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Fear of asking is the number one challenge faced by professional fundraisers and volunteers. I would even venture to guess that most fundraisers are afraid to ask for money.

Although you’re likely competent and capable in many areas of your job, if you are afraid to ask, it’s important to acknowledge it (even just to yourself) so you can work on improving. That’s because asking, of course, is a significant part of the job of raising money.

The Fear of Asking is Entirely Beatable

The good news is that fear of asking is much more common than you might think.

Even better news — the fear of asking a very conquerable fear. In order to be successful, you need to push past your fear so it doesn’t prevent you from getting the job done.

Stop and take minute to think of something you’ve worked up the courage to do — like asking someone out on a date or asking for a raise. Asking for important things takes courage. In those cases, the potential reward is great enough that it surpasses the discomfort caused by the fear.

So, what should an organization do when it has a smart, organized, thoughtful, articulate professional who doesn’t get around to asking? Or doesn’t ask nearly often enough?

Take steps to grow courage.

As much as I wish we could go to the store and buy some extra courage, it doesn’t work that way. Courage builds over time and with experience. It’s something you’ve got to work at.

Courage Develops Over Time, With Practice

I’ll never forget the first summer my daughter was tall enough to go down the water slide at our town pool. I’m sure you can picture all her friends and the other “big kids” racing past her as she hesitantly waved them past her in line. After many kids telling her she could do it, and a few probably calling her a chicken, she finally made her way to the top of the stairs.

But sadly, the idea of getting onto that slide was simply too terrifying and she climbed back down.

The next day, she tried again… and left the line. And the day after that. Same result.

Finally, by the end of the week, she was tired of being left out of the fun, so she mustered all her courage and got herself to go down that slide. You can imagine how proud she was when she got to the bottom. She was still scared, but she did it… again and again and again! And, within a few days or week, she was a pro at going down that slide, wondering why she was ever so scared to begin with.

The same is true with asking. And, when you get good at it, it feels amazing.

Now, maybe I should have told a story about her learning to ride a bike. Because with fundraising, once you learn to ask, it doesn’t mean you won’t ever fall down. You will. We all do. But part of developing your courage muscle is being able to pick yourself up and ride again.

Fear of Asking is Typically the REAL Problem

At the Capital Campaign Toolkit and in my work with the Mastering Major Gifts program, the number one stumbling block to raising more money is not asking. (A close second is not being specific when you do ask.) It takes courage to ask for money.

Not raising money is much less frequently about things like:

  • Not having qualified prospects
  • Not having enough prospects
  • Not having enough research/information
  • Not having enough time
  • Not having support of board members

In other words, those are just excuses. And I should know — I’ve made most of those excuses myself. We all have.

My question to you is twofold:

What will you do to overcome the REAL stumbling block that’s preventing you from raising more money? How will you work to build your courage and overcome the fear?

Over the last few years working with clients, I’ve discovered one of the most powerful ways to grow courage is with the help of regular and ongoing peer support and encouragement. It’s like having all the kids cheering you on as your make your way up the steps to that great, big, intimidating slide.

Peer Support Can Make Big Difference

At the Toolkit, one of the most surprising elements contributing to campaign success is the weekly peer support group. We see this over and over — both in the Monday Toolkit Talks sessions, which are free and open to the public, as well as our Toolkit members-only Wednesday calls.

In addition, in response to COVID-19, one of the solutions we created to help nonprofits was an 8-week Mini-Campaign program to raise $100K or more. Last week, we celebrated the success of the 2nd cohort of organizations to graduate the program.

What we heard from one participant after another is that when they asked, they received. EXACTLY! Asking was something many of them didn’t have the courage to do before.

In fact, one participant proudly declared that he had asked for several gifts and received every single one. That’s the power (and prosperity) of courage.

Of course, it’s not revolutionary that if you ask, you’ll receive more gifts (and larger) gifts. But if asking was easy, everyone would do it and I wouldn’t have written this post. Asking requires courage.

What’s the Best Way to Grow Your Courage?

Overcoming fear of anything isn’t easy, but it’s so much harder to do by yourself. My recommendation? Find a good peer-support network. For example, the ones I mentioned above:

Ideally, you want to join a network facilitated by someone who will push you to take that first step. And then practice asking again and again and again. The more successful you are, the more your courage will grow — and the more successful you’ll become. Something so terrifying eventually transforms into a beautiful cycle.

And just like the cowardly lion in the Wizard of Oz, once you get rolling, you may just find that you had the courage all along.

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