The word transformation is an interesting and inspiring word. It means “a thorough or dramatic change.” It is positive and aspirational, and it carries a lot of meaning when it comes to giving.
There is giving, and then there is transformational giving. Both are of equal importance, because they represent what the donor can do at the moment he gives. Just because one gift is a higher amount does not mean it has more value to the donor than the lower gift.
A $2,500 gift from a donor who can hardly afford it may have more value to that donor than a $2.5 million dollar gift from a donor who can afford even more. The lower gift might be sacrificial. Keep your focus on the donor, and not on the money.
Having said that, giving that is truly transformational both to the donor and to your organization is something that can happen from a few donors in your caseload. Jeff and I are always talking about finding those 1-2 (or 3-4) donors in your file who have the capacity to make a transformational gift. We keep talking about it because it will happen if you spend the time and energy to develop a specific plan around those donors.
It’s important to understand that a transformational gift is a result of an alignment between the donor’s deep passions and interests in addressing a societal problem and an opportunity you have presented to that donor that matches a category of work your organization is involved in.
Notice the words “donor’s deep passions and interests.” This is not just a passing interest of the donor. It is deep. It is all-consuming. It is something that needs to find a resolution. It is a yearning, from the donor’s spirit and soul, which must find some relief and expression.
How do you find these donors in your caseload? Here are some ideas:

1. First, identify these few donors. – Look through your caseload and find those donors who are most involved with you (clues: recency of giving and amount), who also have the capacity to give a much larger gift. There will be 2-5 donors that fit that category. Maybe even only one.
2. Research. Specifically figure out if they have given other transformational gifts to any other organizations, and what they gave to. You need to have a complete understanding of what that deep passion is. Having brought that information to light, …
3. Create a “transformational gift team.” Involve others on staff – and perhaps on your board – to help you develop a strategy for the donors you have identified. You might have someone from program and finance there as well. You don’t have to do this all on your own. You need others to help you plan for the right approach and solicit this kind of gift. Jeff and I suggest you spend a considerable amount of time on each donor. And the first question you need to ask is this: “What can we propose that most closely aligns to this donor’s deep passions and interests?” Start with that one and work on it, paying close attention to the alignment. Once you land on the right program or cluster of projects, then answer the question on strategy: “What is the best amount to ask for, and what is the best way to approach this donor?” Spend a lot of time on this as well. Remember, your ask might follow an eight-month series of steps and engagements where you show the donor, before the ask, that this program/project is the perfect one to express her interests and passions. Do not just run out of your strategy session and ask for the money. You need to bring the donor into alignment with the idea through exposure to the problem (this may take 2 to 3 steps), exposure to the solution (this may take another 3 steps), the input of third parties (this may be one step where an outside authority figure endorses your solution to the problem), the endorsement of friends and colleagues (this might be friends or acquaintances of the donor who give credence and support to the idea) and finally the ask. See how it builds up? Plan for that.
4. Execute. Once you have your strategy, develop a communication plan and a timeline to obtain that gift in 6-18 months.

It’s easier said than done, that’s for sure. But if you follow these steps, you will be well on your way to securing a transformational gift. Always remember, though, that a transformational gift is NOT about the money. It is about helping the donor find expression to her deepest yearnings to make a difference in this world. THAT is what you are facilitating.
Richard