Fundraising is not for the faint of heart. It takes courage, persistence, and a willingness to step outside your comfort zone. But more than anything, it requires taking calculated risks—especially when it comes to asking for major gifts.
Too often, nonprofit fundraisers and leaders shy away from big asks. They’re worried they’ll hear “no” or even offend the donor by asking for too much.
The reality is, if you don’t ask, you don’t get. And when you avoid making bold requests, you’re not just shortchanging your organization—you’re also denying donors the opportunity to make a real impact.
Taking the Ever-Important Risk of Asking for Major Gifts
Your mission deserves significant investment. Major gifts have the power to transform your organization, fueling programs, expanding services, and amplifying your impact.
An example:
For example, let’s say your annual fund raises $500k from a combination of activities, including your year-end appeal, grant writing, online giving, and a gala.
Let’s say your goal is to raise an additional $100K (or increase your annual fund by about 20%). You could do that with ten donors or less.
But these gifts don’t simply appear. You need to actively cultivate relationships and confidently make the ask.
Engaging in thoughtful conversations with donors about their philanthropic goals and showing them how their generosity can make a difference is key. If you’re not inviting them to be part of something bigger, you’re missing an opportunity.
What It Means to Take a Calculated Risk in Fundraising
Taking a calculated risk means making informed, strategic decisions based on research. It’s about weighing potential outcomes and taking steps to minimize uncertainty before making a bold move.
In fundraising, this means:
- researching donor history
- understanding giving capacity (whenever possible)
- developing relationships with donors to learn about them
For example, imagine you have a long-time donor who has steadily given $1,000 annually for the past few years. Through conversations, you’ve learned they just sold a business and are looking for meaningful philanthropic opportunities. Asking them for a $50,000 gift might feel risky, because you don’t want to lose their annual support.
If you’ve built trust, aligned your request with their interests, and demonstrated impact, the risk is well-calculated. Also, you’ll want to express genuine gratitude no matter their response.
The real risk isn’t in asking — it’s in not asking and leaving potential support untapped.
Engaging Donors is Key to Your Mission
The best fundraising is not just about raising money — it’s about building partnerships.
Your donors care about your mission, and they want to be engaged in meaningful ways. Keep them informed, involve them in decision-making, and most importantly, treat them like valued members of your team.
3 Ways to Improve Donor Engagement
Here are three ways to deepen donor engagement:
- Personalized Communication – Tailor your outreach to show donors you understand their interests and priorities.
- Impact Storytelling – Share compelling stories of how their support is making a tangible difference.
- Opportunities for Involvement – Invite donors to experience your work firsthand — through site visits, events, or volunteer opportunities.
Yes, asking for major gifts can feel intimidating. But calculated risks in fundraising lead to greater rewards. When you engage donors with confidence and a clear vision, you inspire generosity at the highest levels.
So take that next steps: Send an email (to invite a meeting). Have the conversation. Make the ask. Your mission depends on it.
Leave a Comment