Preparing To Pay Attention

When I’m driving to meet with a giver, I often find myself imagining the conversation in my head. Sometimes I’m rehearsing a presentation.  But more often, I’m preparing to pay attention. I’m thinking about what I already know about them. Recalling details from previous conversations. Wondering what has changed since we last met. Thinking about which stories might be helpful if they ask about the work. I often jot down a few questions in the small pocket journal I almost always carry.

Sometimes I'm even thinking about something as ordinary as how I’m going to pay for lunch. That might sound like a small detail, but I don't think it is. Hospitality begins before the conversation starts.

Earlier in my career I spent much more energy preparing what I wanted to say. I wanted to make sure I explained the vision well. I wanted to anticipate objections before they surfaced. I wanted to demonstrate that I knew the work inside and out. 

Time has changed a lot of that. 

These days I spend much more time thinking about the other person than about the cause.

One of the best conversations I've had happened shortly after I joined an organization. I was meeting with the board chair who was also, by far, the organization's largest giver. 

During our conversation, I asked him a question that had been sitting in the back of my mind. "What would happen to your giving if you passed away?" He leaned back for a moment. "You know," he said, "no one has ever asked me that question."

What followed was a conversation about stewardship. Succession. Family. Leadership. 

We talked about the long-term health of the organization and the role fundraising might play for decades to come. He eventually became a trusted mentor and friend.

I've thought about that conversation many times over the years. My question wasn't brilliant. It was simply the next honest question.

Another meeting taught me a different lesson. 

After reading a wealth profile, I had convinced myself I knew what a particular giver was capable of. I had studied the data and drawn my conclusions. During the conversation, I asked for a $200,000 gift. He smiled. Then he called me on it. "If you're interested in this kind of thing, just ask me." He was right.

I had spent more time interpreting data than paying attention to the person sitting across from me. Thankfully our relationship was strong enough to survive my mistake. Over time, his annual giving grew significantly. But I left with a lesson I still carry. Don't substitute research for conversation.

Preparation matters. Research matters. Neither can replace genuine curiosity. That's why I don't spend much energy worrying about what I shouldn’t say. Instead, I try to listen. I ask questions. And I often find myself saying, "Let me make sure I heard that correctly..."

Sometimes the greatest gift you can give someone is the confidence that they have been accurately understood. When newer fundraisers ask me how to prepare an important meeting, they may be expecting advice about presentations or talking points. Instead, I encourage them to prepare their attention.

Bring two or three current stories that illustrate the work. Write down a few thoughtful questions. Review your notes from previous conversations. Then put most of your energy into paying attention. Watch their expressions. Listen for what excites them. Notice what they return to more than once. And be willing to follow a conversation somewhere you didn't expect it to go.

If the opportunity to extend an invitation comes naturally, wonderful. If it doesn't, that's okay too. One of the ways I evaluate a meeting has very little to do with whether someone made a commitment. I ask myself a different question. Do we have a clear next step?

Sometimes that's another meeting.
Sometimes it's sending an article.
Sometimes it's making an introduction.
Sometimes it's simply giving them space.

A clear next step usually tells me I’ve paid enough attention to understand what makes sense for both of us.

As you prepare for the conversations ahead this fall, consider spending less time polishing your presentation and a little more time preparing your attention. 

Before you walk into the room ask yourself, How do I want this person to experience me? Not, How do I want them to experience my organization? Or, How do I want them to respond to my ask?

But simply: How do I want them to experience me?

If they leave the conversation feeling seen, understood, and respected, you've accomplished something important. 

Everything else develops from there.

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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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