How to Turn Making the Ask from Excruciating to Exciting

This article originally appeared in our November/December 2015 issue of Nonprofit Hub Magazine, a free bi-monthly magazine. You can reserve your free copy today.


Shanon Doolittle was a wreck.

Going into her first major donor ask, she was nervous, hadn’t slept well in days and had no idea what to expect.

The meeting with the potential donor didn’t go much better. She talked too much, fumbled the ask and tried to give the prospect a folder with paper documents, but they didn’t want paper.

“Everything that I thought I was doing right, I didn’t because I was so inexperienced,” said Doolittle, who now works as a fundraising coach. “At the end of the day, it turned out OK. What I learned is you have to know your donor really well…I have to go at their pace and not at my pace. Whatever they need, I adapt to that.”

Now, Doolittle has become a seasoned pro when it comes to making the ask, but her experience isn’t unique or uncommon for many nonprofit fundraisers. When it comes time to make the ask they get queasy, tense up and word vomit all over potential donors, but it doesn’t have to be that way.

When Marc Pitman thinks of fundraising, it excites him. Pitman, who is a fundraising coach and leadership expert, says making an ask can be a joyous occasion.

“It’s an incredible adrenaline rush to have someone excited to give,” he said. “When you experience that a few times, you never know (going into an ask) if this going to be the next hit.”

Doolittle and Pitman offered several tips on how you can overcome the fear and help change those feelings from excruciating to exciting when you make the ask.

Expect Plot Twists

By the time you sit down with a donor, most of your work should already be done. If you’re planning to make an ask for a major gift, they will know what you will be asking because you’ve developed the relationship, learned about the donor and made a connection with them.

Doolittle said you should map out how the meeting is going to unfold. She says to have a few stories of what impact the donor has already made and how a larger donation can make a bigger difference.

“Whenever I am sitting down with a major donor, you have a case study and portfolio, but what they are going to remember is the story,” Doolittle said. “If I talk in statistics, their eyes are going to glaze over unless I know that’s what the donor wants. Regardless, I am always going to throw a story in there because the story is what emotionally connects them to what I am about to ask them for.”

Doolittle compares the preparation and anticipation to the work of a car salesperson. They know every detail about the product, and do their best to remove every obstacle to help you picture yourself in that new car. For every objection (gas mileage, safety, cup holders) they have a response designed to put you at ease and make you want to buy that car.

In fundraising, Doolittle said you have to know your mission inside and out, what other organizations are doing that is similar and why your project is unique and deserves fundraising.

“You’ve prepared for everything, but you totally expect plot twists,” Doolittle said. “You have to anticipate objections. What is that person going to say next?”

Pitman does an exercise with people he coaches where he asks them to write down all of the possible objections they could hear. Then have your team go through and prepare answers for each of the objections, so when a donor raises an sticking point, you’ll be ready with a response.

One obstacle that you should worry about is figuring out the right number to ask. Both Doolittle and Pitman said it’s important to ask for a specific amount regardless of if it is just an estimate. Doing so takes the pressure off the prospect to read your mind and also sets the donor up for what type of donation they can make. Pitman said it is better to ask too high rather than too low.

“We aren’t doing anyone a service if we aren’t clear in what we are asking. Because if you’re supporting the cause it might be $250,000 and to them it might mean $250,” Pitman said. “‘What if I over-ask?’ which seems legitimate until you do it and then once you’ve done it you realize people aren’t offended, they are flattered.”

Find Your Routine

Making an ask is a full-body experience. If you’re not focusing or feeling sick, everything can go wrong. Doolittle said it helps to develop a routine to make yourself as comfortable as possible.

For example, Doolittle says she eats the same food so she knows her body will feel good. She visualizes the donor saying “yes” and then on the way to the ask, she has a pump-up playlist that includes songs such as “Lose Yourself” by Eminem and “Eye of the Tiger” by Survivor.

“For me, most of the problem comes with the fear and the limiting beliefs,” she said. “Whatever you can do to calm those nerves, you’re going to be in a better position to go into the meeting and feel good about it.”

Pitman said another helpful prep tool is talking to the steering wheel. Practice using the exact phrase you want to use to make the ask, so when it comes time to put a number out there, you don’t mess up. If all else fails, admit you’re nervous to the donor, but try to let your passion and excitement for the cause shine through.

“If we stumble over the words of the ask, that can also raise a red flag for the donors,” Pitman said. “If we can make it sound very confident like it’s something people do every day, it removes another roadblock and allows the donor prospect to review the request without our negative emotions and make the path a little more clear.”


Part of what makes the ask scary is the vulnerability that comes once you ask the question. You can control everything up to that point—from the research, meeting, storytelling and presentation. But once you ask the question, the ball is in the donor’s court and you have to wait for a response.

Pitman said most donors don’t have an answer immediately because they will need time to think about everything you’ve told them. Once they are ready to move the discussion forward they will.

“We will know they are done processing because they will be the first to talk,” Pitman said. “It is helpful to have water or something to put in your mouth, instead of your foot.”

Doolittle said one of the big challenges of fundraising is accepting that you can’t control everything. However, if you’ve done your prep work, then it will be easier to make that ask. However, if things don’t work out in your favor, it is not always your fault. Sometimes life happens and the donor isn’t able to give at that moment.

“You can control how many times you ask, who you ask and when you ask—but you will never have control of the answer, so be OK with that,” Doolittle said. “Try to prepare what you can be in control of, but whether they say yes or no is not on you.”

In the end, most of the fear stems from the fact that we are talking about money, which is usually a taboo subject in society. However, you can make the task easier by focusing on the difference you are making for your organization and its mission.

“You’re selling a feeling and that feeling is joy and happiness,” Doolittle said. “At the end of the day, when donors give, they are totally in their joy center.”

It might never be easy for you to make the ask, but knowing that you’re making a difference can help calm those nerves. In the end, don’t think about the money, and instead focus on the positive impact each ask can make.

“When we see it as serving the donors and helping them further their values in a way they couldn’t do, and with more excellence than they could do on their own, it can become really fun,” Pitman said.


Lincoln Arneal

Lincoln Arneal was a Senior Editor at Nonprofit Hub who brought loads of real-world nonprofit experience to the team. He was the past executive director of a nonprofit that provided leadership development to junior high and high school students. He looked to bring the insights from his time forming, developing, and running a nonprofit to help others in their quest to do good. Lincoln also had a legal background and had written for various newspapers (covering high school sports) for the past 15 years. He could be followed on Twitter at @NPLNK.

November 18, 2015

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