30 Reasons To Reach Out

Last week I wrote about a simple discipline I try to maintain in major gift fundraising: three meaningful reachouts every working day. 

That's about 15 a week. Which raises a good question: When it’s time to reachout, what do you actually say or do? Sometimes the answer is easy. There's a gift to acknowledge, a meeting to schedule, or a proposal to discuss. But what about the rest of the time?

Sometimes the relationship doesn’t need another conversation about giving. Not right away. We still want to tend the relationship, but there we are, staring at a name in the CRM wondering: “What meaningful reason do I have to get in touch with this person?”

Here's some good news: You probably have more reasons than you think.

Start with what you know

The best reachouts often come from simply paying attention to someone's life - and remembering what they've told you. 

Maybe they mentioned a business deal the last time you talked. Their daughter was graduating in May. They were headed to Italy for three weeks. Their parents were celebrating their 60th anniversary. They were considering a significant decision and asked you to pray about it.

Those are all reasons to reachout. 

A simple, “Hey, whatever happened with that acquisition you were working on?” communicates something beyond curiosity about the deal. 

It says: I remembered. That's a good place to begin.

Gratitude gives us lots of reasons

We tend to associate gratitude with gifts. Someone gives and we thank them. But there are all kinds of things worth thanking people for. 

Maybe they gave you advice that proved helpful. They made an introduction. They encouraged you during a difficult season. They said something six months ago that stuck with you. They opened a door for your organization. They helped you understand a situation differently.

Tell them.

One of my favorite kinds of reachouts is some version of: “I was thinking about something you told me a few months ago, and I realized I never told you how helpful it was.” 

No ask. No organizational update. No hidden agenda. Just gratitude.

Make connections

This may be one of my favorite things to do. 

Over time, we get to know quite a few interesting people, and every once in a while, you realize two of them should know each other.

I've connected givers with people who share another charitable interest. I've made connections related to business opportunities someone was pursuing. Sometimes I've introduced two people just because I thought they would enjoy knowing each other.  

And here’s the beautiful part: There doesn't have to be a benefit to your organization. In fact, that's part of the fun. You know something about this person and something about that person, and you realize you might be able to help them both. 

So make the introduction.

Let your phone do some of the work

Every once in a while, my iPhone serves up one of those featured photos from years ago. Sometimes it's a picture from a trip or experience I shared with a giver. Those are incredibly easy reachouts. I'll send the picture with something like: “Look what popped up on my phone today!” 

Maybe I'll add a memory from the trip. Or maybe I’ll simply say that it made me smile. That's it. I didn't create a stewardship strategy around the photograph. My phone reminded me of a shared experience, and I thought they might enjoy remembering it too. Shared history is worth tending.

The reachout toolkit

Let’s get down to brass tacks. Here are 30 specific things I’ve done over the years. If you're looking at your three names for today and wondering what in the world you're going to say, here are some possibilities to pull from.

Pay attention to their life

• Acknowledge a birthday, anniversary, graduation, retirement, new grandchild, business sale, or other milestone.
• Remember a difficult milestone or anniversary, when appropriate.
• Ask how the business deal or decision they mentioned is going.
• Ask how their trip or vacation went.
• Ask about a family member they mentioned in an earlier conversation.
• Follow up on a challenge or opportunity they told you about months ago.
• Celebrate something they're doing that has nothing to do with your organization.

Share something useful or interesting

• Send an article connected to something they care about.
• Send a book, podcast, or video that made you think of them.
• Send a travel, restaurant, book, or other recommendation based on something they enjoy.
• Tell them something happened that reminded you of a previous conversation.

Practice gratitude

• Thank them for something beyond their giving.
• Thank them for the advice they gave you.
• Thank them for the introduction they made.
• Tell them how something they said or did ended up helping you.

Make a connection

• Introduce them to someone connected to another charitable interest.
• Connect them with someone who could be helpful in a business opportunity or decision.
• Introduce two people simply because you think they'd enjoy each other.
• Offer to meet a spouse, child, or family member they've talked about.

Involve them in the mission

• Give a quick update on the project they're supporting.
• Send a photo or small moment from that project instead of a formal update.
• Share good news from your organization that connects specifically to why they give.
• Invite them to consider a vision trip.
• Invite them to something you genuinely think they'd enjoy.

Remember your shared history

• Send an old photo from something you experienced together.
• Bring up a funny or meaningful memory from a previous trip, event, or conversation.
• Revisit something you talked about a year or two ago and ask what happened.

Care for them

• Offer to pray about an important business or personal decision.
• Follow up on something they previously asked you to pray about.
• Simply say, “It's been a while. I'd love to catch up.”

Add some of your own things to this list and tape it on the wall above your desk. It's a great reminder for those moments when you know a relationship deserves some attention but aren't quite sure what to do.

Remember the person behind the gift

There's a temptation in fundraising to overthink our interactions with givers and prospects. Every meeting needs a strategy. Every email needs to advance a deal. Every conversation needs to move someone toward a decision. But relationships just don’t work well under that kind of pressure.

We should know why someone is in our portfolio. We should have a plan. And yes, ultimately, we're fundraisers. Giving is part of the relationship we're responsible for tending.

But don’t forget to consult your notes and work to remember:
What they told you.
What mattered to them.
The trip they took.
The decision they were wrestling with.
The person they introduced you to.
The funny story they told three years ago.

Good fundraising relationships are built by remembering so much more than just their giving.

So what would you add? I'm sure my list of 30 is missing some great ideas. Hit reply and tell me one of your favorite reasons to reach out to a giver. Let's keep adding to it together.

And when your phone features a picture of you and me from seven years ago, send it along! I love those memories.❤️🕺🏻😊

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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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