The Missing Middle: Creating an Engagement Strategy for Leadership Donors
In 2026, building and maintaining a strong donor pipeline remained a key concern for philanthropic organizations, which dedicate substantial resources to acquiring new donors at the pipeline's entry point. At the same time, teams invest significant time, research, and personalized strategy in cultivating major and principal/transformative gift prospects.
However, a critical segment lies between these two ends of the pipeline. A donor may give $1,000, $2,500, $5,000, $10,000, or more each year, depending on how an organization defines leadership or mid-level giving. And they often give significantly more than the average annual donor, but they haven't reached the organization’s major gift threshold, yet.
This group is often called the 'forgotten middle,' a term that endures because organizations frequently fail to address their unique needs and potential. These donors typically receive the same communications as the broader annual giving base, perhaps with a giving society invitation or a few incremental benefits, yet they rarely receive the intentional relationship management and strategic engagement reserved for major gift donors. This presents a challenge, as these donors are not simply future major gift prospects.
This segment matters because they are already providing meaningful support to your organization and its mission.
Our opportunity is to deepen these relationships by acknowledging the commitment these donors have already demonstrated and creating intentional pathways for continued engagement.
The Middle Matters More Than Ever
Recent fundraising data makes this conversation especially timely for philanthropy professionals.
In July 2026, the Fundraising Effectiveness Project reported that charitable dollars rose an estimated 4.3% in the first quarter of 2026, while donor counts fell by 0.8%. More concerning, retention declined across all donor groups during the same quarter: Small, Midsize, Major, and Supersize. This also aligns with the full-year 2025 findings: dollars rose 5%, while the number of donors fell 3.6%. These trends suggest that even as fundraising totals rise, our donor pipeline’s long-term health and sustainability remain at risk.
If you know me, you’ve undoubtedly heard me say, “Retention, Retention, Retention!” Retaining your current donors and deepening those relationships is more essential than ever. Higher education leaders recognize this opportunity: EAB’s research shows that mid-level and leadership annual giving are quickly becoming philanthropic priorities. In EAB’s 2025 Advancement Leaders Survey, 92% of leaders rated mid-level giving as a high or moderate priority. Improving engagement with mid-level donors was also the most common strategy leaders identified to address donor decline.
EAB’s 2026 research goes one step further: leadership-giving growth depends on combining better data with structured stewardship and intentional donor engagement, rather than assuming it will occur naturally.
The broader nonprofit sector is reaching the same conclusion. In September 2026, the Chronicle of Philanthropy described donors giving roughly $1,000 to $10,000 as a distinct group deserving its own strategy, noting that they often fall between mass annual fundraising and high-touch major gifts. We must ensure these donors no longer fall through the cracks in our engagement strategies.
Start With Engagement, Not the Gift Amount
Here is where donor relations can shift the conversation. A leadership giving program should not be treated as a scaled-down version of major gift fundraising.
Engagement must go beyond a giving society.
DRG's behavior-based donor relations philosophy encourages us to look beyond the size of a donor's most recent gift and focus on the donor’s behavior. A first gift, recurring gift, consecutive gift, upgrade, event attendance, engagement with communications, volunteer service, or support for a particular initiative all tell us something about the donor's relationship with our organization.
Recognizing this distinction is essential to building an effective donor engagement strategy.
Two donors may each contribute $2,500 this year. One has given $2,500 every December for 15 years and regularly attends alumni programs. Another previously gave $250 and, after attending a presentation on student financial aid, suddenly increased their gift tenfold. Same gift amount. Very different donor behaviors. Very different engagement opportunities.
This is why the donor journey must reflect giving level, giving behavior, interests, engagement, and relationship stage. A well-developed donor relations framework should give mid-level donors a curated experience with meaningful personal touches, milestone communications, and engagement tailored to their behaviors and interests.
Give Them More of What Matters, Not Just More
Engaging leadership donors does not mean developing individualized stewardship plans for hundreds or thousands of donors. It requires thoughtful segmentation and differentiated engagement strategies. The goal isn't necessarily more communication. It is about delivering more relevant and meaningful communication.
That might include a personalized acknowledgment recognizing an upgrade. An impact story tied to the fund the donor supports. A note recognizing ten consecutive years of giving. An invitation to hear directly from a faculty member, student, program leader, or beneficiary. A brief, non-solicitation phone call. Or an insider update on something the donor has repeatedly shown interest in.
A strong leadership giving framework calls for personalized acknowledgment, impact reports tied to each donor's giving area, three to five meaningful touches at strategic intervals, and content tailored to donors’ interests and capacity. Notice what isn't on that list: More generic newsletters.
Mid-level donors should not receive every communication just because they give at a higher level. They need to receive the communications and experiences most likely to enhance their connection with the institution.
Let Donor Behavior Determine the Next Step
This is where data and analytics become especially valuable.
Engagement data helps prioritize where we should focus limited staff resources and attention.
Consider the donor who:
increases their gift two years in a row
begins attending events connected to the area they support
responds consistently to impact stories
makes multiple gifts during the year
becomes a volunteer or mentor
responds to a survey and identifies a specific passion
has given loyally for many years but suddenly stops
Those behaviors should prompt a specific response or action. Not always an ask.
Sometimes the next right move is gratitude. Sometimes it is an impact story. Sometimes it’s an invitation. Sometimes it’s a conversation. And occasionally, yes, it is an opportunity to explore a larger gift.
The key is to let donor behavior guide our next steps.
This approach is fundamentally different from simply producing an annual report listing everyone who gave between $1,000 and $24,999.
Most philanthropic organizations still have room to improve. EAB's 2026 survey found that only 51% of leaders reported using predictive modeling or scoring for likelihood to give, upgrade, or lapse, and only 48% used performance data to refine strategy. Meanwhile, 84% said they use stewardship to help build the pipeline, but only 28% said they do so very consistently across most or all donor segments. That gap is precisely where donor relations professionals can have a significant impact.
Engagement Is Bigger Than Stewardship
This distinction is also important. Stewardship is one component of donor engagement, but it does not encompass the full scope. We steward the gift: we acknowledge it, honor donor intent, report on its use, and demonstrate its impact. We engage the individual behind the gift. That may happen before a gift, between gifts, after a gift, or even during a year when the donor doesn't give at all.
For leadership donors, this broader perspective is essential. Our goal is not only to provide a satisfactory post-gift experience but also to build an ongoing, meaningful relationship. That might include volunteering, mentorship, events, advocacy, surveys, conversations, insider content, institutional updates, or opportunities to share expertise.
CASE's 2025 Voluntary Support of Education findings, released in April 2026, offer another reason to keep impact central to these interactions: 81% of contributions to U.S. colleges and universities were designated for specific purposes, with student success, financial aid, and research among the most common destinations. When donors express their priorities through their giving, our engagement strategies must reflect and honor those interests.
Don't Treat Every Leadership Donor as a Major Gift Prospect
Another common pitfall to avoid. Not every $5,000 donor wants to become a $50,000 donor. And that’s okay. Pipeline development is critical. Leadership giving is a vital bridge between annual and major giving. Investing in this middle segment delivers both immediate revenue and long-term strength for the donor pipeline. However, donor engagement should not be reduced to simply moving individuals to the next giving level.
Some donors will upgrade. Some will eventually make major or planned gifts. Some will give $2,500 faithfully for 25 years. All three can be extraordinary donor relationships. Our responsibility is to recognize and honor these dissimilarities.
Build a System, not a Collection of One-Off Efforts
The best leadership donor programs do not depend on one fundraiser remembering to make the perfect phone call. They create systems.
Determine clear criteria for inclusion in the leadership donor segment. Identify key behaviors to monitor. Set baseline engagement standards that every leadership donor should experience.
Determine which moments require enhanced personalization. Assign clear ownership for each step.
Document interactions in the CRM. Establish triggers for upgrades, lapses, milestones, and major gift referrals. Finally, measure whether these experiences are delivered consistently.
This approach is especially important as advancement teams are being asked to do more with fewer resources and staff. Personalization does not require manually crafting all engagement.
Automate processes where possible and focus staff attention where it will have the greatest impact.
The Chronicle of Philanthropy's September 2026 report reaches a similar conclusion: successful mid-level programs combine robust back-end systems with simple human touches, such as personalized notes, phone calls, recognition of giving history, and communications that show the organization knows who the donor is.
This approach is scalable and achievable for all advancement teams.
The Middle Shouldn't Feel Like the Middle
Our leadership donors have already raised their hands. They have demonstrated generosity, loyalty, interest, or some combination of the three. What happens next should not be determined only by whether a donor’s most recent gift meets a specific threshold.
Pay attention to what they support.
Notice when their behavior changes.
Recognize loyalty.
Show impact.
Invite participation beyond philanthropy.
Give personal attention when the moment calls for it.
When their behavior suggests they want a deeper relationship, be aware and be prepared for that conversation. The goal isn't simply to generate more major gift prospects. It is to foster deeper, more meaningful donor relationships.
When we do this well, retention, loyalty, upgrades, pipeline growth, and lifetime giving become natural outcomes of a strong donor experience, rather than the sole drivers of engagement.
Written by Jenny Jones
