Fearless Major Donor Cultivation

So you had your first visit with a hot prospect. And it went well!

You’re confident they have the capacity to make a big gift. They’re interested in learning more about your organization.

Now what?

Well, now the fun begins.

Welcome to the longest stage of the fundraising cycle: cultivation.

Cultivation is where you connect your prospect’s passion with the work of your organization. And you do this in a way that, ultimately, leads to significant investment – a major gift.

I like to think of it as bridge-building. Or, at least building the support structures on which you can build a bridge.

Here are a few doodles to help the visual learners out there:

You probably noticed the three support pillars labeled “learning,” “trusting,” and “engaging.”

To be sure, there are other variables that impact your cultivation efforts – timing is a big one. But you can’t control your prospect’s timeline.

Since top performers focus on what they can control, that’s what we’re going to do here. Good cultivation can have a major impact on your prospects’ levels of learning, trusting, and engagement.

Why does this matter?

Well, without cultivation, the best you can hope for is some type of transactional gift. These tend to be much smaller, less personal, and they don’t help inspire lifelong attachment.

Now, of course, there’s danger at the other end of the spectrum as well. Too much cultivation and you’ll never ask! It’s the “Ready, aim, aim, aim, aim…” syndrome.

So, how long does it take?

18-24 months is typical, but 36 months certainly isn’t unusual.

And for a donor’s first gift to you of $1,000,000 or more, you’re probably looking at something closer to five years.

So, settle in. You may be here for a while.

And settle into this blog series too. We have a lot to cover. Cultivation is a huge topic. In the weeks ahead, we’ll tackle it in four parts.

Since we can’t cover everything (even in a four-part series), I’m going to make a few assumptions along the way.

Most importantly, I’m going to assume that when we talk about “cultivation,” we’re referring to prospects you’ve already qualified. Someone at the organization has met with them face-to-face, at least once. You know they have the capacity to make a major gift, however your nonprofit defines it. And you’ve confirmed that they have some level of interest in you.

That last part is equally important. Bill Gates certainly has the capacity to make a major gift to your organization. But unless you’ve connected with him and know he’s interested in you, you’re not actually cultivating Bill Gates.

For tips on how to handle your unqualified prospects (aka “suspects”), check out my series on qualification outreach and qualification visits.

I’m also going to assume you have a donor database, an understanding of who your major gift prospects are, and some type of moves management process.

So, let’s get into it. We’ll start with the psychology of major donor cultivation.

Inside Their Heads 

Before you can think about cultivation strategy, action items, or what you’re going to say, you need to get inside your prospects’ heads. Without this foundational work, the tactics and word-for-word scripts I’m going to give you later are useless.

So, let’s get in their heads.

High net worth individuals know when they’re being cultivated. And that’s okay! If they had zero interest in you, you’d know by now.

But, their awareness doesn’t make it a done deal. The process is still important – like dating before marriage.

During this time, your prospect is trying to figure out a few basic things.

Let’s organize them using the “bridge-building” framework:

Learning

• What is the org’s mission? What need are they meeting?
• Do I agree with their understanding/definition the need or problem?
• How are they addressing it?
• Are they truly having impact?
• Am I sold on their plans for the future?

Trusting

• Do I like and trust the leadership of this organization?
• Am I treated well here?
• Are other people like me involved?

Engaging

• Do I have anything to offer? Am I valued for my skills, expertise, opinions, and/or connections?
• If I’m not ready to write a big check, what else can I do?
• Are there people with true expertise here? Are they passionate?
• Do I feel like I’m truly part of something meaningful?

Whether consciously or unconsciously, your prospects are looking for answers to these questions as they’re getting to know you.

So be sure you’re putting yourself in their shoes! Yes, to you it’s “cultivation,” but to them it’s a critical time of learning and deciding.

Another framework I’ve found incredibly useful comes from Russ Alan Prince and Karen Maru File’s book, The Seven Faces of Philanthropy.

It’s no secret that people give to charities for varying reasons. Using academic research, the authors categorize high net worth donors into seven psychographic “types,” or profiles. Donors within each profile have a unique set of values that influence their giving decisions.

The book is worth a read, but I’ll try and summarize. Here are the profiles identified by Prince and File:

1. The Communitarian: Doing Good Makes Sense
   • Values: The community where they live and do business; “We’re all in this together”
   • Motivations: Investing in the community is good business; they do well when their communities do well; they develop valuable personal/business relationships via nonprofit involvement, namely board service
2. The Devout: Doing Good is God’s Will
   • Values: Faith-based causes and institutions
   • Motivations: “It’s God’s will that I give to his work and for the benefit of others”
3. The Investor: Doing Good is Good Business
   • Values: Tax efficiency; sound financial management; more likely to give to community foundations or other umbrella non-profits
   • Motivations: Tax and estate benefits; adviser recommendations
4. The Socialite: Doing Good is Fun
   • Values: Having fun while doing good; more likely to support the arts or collegiate athletics
   • Motivations: Leisure and entertainment; expanding their social influence; networking
5. The Altruist: Doing Good Feels Right
   • Values: Generosity; “Giving is a moral imperative;” most likely to support social causes
   • Motivations: Empathy; personal/spiritual growth; wholeness
6. The Repayer: Doing Good in Return
   • Values: Loyalty; likely to support education and/or healthcare
   • Motivations: Reciprocity; obligation; Helping an organization that helped them
7. The Dynast: Doing Good is a Family Tradition
   • Values: Tradition; legacy; family name
   • Motivations: Continuing family legacy; expectations; peer pressure from other dynasts

Now, this is just a framework. Not every human being will fall squarely within one type. But, understand these profiles and you’ll be well on your way to knowing what motivates your prospects.

And that really is the key, isn’t it? Knowing someone on a values level – a motivational level – is essential to your ability to develop an effective cultivation strategy for them.

Get your cultivation right and asking for a gift will seem like a natural next step in the relationship.

Your Winning Cultivation Mindset

OK, let’s talk about you for a bit.

How do you balance empathy with your agenda?

You have a lot of learning, listening, and understanding to do, but you also need to move things forward. They don’t have to be mutually exclusive.

Today, I want to focus on developing (cultivating?) a winning cultivation mindset.

A winning mindset allows you to strike that ever-important balance between being donor-centered and goal-oriented. Your winning mindset will include the following:

• Curiosity: You’re interested in people. You want to figure them out and get to know them on a motivational level. Only then will you be able to help them learn and engage in a way they find meaningful .
• Friendliness: You’re likeable. People without this trait don’t last long in fundraising! It greases the wheels; it helps you build trust and so much more.
• Confidence: You believe in your cause and are unashamed to fundraise for it. You communicate an air of inevitability.
• Persistence: Goes hand-in-hand with confidence. You’re not shy about keeping in touch with your prospects and finding ways to keep them engaged and connected.
• Patience: You’re able to keep the bigger picture in mind and stay focused. Easy wins are nice, but big wins transform organizations. And careers.

I’m the first to admit that I don’t feel friendly all the time. Same goes for confident, patient, etc. But, over time, I’ve learned how to turn it on when I need to.

How? By faking it.

I’m serious. If those qualities don’t come naturally to you, don’t worry. You can fake them until you get used to adopting this mindset.

To get started, use what I call the “How would I act if…?” technique.

Let’s use curiosity as an example.

How you would act if you were naturally curious about other people? Do you know people like that? What are they like? How do they approach their conversations? Their relationships? If you had an insatiable curiosity about people, how would it feel? What would you say? How would you act?

Now act that way.

If the “How would I act if…?” technique sounds inauthentic, it might help you to know there’s science behind it.

Psychologists have proven that the relationship between emotion and behavior isn’t a one way street. It’s reciprocal, not linear.

It’s not only “I’m sad therefore I cry.” You can also make yourself feel sad by crying. It’s how we’re wired.

The research around body language also shows that you can make yourself feel more confident just by adopting poses, postures, and gestures associated with confidence.

And this is good news! It means that instead of waiting until you feel friendly, confident, curious, etc., you can act as if you’re experiencing those positive, helpful emotions and the feelings will follow.

Over time, and with some practice, this gets easier and faster.

Wrapping Up 

We covered a lot of big picture stuff today. Hopefully its importance wasn’t lost on you!

You’ll never successfully cultivate major donors if you can’t get inside their heads. We worked our way through two frameworks that will help you do just that.

And practicing mindfulness and knowing how your own emotions impact your work is essential to being a professional, let alone a top performer. We outlined a winning mindset for balancing empathy with your agenda.

Have something to add? Leave a comment below!

Things will get more tactical from here on out, so stick around.

Next up, we’re going to cover cultivation planning. We’ll talk about how to take what we know about our prospects’ values and motivations and develop individualized strategies for each of them.

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