As the leader of a nonprofit, I ask people for money as a big part of my job—and I love doing it. Making the ask isn’t as hard as you might think. The most effective leaders I’ve seen in any setting—business, government, nonprofit—are driven by purpose, mission, and the sense that their work is making the world a better place. If you approach donors from that standpoint, you’re really just having a conversation about mission and purpose and then asking them to join you. You simply have to blurt out the number and not worry about how many zeros it has at the end. The most I have ever asked an individual to give is $250 million. That particular person said no, but I’m pretty sure he has made a generous bequest to us in his will. What’s striking about these big donation asks is that for most of its history, United Way had no direct relationship with its donors. In fact, in most instances we didn’t even know their names.

A version of this article appeared in the September–October 2018 issue (pp.38–44) of Harvard Business Review.