This question is often posed by those involved in a campaign for the first time:

Don't we only get to ask a donor ONCE for a campaign gift? If they say no, don't we need to move on and cross that donor off our list for the campaign?

I usually respond: Wow, that's a lot of pressure you're putting on yourself! I understand it, however, because when I was early in my career, I assumed that you only got one chance to make an ask. Asking seems so "peak of the mountain" that it's natural to assume there's only one direction to go from there - down, and fast!

However, the first thing to remember is that asking the donor to consider a gift to your campaign is not a performance on your part. If it is just a performance, your chances of getting a "yes" at the level your donor can actually give are not great.

Instead, it needs to be part of a continuing conversation you have with the donor - a conversation that may have started months or years ago as the donor first became involved with your group or when you joined the group as a board member, executive director, or major gifts officer. Or it may have started as a result of good networking and donor engagement work on your part.

Getting to the ask should be less like climbing a mountain and more like following a meandering stream to a beautiful waterfall that you know is there ahead of time!

In any case, what might this continuing conversation look like?

It's a conversation in which you listen more than you talk.
A conversation that focuses mostly on the meaning your group's work has for the donor, and what this special project will mean to the impact your work can make.
A conversation in which you tell them about the project and the campaign and how many gifts at what levels your group will need to receive to make it happen. (Briefly and fairly early in this ongoing conversation).
And a conversation that eventually takes you together to the point where you can say, "Would you like to talk about how you can help with this project?", and get their permission to move forward with the ask.

If your ongoing conversations with the donor have been warm and supportive and filled with mutual appreciation, once the campaign starts you can often get to "the ask" conversation fairly quickly (maybe even within a couple of conversations). Be open to them offering to make a specific gift during these ongoing conversations -- let THEM make the ask of themselves! (Here, I'm not including "pre-emptors" - supporters who try to "get away with" a much smaller gift than they could make by springing it on you right away. You know the difference.*)

But when you ask for the gift, what if the donor says "No, I'm afraid we can't do that" (for whatever reason or no reason)? Or they seem hesitant or a lot less enthusiastic than you've seen them be in the past?

Have you blown it? Not at all.

But you do need to understand whether they are really saying "not now" versus "not at that level" versus "I need to consult with my spouse/ partner/ children/ siblings, advisers, etc." versus "I still have some questions". The relationship you've built with them will help you ask the discovery question, which can be something like, "You are so enthusiastic about what we're trying to do. Is there something else you need to know or someone else you'd like to include in our next meeting or something that needs to happen for you to continue our conversation about how you'd like to be involved?"

And then listen. And be prepared to say, "That makes so much sense. We can talk about this again after you feel better informed about X or have [done what they need to do]." Then write them a brief note or email the following day, and pick up your ongoing conversation within a week or two if possible. It will work out because the donor genuinely wants to help your group.

And remember - a pledge over two or three years may work best for them. Or they might want to make a smaller gift now to help the campaign take off, and then a larger one later in the campaign or vice versa. Be as flexible as your campaign policies allow.

If the donor lets you know that something private is happening that they just can't share with you right now and it's the reason they can't make a gift commitment right now, be gracious and say, "I know you will tell us when the right time to discuss this might be in the future. In the meantime, just know how much we appreciate you, and how much your support means."

If you have a good relationship and ongoing discussion about the campaign with your donor, it may take a while - perhaps a year or more - but they will make a gift that's right for them, maybe even the amount that you ask, or more. But it's not one and done.

It's a continuing conversation that will extend through and beyond this campaign and you just need to stay engaged.

Next time – when to truly give up on getting a major gift from a prospective donor when you know they have the financial capacity. (It happens.)

* See my article "When a Donor Preempts Your Ask "