There are a number of misconceptions about what being a successful nonprofit leader and fundraiser looks like.

One of the most common is that the leader needs to be 100% confident. Completely sure about themselves at all times.

If they aren't sure, how can they ask donors to give?

Looking in all the wrong places

Since no one starts a nonprofit because they want to ask for money, fundraising feels like an annoyance. The nonprofit leader may be a genius at solving a problem or at leading a team.

But fundraising shines a blinding light on all the leader's insecurities. What should be a simple act of inviting someone to give to something amazing becomes a mess of self-worth issues, self-doubt, and vacillation.

  • Will the donor now think that I only wanted a relationship with them to get their money?
  • Will I offend them by asking for too much? Or for asking at all?
  • Will showing a need reflect poorly on my nonprofit?

So the nonprofit leader tends to put off the fundraising. Or gets caught up in an endless process of research - desperately seeking the exact right amount to ask a person.

Or they get fed up with the lack of ease they feel from thinking about money and decide to "subcontract" it out by hiring a fundraiser.

What are you sure about?

All the while, the nonprofit leader's doubt grows because that emotional agitation seems out of sync with how a strong leader should be. I bet this is why 67% of nonprofit CEOs are looking to leave their position in the next five years.

But this doubt doesn't need to mean you aren't leadership material. If you talk to most leaders, doubt is common.

One of the surprising gifts of doubt is that it invites you too look inwardly. To find what is stable.

As nonprofit leaders clarify why they're in the nonprofit, they move to a steady center. A place of stability. They get clear on what fight they're in. On what values they stand for.

Then fundraising moves from being a referendum on you as a person. It becomes a joy-filled adventure of looking for others who share those values.

A way to start moving to stability

The pressures of running a nonprofit are so great, it can be hard to get clear on those core values. Fortunately, one of the best ways to learn how to express your values is to talk to your donors. Find out

  • what they love about giving
  • what they love about giving to the nonprofit
  • what they look for in causes they support

And be interested enough to want to know more. If they answer "Why do I give? Because you all are so awesome," that's lovely. But unhelpful. So thank them and ask, "What part is particularly awesome to you?"

You'll find yourself getting even more committed to your work. And you'll find common themes and values emerging. Those will give you greater confidence in asking. You'll be able to choose from a few values to invite people to give to knowing you're likely choosing the right values.

Why not start making some of those calls now? All it takes is some sincere gratitude and honest curiosity. "Hi ____. I'm so grateful for your long-time support of us. But I was just realizing, I'd love to know what inspired your first gift. What got us on your radar the first time?"

When they've answered that, express gratitude and ask "And what keeps you giving?" And be curious enough to ask them more as they share more. This isn't an interrogation. This is a conversation between two like-minded people sharing common interests.

A final thought

I'd strongly encourage you to use the phone to do this. It's too easy for the donor to misread your tone in an email or text. But on the phone, even in a voicemail, people will hear your integrity and curiosity.


If this idea of doubt being a gift intrigues you, check out my new book The Surprising Gift of Doubt. It's coming out March 23rd but is available for pre-order now. (And their are bonuses for pre-ordering!) https://SurprisingGiftofDoubt.com/

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