, we spend hours researching donors, refining our case for support, and crafting the perfect pitch. But how often do we actually rehearse what we’re going to say out loud? As Amy Eisenstein points out in How to Practice and Prepare for a Strategic Pair Ask, “You would never wing a meeting with investors—why would you wing this?”
Fundraising role-play gives you the chance to simulate high-stakes conversations without real-world pressure. You can test different approaches, build muscle memory, and receive actionable feedback, all in a safe space. Research shows that deliberate practice, a term popularized by psychologist K. Anders Ericsson, is the key to developing expertise in any field, including fundraising. It’s about purposeful repetition paired with feedback, reflection, and continuous improvement.
Want to go deeper? Megan DeVoe explores this beautifully in The Power of Practice, showing how role-play is a cornerstone in advanced sales training and remains underutilized in our sector.
How to Set Up a Major Gift Role-Play Session
Here’s a simple exercise you can try with your team:
Scenario: A donor has given $100 annually for two years. They recently received an invitation to increase their gift to $250. A follow-up call is scheduled. Time to prepare.
Assign one person to play the fundraiser and another the donor. The fundraiser’s job? Open the call with warmth, explain why the larger gift matters right now, and make a clear, confident ask. From there, the conversation might twist, stall, or soar, just like in real life.
Use this format, adapted from Nonprofit Quarterly’s role-play guide, to create a three-person triad:
Asker
Donor
Observer
Afterward, take a few minutes to reflect. What felt strong? What could be improved? What would you try differently next time? These short debriefs are where the real growth happens.
Make the Scenario Realistic and Impactful
For the role-play to be useful, the scenario should feel authentic. Start by setting the stage: What’s the donor’s history with your organization? What recent programs or campaigns might they be excited about? Then, think through how you’ll structure the conversation.
Begin with a natural, relationship-driven opening. Then pivot into the case for support, why you’re reaching out now and what impact a larger gift could make. When it’s time to make the ask, be specific. Instead of saying “Would you consider increasing your support?” try “Would you consider making a $250 gift to help us expand our youth mentorship program this fall?” Anchoring the ask in a real, tangible need helps donors feel more connected to the impact.
Finally, listen carefully. Some of the best moments in a donor conversation happen when you’re fully present and responsive, not rushing to the next point. Practicing that kind of listening in a fundraising role-play makes it second nature during the real thing.
Building a Culture of Practice and Feedback
Role-play isn’t just a one-time training tool; it can be a regular part of your team’s culture.
Incorporating it into staff meetings or using it to prepare for big campaign launches helps normalize the idea that practice is part of the process, not a sign of weakness, but a commitment to growth.
Encourage your team to give each other supportive, actionable feedback. When people feel safe and empowered to practice and reflect, they’re more likely to stretch themselves and improve. Over time, this creates a culture of shared learning and continuous improvement.
Want more evidence? The team at Nexus Nonprofits reinforces how deliberate practice not only builds confidence but helps fundraisers handle rejection, recover quickly, and keep showing up prepared in their article, Mastering ‘The Ask’ in Fundraising: A Transformative Skill for Nonprofit Leaders.
How Practivated Makes Practice Easier
While team-based fundraising role-play is powerful, it’s not always easy to find time for live practice sessions. That’s where Practivated comes in. Practivated is an AI-powered donor conversation simulator that lets fundraisers practice realistic asks anytime, anywhere.
Whether you’re new to fundraising or preparing for your next big campaign, Practivated helps you refine your pitch, get comfortable making the ask, and receive real-time feedback. It’s a low-pressure environment designed for high-impact growth. You can rehearse difficult scenarios, experiment with different messaging, and walk into your next donor meeting feeling prepared and confident.
Practice That Pays Off
The truth is, most fundraisers aren’t nervous because they don’t know their stuff. They’re nervous because they haven’t practiced saying it out loud. Fundraising role-play bridges that gap. It takes all the strategy and planning you’ve done and helps you deliver it with clarity and confidence in the moment.
So before your next big donor meeting, take some time to rehearse. Whether it’s with a teammate, a mentor, or a platform like Practivated, a little practice can go a long way. It won’t just make you a better fundraiser—it will help you build stronger relationships and raise more for the mission you believe in.
