Before The Ask Ever Happens

This is the Post #4 in a series called The Invitation: Rethinking the Ask in Major Gifts

If you’re new to this, you can start here with the first post in the series:  🎉 Let’s Party! 🥳

Over several weeks we’re exploring a different posture - one that reshapes how we approach the ask. When an invitation is extended at the right moment, to the right person, for the right reasons, something shifts. The work feels lighter. More human. Even energizing.

I’d love to hear how this is landing for you. What are you noticing? What’s working? What still feels uncertain? Hit reply - I’d love to hear from you.

Let’s keep learning together.

“I think I should go… I just don’t want it to be a wasted trip.”

A friend said that to me recently while deciding whether to travel to Portland. He’d been circling the idea for months.

Flights. Rental car. Hotel. Meals. A few days away from home. By the time he added it up, the trip would cost around $1,500. Not insignificant, especially without a large travel budget behind him.

But logistics weren’t actually the issue.

He was trying to answer a deeper question: What makes a trip worth it?

What justifies the trip?

To get beyond the financial cost, I decided to ask him a different question: “Do you have one or two anchor appointments?”

An anchor appointment is simple. Someone already meaningfully engaged - often around the $10k level or beyond - or someone with clear capacity and genuine interest. One anchor appointment is often enough to justify the investment.

He paused for a moment, then said, “Actually… yes.” There was someone he had been connected to and was already engaging by phone. They showed strong interest. He knew through a connector that they had capacity. And they had already said they’d be glad to meet if he came into town.

Recognizing what’s already in motion

“Book the trip,” I told him. I couldn’t guarantee the outcome, but I could see that something was definitely in motion.

Sometimes you just need to pull the trigger.
Once he did, everything became easier.

He started reaching out to other people in the area - connectors, existing supporters, a few emerging relationships.  Once people know you’re already coming, calendars open differently. The trip slowly began organizing itself around his arrival.

I spent ten years working with a CEO who had an unusually simple instinct about travel. If there was even one meaningful anchor appointment, that was often enough.

Sometimes there wasn’t much else scheduled at all.

He would still say: 
“Just head on out there. Make your presence known. Work your network. Do what you do.”

There were trips where almost nothing came together.

His response never changed: “Plan the next one. Just keep showing up.”

I’m deeply grateful for that posture because it changed how I think about this work. It gave me permission to show up before everything was perfectly arranged.

Most travel decisions are practical on the surface:

Flights.
Calendars.
Budgets. 

Underneath those decisions, something larger is being shaped: the movement of relationships.

There’s a kind of clarity that comes when you begin paying attention to what’s already unfolding.

Is there genuine movement here?
Is there a reason to show up?
Would I actually want to spend meaningful time with this person?

And when you keep showing up consistently, it changes the way you relate and are received.

You’re no longer trying to squeeze in a visit.
You’re part of the rhythm.

When I was doing frontline fundraising fulltime, I had a handful of folks who always had a room available for me when I came through. I could text ahead as little as a few days and the response was, “yep, the J.Paul room is ready for action.”

It’s such a great experience. Conversations pick up where they left off. Opportunities feel less manufactured.  Trust grows naturally.

The risks

Of course, there is risk in this.

The trip may not unfold the way you hoped.
Meetings cancel.
Schedules shift.
You board the flight home wondering if it was worth it.

It happens. And it’s okay.

Not every investment produces immediate visible return.

But over time, showing up consistently in the right places - with the right people - builds something you can’t manufacture from a distance.

So much of major gift work is shaped before an ask is ever made. It’s in the decisions you make about where to go. Who to prioritize. And what’s already in motion.

A blessing for you
May you recognize the relationships already carrying momentum.
May you trust them enough to move toward them.
And may your time, presence, and energy be invested where something real is already beginning to grow.

Let’s take action on this today:

Choose three people in your portfolio.
Invite one.
Invest in two.

* * * * * * * * * *

If you haven’t explored the free resources I’ve created for major gift fundraisers, this is a great place to start:

• Follow me on LinkedIn for daily pro tips and reflections.
• Major Gift Fundraising MRI Scan - a short, story-based assessment to help you name your instincts and clarify your posture.
• JappaFry Writer - an AI tool shaped by 30+ years of real-world experience, teaching, and strategy.
• Breakthru Newsletter, Blog, and Podcast - ongoing reflections, conversations, and practical guidance for the work you care about most.

These resources are designed to meet you where you are - and help you move forward with clarity and confidence.

If you’d ever like to talk, you can always schedule a free introductory call. I'd love to get acquainted and hear what you’re navigating right now.

‍For organizations ready for more structured support:

‍You may not need a full-time development leader - at least not yet. Sometimes what’s needed is clearer thinking. Sometimes more consistent action. And sometimes, for a season, real leadership.Here are a few ways we can start building momentum together:

* Online Catalyst Course ($199) - A complete brain dump of 30+ years in major gift fundraising - the good, the hard, and the surprisingly joyful. Built around strong fundamentals, the sacredness, and yes, even the fun. Infused with insights from Henri Nouwen. Many who take this course find it gives them everything they need to build healthy, sustainable systems.

* Live coaching ($300-400 / 90 minutes) - Think of this as "brain rental". Focused, strategic, and highly practical. The kind of time that brings clarity quickly and creates real momentum.

* Laser-focused session ($99 / 45 minutes) - For one specific moment that matters - preparing for a high-stakes conversation, navigating an invitation, or working through a decision that needs clarity.

* Fractional Director of Development - For a small number of organizations, I step in more deeply - bringing clarity to your message, movement to key relationships, and structures your team can sustain long after I’m gone.
In the first 90 days, you can expect:

• clearer, more confident communication of your vision
• more meaningful engagement with top givers and prospects
• renewed movement in relationships that may have stalled
• simple, actionable next steps after each interaction
• a sharper sense of who is ready to be invited - and who is not

Most fractional engagements range from $2,500 - $7,500+ per month depending on the level of involvement.Not sure what kinds of support you need? I can point you to a simple Development Readiness Assessment -  just reply and let me know.

And don’t miss connecting with my colleague Ivana Salloum - she's wonderful and can help with scheduling, resources, and getting you where you need to go.

Thank you for the work you do. Truly.I’d love to hear what’s unfolding in your world - and how I can come alongside you.

‍