1. "How familiar are you with this issue?"
This simple question tells you so much. It helps you understand where someone is in their awareness journey about the issue your nonprofit is addressing, and how much context they might need before they're ready to give.
If they haven't heard much about the issue yet, that's not a barrier. It's just a signal. It means some education and storytelling will go a long way before you make any kind of ask. Meeting people where they are is one of the most important things you can do as a fundraiser.
💡Try this: Create an issue fact sheet with a few key data points and a short but compelling story about someone impacted by the issue that you can offer up interested potential supporters.
2. "Where have you seen this issue show up in our community?"
This question does something really powerful. It invites the person to connect your mission to their own observations and experiences, which starts making the issue feel real and personal to them.
When someone can point to a specific moment or place where they've been affected by or witnessed the issue you're working to solve, it stops being an abstract cause and starts becoming something they genuinely care about. That personal connection is what turns a casual conversation into the beginning of a meaningful donor relationship.
3. "Which area of our work feels most relevant to you right now?"
Before you ask this question, give them 2-3 options to choose from.
For example: "Is it the mentoring piece, the emergency support piece, or the bigger systems-change piece that stands out most?"
This does two things. It helps you understand what aspect of your work resonates most with this particular person. It also makes the conversation feel more collaborative and less like a pitch.
When donors feel like their interests are being considered, they're much more likely to stay engaged.
4. "Have you ever connected with a mission like this through volunteering, giving, attending events, or other forms of support?"
This question helps you understand a potential donor's history of giving and community involvement. Past behavior is one of the best predictors of future behavior.
If they've donated to similar causes before, you know they're already comfortable with giving. If they've volunteered, they might be more interested in getting involved hands-on before making a financial gift. Either way, their answer gives you a clearer picture of how they're most likely to want to participate, and how to invite them in.
5. "What questions do you have?"
I love this one.
This might be the most powerful question on the list.
When someone asks a question, they're telling you exactly where their curiosity, confusion, or hesitation lives. That is incredibly valuable information. It reveals trust gaps you might not have known existed, objections you can address, and next steps to keep the relationship moving forward.
💡Try this: Whatever they share, write it down and follow up with a thoughtful response within the next week. That follow-up is where the relationship really starts to deepen.
Try it this week 🚀
Pick one conversation you already have scheduled this week, whether it's a coffee meeting, a donor call, or a community event, and try working one or two of these questions into it naturally. You don't have to ask all five at once. Just start listening more intentionally and notice what you learn.
