Mighty Penguin Speaks

In today’s fundraising environment, meaningful donor engagement is more important than ever. High-capacity donors typically support fewer nonprofits—and those they choose must demonstrate measurable impact, financial responsibility, and visionary leadership. These donors see their contributions as investments in change.

This guide offers practical strategies for building strong relationships with major donors, cultivating meaningful conversations, and making confident, effective asks.

Understanding Major Donors: Who Are They and What Do They Value?

Major donors often:

• Prioritize fewer organizations where they can make a significant impact
• Seek out nonprofits with clear missions and strong leadership
• Expect transparency, accountability, and results

Understanding their values:

• Spend time learning about their values, interests, and giving philosophy
• Cultivate relationships rooted in trust and shared purpose
• Treat them as mission partners, not just check writers

The Five I’s: A Relationship-Driven Approach to Major Giving

Strong donor relationships are built over time. One proven framework is the Five I’s:

• Identify – Use your data to find high-potential donors
• Inform – Share stories of impact that resonate with their values
• Interest – Spark curiosity with tailored outreach
• Involve – Engage them meaningfully in your mission
• Invite – Extend a clear, timely ask for their support

Common Pitfalls to Avoid

Many fundraisers spend too much time behind a desk. While reports and newsletters are useful, transformational giving happens through personal connection.

Ask yourself:

• When was my last in-person meeting with this donor?
• Am I relying too much on mass communication?
• Do I make important requests face-to-face?

Fundraising is relationship-building. You wouldn’t deepen a friendship through email alone—apply the same thinking here.

Who Should You Prioritize?

Use your time and energy wisely by zeroing in on those most likely to give generously and consistently. Start with:

• Top Lifetime Supporters – Your most loyal donors are often your best prospects for transformational gifts.
• Recent High-Level Donors – Look at the top 50 donors from the past few years—they’ve already shown strong interest.
• Active Foundation and Corporate Funders – These partners may be open to increased support or multiyear commitments.
• Long-Term Engaged Supporters – Volunteers, board members, or advocates with deep mission alignment can become major donors.
• Wealth-Screened Prospects – Use wealth indicators and capacity ratings to surface new high-potential individuals.

Pro Tip: Don’t just pull a list—dig into the story behind the giving. Look for patterns, passions, and relationships that can guide your outreach strategy.

Key Habits for Successful Donor Engagement

Strong donor relationships are built through consistency and intentional effort. These habits can help you stay focused, build trust, and move relationships forward.

• Prioritize in-person meetingsFace-to-face conversations build connection and trust. Schedule regular donor visits.
• Set clear goals and track your progressDetermine how many donor touches or meetings you want each month. Monitor your results.
• Create accountability structuresAsk a colleague or supervisor to help keep you on track with your outreach.
• Follow up on milestonesReference birthdays, anniversaries, or professional achievements to reconnect meaningfully.
• Take time to understand their interestsAsk thoughtful questions about their passions and values. Show you’re listening.
• Vary your communication channelsMix emails with phone calls, handwritten notes, and text messages to keep things fresh.
• Be persistent, not pushyKeep reaching out until you get a clear yes or no—most gifts take multiple touchpoints.
• Time your outreach strategicallyTry calling on Friday afternoons or early weekday mornings when schedules may be more open.

Don’t underestimate the power of consistency. Small, genuine efforts add up to long-term, transformational relationships. Be bold and gracious. Donors want to help. You’re giving them a chance to create real change.

What Do You Talk About? Begin with Discovery

Great fundraising starts with listening. Use open-ended discovery questions to better understand your donor:

• What first drew you to our organization?
• Are there particular programs or areas of our work that resonate most with you?
• Can you share what motivated you to give in the past?
• What aspects of our current work are you most passionate about?
• Where do you see the greatest potential for our organization’s growth or impact?
• When your family thinks about giving, how do you typically decide where to focus?
• What gives you a sense of fulfillment or joy when you make a charitable gift?
• Is there anyone in your network who might also be excited about what we’re doing?

Remember, it's not always appropriate to ask for money at the first meeting. Let the donor know that this is just a conversation and you’re not asking for a gift today. However, it's okay to ask if it would be okay to come back in a few weeks to discuss support or a larger leadership gift.

Bring a concise, well-designed take-home packet that outlines giving options. Make sure it’s powerful, polished, and brief.

Track all insights and updates in your donor database—it’s your most powerful tool.

Framing the Ask: Align, Inspire, Invite

Once you’ve built trust and laid the foundation, schedule another meeting to make the ask. Aim to make the ask within the first 15–20 minutes—you’ve already done the groundwork.

Suggested Meeting Flow:

• Reconnect around your shared commitmentReflect on the relationship and emphasize your mutual dedication to the cause.
• Cast a compelling vision and outline the opportunityShare the big picture, along with the specific funding need that aligns with the donor’s interests.
• Extend the invitation to giveMake a confident, respectful ask—clearly stating the amount and purpose, then giving space for reflection.

Sample Ask Phrases:

• “Would you be open to making a leadership gift of $25,000 to move this work forward?”
• “You spoke about how much [program] resonates with you. Would you consider supporting it with a $10,000 contribution?”
• “This initiative is ambitious, and we’re turning to our most committed partners to help lead the way. Would a $50,000 investment be something you’d consider?”

Set a follow-up plan:

“Would it be okay if I followed up in two weeks after you’ve had a chance to talk with your spouse or partner?”

Following Up with Purpose

Follow-up is where many fundraisers lose momentum—but it’s also where relationships deepen. Be proactive, confident, and thoughtful in how you re-engage.

• Call or email with a polite, confident check-in:
  • “Have you had a chance to consider the leadership gift?”
  • “We’re wrapping up this campaign soon—can I answer any questions?”
  • “Is there any additional information I can provide to help with your decision?”
  • “Have you had a chance to discuss this with your family or advisor?”
  • “Does this opportunity still align with your giving goals this year?”
• Keep the relationship warm and engaged

Finding Organic Ways to Connect Again:

Follow-up doesn’t always need to be about the ask. Offer value and build connection through updates and shared interests:

• Share a success story tied to the program they care about
• Send a photo or short video that shows their impact
• Forward a media article that features your work or a relevant issue
• Let them know about a new partnership or milestone you’ve reached
• Congratulate them on a personal or professional accomplishment (based on social media, news, or conversation)
• Invite them to join you at an upcoming community event or behind-the-scenes tour
• Offer a quick “thinking of you” note or check-in to keep the connection alive

Practical Tips for Major Donor Success

Consistent, personalized touchpoints build trust and show that you see the donor as a partner.

• Nurture those already engaged
• Thank generously, often, and personally
• Show them their impact
• Create a system for staying in touch
• Offer meaningful engagement beyond the ask
• Tailor your communication to their preferences
• Celebrate milestones together

Donors want to feel seen, valued, and essential to your success. Personalized communication builds trust and loyalty over time.

Don’t Forget: Planned Giving Can Be a Powerful Strategy

In 2025, successful fundraising is all about building genuine relationships, sparking meaningful dialogue, and offering donors opportunities to create long-term impact. One powerful yet underutilized strategy is integrating planned giving into major donor conversations. Planned giving refers to charitable contributions that are arranged in advance and typically allocated from assets such as wills, trusts, life insurance policies, retirement funds, or appreciated stock. Read a previous article about how to Weave Planned Giving into Major Donor Conversations to learn more about this powerful strategy.

Need Support? Partner with Mighty Penguin

Looking for expert support in developing your major donor strategy, refining your messaging, or building a sustainable fundraising program?

Mighty Penguin specializes in helping nonprofits build brave messaging, design high-performing development systems, and create authentic donor engagement strategies that lead to transformational gifts.

From customized coaching to campaign consulting, we’re here to help you succeed.

Final Word: You’ve Got This

Major gift fundraising isn’t about pressure—it’s about partnership. When you lead with curiosity, respect, and boldness, donors feel inspired to join you. You’re offering them a chance to make a real difference. That’s a powerful invitation—and one worth accepting.