Picture this: I am sitting in my front bench. The cool mountain air is crisp in my lungs. The sun is bright and I am excited. As I laced up my running shoes, I knew that the day held both a challenge and an opportunity for growth. Hey there, fellow fundraisers. Clark Vandeventer, your devoted Major Gifts Fundraiser, is excited to share an analogy that bridges the gap between my recent exhilarating trail run and the art of cultivating donors. So, grab your favorite beverage, get comfortable, and let’s embark on a journey through the intriguing world of fundraising, where timing, strategies, and impactful connections converge.

The Power of Breaking it Down: From Runs to Asks

Much like the trail run I embarked upon—a strenuous 15-mile route through nature’s rugged terrain—successful fundraising often hinges on breaking down monumental tasks into smaller, more manageable steps. As I tackled the trail, I realized that the seemingly insurmountable distance became attainable by focusing on each leg of the journey. In the realm of fundraising, a similar principle applies to how you approach your donors.

Imagine this scenario: you’re striving to achieve a remarkable $6 million fundraising goal. However, presenting donors with the entire amount can be overwhelming. Much like my run, which was divided into segments, consider initiating the fundraising conversation with a smaller, more digestible ask. This “qualifier ask” allows you to engage donors early on, building a bridge between their immediate contributions and the grander vision.

For instance, let’s delve into a specific example from my journey. In a scenario where your ultimate goal is $6 million, consider starting the conversation with a $5,000 ask. This initial step serves as a foundation for your relationship with the donor, while also demonstrating how their support contributes to the larger mission.

Understanding Timelines: The Complex Dance of Cultivation

The question of how long to cultivate a donor before making a major ask is much like a puzzle with intricate pieces. My personal record includes an impressive 19 meetings with a donor before finally making a substantial ask—a strategy that ultimately bore fruit. However, it’s important to note that this approach may not be universally applicable. In fact, I’ve also had success by asking for a gift on the very first meeting, a tactic I’ve employed multiple times.

This distinction, however, is tied to the types of gifts and the nature of the relationships. Consider the scenario where a donor is already contributing $10,000 annually. This donor may have a long history with the organization, and it may be easy to move them up quickly. If it is a new donor, even if they have capacity and philanthropic disposition,  cultivating  them for a million-dollar gift requires a longer timeline to establish rapport and emphasize the transformative impact their contribution can have.

One other distinction is the type of ask. I call these “qualifier asks’ ‘ or “nonchalant asks” that serve as icebreakers in the initial stages of a campaign or relationship. This would be asking someone to join your giving clubs. These carry certain levels of giving, maybe 10,000 annually or more depending on the organization. These asks can just be suggested in conversation, and if the donor comes through you now have a better idea of where you are in the dance.

Leveraging Different Gift Types: Setting the Stage

Let’s delve deeper into the concept of different gift types. Take the aforementioned donor contributing $10,000 annually—they’re on track for a million-dollar gift with proper cultivation. On the other hand, “qualifier asks” are crucial in laying the foundation for future engagement. Imagine you’re seeking a million-dollar gift, but you encounter a donor with the capacity to contribute substantially. Instead of years of cultivation for the million-dollar ask, you initiate with a qualifier ask that aligns with their immediate capacity.

To exemplify, you might invite them to join your organization’s President’s Club by contributing $1,000 or more annually. This initial engagement serves as a stepping stone towards larger contributions down the line, while also fostering a sense of belonging to your cause.

Strategic Early Engagement in Campaigns

The strategy of early engagement holds immense significance for successful fundraising campaigns. Consider a scenario where you’re aiming for a $6 million goal over three years. When encountering a potential donor who has never contributed before, starting their involvement with a $5,000 gift lays a strong groundwork. This gift, received sooner rather than later, allows you to initiate stewardship and begin cultivating larger contributions.

The beauty of this approach lies not only in the immediate gift but also in the journey it sets in motion. These donors are likely to contribute additional gifts over time, their commitment growing as they align with your mission. Months down the line, when you approach them for a $25,000, $50,000, or even a hundred-thousand-dollar gift, they’re already invested in your organization’s vision.

Conclusion: A Dynamic Symphony of Strategy and Timing

As we conclude this exploration into the art of donor cultivation, remember that fundraising is a harmonious blend of strategy, timing, and connection. By embracing the nuances of different gift types and harnessing the power of early engagement, you’re equipped to navigate the intricacies of fundraising campaigns. Whether you’re initiating a qualifier ask or embarking on a carefully orchestrated cultivation journey, each step contributes to the symphony of positive impact.

So, fellow fundraisers, go forth with these insights in hand. Your ability to master complex timelines and tailor strategies to donors’ unique characteristics will create a wave of change that extends far beyond initial interactions. As always, I’m here to support you on this dynamic journey. If you’re seeking advice or yearning to explore these strategies further, feel free to reach out. Until our next exploration, keep cultivating, keep inspiring, and keep making a difference. Peace.

This post was created from podcast #155: How long should you cultivate before you ask?


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