Author: Seize The Weekday

Your best prospects are often your busiest—balancing demanding careers, family responsibilities, and packed schedules. Yet, one of the most effective ways to engage these high-potential individuals is by involving them on advisory or leadership boards. The challenge? Board meetings typically require a significant time commitment and, in many cases, travel. So how do you ensure your top prospects show up in person?

Here are a few proven strategies to boost attendance and deepen engagement:

1. Invite Them to Present

People make time for what feels meaningful. Ask your prospect to present at an upcoming board meeting on a topic aligned with their expertise and interests. Reach out a month or two in advance so they can prepare—and prioritize being there. For example, one of our computing advisory board members had a background in K–12 education and AI. We invited him to share insights on how artificial intelligence is impacting high school students’ interest in computing. He made the effort to attend—and gave one of the most memorable talks of the year.

2. Make Room for Industry Spotlights

Top prospects love to share what’s happening in their world. Build in an agenda item for board members to offer brief updates about trends, milestones, or news from their industries. One board member I worked with had just closed a major deal with a large tech firm. When we gave him the chance to talk about it at the meeting, it confirmed his attendance.

3. Anchor the Meeting Around a Signature Event

Plan your board meeting around a high-profile university or organizational event that members will want to attend anyway. Whether it’s Homecoming, a campaign launch, or a naming ceremony, tying the meeting to a memorable occasion adds extra incentive. One of our board members had recently named a space on campus, so we scheduled a ribbon-cutting as the final item on the agenda—it guaranteed his attendance.

4. Eliminate the Zoom Option

While virtual participation can be convenient, it often becomes a fallback that reduces in-person engagement. If your goal is meaningful relationship-building, skip the Zoom link. When board members know the only way to fully participate is by showing up, they’re more likely to make the trip.

By implementing these strategies, you’ll not only improve attendance at your board meetings—you’ll deepen engagement, spark meaningful conversations, and create moments that move your top prospects closer to transformative giving.

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AI tools like ChatGPT are giving major gift fundraisers a whole new way to work smarter and faster. But to truly unlock their potential, you need to understand prompt engineering—the art of crafting strategic prompts that guide AI to deliver high-quality results. At its core, prompt engineering is about giving AI the right instructions. With the right structure, context, and constraints, you can turn AI into a powerful ally that helps streamline your work. For those of us in major gifts, this means saving time and increasing efficiency. Whether it’s writing donor communications, conducting prospect research, or brainstorming cultivation strategies, AI can do a lot—so you can focus on what matters most: building relationships and closing gifts.

Here are a few effective ways to get the most out of AI using prompt engineering:

1. Assign a Persona

AI performs better when you tell it who it should be. For example, if you need help with messaging, try:

“Act like a marketing executive and draft an appeal email for a donor who supports student scholarships.”

For fundraising-specific tasks, you might say:

“Act like an expert major gift fundraiser and create a cultivation strategy for a tech entrepreneur interested in STEM education.”

This approach leads to more relevant, tailored outputs.

2. Provide Context and Constraints

The more background you provide, the better the AI will perform. Don’t just say, “Write a proposal.” Instead, try:

“Act like a senior advancement officer. Draft a one-page proposal to a long-time donor who previously gave $25K to support sustainability initiatives and is now interested in funding student-led research. Keep it under 300 words and use a warm, conversational tone.”

Include what you want—and just as importantly—what you don’t want. A great prompt is typically a paragraph, not a sentence. But do not put in any information that is unnecessary.

3. Test and Iterate

Don’t stop at one prompt. Try a few variations to see what works best. Change up the wording, try different personas, or adjust the tone. Think of it like AB testing your fundraising messages—you’re looking for the best version to move your work forward.

4. Quality In = Quality Out

AI is only as good as the prompt you give it. Tell it clearly who it should be, what it should do, and how it should do it. Specificity is your friend.

A Quick Word of Caution

AI tools pull from a wide range of sources on the internet, which means not everything they generate will be accurate—or appropriate for your audience. Always fact-check and apply your professional judgment before using AI-generated content in donor-facing materials.

AI can be a powerful tool for fundraisers—but only if used thoughtfully. That’s where prompt engineering comes in. The way you frame your prompt can make all the difference in the quality of the response. Below, we’ll show two examples: one with minimal instruction and another with a well-crafted prompt that includes persona and context. You’ll see firsthand how the right prompt can unlock AI’s full potential.

Minimal Instructions Prompt Example

Prompt:

“Analyze this donor’s giving history and interests to recommend the best engagement strategy: Tony is a class of 1983 alum of the Mumford engineering college, which he supports annually with a $500 a year gift.”

ChatGPT Output:

Donor Profile: Tony

• Class Year: 1983
• College: Mumford College of Engineering
• Giving History: $500/year annually
• Engagement Status: Not specified—assume passive donor without recent deep involvement unless otherwise noted

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Philanthropic & Engagement Insights:

1. Loyal & Consistent

• A consistent annual donor for many years—this demonstrates clear loyalty and likely a positive student experience. He’s “quietly committed,” which is valuable.

2. Affinity to Engineering

• His gift designation directly to the College of Engineering suggests he still identifies with his academic roots. This opens the door to content that aligns with engineering education, innovation, and student experience.

3. Untapped Engagement Potential

• Without known deeper involvement (advisory roles, event attendance, volunteering), Tony is a classic candidate for discovery-level engagement: someone who may give more and do more if personally invited.

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Recommended Engagement Strategy:

1. Discovery Outreach

• Personalized Outreach: Send a personalized email or letter thanking Tony for his loyalty and asking if he’d be open to a short conversation to learn more about what motivates his giving.
• Key Questions: Ask what inspired his annual giving, what his most impactful RIT memories are, and what issues he cares about in engineering today.

2. Connect to Meaningful Opportunities

• Showcase Impact: Share a story or brief report showing how his gifts support current engineering students or capstone projects.
• Invite to Engage: Based on his interests, invite Tony to:
  • Join a virtual engineering alumni roundtable or mentorship session
  • Attend an upcoming regional or college-specific event
  • Visit campus for a lab tour or capstone showcase

3. Introduce the Idea of an Increased Investment

• Next-Level Giving: Depending on his response and capacity, introduce an upgrade path:
  • Senior Design Team Sponsorship (e.g., $2,500–$5,000/year)
  • Multi-year Pledge toward a student-focused initiative
  • Naming Opportunity for a piece of lab equipment, workspace, or scholarship fund
• Planned Giving Introduction: As a 1983 alum, Tony is entering the stage where planned giving (IRA, bequests) could be relevant. Lightly introduce that Mumford has resources to help alumni create a legacy in line with their passions.

Well-Crafted Prompt Example

Prompt:

“Act like an expert major gift fundraiser and Analyze this donor’s giving history and interests to recommend the best engagement strategy: Rob is a class of 1982 alum of Mumford who had a long career engineering and robotics. He gives $500 a year to the college of engineering and lives in Boston, MA where he recently retired. He says the senior team was his most valued experience at Mumford and was also part of the cross country team as a student. He still meats up with cross country teammates on an annual trip. As an alum he attended some regional events but has mentioned wanting to be more involved, maybe in an advisory board capacity.”

ChatGPT Output:

Donor Analysis: Rob – Class of 1982, Mumford College of Engineering

Giving History:

• Annual Gift: $500/year to the College of Engineering
• Consistency: Indicates loyalty, likely decades of uninterrupted giving
• Designation: Academic unit—shows sustained affinity to his discipline

Professional Background:

• Field: Engineering & Robotics (likely high technical expertise and potential capacity)
• Status: Recently retired in Boston—available time + reflective life stage = ideal for deepening engagement
• Geographic Relevance: Active alumni population in Boston; potential for regional volunteerism or event leadership

Student Experience:

• High Affinity Touchpoints:
  • Senior Design Team: Cited as most meaningful experience—signals deep emotional connection to hands-on, team-based learning
  • Cross Country: Maintains annual meetups with teammates = powerful emotional loyalty + built-in peer network

Alumni Engagement:

• Has attended some regional events
• Expressed interest in doing more—specifically advisory board involvement

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Engagement Strategy

1. Deepen Personal Connection

Objective: Transition Rob from loyal donor to invested partner by honoring his Mumford identity and listening for passion points.

• Action: Reach out for a discovery meeting (Zoom or in-person in Boston) framed around gratitude and curiosity.
• Focus Areas to Explore:
  • Why the senior team experience meant so much
  • What excites him about current engineering trends
  • How he’d like to contribute (time, expertise, financial support)

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2. Leverage His Affinity for Experiential Learning

Objective: Tie his giving and potential involvement to the student experience he valued most.

• Position a Giving Opportunity:
  • Sponsor a Senior Design Team ($2,500–$5,000/year) named in his honor
  • Create a fund supporting student innovation or team-based capstone projects
  • Option for multi-year pledge or IRA charitable rollover post-retirement
• Involve Him Beyond the Check:
  • Virtual or in-person judging of capstone presentations
  • Mentor a senior team aligned with robotics or systems engineering
  • Invite him to the engineering building to meet faculty or students and see labs he could impact

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3. Acknowledge His Athletic Affiliation

Objective: Reinforce emotional connection through athletics and peer identity.

• Connect him with alumni athletics engagement team to explore:
  • Legacy giving in honor of the cross country program
  • Special recognition at future reunions or athletic events
  • Naming opportunities tied to athlete scholarships or travel funds
• Facilitate a cross country alumni reunion—he could be instrumental in helping lead or host this event

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4. Offer Leadership and Recognition Pathways

Objective: Tap into his interest in being more involved—and signal that his experience and loyalty are valued.

• Advisory Board: Invite him to join the College of Engineering Advisory Council or a Senior Design Committee
• Alumni Mentorship: Offer short-term, low-lift options (e.g., mentoring one team or a speaking role at alumni-student events)
• Recognition:
  • Profile him in alumni communications (e.g., “Why I Give Back” series)
  • Celebrate his years of giving with a special acknowledgment at a Boston-area event

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Next Best Actions

1. Discovery Call or Visit: Schedule a personal conversation focused on listening and exploring his interests.
2. Prepare a Custom Engagement Deck: Include senior team sponsorship options, advisory opportunities, and impact stories.
3. Coordinate Internal Partners: Loop in engineering dean’s office and alumni engagement team for athletics/council connections.

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Bringing on a new major gift fundraiser is both exciting and critical for the growth of your organization. But here’s the truth: if they don’t learn to do the job in a way that works best for your organization, they’ll end up being ineffective — and you will have wasted valuable time and resources.

One of the best ways to set a new major gift officer up for success is by creating a comprehensive onboarding binder. This resource isn’t just about policies and procedures — it’s about ensuring they know how to build relationships, represent your mission authentically, and drive philanthropy in a way that aligns with your team’s culture and strategy.

Why an Onboarding Binder Matters

Every nonprofit has its own processes, expectations, and relationship-building style. New fundraisers often come from organizations with different approaches. Your on-boarding binder becomes their roadmap for learning your organization’s approach and maintaining consistency across the donor experience.

By giving new fundraisers a clear structure from day one, they gain confidence, clarity, and direction — and ultimately, they’ll close gifts faster and cultivate donors more effectively. The binder also serves as an ongoing resource they can rely on throughout their entire tenure. Whenever a question arises or clarity is needed, they can easily reference it to ensure they’re aligned with your organization’s expectations and best practices.

What to Include in Your Major Gift Fundraiser Onboarding Binder

A great binder goes beyond policies. It should teach strategy, set expectations, and provide practical tools for every stage of the donor pipeline. Here are important topics to include in the binder.

1. Team Priorities
Clearly define your team’s priorities — doing so will help shape and reinforce the culture you want to build. For example, three key priorities might be: fostering strong internal relationships, maintaining a donor-first focus, and committing to continuous learning through professional development.

2. Metrics
Outline what success looks like: how many visits, proposals, and closures fundraisers should aim for — and how you measure progress. Be sure to emphasize the importance of entering information into your CRM in a timely manner. For instance, visit contact reports should be entered within 24 hours of the visit.

3. Visits
Explain what qualifies as a visit and the correct format for entering visit contact reports into your CRM.

4. Proposals
Show how proposals are created, reviewed, tracked, and presented, including templates and examples.

5. Giving Societies
Provide an overview of your giving societies, the benefits they offer, and how fundraisers can use them to engage donors.

6. Fund Documentation
Include templates and examples of fund agreements and ensure they meet internal guidelines.

7. Naming Guidelines
Explain what gift amounts trigger naming opportunities and outline the process for securing naming approvals.

8. Meetings/Appraisals
Outline team meeting schedules, performance check-ins, and how fundraisers will receive coaching and feedback. Emphasize the importance of strategy sessions — dedicated meetings where fundraisers can present challenging prospects and collaborate with the team to brainstorm creative next steps for moving those prospects toward making a gift.

9. Travel
Communicate clear travel expectations, policies, and reimbursement guidelines, along with best practices for planning effective donor visits. Set expectations around visit volume — for example, how many donor meetings a fundraiser should aim for each day while traveling.

10. Using AI for Efficiency
Share practical examples of how fundraisers can leverage AI tools like ChatGPT to streamline their work. From drafting donor communications to brainstorming cultivation strategies, AI can help make their daily tasks faster, more creative, and more effective.

11. Internal Relationships
Introduce key internal partners — including advancement services, communications, and academic leadership — and outline how to collaborate effectively with each. Include guidance on building strong internal relationships, fostering trust, and working together to advance shared goals.

12. Follow-Up
Provide templates and best practices for timely follow-up after visits and meetings. Stress that follow-up should happen within 24 hours of the visit.

13. Qualifications
Clarify the prospect qualification process at your organization so your team understands each step. Share best practices for identifying new leads and effectively reaching out to potential donors.

14. Outreach Emails
Outline the types of communications and email strategies that are most effective at your organization to help ensure stronger engagement and higher response rates. Sample emails:

• Career Self-Interest Email: Templates for prospects who care about career outcomes.
• Target Self-Interest Email: Templates for donors interested in specific strategic initiatives.
• Parent Self-Interest Email: Templates for parents motivated by their child’s experience.

15. Preparing for the Visit
Provide step-by-step guidance on how to research donors and build an effective visit plan.

16. During the Visit
Outline best practices for building rapport, asking the right questions, and reading body language.

17. Visit Follow-Up
Include detailed instructions for writing follow-up emails, updating CRM systems, and communicating with team members. Reinforce that follow-up should happen within 24 hours of each visit.

18. Cultivation
Share strategies for deepening donor engagement between visits and keeping relationships warm. Highlight the most effective ways to involve prospects with your organization, such as serving on advisory boards, mentoring students, volunteering at events, hosting gatherings, and other meaningful touch points that strengthen their connection.

19. Solicitation
Provide a clear breakdown of the entire solicitation strategy and timing.

20. Priming the Ask
Offer guidance on how to prepare donors for the ask through intentional conversations and subtle cues.

21. The Real Ask
Include scripts, language suggestions, and confidence-building techniques for making the ask directly and effectively.

22. The Response
Train fundraisers on how to handle responses — whether it’s “yes,” “no,” or “not now” — with professionalism and thoughtful rebuttals.

23. Closing
Provide clear instructions for formalizing gifts, completing documentation, and effective strategies for securing signed gift commitments. Every organization has best practices for closing gifts — make sure to outline what works best within your institution’s unique framework.

24. Stewardship
Share best practices for keeping donors informed, engaged, and feeling valued long after their gift has been made.

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A major gift fundraiser onboarding binder isn’t just a document — it’s a playbook. It’s the difference between someone who’s “learning as they go” and someone who hits the ground running, fundraising with confidence and integrity.

Set your team up for long-term success by giving them this tool. Your donors — and your mission — will thank you.

Interested in having us create a custom onboarding binder for your team? Simply fill out the form below, and we’ll reach out to get started.

One of the biggest challenges for major gift fundraisers is getting “stuck” with a prospect. They’ve made the ask, but the donor isn’t moving forward—or worse, they’re unresponsive. When a gift stalls, it takes creativity and strategy to get it across the finish line.

One of the most effective ways to overcome this roadblock is through a Prospect Strategy Session—a collaborative brainstorming meeting designed to generate fresh ideas and new approaches for closing gifts. By bringing together multiple fundraisers, these sessions introduce diverse perspectives, innovative tactics, and renewed momentum.

Structuring an Effective Prospect Strategy Session

Who Should Be Involved?

1. Experienced Fundraisers Familiar with Your Organization
   These individuals understand the institution’s priorities and can suggest angles the primary fundraiser may not have considered. Their knowledge of university initiatives or programs can help tailor the ask in a more compelling way.
2. Fundraisers with a Track Record of Closing Gifts
   Those who have successfully closed similar gifts can offer real-world insights and share proven strategies that have worked in the past.

How to Prepare

To maximize the session’s effectiveness, the fundraiser presenting the prospects should send an advance briefing to all participants. This should include:

• A list of 4–8 prospects they are struggling to move forward.
• A brief summary (one paragraph per prospect) outlining the donor’s background, giving capacity, and the potential gift opportunity.

Providing this information ahead of time allows participants to come prepared with thoughtful strategies and recommendations.

Meeting Format

• Overview (1–2 minutes per prospect) – The presenting fundraiser gives a concise summary of the donor, their engagement level, and the current roadblock.
• Brainstorming Discussion (10–15 minutes per prospect) – Participants collaborate to generate ideas, suggest alternative approaches, and offer potential next steps.
• Action Plan – Each prospect should have clear, actionable next steps for the fundraiser to implement.

Post-Session Follow-Up

The real value of a Prospect Strategy Session comes from execution. Fundraisers should leave with a set of specific action items for each prospect and follow up on the results. Did the new strategy work? What adjustments are needed? Keeping the group informed on progress fosters accountability and continuous learning.

Prospect Strategy Sessions are a powerful tool for unlocking major gifts that might otherwise remain stalled. The more perspectives and ideas you bring into the process, the higher the likelihood of success. By leveraging the collective experience of a fundraising team, you can increase your chances of securing transformative gifts for your organization.

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