Treating this like a first date is a great idea. But some people are really bad at dating...so let's elaborate.
We all know this person: as soon as they make plans to have drinks with someone, their mind starts spinning wild stories into the future, envisioning a winter wedding, picking out names for their children...and that never works out, because that kind of craziness makes it impossible to simply be there on that first date. There's no getting to know each other, there's no sense of togetherness - it's just the poor date, tagging along with you and your dreams.
You can't go into a first date hoping that you'll be ready to pop the question by the end of the hour. So? Don't approach a first meeting with a prospect thinking that you need to be ready to solicit them by the end of the meeting.
Your job on a date is to get a feel for each other, establish some common ground, introduce yourselves. Donors have a lot of causes competing for their support. You have a lot of potential donors to court. Just like dating, the purpose of these meeting is to see if you're a good fit for each other, and if things go well, it's a relationship you build up over time.
It's a two way street. A lot of folks get thrown by perceived power dynamics - if you're lucky, you're a working stiff, raising money for an organization you love, across the table from someone who is ridiculously, almost unimaginably wealthy. But on a first date, you cannot see yourself as powerless. You're trading information, you're feeling each other out. The second you believe you're begging for table scraps? Well, it's like someone who goes on a first date and leads with "I'm so grateful you agreed to go out with me. I'm ugly, boring, unlovable and completely unworthy of your interest, but I'll worship you if you date me." Won't go well.
Ideally, you are listening more than you're talking, after you make sure that the prospect has a reasonable foundation of knowledge about your organization. You have a lot to learn about this other person. What are their likes and dislikes, what missions and causes speak to their heart, what do they support because of a sense of obligation or inherited responsibility, what do they look for in projects to support, what motivates their giving...and also, what do they like about their job, what kind of family do they have, what things might you (your professional persona) and they have in common...and that's just the general questions. Depending on what kind of organization you're fundraising for, you also want to know how they relate to your cause? Are you in the arts? What was the first performance they remember? Are you working for a homeless shelter? Have they ever been to one?
Think about your excitement, meeting a potential mate for a date in a swanky restaurant. You're dressed up, you have every reason to believe this person is amazing...what do you want the evening to look like? Well, there may be some awkward introductions at first (hopefully not so awkward!), but you want to settle into an easy conversation where you're asking questions, listening intently to the answers, and responding with tidbits of your own (stories, anecdotes, observations) and then asking the next question based on where the conversation has gone. You're laughing, you're talking...you want more, when it's time to end the date.
Just make sure you're steering - not just letting the conversation ramble and run away. A fun coffee date with a prospect that doesn't give them new appreciation for your organization and/or doesn't give you any better sense for who that prospect is as a supporter may be pleasant...but you're not likely to get more of their time. (That's where the date comparison ends...it's not enough to enjoy each other's company - you're not looking for friends, you're developing a professional relationship, and if you don't provide them with a clear answer to the question "is this worth an hour of my time?" then these prospects will be spending their valuable time elsewhere.)
Be engaging, be charming, make connections. Leave them wanting more, and make sure you have enough information to be able to follow up in a way that will strengthen that connection. And most importantly - don't put too much pressure on the date. Give yourself breathing room, and just enjoy the chance to get to know an amazing person a bit better.
Next up: a little more structure. What do you want to be sure to communicate, and what do you really want to find out?
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