When They Start Asking You

This is Post #5 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.

There’s a moment in some major gift conversations where something changes. 

You can feel it before you can explain it. But if you’ve been in this work long enough, you start to recognize it.

The questions start coming from the other side.
They begin imagining possibilities out loud.
You’re not carrying the conversation anymore.

I was sitting with a friend of mine - Ed. We had known each other for years. There was trust between us. Ease. Shared history.

We were talking about the possibility of him serving on the advisory board of an organization I knew he cared deeply about. 

He asked a natural question:
“What are the expectations?”

I told him how we think about it:
* Some people come alongside as connectors. They introduce three to five new prospective givers each year to the mission.
* Others step in as lead givers. They make the organization one of their major priorities. They give at a level of $50,000 or more - sometimes far more than that. Their name carries weight. Their involvement signals belief in the work.

I didn’t need to tell him which category I thought he fit into. And I didn’t need to ask him for anything.

He paused for a moment and then said:
“For me, money isn’t going to be the issue… but I will be limited with my time.”

That’s when I knew he was ready.

We talked a bit longer. Then he said,
“Give me about a month to think and pray about it. I’ll be in touch.”

I told him that sounded great. 

As we wrapped up, he smiled and joked,
“If I don’t call you, I know you’ll be knocking on my door.”

When the conversation changes

That moment with Ed didn’t build toward a decision. It revealed one.

I’ve come to believe this:
The best asks in fundraising are often the ones the giver initiates.

Not always directly.
But in the way they lean in.
In the way they joke with you.
In the way they start imagining the future out loud.
In the way they begin helping build what comes next.

This happens more than we think

Recently, one of Julie’s coworkers gave us a kayak. It sat on the beach for a few weeks before anyone used it.

Then one beautiful afternoon, I suggested she take it out. 

She stayed on the water for four hours.

Later she thanked me - not just for suggesting it, but for letting her be the first to enjoy it.

The best moments in major gift fundraising feel more like that. 

You begin noticing who’s already leaning in.
Who’s asking thoughtful questions.
Who’s already moving toward the water.

And when you see it, you don’t have to force anything.
You simply step into it with them.

A blessing for you
May you recognize the moments when something begins to shift.
May you have the wisdom to name what is already becoming true.
And may your invitations be shaped by clarity, not pressure.

Three simple actions for today:

Choose three people in your portfolio.
Invite one.
Invest in two.
And… pay attention to who’s already leaning forward.

* * * * * * * * * *

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.

‍