Naturally great fundraisers love people, they can and will talk to anyone, they can find common ground with anyone, they're your friends that talk to people in the elevator or at the grocery store. They believe in the work required to both build relationships and keep them. And they naturally have a high tolerance for rejection.
But I don't expect everyone to be a natural, and you don't have to be a natural to raise money. You just have to respect the people and the process, and do the work. Will you reconcile your baggage? Will you commit to build relationships? If you will, you're ready to make the ask. And the ask is oftentimes as simple as using the phrase "Would you consider?" Would you consider becoming a monthly donor? Would you consider increasing your support to 100 dollars? Would you consider investing in our work at the one-million-dollar level?
"Would you consider" does a couple of awesome things. One, it gives the donor an easy way out. Like, they can say "no" without it being "yes-no." And two, it gives you a second ask. "Well, what would you consider?" It's good, right?
When you do this, remember, you're not asking for yourself. You're asking on behalf of all of the people you serve or are touched by your genius. This isn't a personal favor, right? Feel proud of the ask - it's incredible that you do this work. Don't try to be someone you're not, you're going to go to these meetings and think you need to big-shot it. Be yourself, authenticity matters, nobody likes a phony. Just be yourself.