You are dedicated to the cause. Your nonprofit is wonderful. You hate asking for money. 

Why is that? 

Why do so many passionate and otherwise engaged board members and, secret be told, staff members, too, run in the opposite direction when it comes to major gift “asks”?

Seven Reasons You Might Hate Asking for Money–and Possible New Perspectives

1. The arm twist.
   These are not gifts based on passion and connection to your organization. They are often based on repaying a favor, currying favor or playing a power card of some sort. I’d hate this too. 
2. I’ll give to yours if you give to mine.
   This is a variation of the arm twist, in that you are asking someone to make a gift to an organization with which he or she has limited or no involvement. In the short-run, money swirls around. But there is no real long-term gain unless connections develop.
3. You don’t know what to do and what to say.
   You can’t possibly know how to make an “ask” if you haven’t been trained. In addition to training, I recommend a practice round or two with mid-tier donors who are not your prime prospects.  (Training note: You are over half way there if you are passionate and knowledgeable about your organization and a good listener. Be the ambassador for your organization that you usually are.  You’ll just be adding a few techniques to your repertoire.)
4. You don’t trust the ask amount.
   Should I really be asking this person for this much?  Not to worry. Donors are typically flattered by the “over ask.”  Why wouldn’t they be? And there are strategic “negotiation” benefits for starting high—but that’s a subject for another day. (Yes, there is a too much—but it needs to be way off base.) If you properly research the donor, you will be in the right ballpark.
5. Money talk is taboo in our culture.
   True, but what you are doing is inviting someone to support a cause and organization in which he or she believes.  The connection and desire to give have already been expressed with smaller gifts.  You are providing the donor with the opportunity to play a larger role. Research assures us that this donor has the financial wherewithal to make this level gift if he or she so chooses.  And that’s all it is—a choice.  A choice that comes with a slew of benefits, both tangible and intangible.  This is bad?
6. The prospect might say, “no.”
   You can count on “no’s.” In fact, fundraising research tells us that you are likely to have to make anywhere from two to five asks per gift. That’s lots of “no’s.” The path to success is to keep asking. Plus, there is a benefit to every in-person conversation with a donor. It builds the relationship. Check out my blog entry, “Every ‘no’ is a ‘yes’” and move right past the “no’s.”
7. You believe the experience of giving is negative for the donor.
   I may have saved the best for last:  There is a body of scientific research that tells us giving is good for your health. When you make an “ask,” you are not harming the donor or otherwise inflicting pain. Quite the contrary!  You are opening the door to the pleasure center of the brain lighting up, blood pressure dropping, immune system boosting, stress reducing experience.  The donor will feel good!  And, by the way, so will you!  (For more about this research, visit my blog entry: “Giving is good for your health!”)

May I suggest that you are doing a major gift prospect a favor when you invite the opportunity for greater involvement in a cause he or she believes in—that’s right, a favor.

Feel any better?