--- title: 4 Hang-Ups About Making an Ask description: Overcome four common hang-ups about asking for major gifts, with practical tips to help you feel more prepared and confident when making the ask. image: https://blog.chorusconnection.com/hubfs/chorus-connection-racetrack-hurdles.jpg --- - [About](https://www.chorusconnection.com/about) - [Features](https://www.chorusconnection.com/features) - [Pricing](https://www.chorusconnection.com/pricing) [![Chorus Connection](https://blog.chorusconnection.com/hubfs/Chorus_April2019%20Theme/image/download.png)](https://www.chorusconnection.com) - [Blog](https://blog.chorusconnection.com/) - [Login](https://app.chorusconnection.com/sign_in) - [Book a Demo](https://pages.chorusconnection.com/request-a-demo) [![Chorus Connection](https://blog.chorusconnection.com/hubfs/Chorus_April2019%20Theme/image/download.png)](https://www.chorusconnection.com) - [About](https://www.chorusconnection.com/about) - [Features](https://www.chorusconnection.com/features) - [Pricing](https://www.chorusconnection.com/pricing) - [Blog](https://blog.chorusconnection.com/) - [Login](https://app.chorusconnection.com/sign_in) - [Book a Demo](https://pages.chorusconnection.com/request-a-demo) # 4 Hang-Ups About Making an Ask [Courtney Huffman](https://blog.chorusconnection.com/author/courtney-huffman) Oct 01, 2026 Learn more: [fundraising](https://blog.chorusconnection.com/topic/fundraising) ![curving racetrack with hurdles in each lane](https://blog.chorusconnection.com/hs-fs/hubfs/chorus-connection-racetrack-hurdles.jpg?width=700&height=394&name=chorus-connection-racetrack-hurdles.jpg)   Major gifts are the largest source of contributed revenue in the nonprofit sector, and that's only becoming more true. Giving overall is actually growing — but almost all of that growth is coming from large donors. Smaller gifts? Those are shrinking. Major gifts also give you a far better return on your time than chasing a large volume of small gifts ever will. So getting comfortable with asking (making “the ask”) isn't just good practice — it's how you raise more money while doing less work. Here's the best part: you don't have to go find these donors. They're already in your database. If someone is giving you $500, $1,000, or $2,500 a year, they've already told you two things — they believe in what you do, and they have the means to do more. Asking them to grow that gift isn't a “cold” ask. It's just the next conversation. If all of this is true, why is it that many of us aren’t capitalizing on major gifts? Asking for a major gift can be a daunting task for even the most seasoned fundraiser, but when you consider that many of us in the choral world are accidental or default fundraisers, it's only natural to find that there are a few hurdles that can hold us back from our major gift potential. As someone who sort of ended up in fundraising, I have experienced them all, and I'm here to share the most common hang-ups and how to work through them. After all, major gifts are literally where the money is at!     ## **1. The Capacity Problem: “I don't know how much to ask for”** **The hang-up:** not understanding the donor's actual capacity to give. The biggest issue I see is people not feeling clear about how much they should be asking for. **This issue typically arises because we are unfamiliar with our donors' capacity to give** — we don't actually know how much they might be able to give to our organization. Luckily, tools exist for exactly this issue: wealth screenings. For those who are not immersed in fundraising, this tool can cause feelings of discomfort (a hang-up that could be a whole blog post on its own!). It can feel like an invasion of privacy, and I get that. But wealth screenings are accessing publicly available information, meaning, if you wanted to, you could find this information on your own through a few good web searches. In fact, that's how this was done before technology made life simple for everyone. Fundraisers would spend hours doing research online, in meetings, and through other channels to try and understand their donors' true ability to give. And if a wealth screening is beyond your budget, you will have to take this alternate route of doing your own research. So what does that actually look like? A few free, low-lift places to start digging: - **Home value and property records** — your county assessor or auditor's website (often searchable by name) will show property value, which gives you a rough proxy for wealth. - **Other philanthropic giving** — donors love recognition, so their name is probably showing up somewhere: annual reports, gala programs, donor walls at other local nonprofits, universities, or arts organizations. A quick search of "\[donor name\] + gift" or "\[donor name\] + donor" can turn up more than you'd expect. - **Political contributions** — these are publicly searchable at the state and federal level (FEC.gov is a good starting point for federal races), and the size of the gift can tell you something about a donor’s capacity to give. - **LinkedIn and company bios** — job title, company size, and career trajectory all factor into the picture you're building. None of this requires a subscription or a research department — just some time and a search bar. Whatever you do, it's vital that you understand what your donor is able to give so you can make the most informed ask and get the biggest donation possible. **The fix:** Conduct front-end research and cultivation work to make an informed ask.   ![metallic gold dollar signs raining down in front of a blue sky](https://blog.chorusconnection.com/hs-fs/hubfs/chorus-connection-gold-dollar-signs-raining-down.jpg?width=1920&height=1080&name=chorus-connection-gold-dollar-signs-raining-down.jpg)   ## **2. The Money-Mindset Problem: “Big numbers make me uncomfortable”** **The hang-up:** your own relationship to money is projected onto the ask This was a big one for me when I first started out in fundraising. I grew up in a standard middle-class household, with a large family, so my relationship to money is very different from that of the typical major donor. **The idea of asking for sums I could only dream of being able to donate felt incredibly uncomfortable.** The mindset shift came when I had the opportunity to work at a large nonprofit with major donors every day. It became so clear to me that they thought about money very differently than I did. I came to realize that a $100,000+ donation to them was equivalent to a $500 donation for me — meaningful, significant, but comfortable. Consider for yourself what that size of donation would be for you, and make the same comparison. Donors with major giving capacity are traditionally giving from assets, not cash. That's a very different kind of wealth and a different reality than most of us are familiar with. So set aside your personal relationship with money and remember your major donors are in a very different financial situation. **The fix:** Level-set: mentally separate your finances from theirs to better understand how wealth-holders actually think about giving.   ![female writing no with red lipstick on a mirror](https://blog.chorusconnection.com/hs-fs/hubfs/chorus-connection-lipstick-on-mirror-spelling-no.jpg?width=1920&height=1080&name=chorus-connection-lipstick-on-mirror-spelling-no.jpg)   ## **3. The Rejection Problem: “What if they say no?”** **The hang-up:** internalizing a donor saying “no” as personal failure, or catastrophizing the organization’s need for support. **The key to a yes is preparation.** By the time you get to a meeting with your donor where you are making an ask, the groundwork should have been laid for this specific moment. Your donor should know exactly why you are meeting and be prepared for you to make the ask. A cultivation or get-to-know-you meeting is NOT the place to make an ask. A stewardship or catch-up meeting is also NOT the place to make an ask. A solicitation meeting is very specific, and there should be no mystery about what you are both doing at the table. Sometimes, even when we are fully prepared, our nerves get the best of us because we know the organization is counting on us to secure this contribution, and that pressure can lead to anxiety that we'll mess it up. **Take time before you ask to practice.** Practice your pitch and say the exact amount you want to ask for out loud. Prepare yourself for questions that may come up — you can work with a partner or AI to consider what might be asked and have answers prepared. And finally, remember that a “no” can feel personal, but it isn't. Keep in mind: if it's a “no,” it's not about you. Sometimes a “no” means “not right now.” **The fix:** Do the prep work so a “no” is unlikely, but take yourself out of the equation — it's not about you.   ![serious female in striped shirt holding out her hand palm out indicating stop](https://blog.chorusconnection.com/hs-fs/hubfs/chorus-connection-hand-held-out-making-stop-symbol.jpg?width=1920&height=1080&name=chorus-connection-hand-held-out-making-stop-symbol.jpg)   ## **4. The Reluctant Board Member: “I don’t like asking for money.”** **The hang-up:** Here's a not-so-secret, secret — your board members are dealing with the exact same hang-ups you are. They have their own complicated relationship with money. They don't feel prepared enough to ask. And on top of all that, they're often being asked to solicit their own friends and peers, which adds a whole extra layer of discomfort. What if it hurts my relationship with this person? It's the same fear you have about a donor saying no, just with higher personal stakes. But here's the thing: board members love your mission, and they usually do want to help. The fix isn't to push past their discomfort and make them ask anyway — it's to recognize that asking is only one piece of the process, and there are plenty of other ways to bring them in without ever putting them in that position. **The fix:** Give them an entry point that isn't the ask itself. - **Identify, don't ask.** They already know people with capacity and affinity for your organization in their own network — connecting the dots is half the battle, and it doesn't require asking anyone for anything. - **Warm the door.** A quick email, or a casual "you should really talk to our ED about the anniversary campaign" over coffee, does more heavy lifting than people realize — and it costs your board member nothing. - **Bring a partner.** Let staff make the actual ask while the board member is in the room for relationship and credibility. They get to show up without carrying the weight of naming the number. - **Say thank you.** A phone call or a handwritten note after a gift comes in is about as low-pressure as it gets — and it might be the highest-impact five minutes of their whole board term. Once board members see that fundraising has room for more than one role, "I don’t like asking for money" stops being an excuse.   ## **The Bottom Line** None of these hang-ups disappear overnight, but each one has a concrete fix: do the research, reframe your relationship to the numbers, and prepare so thoroughly that a “no” loses its sting (side note: a donor saying “no” often actually means “not right now). Start small by reviewing your donor list and identifying 3-5 donors to focus on. Then pick one hurdle from this list and take a small step on it this week. Major gifts really are where the money is at — and the fundraisers who get comfortable asking for them are the ones who unlock it. Which of these hang-ups resonated most with you? Do you have other hang-ups or solutions around fundraising? Share in the comments below so we can learn from your experiences.   ## [![New call-to-action](https://no-cache.hubspot.com/cta/default/1860171/f9d3fb88-6947-4fbd-8454-03e1748c7b7c.png)](https://cta-redirect.hubspot.com/cta/redirect/1860171/f9d3fb88-6947-4fbd-8454-03e1748c7b7c) ![Courtney Huffman](https://blog.chorusconnection.com/hubfs/courtney-huffman.jpg) Courtney Huffman serves as Executive Director of Kantorei in Denver, bringing more than a decade of experience in arts management, nonprofit leadership, and business management. A passionate arts advocate, Courtney combines strategic insight with a commitment to building strong, inclusive arts communities. She holds a bachelor’s degree in psychology, a master’s degree in organizational leadership, and the Certified Fund Raising Executive (CFRE) credential. Prior to joining Kantorei, Courtney served as Executive Director of several arts organizations, including the Columbus Symphony Orchestra, The Arts Hub, Boulder Chamber Orchestra, and St. Martin’s Chamber Choir. She also served as Senior Manager of Individual Giving at the Denver Art Museum, advancing major gift strategy and donor engagement. As a singer herself, Courtney has a personal connection to Kantorei’s work and is excited to help advance the organization’s artistic vision, community impact, and future growth. 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