"Relationally intelligent" is probably the best way to describe how fundraising should be approached. So, what does it mean to be "relationally intelligent" when it comes to fundraising--and specifically, when asking someone for money?
At the beginning of the meeting, set the context. Let those you are meeting with know that you are there to challenge them to do something big for God, but in the end, your relationship is going to be okay whatever they decide. This lets them know that their decision should be based upon God's leading, not on any pressure they may perceive from you.
Next, make the ask clearly and succinctly. Here's what I’ve said to high capacity donors: "I'd like to ask you to pray about giving more of your hard-earned money to God's purposes in the world."
Then I add, "I have no idea what you are capable of giving or what you had in mind, but would you prayerfully consider a gift of [insert dollar amount]." I literally ask them for a specific donation amount.
Here's why: If you don't make the request specific, the person or couple you are with won't have any idea if you want them to consider a gift of $500, $5,000, $50,000, $500,000 or even $5 million!
Think of it this way, if your neighbor were going to take a trip and asked you to care for their lawn while they were gone, you'd want to know how long they will be gone (a week, a month, the whole summer?), what they would want you to do (mow, water, fertilize?), and how often they would want you to do it (weekly or when it looks like it needs it?). It's the same with fundraising. The more specific you are, the easier the conversation is.
Before you leave, agree upon a time to get back together. "Could we meet again in two weeks to see where you are with this?" I find it easiest to set a time and location right then and there while everyone has their calendar handy.
If you do all of this, at your next meeting, all you need to ask is, "So, how is God leading you?"
It's normal to get nervous or feel a lump in your throat! But leadership requires growing in this skill. The more confidently you can do this, the easier the conversation goes!