Tell Me Again… How Did That Ask Happen?
Reminder: Check out the Major Gift Fundraising MRI Scan - A story-based self-assessment that helps you name your instincts, clarify your posture, and grow with intention. Takes less than 20 minutes and gives you a custom coaching summary based on your responses.
It started with a lake house invitation from a friend who’d never given to our work before. I told this story in three short LinkedIn posts… and some of you said, “Please tell that story again more fully in your weekly Breakthru Guide…and this time, include the parts you left on the cutting room floor.”
While I’ve blurred a few names and details for privacy, Mark will definitely recognize himself here - and I know he’ll love that I’m telling it.
So here it is - the Director’s Cut - complete with things that didn’t make it into the LinkedIn posts... Deleted scenes, behind-the-scenes commentary, and a surprise bonus track at the end: four actionable learning points for all of us in major gift fundraising.
🎥 Scene 1: Lake Cabin
While reviewing a giver prospect list with my team for a new project, Mark and Jennifer kept rising to the top. It was unusual, since they knew about our work, but had never given financially before. Yet in prayer, I kept returning to my relational history with them - especially with Mark.
I picked up the phone, and after some pleasantries and catching up, I got to the point:
“Mark, I’d like to know if you and Jennifer would be willing to consider a gift to the cause. And if so, what’s the best way to pursue that discussion?”
Our Strength of Relationship score was a 4 out of 5 - solid enough to know I wasn’t risking the relationship even if they said no.
Mark paused, then said: “That would be fine - no guarantees - but we’d love to hear you out. Why don’t you come to the lake house for 24 hours? We can ‘retreat’ - pray, catch up, and talk more about your offer.”
Booking my flight on United Airlines was my next move.
Deleted Scene
Mark and I first met in 2016 in Singapore. Our mutual friend Adam introduced us and set up a dinner featuring dim sum, hot pot, and my secret peanut sauce recipe. Oh man… Hot pot is one of my favorite meals in the world… mmmmm…
Wait, what was I saying? Right… meeting Mark for the first time. I remember his kind face and genuine curiosity. I remember having my wife Julie with me. And I definitely remember my special peanut sauce recipe.
🎥 Scene 2: Rudy’s BBQ
We talked, caught up, prayed, and let the slow rhythm of the lake set the pace. The highlight? Dinner at Rudy’s. Cut to brisket, creamed corn, and zero pretense.
I clearly remember when we started talking about dinner plans. Mark grinned and said, “Since the wives aren’t here, let’s be a little naughty and indulge at Rudy’s.” I laughed. It was perfect.
I know it might seem like I’m talking about food a lot. Sashimi! (thanks Will Arnett)
But feasting like this matters. It’s not “extra” - it’s the trust-building montage before the big scene.
Deleted Scene
We spent focused time with Mark sharing about a charity which he helped start, one that’s been experiencing a lot of success. We discussed fundraising strategy, and I was grateful to have some professional value to offer him in return.
I thought of another friend, also a very successful entrepreneur running a similar charity in another city. “Let me see if I can get him on the phone and introduce you”, I suggested.
Mark was delighted. He knew my friend by reputation and appreciated the connection.
My friend, with whom I have a 5 out of 5 on the Strength of Relationship scale, was available to talk. He joined on speakerphone and in just a few minutes, a new friendship was born.
🎥 Scene 3: Tom Joad
The next morning, Mark made breakfast: scrambled eggs, bacon, toast. We sat on the porch overlooking the water. I was a bit anxious about finding my opening… but then he gave it to me: “Alright - let’s get specific. Tell me about the project.”
I was ready. I’d rehearsed it a dozen times. And - slight cringe here - I played him a song as part of the pitch: The Ghost of Tom Joad (Rage Against the Machine covering Springsteen). Lyrics printed out and everything.
He loved it. He didn’t commit right then - just said he’d talk and pray with his wife, Jennifer.
The ask: $300,000 over three years for a cause they’d never financially supported before.
I flew back to Seattle feeling good. Before my plane landed, his email came in: “We’re in.”
📀 Special Features (Bonus Track Learning Points)
1. Informed Casting - Use the SToR Tool Before the Ask.
Don’t assume someone will take a “lead role” just because of their capacity. Mark and Jennifer scored high on Strength of Relationship - and that helped me know the appropriateness and timing of the invitation.
2. Location Is a Character - Invest in Unhurried Time.
The lake cabin wasn’t just a backdrop - it set the tone and created the perfect setting for connection.
3. Never Cut the Dinner Scene - Honor the Table.
Rudy’s brisket wasn’t filler. Meals are a sacred set piece - part of the spiritual and relational work.
4. Stick the Landing - Be Ready, But Don’t Rush.
I had my lines ready, but I let Mark cue the scene. The song was a creative risk - but in the right relationship, risks make memories.
A “yes” to $300k is wonderful, but the real win was the story: one that honored the relationship, infused joy, and made the invitation feel both natural and sacred.
Roll credits. 🍿
Here’s to more asks that feel like stories worth retelling. What are some scenes from your own fundraising journey you’d put in your Director’s Cut?
* * * * * * * * * *
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:
* Major Gift Fundraising MRI Scan - A story-based self-assessment that helps you name your instincts, clarify your posture, and grow with intention. Takes less than 20 minutes and gives you a custom coaching summary based on your responses.
* JappaFry Writer - A freely available AI tool that draws from over 175 pages of original teaching, storytelling, frameworks, and strategy from my 30 year career in major gift fundraising.
* 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,
