Recently, I had the pleasure of meeting with an old friend, who happens to be a rabbi of a mid-sized congregation on the East Coast. In the late 1990s, I “coached” his synagogue through a successful multimillion capital campaign. We’ve kept in touch, but hadn’t seen each other for a long time. As we settled in to his office, surrounded by tomes of wisdom, a flood of memories returned to each of us. As we engaged in spirited banter, it was almost as if no time had passed, except where we might once have spoken about our children, the conversation now gravitated toward grandchildren.

But soon, the conversation reverted to the work we did together, to the campaign’s one honest-to-goodness, moment of reckoning. The meeting came at the outset of the 2015 installation of March Madness: Like many Americans, for a few weeks, I somehow get basketball on the brain. I must admit that, throughout the year, I pay must closer attention to the Dancing with Stars standings than who is on top of the ACC or Big East. But it hit me, flipping on a late-night tournament game, how well the basketball metaphor works for fundraising. There is the moment, the last second shot, where some players want the ball and others hope and pray the fate of their team doesn’t rest upon them. And, years ago, I had no doubt that the ball needed to be in the rabbi’s hands.

“You really put me through it,” the rabbi told me. “You made me sweat.”

We were building a major addition to the rabbi’s synagogue complex and needed a substantial lead gift to inspire other donors and, ultimately, make the numbers work. One particular couple could easily have afforded to make a $1 million pledge. The rabbi had a good conversation with them, but at the end of the meeting, they offered a generous but disappointing $500,000 pledge. The rabbi called me in something of a panic.

“Our campaign is doomed to failure,” I remember him saying, his voice almost quivering, sounding as if all were lost.

I recall thinking about the situation for about three seconds before I blurted out, “You can’t accept the gift. You failed to make the most compelling case for why this campaign is so important. You must call them back and ask for another meeting.”

“How can I not accept a half a million dollar gift?” he asked, seemingly expecting instant gratification.

You would have thought I’d just asked the rabbi to run into live cannon fire, or to stick with the basketball analogy, to try to drive to the hoop through Kentucky’s defense. But I knew that the $500,000 figure just wasn’t good enough, not for this particular couple, or to meet the needs of this transformative project.

I didn’t send him in blind. We drilled. We trained. We drew up a playbook. We discussed what he would say on the call and then rehearsed what he would say in the meeting. He had to be passionate, forceful and convincing. He was all of those things and, wonder of wonder, miracle of miracles, the synagogue ultimately received a $1 million pledge.

I recall this story because, too often, nonprofit leaders are content to settle. It makes sense; they are called donations for a reason. Nonprofit executives tend to be grateful and polite and tell donors what they want to hear. But sometimes, it pays to say, “No, I’m sorry, that just isn’t good enough.” Even I could use a reminder at times that sometimes we can’t accept generosity and must demand more. Obviously, this needs to be undertaken sparingly and with great care. It is possible that, by refusing a gift, your organization can end up with nothing. It is certainly a risky strategy, one that is sometimes worth taking. Weigh the risks, consider the options and seek second and third opinions. Sometimes it is best to play it safe, sometimes it pays to go for it all.

Too often, I get the sense that the nonprofit world – even including fundraising “machines” run by big hospitals and universities – is settling, that our leaders are not demanding more of our donors or laying out the best cases. A new class of donors has forced nonprofits to develop creative, innovative approaches to fulfilling their missions. Some of these ideas are being funded, others are languishing due to a lack of resources. Let’s be bold. Bold in our ideas, bold in laying out visions and bold in our asks. Let us all be willing to take the shot, with the game on the line, with all eyes upon us. The rabbi was terrified when he learned the ball would be put in his hands. But he’s never regretted taking the shot. It transformed his life and the life of his congregation. Sure, we can go for it and miss. But sometimes, I think, if we don’t go for it, we’ve already lost.

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