Call Me, Maybe?

I try to make at least three meaningful reachouts every working day. That works out to 15 a week and roughly 60 a month. And yes, I keep track.

Those reachouts get documented in the CRM, and I have a report that tells me how I'm doing. If I get to the end of a month and that number isn't somewhere around 60, it's usually a sign that something has gotten in the way of one of the most basic parts of my job: interacting with people and tending to relationships.

Of course, hitting 60 isn't particularly impressive if I'm reaching out to people simply so I can count the activity. The more important question comes before the call, text, or email: Who should I reach out to this week?

Start with the CRM

Start with the plans you've already made for the people in your portfolio. If you're tracking Strength of Relationship, anticipated asks, and next-action dates, the CRM should give you a pretty good starting point.

Sometimes a name will pop up that you haven't thought about in weeks, maybe even a few months. That's okay. You made the plan for a reason. One of the reasons we have a CRM is so we don't have to keep every relationship constantly swirling around in our heads.

Then consider whether the plans you made are still relevant. Does the action that made sense six weeks or three months ago still make sense today? In my experience, about 70% of the time it does. Make the call, send the text, write the email, or start working on getting the visit scheduled.

The other 30% is where judgment comes in. Maybe you know that they're heading into a particularly busy season at work. Maybe they're traveling, experiencing an important family milestone, or dealing with a tragedy. Maybe a trusted connector has given you new information that suggests you should pause or approach the relationship differently.

We make plans with the best information we have at the time. When we have better information, we pivot.

Look beyond the CRM

I also keep a running list in my journal of names that come to mind while I'm praying, meditating, listening, or simply thinking about the work. You may have your own version of that. The point is to pay attention to the people who keep surfacing outside the machinery of your portfolio plan.

Then look at gifts that have come in during the previous month. You've probably already thanked those people, but thanking someone for a gift and actually having a conversation with them aren't always the same thing. There may be a call or visit worth pursuing.

Finally, look at your active connectors. Those relationships need tending, too. It's surprisingly easy to become so focused on prospective or current givers that we neglect the people who have opened doors for us.

Somewhere in all of that, you should find at least three people for today.

What counts as a reachout?

Be open about the form and fairly strict about the purpose. A thoughtful phone call counts. So does a meaningful text or email. The person might be an active giver, a lapsed giver, a prospective giver, or a connector. And several reachouts with the same person can count, especially when an actual conversation is unfolding through texts or emails.

There should still be a legitimate reason that relationship belongs in your fundraising work. I've found it helpful to keep that reason incredibly simple. Ultimately, there are only four things a giver can do:

• Start giving
• Continue giving
• Restart giving
• Increase giving

A connector can help create relationships with people who might eventually do one of those four things. That's a useful filter. We're fundraisers, after all. We don't need to pretend there isn't a fundraising purpose behind the relationships we're responsible for tending.

At the same time, the relationship can have a purpose without every conversation having an agenda. That's where this gets interesting.

You don't always know where a reachout will go

I once called a giver for a normal catch-up conversation. There wasn't anything particularly strategic happening. Somewhere during our conversation, I mentioned something personal that was going on in my own life, almost in passing.

We finished our conversation and hung up. About 15 minutes later, my phone rang. It was them calling back. They wanted to hear more about what I had mentioned because they were experiencing something similar in their own life. Our call went somewhere the first one never could have gone if I'd tried to engineer it. It was personal and meaningful, and it had nothing to do with giving. But it was an important moment in our relationship. Subsequent conversations about their giving were more grounded than they had been before. There was context and understanding between us that hadn't been there previously.

I couldn't have put that into a cultivation plan. I simply had to make the first call and be available for the conversation that actually happened.

That's one of the reasons I think the discipline of reaching out matters. We can plan the contact. We can't always plan what happens once they respond.

And don't forget your connectors

Another time, I called a connector just to catch up. This was someone whose relationship I wanted to tend, and I wasn't calling with a list of people I wanted them to introduce me to.

During the conversation, however, names started surfacing. One became two, and eventually we were talking about four people who hadn't seemed particularly obvious to them before our conversation. Those referrals eventually produced some significant giving.

There's absolutely a place for thoughtfully planning how we're going to activate a connector. Sometimes we know exactly who we'd like to meet and why an introduction makes sense. But there's also something to be said for staying close enough to our connectors that opportunities have somewhere to emerge.

That particular call could easily have looked unproductive on a calendar. It turned out to be anything but.

Who are your three?

So here's a very practical exercise for this week. Look at the plans you've already made and ask whether they still make sense. Look at the people who have been coming to mind. Look at recent gifts. Look at the connectors you haven't talked with lately. Somewhere in there, identify three people and thoughtfully reach out to them.

Do it again tomorrow, and keep going through the week. Document those interactions so you can look back and see whether you're somewhere around 15. The number isn't sacred. It's simply a discipline that keeps us doing the relational work that matters.

When someone answers the phone (or responds to the message), hold your plan loosely enough to pay attention to the person you're actually interacting with. Something may have changed since you put a plan in the CRM. Something may be happening in their family, their work, or their life that matters much more today than whatever you planned to discuss.

Or nothing unusual may happen at all. You'll still have reached out and tended the relationship.

And every once in a while, an ordinary call will become something you never could have planned.

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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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