It’s almost Halloween, which means we’re surrounded by ghosts, goblins, and things that go bump in the night. But if you’re a fundraiser, your biggest fears probably aren’t related to haunted houses or evil creatures.
I know what it’s like this time of year. You’ve got to pick up the phone to call a donor who hasn’t responded to your last few emails. You’ve got to schedule an in-person meeting because it’s time to finally ask for a major gift. You’re thinking about sending one more email and whether that will make you seem pushy.
That can be scary! Even experienced fundraisers struggle with these moments. When you care about your donors and the relationships you’re building, the last thing you want to do is make someone uncomfortable or allergic to your mission.
But here’s something that might sound strange: Fear can also help us become better fundraisers. You just need to find a way to work through it.
Let's look at three common fundraising frights and how you can face them.
Fear No. 1: Asking for a Gift
Have you ever walked into a donor meeting knowing you should make an ask, only to walk out without doing it? You couldn't find the right moment, you weren't sure how much to ask for, or you worried the request would make things awkward.
It happens more often than you might think. Many fundraisers were never taught how to ask for a gift, so the conversation can feel like a sales pitch, especially when there's not a strong relationship behind it.
Here's how I think about it. Your job isn't to convince someone to give, but to help a donor find a meaningful way to make a difference.
That's why we teach Permission-Based Asking™. When you understand a donor's passions and interests, you can share an opportunity that aligns with what matters to them. You might say, "You've shared how much you care about this program. Would you be open to me bringing you a specific opportunity to support in the spring?"
Now the donor knows what to expect, and your next conversation has a clear purpose. You're offering an opportunity, not demanding a gift, and the donor gets to decide whether it's right for them.
Try this: Before your next meeting, identify what the donor cares about and what opportunity might interest them. If you're not ready to ask, start by asking permission to bring an opportunity forward.
Fear No. 2: Hearing No or Getting No Response
You leave a voicemail, send an email, and wait. When you don't hear back, you start wondering what you did wrong. Your brain goes through every worst-case scenario. Did I ask too much? Is the donor upset? Do they want to hear from me anymore?
I understand how easy it is to take silence personally, but silence doesn't tell you what a donor is thinking. It only tells you that you don't have an answer yet.
Look, donors have busy lives, competing priorities, and their own reasons for responding when they do. Follow up thoughtfully, give them space between contacts, and share useful updates rather than making every interaction another request for a decision. If several attempts go unanswered, it's OK to step back.
It's also worth asking whether you're spending time with donors who actually want a relationship with you. At Veritus, we believe major gift and mid-level caseloads should be built around donors who have been qualified and agreed to a two-way relationship. When you know someone wants to engage, picking up the phone becomes a little easier.
And remember, a “no” can be useful information too. The timing may be wrong, the amount may need to change, or another opportunity may be a better fit.
Try this: Make a follow-up plan before you reach out. If you hear no or get no response, consider what you can learn and decide on an appropriate next step. You can control how thoughtfully you follow through, not how someone responds.
Fear No. 3: Seeming Too Pushy
This one can be quite common. I’m sure you’ve had times where your board gets worried that you’re contacting major donors too often. Or you’re still a bit traumatized from the time a donor told you that you were being too solicitous. Now you second-guess every email or text or call.
It's understandable. You care about your donors, and you don't want them to feel like you're constantly asking for something. But consider whether you’re actually bothering the donor, or you’re just uncomfortable with the idea of reaching out.
Those aren't the same thing. Some donors prefer less contact, and we need to respect that. But a personal note with a photo from a program the donor helped fund, or an update about something they care about, can strengthen a relationship rather than burden it.
The key is to understand how each donor wants to engage. Ask what information they'd find useful, how they'd prefer to stay in touch, and how often they'd like to hear from you. If your board is nervous about outreach, show them the difference between a generic appeal and a personalized impact update. Help them see that you're not simply sending more messages; you're building relationships with people who have agreed to engage.
Try this: Before reaching out, ask yourself whether you're sharing something relevant, respecting the donor's preferences, and helping them see the difference their giving makes. If you're unsure, ask the donor how they'd like to stay connected.
Don't Let These Fears Keep You From Building Great Relationships
These fears (and plenty others) can cause us to focus more on our own discomfort than on the donor in front of us. We put off calls, avoid asking for gifts, or stop sharing updates because we're afraid of getting it wrong.
The answer isn't to ignore those feelings. It's to build a process that helps you understand your donors, prepare for conversations, and make thoughtful decisions about how to move each relationship forward. You may still feel nervous, but you don't have to let that nervousness make the decisions for you.
And you don't have to figure it all out alone.
Our January Certification Courses can help you develop the skills, structure, and confidence to handle the challenges that come with fundraising.
Hiding behind much of a fundraiser’s anxiety is the feeling of uncertainty and not knowing if you’re going about things the right way. Having a proven plan and system in place can make your work more rewarding and less stressful.
Register now to take advantage of the early-bird deal (a $200 discount). Invest in yourself and start the new year feeling better prepared for whatever comes your way.
Happy Halloween and happy fundraising!