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High Risk, High Reward: Why Raising More Money Requires a Culture of Risk-Taking

High Risk, High Reward: Why Raising More Money Requires a Culture of Risk-Taking

Picture of Summers Hammel, CFRE

Summers Hammel, CFRE

Senior Consultant

When you swing big, sometimes you hit a home run. And sometimes, you strike out. If your organization’s culture doesn’t reward risk-taking, striking out is scary. The result? Annual fundraising that remains flat, philanthropy officers that are asking donors for “safe” amounts that they know they can secure, and a team that is less than inspired.

And if your organization does reward risk-taking? The growth opportunities are endless.

Big Ideas Are Powered by Philanthropy

We work with organizations that embrace transformational visions. Pie-in-the-sky ideas, from increasing access to genomic screening for infants, ensuring no one faces epilepsy alone, creating rich campus environments that will foster the next generation of leaders, and changing visitors’ worldview through art. And these big ideas are powered by philanthropy.

Annual fundraising for the programs and operations that make progress toward these grand visions possible every day is the foundation of your organization. Successful annual fundraising requires clear strategy, the right people structure, efficient processes, effective technology, and a culture that values risk-taking.

Nonprofit Fundraising Backed by a Culture of Risk-taking

So what about the culture piece?

We partner with organizations across the nonprofit sector who want to raise more money to fund their transformational visions for years to come. With year-over-year sustainability and growth in mind, we build a custom path forward together to shape revenue for the next three to five years. It is informed by your current operations and fundraising performance, goals, industry best practices, philanthropic potential, and more. The goal is to create a revenue model that is ambitious but achievable.

Three Ways to Build a Culture that Rewards Risk-Taking

A culture that rewards risk-taking and encourages development teams to take appropriately big leaps is a critical ingredient for success. Appropriately big doesn’t mean reckless—it means informed by relationships, data, and strategy, stretching past what feels comfortable in favor of embracing what could be. So, how do you do that?

Set metrics that reward risk-taking.

Incorporate metrics like number of solicitations and average increase in gift size in addition to dollars raised and number of gifts closed. If your gift officers are having a high number of solicitation conversations but receiving a low number of dollars, that invites a discussion about how they are arriving at the target gift amount and gauging donor readiness for a gift conversation. If win rate is high but predicted ask ratio (i.e., amount you’re asking for compared to the total capacity in your portfolio) is low, that invites a conversation about how to thoughtfully increase target gift amounts.

For example: a gift officer has 10 solicitation conversations this quarter and three result in a closed gift agreement. Under an outcomes-only model, that may read as a weak quarter. Under a model that rewards risk-taking, it’s the opposite—she’s reaching past the safe list of donors she knows will say yes. Even if the conversations don’t result in an immediate gift, it helps build the relationship and prompts the donor to think about the impact their gift would have.

Set big goals with your team and serve as an accountability partner.

Work with your team to set two to three goals each quarter that scare them. It might be a conversation with a prospect that excites them, leading an all-staff exercise at the next team meeting, or a personal goal that’s felt out of reach. Make sure success within that goal is defined as taking the risk, not the outcome.

For example: one gift officer’s quarterly goal might be asking a longtime $5,000 donor for an increased investment of $25,000—a number that feels like a stretch for both of them. If the donor says yes, celebrate it! That’s a big leap for both the donor and gift officer. If the donor gives $10,000 but responded positively, celebrate! The gift officer took the risk. The next team conversation should be about what you learned about that donor’s readiness and what the appropriate next steps are.

Model the behavior you want to see on your team.

As a leader, identify one or two goals each quarter that may or may not come to fruition in the way you imagine. Share them with your team and be vulnerable.

For example: Next month, you plan to ask your board chair to personally reach out to five of your lapsed major donors and ask for renewed support. You think it will work because of the relationships the team has built, the board chair’s eagerness to help your mission, and the strategy the leadership team has put in place. It may not be successful because this is the board chair’s first time putting her philanthropic training into action, and that’s okay.

An Environment Where It’s Safe to Fail Leads to Fundraising Successes

A team where everyone feels psychologically safe and encouraged to take big risks rewards everyone. From fundraising goals to personal and professional growth, risk-taking isn’t something that people wake up and decide to embrace overnight. It requires thoughtful planning, leadership buy-in at the staff and board level, and willingness to fail.

Ultimately, the hard work is worth it. A culture that encourages taking appropriate risks is critical for annual fundraising success.

If your annual fundraising has plateaued and you’re not sure whether it’s a strategy problem or a culture problem, let’s talk. We’ll help you diagnose the issue and plan its remedies.

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