The Conversation You Almost Had

Last week, we explored 30 reasons to reach out. 

Suppose you picked one, made a call to someone on your list, and got a coffee on the calendar. Now you’re sitting across from them - the conversation is underway and you’re looking forward to sharing an exciting update about your cause.

While exchanging pleasantries, they say something seemingly ordinary. You acknowledge it, knowing the conversation could go several ways. But there’s an update you’re eager to share. Do you acknowledge the comment and ask another question? Or do you let it go and get into what you were planning to present?

Let’s imagine a moment like that played out three different ways.

Here’s the setting: You’re having coffee with Anne, one of your top givers. You’ve known her for several years. Her youngest son, Chad, participated in your organization’s mentoring program during high school, and the family has continued supporting it. You’re meeting to catch up and share how the program is doing.

With coffees in hand, you ask her how the family is doing.

She looks away briefly.  “Pretty good. Chad just moved out, so the house is suddenly quiet. I’m still figuring out what to do with that.”

Nothing about this moment announces itself as significant. It feels like a normal life transition. Let’s examine a few ways to respond.

First - The encouraging connection

Anne just finished her response to your question, “I’m still figuring out what to do with that.”

You nod affectionately and respond: “Well, Chad has certainly come a long way. I still remember how much he enjoyed spending time with his mentor. We’ve had some really encouraging stories from the program this year.”

Anne smiles. “Yes, it was good for him. How’s everything going?”

You share the update. Anne asks about new mentors, you tell her about a few students, and the conversation moves comfortably along. There’s warmth and gratitude. You shared more Chad memories and connected his experience to something the family cares about.

But Anne’s earlier comment, I’m still figuring out what to do with that, quietly slips away.

Second - The familiar experience

Let’s return to the same opening. Anne just said, “I’m still figuring out what to do with that.”

This time you ask, “What’s that been like for you?”

Anne hesitates and thinks about it. “Honestly, a little strange. You spend so many years being needed every day. Then suddenly you aren’t, at least in the same way.”

You respond: “I get that. When our kids left, we hardly knew what to do with ourselves. We eventually started traveling more. Do you have any trips coming up?”

She does. You spend a few minutes talking about destinations, flights, and the pleasure of traveling whenever you like. It’s an enjoyable conversation. 

You asked a good question, heard something familiar, and offered a little of your own experience. 

Finding common ground comes naturally to many of us. Somewhere along the way, though, Anne’s comment about being needed gave way to travel plans. There may have been more available in her answer than the conversation allowed.

Third - Staying with the answer

One more time. “I’m still figuring out what to do with that.”

“What’s that been like for you?”

Anne gives a hint of a weary smile. “Honestly, a little strange. You spend so many years being needed every day. Then suddenly you aren’t, at least in the same way.”

You stay with her story and ask, “What do you find yourself missing?”

“I think it’s having a part in someone’s everyday life. Knowing what’s happening with them. Being there for the little things.”

She shares more about the adjustment, how Chad is settling into his new digs, and how much she enjoys his occasional calls. There’s tenderness in the conversation, along with some uncertainty about the new season.

Eventually, there’s a natural pause.

You make a suggestion. “Shall we talk a bit about the mentoring program? I know Chad was a big fan, and I’ve been looking forward to sharing how things are going.”

Big grin. “Absolutely. How’s it been?”

You move into the update. But you realize that you’re not just simply giving Anne a project report. You’re talking about the transformation her young adult son experienced through the mentoring initiative.

A few things to try

All three scenarios are appropriate and could happen on a perfectly ordinary Tuesday. Each has warmth.

But, wow, in that third conversation, you stayed with Anne’s answer long enough to discover what she loves about your cause. My suspicion is that there are some volunteer roles which may hold interest for her. Maybe a board role?

Let’s practice this kind of awareness. What would you have asked Anne? I’d enjoy hearing how you would approach that moment.

As you go into upcoming giver visits, listen for a phrase - or even just a few words - you can stay with:
Still figuring it out.
Being needed.
That didn’t go quite how we expected.
I’m ready for something different.
It’s been a bit of a season.
I’m not sure what comes next.
That meant more to me than I expected.

You don’t have to know what the phrase means. You don’t have to interpret it correctly. You simply can give the person room to explain. “Tell me a little more about that.” That’s often enough.

When an answer reminds you of your own experience, consider asking one more question before sharing about yourself. Your story may belong in the conversation. Or it may not. Give theirs a little room first.

And when it’s time to talk about your cause, make the transition plainly. 

“Shall we talk about the program?” That’s often enough too. 

A meaningful personal conversation can sit comfortably alongside the business you came to discuss. The two don’t have to compete for space.

So try it this week: Ask a question. Hear the answer. Then let that answer help you choose your next question. 

A little curiosity makes a lot of difference.

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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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