Only negotiate if you hear a flat-out: “there is no way in the world I/we can do that” or “I/we can’t possibly afford that much.”  You are listening for an absolute “no” that will be expressed through words, voice tone and body language.

 The following are not negotiating triggers:

•  “Wow, that’s a lot of money.”  [An observation, not a definitive statement that the donor can’t or won’t make the gift.  Respond with an “impact statement,” e.g., “With that gift, you will be <describe impact>.”]
•  “I wasn’t expecting that.” [Surprise is not a definitive “no.” Donors are often surprised. Keep the focus on the project and help the donor determine how involved s/he wants to be in the opportunity.]
• “How did you come up with that number?” [Respond with impact, not process: “We know how much you care about <nonprofit> and thought you would want to take a leadership role” [or thought this might be the level at which you would want to be involved].
•  The classic: “Let me think about it.”  The donor may simply need time.  Your job becomes to understand what the donor is thinking about and to determine if you can help that process.  If not, let the donor think.

Donor-respectful Negotiation steps

1. If you do receive a flat-out “no way” and want to negotiate:If you asked for the gift as a lump-sum, e.g., for an outright $50,000, test a timing solution:  “Would you be able to fund this project the way you’d like to if we spread your gift over time—would $10,000 a year for 5 years for a total of $50,000 make it possible?”
2. If timing doesn’t get you to “yes,” then negotiate the amount.  Reduce the amount by 50% and re-ask using the “ask” format:  “So John, would you consider a gift of $25,000 to support this project?” 
3. If a 50% reduction does not get you to “yes,” then shift to letting the donor tell you what amount will work: “So John, I can see that you want to support this project–what amount will make that possible for you?”

 Why 50%? 

1. If the donor could come close to the amount you asked for, you wouldn’t hear an emphatic “no way.”
2. You want the donor to feel listened to and respected.
3. This is not a bazaar—you don’t want to be in the position of haggling.

Note:  There may be different advice for potential gifts of $10M+.  That’s not my space.