A year ago I was sitting down with the Director of Development of a new client, discussing his many challenges with his non-profit’s leadership. He was depressed. His CEO thought there was no way cultivating individual major gifts was going to work for their non-profit. He also had a board chair who, while extremely wealthy and well connected, had an aversion to asking for money.
You see, this particular non-profit grew up on foundation and government grants. In the past they were really good at creating proposals and getting funding for specific projects. But those funds were becoming harder to obtain. The Director of Development was hired to figure out what do to.
His solution was to start building an individual major gift program. It was exactly what this non-profit needed… except that no one in leadership believed it was going to work.
Together, we got working to build a caseload of donors from their database. We qualified those donors, created goals and developed a plan for each donor. The program was now on a solid foundation. Yet we had the challenges of the CEO and board chair.
The Development Director and I created a plan to get the CEO to believe that major gifts could work. Here is what we did:

1. Created a personal portfolio of donors for the CEO — The CEO had 20 donors that he was responsible for. Obviously the Director of Development was behind the scenes supporting the CEO, but the CEO felt ownership that these donors were his responsibility to cultivate, steward and solicit for gifts.
2. We started with the low-hanging fruit — Remember that this CEO was skeptical that going after major gifts from individuals was going to work. The Development Director and I knew that if the CEO could get a “win” early, it would be much easier to move forward. So we took time to really figure out who was most ready to be solicited, developed a plan and then took the CEO by the hand to cultivate those donors and set up a solicitation plan.
3. Coach, Coach, Coach — We took many hours to sit down with the CEO and walk him through how to approach the donors, what we should ask for, how it should be done… every little detail so that he would feel comfortable.

After a couple of months it was time for the CEO to solicit one of the “low-hanging fruit donors.” It turned out to be a great experience, and the non-profit received a $500,000 gift from an individual for operations! Not only was it wonderful that the gift came in, but we made a believer out of the CEO. Since that first gift, the CEO is “all over it” and has solicited multiple gifts from individuals. In one year, over one million dollars has come in from individuals. Now, this CEO is “an old pro” at it.
At the same time, we had work to do with the chair of the board. Remember, this board chair was adamant that she could not – and would not – raise money. Yet no one had ever taken the time to ask her why.
So we sat down with her and did just that. We asked her why she had such a tough time with fundraising. It was an amazing discussion. It turns out she’s had some pretty bad experiences in the past with people soliciting her for a donation, and she said she never wanted to do that to anyone herself.
We probed deeper. We asked her to tell us about some of her good experiences and how they made her feel. Her demeanor changed. She started to see how helping others give away money could be a good thing, because it made her feel good when she gave it away herself. It also started to feel like a spiritual thing for her. It was like a light bulb going off in her head, and now it all seemed to make sense.
We have now been working with her for many months, and she is doing amazingly. She’s been asking for large five- and six-figure gifts from her friends and contacts, and the money is flowing in. This was from someone that “never wanted to fundraise” before.
Here were two people that had a negative attitude toward fundraising, but because we approached these two with compassion and understanding (and good strategy), we were able to turn them around and do something amazing for the organization.
Here are some of things the Development Director and I learned in this process:

1. Creating an individual major gift program will work with any non-profit. You have individuals who care about your mission. They will give… if you ask. (Okay, we knew this, but we certainly made a believer out of the CEO.)
2. Take great care in helping the “naysayers” move toward a “yes.” Be gentle, be compassionate toward their fear and skepticism, then provide a plan and coach them well. Hold their hands through the process. It will work.
3. Listen to people. The reason we were able to turn the board chair around was because we listened to her story and then we kept asking questions. I hear from too many Development Directors who just haven’t taken enough time to help someone in leadership understand the power of fundraising and the enormous benefits it has for the giver.
4. Encourage leaders. Yes, even leadership needs ongoing encouragement in fundraising, especially if they don’t think they are good at it. I think we forget this sometimes, and we think that leaders will be fine on their own. They need YOU to be successful.

So yes, it is possible to teach “old dogs” new tricks. Very possible. But you have to have patience, understanding and persistence to help make those “new tricks” a way of life. You can help make that happen.
Jeff