The Cost Of Getting It Wrong

This is the Post #3 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 once brought a CEO of the charity I worked for to meet a close friend of mine. We met in a hotel lobby café - casual, comfortable, low pressure.

My friend arrived relaxed and open. The kind of person who enjoys meaningful conversation and thoughtful relationships.

Then my CEO walked in. 

Three-piece suit. Pocket square. Fully dialed in.

He had a rule: If you’re asking someone to give, you wear a suit and tie.

I hadn’t prepared him for anything different. 

The moment I saw him, I knew we were in trouble. I can still, to this day, see him in that suit.

We sat down. My friend respected me, so he gave us his attention. 

And then my CEO began talking.
And kept talking.

Seventy-three minutes. 

Slides. Vision. Strategy. Numbers.

No questions.
No curiosity.
No real invitation.

Just… a monologue.

Nothing went wrong… and nothing truly connected

Afterward, my friend pulled me aside. He was gracious about it, even playful, but clear: 

“Hey… please don’t ever do that to me again.”

We were okay. Our friendship had years of trust behind it. We played golf not long after, and he teased me the entire round.

But something had shifted. Not much. But enough.

I found myself slower to bring new opportunities to him. More cautious. A little less free.

What it costs

And that’s the part that’s easy to miss. 

When an ask comes too early - or arrives in the wrong way - the cost usually isn’t dramatic. It’s subtle.

A little less openness.
A little less trust.
A little more hesitation next time around.

I’ve seen it play out at a much larger scale, too. 

Organizations that consistently rush the moment…
They treat the ask as something to complete instead of something to discern…

They don’t slow down long enough to understand the person in front of them…

They often live under constant pressure.
Always trying to catch up.
Always pushing for the next gift.
Rarely experiencing real momentum that comes from deeply rooted relationships.

There isn’t enough space for trust to mature.

And I’ve gotten this wrong myself. I once made a significant ask based largely on a wealth profile. The relationship was strong enough that we recovered easily, but the experience stayed with me.

It reminds me of something important.

Capacity may help shape the number. But it doesn’t determine the moment.

Starting over

When something like this happens, the most helpful move is often the simplest one.

Name it.

Pull out your metaphorical clabberboard and say, “You know what? I’m better than that. Let me try again.”

A little humility helps. Maybe even a little humor.

It releases tension.
It rebuilds trust.
It reminds the other person that the relationship matters more than getting the moment right.

And not every misstep causes damage.
But enough small moments, left unaddressed, begin shaping a relationship in ways that are difficult to notice… and even harder to reverse.

So the question isn’t only: Is it time to ask?

It’s also: What do I do when a moment doesn’t land the way I hoped?

Here’s my prayer for you this week:
May you notice the moments that don’t quite connect.
May you have the humility to name them when they happen.
And may your relationships be strong enough to hold both the invitation - and the occasional misstep.

Let’s put this into motion 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.

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