From Cha-Ching! to Changemakers

I vividly remember my first fundraising role, in 1995, as Annual Fund Director for a small seminary in Tigard, Oregon. Part of my attraction to the role was having the privilege of working with a new friend and mentor, Dave Jeffery. Dave amazed me. He operated like a boss in the world of major gift fundraising with an uncanny knack for going ‘toe-to-toe’ with wealthy, influential givers, ultimately winning them over for large gifts.

A particular memory I have occurred early one Tuesday morning (at 6:30 am!) when I walked into Dave’s office and found him talking on the phone with a mutual friend (let’s call him Ned) from the Seattle area. Ned was a very successful businessman whom I had known for several years. I was completely intimidated by him. But Dave was speaking to him as if they were peers. There was no pandering. No gratuitous compliments or fake chuckles at bad jokes. It all felt very normal.

And then came the part that really shocked me. Dave ended the call, greeted me and said, “That was Ned Jones…do you know him?” I nodded and Dave stated, “We talk every Tuesday morning at 6:30 am.”

To my knowledge, Ned never gave a dime to our seminary. So why was Dave talking with him every Tuesday morning at 6:30am? I later learned there were many good reasons for the weekly call, but at the top of Dave’s list was simply being a ‘no-strings-attached-friend’ to Ned. They talked about family, church, religion, business, etc. And I’m sure much of the time they spoke about things that Ned shared confidentially only to Dave.

Of the many things I learned from Dave throughout our working relationship, what lingers the most, is that I don’t have to sell a vision to convince people to be generous with their wealth. What matters most is cultivating a strong relational connection which allows us to speak openly and transparently about what we need from each other, and how we can support each other.

Years later, in the early 2000s, I sat down with a prominent giver - someone I was certain would contribute generously to our cause. Armed with data and stories, I prepared to make the pitch. Instead, channeling a bit of Dave Jeffery, I began by asking about his life. What he shared was unexpected: his wife was feeling drawn to a different type of giving, one aligned with her heart and their shared values. And one that had nothing to do with our cause. Rather than pressing forward with my pitch, I paused and said, “How can I help you and your wife connect with those causes?”

The result? Not only was a lasting relationship cemented, but over time, their contributions to our mission far exceeded what I originally envisioned. They are special friends to this day. One of their sons receives this weekly newsletter even though he never reads it… (Hey KJ! If you’re reading this now, text me and I’ll let you choose my LinkedIn profile picture for the next 7 days.)

KJ and I don’t talk every Tuesday morning at 6:30am, but I imagine he fits into the same category for me as Ned did for Dave. And I get it now.

Understanding the mindset of givers isn’t about transactional exchanges - it’s about relational transformation.

Here are five insights I gleaned from my first mentor, Dave Jeffery, which can help us better understand the mindsets of major givers and prospects:

1. Listen First, Speak Later

Givers often feel misunderstood when people talk at them, not with them. Start conversations by asking open-ended questions about their lives, passions, and values:

• “What excites you most about your active business interests?"
• “What causes have made the biggest impact on your life?”

Action: Before your next meeting, prepare three thoughtful questions. Your role is to listen actively, not to pitch. For extra credit, listen for ways that you can help them with connections or other resources to further their business or charitable interests.

2. Discover Shared Vision

Givers aren’t ATM machines for your cause; they are partners in a shared mission. Align your pitch with what matters most to them. One giver might care deeply about education, while another prioritizes climate change.

Reflection: Ask yourself, “How does our mission resonate with their story?” Then articulate this alignment during your conversation.

3. Focus on Strength of Relationship (SToR)

It's tempting to approach someone just because they have capacity. Remember, the success of a major pitch is directly tied to relational trust. Use a simple assessment to evaluate readiness:

• Do I know their family dynamics?
• Do I understand their philanthropic priorities?
• Have we built enough relational equity?

Action: Score your connection using a relationship rubric. If you’re missing key elements, prioritize building rapport before making the ask.

4. Balance Boldness with Empathy

Presenting a large pitch can feel like ‘swinging for the fences’ in baseball. The key is not just the amount you request but how you frame the invitation. Consider their life stage, recent milestones, or even potential challenges they’re navigating.

Example: Instead of starting with numbers, lead with: “Here’s a vision I believe aligns with your heart. I’d love to explore with you if this resonates.”

Reflection: Be bold and attuned to their circumstances.

5. Lead with Gratitude and Blessing

It’s easy to fixate on what you need from a giver. Instead, reflect on how their contributions are already changing lives. Sharing impact stories - centered on transformation, not just metrics - can deepen their connection to your mission.

Action: Send a handwritten note or small, meaningful token after you meet , expressing genuine thanks and sharing a story that connects them to the cause.

Understanding the mindset of major givers begins with shifting your perspective from “how do I get them to give?” to “how can I serve their journey of generosity?” Each conversation is an opportunity to build a bridge. Step into those moments with humility, empathy, and a shared vision for transformation. When you do, you’ll find the relationships you cultivate often lead to outcomes far greater than you could have imagined.

What’s been your experience in understanding the mindset of major givers? I’d love to hear your stories and insights.

Praying you all have a great week!

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If you haven't taken advantage of some of the resources I've created to help major gift fundraisers, take a look now!  Initial calls with me are free and "no strings attached".  Sometimes folks feel like they need to wait and not 'bother' me until they have a pressing issue.  No need for that...just make the call. 🕺

‍Here's where you can access a lot of content for free:

‍* Follow me on LinkedIn - You'll get short pro-tips and reflections on major gift fundraising every day between 5-7am pacific.

* Breakthru Newsletter - As you've seen here, these are longer weekly posts (audio and written) sent directly to your email.

* Breakthru Blog - the newsletter from the previous week gets posted here each week for everyone (so email subscribers get it a week early).

* Breakthru Podcast - Interviews with high net worth givers about how we as fundraisers can get better at inviting them to the party.  And audio readings of Breakthru Blog posts.

‍Before getting to the PAID stuff: My opinion is that no small ministry with a tight budget should be spending more than $3-5k (total) for major gift coaching/consulting.  Most of you will be good-to-go spending far less than that.  This was a major issue for me when I was a frontline fundraiser - major gift consultants were an expensive 'black-box-of-confusion' for me.  That stops now.

‍Here's the PAID stuff:

‍* Online Catalyst Course - This is a full brain dump of my 28+ years of experience - good, bad, ugly.  It's built around the fundamentals, the sacredness, and the fun, of major gift fundraising.  It's infused with Henri Nouwen reflections.  Many people can take this course and they will be 'cooking-with-gas' and not need any additional coaching from me on the core systems.  I'm grateful that this course has gotten *great* reviews.

* Live coaching with me - I refer to this as "brain rental".  The ROI on live coaching, as you might imagine, is extraordinary.

Finally, be sure to connect with my colleague Ivana Salloum.  She's super awesome and can help with scheduling and access to resources, etc.

I look forward to hearing about your good work!

Blessings,