3 Steps to Optimizing Small Group Dinners for Major Gift Fundraising

Small group dinners can be a powerful tool in major gift fundraising, offering a unique setting to build relationships, cultivate prospects, and inspire philanthropy. Unlike large events, these intimate gatherings allow for meaningful conversations and deeper engagement. However, to maximize their effectiveness, careful planning and strategic execution are essential. Here’s how to optimize these dinners to drive successful fundraising outcomes.

1. Identify Key Attendees First

Start by selecting the top three prospects you want at the dinner. Instead of simply sending invitations, engage them early by seeking their input on key details:

• Where should we host it?

• What dates work best?

• What topics should we discuss?

By involving them in the planning process, you give them ownership over the event, increasing their commitment and making it far more likely they will attend.

2. Leverage Social Proof

Once your top three prospects are confirmed, extend invitations to the next tier of 8–12 attendees. The key is to highlight the presence of the top prospects—successful alumni or key industry leaders—who will be at the dinner. This creates an additional draw, as others are more likely to accept an invitation when they know they’ll have the opportunity to connect with influential peers.

3. Reinforce Commitment

As the guest list is finalized, send out a confirmation email listing all attendees. This step helps minimize last-minute drop-offs by reinforcing the value of the event. When attendees see who else will be there, they are more likely to follow through on their commitment, ensuring a well-attended and productive dinner.

Small group dinners can be a game-changer in major gift fundraising when executed with intentionality. By strategically selecting key prospects, leveraging social proof, and reinforcing commitment, you can create an engaging experience that strengthens donor relationships and drives meaningful philanthropic support.

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5 Specific Takeaways from The Smart Nonprofit by Beth Kanter and Allison H. Fine

The Smart Nonprofit by Beth Kanter and Allison H. Fine provides a roadmap for nonprofits to integrate technology in ways that enhance their mission while staying true to their human-centered values. Here are five specific takeaways from this excellent book which can be purchased here on Amazon:

1) Automating Routine Tasks to Free Up Staff

The authors share an example of a nonprofit that used a chatbot to answer frequently asked questions from volunteers, saving staff time. This allowed team members to focus on building deeper relationships with volunteers and improving program quality.

2) Using Predictive Analytics for Fundraising

Kanter and Fine highlight a nonprofit that implemented predictive analytics to identify donors most likely to upgrade their giving. This approach increased efficiency and allowed fundraisers to prioritize high-value prospects while maintaining personalized engagement.

3) Addressing Bias in AI Tools

The book discusses a nonprofit that implemented AI-driven hiring software but discovered biases against candidates from underrepresented groups. By auditing and adjusting the algorithms, the organization ensured fairer hiring practices and a more inclusive approach.

4) Creating Ethical Data Policies

One example involves a nonprofit that developed a clear data-use policy, outlining how donor and beneficiary data would be collected, stored, and shared. This transparency built trust with stakeholders and set a precedent for ethical data management in the sector.

5) Human Oversight of Automated Decision-Making

The authors describe a nonprofit that used AI to recommend beneficiaries for specific programs but required human staff to review and approve all decisions. This ensured that the technology supported, rather than replaced, nuanced and empathetic decision-making.

These examples illustrate how nonprofits can adopt technology responsibly while keeping human connection and ethical practices at the forefront. Again, we highly recommend this excellent book!


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Winning Over Gatekeepers: The Critical Role of Executive Assistants in Nonprofit Fundraising

In the world of nonprofit fundraising, executive assistants (EAs) are often overlooked, yet they have significant influence over a key aspect of the fundraising process: access to top prospects. These professionals are more than gatekeepers; they are trusted advisors, managers of their executive’s time, and can help ensure meaningful engagement with potential major donors. Winning over an executive assistant can be the difference between securing a high-impact meeting or being perpetually stuck in the “we’ll get back to you” zone.

Why Executive Assistants Matter

1. Time Managers
Top executives, especially high-net-worth individuals, operate on tightly packed schedules. Their executive assistants hold the keys to that calendar. Understanding this makes the EA a valuable ally in navigating the complexities of scheduling.

2. Trusted Advisors
Executive assistants are privy to their employer’s preferences, priorities, and philanthropic interests. They often filter requests and decide which are worthy of the prospect’s attention. Building trust with an EA means they are more likely to champion your cause internally and get back to you in a timely manner.

Strategies to Win Over Executive Assistants

1. Treat Them as Decision-Makers
Approach executive assistants with the same level of respect and professionalism you would extend to their boss. Recognize their authority and acknowledge the critical role they play.

2. Build Genuine Relationships
Take time to connect with the EA on a personal level. Learn their name, remember their communication preferences, and inquire about their schedule and workload. A thoughtful and genuine connection can open doors.

3. Be Concise and Clear
Executive assistants are often juggling multiple priorities. Ensure your outreach is succinct, professional, and focused on the value your nonprofit offers. Provide clear reasons why a meeting would be beneficial to the executive, and outline the alignment between their interests and your organization.

4. Respect Their Time
Understand that EAs are busy professionals. Be flexible and accommodating when proposing meeting dates and times. If an EA declines a meeting, thank them for their time and ask when it might be more appropriate to follow up.

5. Provide Value
Whenever possible, share information or materials that could interest the EA or their executive. This could be a summary of your nonprofit’s impact, a newsworthy success story, or an invitation to an exclusive event. Adding value upfront demonstrates respect for their role and helps differentiate your organization.

6. Show Gratitude
Small gestures of appreciation go a long way. A handwritten thank-you note or a follow-up email acknowledging their effort can make a lasting impression.

Engaging executive assistants isn’t just a means to an end. Establishing positive relationships with them fosters goodwill and trust, making future interactions smoother. Over time, a well-nurtured relationship with an EA can result in access to opportunities that may otherwise be off-limits. In nonprofit fundraising, success often depends on the ability to forge connections with the right people. Recognizing the pivotal role of executive assistants and employing thoughtful strategies to engage them can significantly enhance your chances of connecting with top prospects and achieving transformative results. By respecting and valuing EAs, fundraisers not only open doors but also pave the way for long-lasting relationships that drive impact.

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