The Road Less Traveled: Navigating the Pitfalls of Major Donor Strategy

Written By Trent Thompson

Scaling Major Gifts. Strategies, action steps, and ideas for scaling major gifts by Tammy Zonker, Major Gift Expert & Keynote Speaker. 

If you’ve spent any time in the nonprofit world—as a major gift officer, development director, executive director, or board member—you know that major gifts are the lifeblood of transformational change. After nearly 30 years in this field, I’ve seen firsthand how the right major donor strategy can propel an organization’s mission to new heights. But I’ve also seen the common pitfalls that can stall even the most passionate teams.

Today, I want to share the most persistent challenges major gift officers face when implementing a major donor strategy—and, more importantly, the practical solutions I’ve found to move past them. Whether you’re building your program from scratch or looking to take your results to the next level, these insights are for you.

The Major Gift Officer’s Reality: Common Pain Points

1. Difficulty Engaging and Qualifying Prospects

One of the most frustrating hurdles is simply finding and connecting with the right donors at the right time. Too often, organizations spend precious hours reaching out to prospects who are lukewarm or unfamiliar, only to be met with silence or polite brush-offs. In my experience, this is usually a symptom of insufficient pre-qualification—reaching out without a clear sense of a prospect’s interest or capacity leads to wasted effort and missed opportunities.

2. Lack of Response and “Ghosting”

If I had a dollar for every time a promising prospect failed to reply, I’d have a major gift myself! In fact, a recent survey found that 60% of gift officers cited “no response at all” as their greatest challenge when securing meetings with potential major donors. Even after initial contact, prospects may agree to meet but then postpone or avoid setting a firm date—what I call “the runaround”.

3. Insufficient Relationship Building

Major gift fundraising is fundamentally relational. Yet, under pressure to deliver quick results, many officers rush the process or treat major donors as a monolith. This one-size-fits-all approach misses the mark, failing to connect with donors’ unique motivations and interests.

4. Inexperience and Lack of Training

Especially in smaller organizations, I often see major gift officers thrust into the role with little specialized training. The result? Inconsistent performance, missed opportunities, and a lack of confidence when it comes to high-stakes asks.

5. Discomfort with Solicitation

Let’s be honest: asking for a major gift can feel daunting, even for seasoned professionals. Organizational culture and personal discomfort can both play a role, particularly for teams more accustomed to event-based or transactional fundraising.

6. Time Constraints and Administrative Burden

Major gift officers are frequently bogged down by reporting requirements, data entry, and other administrative tasks—leaving little time for what matters most: building relationships with donors. Unrealistic metrics focused solely on dollars raised can exacerbate this problem.

7. Poor Donor Stewardship and Retention

Finally, even after a gift is secured, many organizations falter in maintaining regular, personalized communication. This erodes trust and reduces the likelihood of future support—a critical issue as donor retention rates continue to decline across the sector.

What Works: Practical Solutions from the Field

Over the years, I’ve learned that overcoming these challenges requires a blend of smart strategy, the right tools, and a relentless focus on relationships. Here’s what I recommend:

1. Invest in Robust Prospect Research

Don’t guess—know. Use tools like DonorSearch, Blackbaud Raiser's Edge NXT, or your CRM’s wealth screening features to identify prospects who have both the capacity and affinity for your mission. I’ve found that collaborating with board members for warm introductions can dramatically increase your success rate.

2. Persistence and Personalization in Outreach

Don’t rely on a single email or call. Use a multi-touch approach: handwritten notes, LinkedIn messages, or invitations to exclusive events. One approach I’ve seen work well is referencing a mutual connection or shared interest in your outreach—it immediately makes your request more relevant and less “cold”.

3. Build Authentic, Individualized Relationships

Develop individualized cultivation plans. Take the time to learn about each donor’s motivations, interests, and history with your organization. Involve them in your mission through site visits, advisory roles, or special events. I’ve watched donors move from “maybe” to “absolutely” when they feel seen and valued as individuals.

4. Prioritize Professional Development

Major gift fundraising isn’t intuitive—it’s a craft. Attend workshops, seminars, and seek mentorship from experienced colleagues. Organizations that invest in ongoing training see dividends in performance and morale.

5. Practice Solicitation and Develop a Compelling Case

The more you practice, the more confident you’ll become. Role-play solicitations with colleagues and develop clear, mission-aligned asks. I’ve found that being transparent about the need helps both the asker and the donor feel comfortable.

6. Leverage Technology to Reduce Administrative Burden

Adopt donor management systems like DonorPerfect, Neon CRM, CharityEngine, or Bloomerang to automate routine tasks and centralize donor information. Delegate or streamline reporting where possible so you can focus on building relationships.

7. Make Stewardship as Intentional as Cultivation

Thank donors promptly and personally, share impact stories, and maintain regular touchpoints. Set stewardship reminders in your CRM to ensure no donor falls through the cracks. In my experience, consistent stewardship is the single best predictor of donor retention.

Real-World Results: A Case Study in Major Gift Transformation

Let me share a recent example that illustrates the power of these strategies in action. An education institute I consulted with was struggling to grow its major donor base. By introducing a formal Major Donor Club, implementing structured upgrade systems, and personalizing communications, they achieved a staggering 453% increase in donors contributing $1,000 or more. Revenue from major donors skyrocketed from $117,000 to over $1.3 million annually.

What made the difference? According to the team, it was:

  • Structured upgrade systems to encourage increased giving

  • Personalized communication and invitations

  • Adequate recognition and appreciation for significant donors


This transformation didn’t happen overnight, but it’s proof that with the right approach, major gift fundraising can be both sustainable and scalable.

Recommended Tools and Resources

Here are some of the products and services I’ve found most effective for major gift fundraising:


Actionable Takeaways for Your Organization

  • Invest in prospect research to focus your efforts on high-potential donors.

  • Use a multi-channel, personalized approach for outreach and follow-up.

  • Develop individualized cultivation and stewardship plans for each major donor.

  • Prioritize ongoing training and mentorship for your fundraising team.

  • Leverage technology to automate administrative tasks and track donor engagement.

  • Set clear, relationship-focused metrics (not just dollars raised).

  • Celebrate and recognize your major donors in meaningful ways.


A Word of Encouragement—and a Call to Action

If you’re feeling overwhelmed by the challenges of major gift fundraising, know that you’re not alone. The landscape is shifting—recent data shows that while total giving is near all-time highs, donor retention and acquisition remain tough nuts to crack. But with the right strategy, tools, and mindset, you can build a major donor program that not only meets your goals but transforms your organization.

In my own journey, I’ve learned that persistence, empathy, and a willingness to adapt are your best allies. I encourage you to share your own experiences, questions, or success stories—let’s learn from each other and keep raising the bar for our sector.

What’s your biggest challenge in major gift fundraising right now? What’s one strategy you’re excited to try? Connect with me on LinkedIn or leave a comment below, and let’s start a conversation!


Keep transforming,
Tammy Zonker
Major Gift Expert & Keynote Speaker
Fundraising Transformed

ps – If you're thinking about a capital campaign, let's explore your vision together. Schedule a complimentary strategy session with me to discuss your campaign goals and how we can help bring them to fruition.

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Trent Thompson
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100. Overcoming the Top 7 Major Gift Fundraising Hurdles