Crafting Personalized Cultivation Plans for Top Prospects in Your Annual Strategy
Scaling Major Gifts. Strategies, action steps, and ideas for scaling major gifts by Tammy Zonker, Major Gift Expert & Keynote Speaker.
In my nearly 30 years as a major gift strategist, I’ve seen firsthand how a well-thought-out, personalized cultivation plan can be the difference between a top prospect becoming a transformational donor—or a missed opportunity.
Whether you're a major gift officer juggling a full portfolio, a development director trying to hit year-end targets, or a board member wondering how to move key relationships forward, this topic hits home. Cultivation isn’t just stewardship lite—it’s strategic, intentional relationship-building. And when done right, it moves the needle in powerful ways.
The Pain Points: Sound Familiar?
Over the years, I’ve sat in dozens of boardrooms and staff meetings where the same cultivation challenges surface again and again:
Too many prospects, not enough time
Unclear ownership of the cultivation process
Generic, one-size-fits-all outreach
Inconsistent follow-up that causes momentum to fizzle
Difficulty translating passion into action (and ultimately, into gifts)
One of the biggest pain points I’ve seen? A team spends months identifying top prospects… but then hits a wall when it comes to what happens next.
Strategies That Actually Work
The good news? These challenges are solvable with a structured, personalized approach. Here are a few strategies I’ve used—or seen used—with great success:
1. Create a Cultivation Calendar
One approach I’ve seen work well is to build out a 12-month cultivation calendar for each top prospect. This doesn’t need to be complicated. At minimum, it should include:
Touchpoints every 6–8 weeks
A mix of personal contact (calls, visits) and mission-focused engagement (program updates, invites to events)
Assigned staff or board member for accountability
2. Use a Personalization Matrix
I've found that tailoring plans based on interest, capacity, and relationship stage helps prioritize efforts. For instance:
3. Lean Into Board Champions
Board members can be incredible bridge builders. One nonprofit I worked with in Chicago trained their board to use “Mission Moments” when speaking to prospects—short, powerful stories that made cultivation authentic, not transactional.
4. Track and Optimize With Tech
Using a CRM like Neon CRM, DonorPerfect, or Salesforce Nonprofit Cloud has helped teams manage their cultivation plans consistently. These tools make it easier to track interactions, set reminders, and evaluate what's working.
A Real-World Win
A few years ago, I worked with a regional health nonprofit that was struggling to move mid-level donors into major gift conversations. We identified their top 25 prospects and built personalized cultivation plans for each. After 12 months of consistent, tailored engagement—one-on-one meetings, handwritten notes from leadership, and strategic touchpoints—they closed $1.2 million in new gifts from that group alone. That was a 37% increase over the previous year.
And here’s the kicker: most of those donors had been giving under $1,000 annually.
Your Action Steps
Here are three things you can start doing this week:
Select your top 10–15 prospects and draft individualized cultivation plans
Assign internal champions—staff or board—for each relationship
Schedule your next three touchpoints on the calendar right now
Remember, a cultivation plan doesn’t have to be perfect—it just has to be intentional.
We’re All in This Together
If there’s one thing I’ve learned over three decades, it’s this: the relationships you nurture today become the impact stories you tell tomorrow.
Connect with me on LinkedIn and let’s keep the conversation going! Have you tried any of these strategies? What’s worked for you—or where have you felt stuck? Drop me a note, or forward this to a colleague who could use a little inspiration.
Because, at the end of the day, fundraising is about people. And that’s something worth doing well.
Keep transforming,
Tammy Zonker
Major Gift Expert & Keynote Speaker
Fundraising Transformed
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