The Biggest Challenge for Fundraisers: Getting That First Prospect Meeting

If you’re a fundraiser, this might sound familiar: An experienced development team at a mid-sized university foundation is doing everything right to hit their goals for prospect meetings. They have a well-researched prospect list and a personalized outreach plan. What’s the problem? They’re not getting that first one-on-one prospect meeting. Time and again, they find their meeting requests with prospects ignored or rejected.

Ron Cohen, former vice president of University Relations at Susquehanna University, can relate.

“In the 90s, you’d tell people about a project you were planning and people would ask, ‘How much do you need?’” Cohen said. “Nowadays, there’s much more skepticism. It’s more about, ‘Explain to me why this is important to the organization and, by the way, what about these other areas that I care about?'”

This challenging evolution in donor engagement isn’t isolated. According to the 2024 State of the Development Profession Survey conducted by the Donor Participation Project and Langley Innovations, 53% of fundraisers cite securing that first meeting as their biggest challenge in prospect engagement. No other challenge comes close.

This finding is particularly puzzling because the majority of those surveyed expressed confidence in their abilities, in the effectiveness of their fundraising materials, and in the fairness of their performance metrics. So why, with increasingly sophisticated tools at our disposal that allow us to identify more potential donors and gain greater insight into giving propensities, are fundraisers struggling to start philanthropic conversations?

The Changing Landscape of Donor Engagement

The fundraising landscape has transformed dramatically over the past decade. Donors are bombarded with more communications than ever before, attention spans have shortened, and traditional outreach methods have lost effectiveness. What worked five years ago often falls flat today.

Consider these sobering statistics from our survey:

• 41% of fundraisers report that fewer than 20% of prospects respond positively to initial outreach
• Only 8 respondents out of 571 reported an 81-100% positive response rate to initial outreach

The old playbook doesn’t work anymore. Donors expect personalization beyond just seeing their name in an email subject line. They want to know you understand their specific interests and values before they’ll agree to spend time with you.

Balancing Technology and Human Connection

The solution to this challenge depends on thoughtfully integrating data-driven strategies with authentic human connection.

Using Technology to Prepare More Effectively

Before reaching out to prospects, savvy fundraisers are using technology to do the prep work:

1. Identify the right prospects. Rather than casting a wide net, use wealth screening and predictive modeling tools to focus on prospects with both capacity and likelihood to engage with you and your mission. This allows you to concentrate your efforts where they’re most likely to yield results.
2. Understand prospect motivations. Advanced prospect research tools can help you uncover a prospect’s philanthropic interests, giving history, and connections to your cause. This information is invaluable for crafting personalized outreach that resonates.
3. Develop tailored messaging. When you understand what motivates each prospect, you can create outreach that speaks directly to their interests. This isn’t about manipulation—it’s about respecting their time by showing you’ve done your homework.
4. Time your outreach strategically. Use your CRM to track prospect interactions and identify optimal times for outreach. Has the prospect recently engaged with your organization in some way? That’s often the perfect moment to suggest a meeting.

The right technology stack doesn’t just make these tasks possible—it makes them efficient. With better systems, fundraisers can spend less time researching and more time building relationships. In fact, the right technology can transform the first-meeting hurdle into a pipeline management opportunity.

Longwood University uses AI to identify best-fit prospects: See how it works

For Frank Jenkins, Managing Director at the Austin Chamber Music Center, employing technology-enhanced personalization as a beta tester of the AI assistant, WIZE, has helped him produce significantly higher response rates from donors.

“I’m already having trouble keeping up with the people I need to follow up with about specific asks and opportunities,” Jenkins said.  

Humanizing Your Approach

While technology provides the foundation, the human side of fundraising remains crucial. Our survey found that relationship building was considered both the strongest skill (32% of respondents) and the most crucial skill for fundraisers (37%).

Here are strategies that successful fundraisers are using to secure more first meetings:

1. Lead with value, not need. Instead of immediately focusing on your organization’s needs, offer something of value to the prospect—insights, connections, or information relevant to their interests.
2. Leverage warm introductions. The survey data suggests that personal connections significantly increase response rates.
3. Create multiple touchpoints. Develop a strategic sequence of touchpoints across different channels, including email, phone, social media, handwritten notes, or small, thoughtful gifts that relate to the prospect’s interests.
4. Personalize beyond the superficial. True personalization goes beyond using someone’s name. Reference specific information about their past engagement, philanthropic interests, or connections to your cause.
5. Offer flexibility. Give prospects options for how they’d like to connect—virtual or in-person, formal or informal, one-on-one or with others present. This demonstrates respect for their preferences and schedule.

Reframing the First-Meeting Hurdle as an Opportunity

What if we viewed the difficulty of securing first meetings not as an obstacle but as an opportunity to elevate our approach? This shift in perspective can transform how we engage with prospects.

Developing More Holistic Metrics

Our survey revealed that 52% of respondents feel total dollars raised is overemphasized as a performance metric. This suggests a need for more nuanced evaluation that considers the quality of donor relationships.

Consider tracking metrics like:

• Conversion rate from first meeting to second meeting
• Donor satisfaction scores
• Long-term retention and upgrade rates
• Referrals from existing donors

Several survey respondents highlighted the overemphasis on “face-to-face visits rather than meaningful contacts” and “number of visits made,” suggesting that quality of engagement should take precedence over simple counting of interactions.

Investing in Skill Development

While relationship building was identified as the strongest skill among fundraisers, data analysis was highlighted as the area needing most improvement (21% of respondents). This indicates a growing recognition of data’s importance in modern fundraising.

Organizations that invest in training their teams in both data analytics and interpersonal skills are seeing higher success rates in securing first meetings. This dual approach ensures fundraisers can identify the right prospects and engage them effectively.

Communicating So Effectively, Prospects Feel Called to Act

The way we communicate with prospects can significantly impact their willingness to meet. Our survey found that emotional storytelling was the most successful type of fundraising material (299 respondents), followed by personalized proposals (260) and impact reports (222).

Improving Impact Reporting

Despite 56% of respondents believing their fundraising materials effectively communicate mission and impact, the same percentage identified demonstration of impact as the area needing most improvement. This paradox suggests a gap between perceived and actual effectiveness of communications.

To bridge this gap:

• Use concrete examples and specific outcomes rather than general statements
• Incorporate both data and personal stories to appeal to different types of donors
• Connect the prospect’s potential contribution to specific, measurable impact
• Create visual representations of impact that are easy to understand at a glance

Focusing on Emotional Storytelling

For fundraisers’ own giving experiences, personal connection to the cause was overwhelmingly the most memorable factor (39% of respondents). This underscores the importance of emotional engagement in fundraising strategies.

Effective storytelling for first meeting requests:

• Share a brief, compelling story that illustrates your mission
• Create an emotional connection without overwhelming the prospect
• Invite the prospect to become part of the story through their engagement
• Be authentic and avoid manipulation or exaggeration

Leveraging Technology for Personalized Communication

Modern fundraising platforms allow for unprecedented levels of personalization in communications. By integrating your CRM data with communication tools, you can:

• Segment prospects based on interests, giving history, and engagement patterns
• Create tailored content streams for different prospect segments
• Automate personalized follow-up sequences while maintaining authenticity
• Track engagement with your communications to refine your approach

This technology-enabled personalization can significantly increase positive responses to meeting requests.

Putting It All Together: A Strategic Approach to Securing First Meetings

Based on our survey findings and conversations with successful fundraisers, here’s a strategic framework for improving your success rate with first meetings:

1. Prepare thoroughly. Use your technology stack to identify the right prospects and understand their interests, capacity, and connection to your cause.
2. Develop a personalized outreach plan. Create a sequence of touchpoints that provides value to the prospect and demonstrates your understanding of their interests.
3. Lead with impact. Show how your organization is making a difference in areas the prospect cares about, using both emotional storytelling and concrete data.
4. Make a clear, specific ask. Request a meeting with a defined purpose that benefits the prospect as well as your organization.
5. Follow up thoughtfully. Use your CRM to track follow-up communications and ensure you’re persistent without being pushy.
6. Analyze and refine. Track your success rates and continuously refine your approach based on what works.

Conclusion: Focus on the Human Connection

The challenge of securing first meetings reflects a broader shift in how people engage with organizations and causes. When we all defer to digital communication, the human connection becomes both more difficult to establish and more valuable when achieved.

By thoughtfully integrating technology with authentic human connection, fundraisers can overcome the first-meeting hurdle and build meaningful relationships with donors. The organizations that will thrive in this new landscape are those that embrace both the science and the art of fundraising—using data-driven strategies to enhance, rather than replace, the personal touch that remains at the heart of philanthropy.

In the end, securing that first meeting isn’t just about getting on someone’s calendar—it’s about beginning a meaningful relationship that benefits both the donor and your mission. And that’s a goal worth investing in.