The Story Before The Trailhead⛺

From as far back as I can remember, my dad shared stories with me about the Grand Canyon - tales of his own adventures and the beauty he experienced while camping, backpacking, and hiking there.  We looked forward to a day when he could introduce me to the amazing spectacle.

However, when we moved from Arizona to Washington state it seemed unlikely that we would ever make the trip. Then, when I was 10, dad brought me some great news. We were going to visit the Grand Canyon and do a 3-day backpacking trip with my Uncle Steve! I couldn’t believe it. We planned and packed, prepared, and anticipated. It was going to be epic.

Today, at 53, I still haven’t been to the Grand Canyon. Not once. Not yet.

Stories are just amazing, aren’t they? So - how eager are you to hear more about me, my dad, and the Grand Canyon? Do you feel compelled to respond in some way?

In previous Major Gift Fundraising MRI posts we have:
…explored how you build relationships.
…looked at how you communicate your message.
…examined how structure shows up in your daily work.

Now we come to the fourth diagnostic prompt - one of the most vulnerable moments in major gift work:
‍What is your posture when it’s time to present a giving opportunity?

‍When you extend the invitation - how do you do it?
What leads?
What holds you back?
What’s your default instinct?

Here’s the specific prompt in the MRI assessment:
‍Which statement below describes how you present giving opportunities?
A. I lead with the cause’s top priorities and tangible opportunities - what’s needed and what could happen.
OR
‍B. I tell stories that position the giver inside a larger narrative - one of purpose, calling, and partnership.

Like the other questions, there’s no right or wrong answer. Both are extremely effective in raising major gifts. But this choice reveals more than technique. It tells us something deeper about what we believe givers are being invited into.

In 1981, my dad and I almost made it to the Grand Canyon. We were within 50 miles of the trailhead when a water hose in our Volkswagen Rabbit decided to burst. It was the middle of night… the middle of nowhere… and well before the convenience of mobile phones… The Grand Canyon would have to wait.

14 years later, when I turned 24, my dad surprised me with plans to redeem that first misadventure and travel to the Grand Canyon together. This time it was my budding career that interrupted our plans. I had just been hired in my first major gift fundraising role to work alongside Phill Butler and the mission of Interdev. Phill was eager to expose me to the work happening in Cyprus and Lebanon - precisely during the time dad and I were planning to visit the Grand Canyon.

We sadly agreed that, yet again, the trip would have to be postponed.

Just like preparing for a big trip - before ever seeing the destination - some fundraisers anchor their invitation in what’s needed and what’s next. Others lead with the story, stirring desire for the journey ahead.

‍If you lead with the need…

‍You’re clear, concise, and grounded, presenting opportunities like a veteran engineer who explains about a project: “Here’s what needs to happen. Here’s what it will cost. Here’s what’s at stake.”

Your approach is straightforward. Honest. Practical. The opposite of manipulation.

This approach builds trust, especially with givers who value urgency and impact.

Just be mindful of the potential sterility of this approach - sometimes the heart of the work gets flattened into bullet points.

‍If you lead with the story…

‍You’re not just presenting an ask - you’re offering them a part in the big show.

You invite the giver into a larger narrative - one of purpose, calling, and momentum. You want them to feel the stakes, the invitation, and the meaning of their participation.

For many givers, this posture is deeply energizing. It elevates the ask from transaction to transformation.But be mindful that the story is anchored - that the “what could be” is clear - otherwise it can drift into abstraction.

None of the unfulfilled plans caused me and my dad to feel bad or ashamed. Disappointed? Of course. I remember watching him crying at my nana’s dining room table after our first attempt fell through. But to this day I have a quirky and sacred premonition that some day, dad and I will finally make it to the Grand Canyon together.

Some things to experiment with in your storytelling…

1. Tell the story like it’s still unfolding.
‍Not every story has to close with an invitation to commit. But it should open the imagination, helping your givers see the end goal in their mind’s eye - and feel the hope of the journey.

‍2. Notice what lingers.
‍Which stories have stayed with people, even if they didn’t give right away? What made those moments memorable?

‍3. Craft invitations that wait well.
‍Just because the gift doesn’t come today doesn’t mean the story isn’t working. Leave the door open. Let your posture say: “When you’re ready, this story still has room for you.”

The storytelling that happens - both from you and the giver - leading up to the invitation is really important. It’s tactical, sure. But more importantly it reveals what you believe about the giver’s role.

Do you see them as a walking wallet - or a character in the unfolding story of hope?

Do you offer them an opportunity - or an identity?

In the very best fundraising moments, the invitation becomes more than a transaction. It becomes a calling.

Two essential things to practice in the invitation:

‍1. Practice the “pivot.”
‍Start with a story or need (or a hybrid of both) - something alive and specific. Then try various segues with questions like: “What would it look like for you to help write the next chapter?”

‍2. Write some bolder asks.
‍Take an invitation that feels soft or ambiguous. Rewrite it with more clarity and vulnerability. Do you feel a bit of nervous energy putting it out there? That’s good. Channel that spark into your ask.

The way you invite someone to give is more than a skill. It’s a reflection. So the next time you feel hesitant before asking, pause.

Don’t aim for perfection.
Aim for resonance.

Think about the story. Name the need. Extend the invitation with warmth, courage, and joy.

I don’t know how it will happen, this trip to the Grand Canyon with my dad. But I know it will still be my first time. It will still be epic. And maybe I’ll even see if Uncle Steve can plan to come along… Let me know if you would like to join us!

Are you thinking now about the next invitation you hope to extend? The Major Gift Fundraising MRI might be a big help.
Try it here:
👉 https://tally.so/r/mYKrAB

The initial assessment only takes 20 minutes, and it’s free.

* * * * * * * * * *

‍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:

* 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,