At Infinite Giving, we work with nonprofits across the country to help them build financial strength, whether that’s managing cash reserves, investing long-term funds, or helping organizations receive stock, crypto, and donor-advised fund (DAF) gifts.

One pattern we see consistently is this: when financial pressure rises, fundraising conversations start to feel different.

Leaders feel the stakes more intensely. Boards become more engaged (sometimes more anxious), and donor conversations that once felt relational can suddenly feel urgent.

That tension was the focus of our recent webinar, “Major Gifts When the Stakes Are High,” featuring Karen Houghton, our CEO and Founder, and Joanna Hogan, Founder and CEO of Inspire Generosity.

Joanna has worked on major gift efforts totaling more than $100 million, serving in institutional leadership roles, advancement teams, and alongside nonprofit boards. Her work today focuses on helping nonprofit leaders build relationships that inspire extraordinary generosity.

But this session wasn’t about fundraising scripts or persuasion tactics; instead, the conversation centered on something much more foundational: the leadership decisions that happen before a major gift meeting ever takes place.

What Happens Before the Meeting Matters Most

Many nonprofit leaders prepare for a major donor conversation by asking a simple question: what should I say?‍

But Joanna encourages leaders to ask a much more strategic question: what decisions need to be made before the meeting happens?

Because very often, what determines the outcome of a major donor conversation happens long before anyone sits down at the table.

The situation will feel familiar to many nonprofit leaders. A funding gap appears. A project needs support sooner than expected. Or the board begins asking questions about the organization’s financial runway.

Suddenly, conversations that might have happened months from now get scheduled next week.

In those moments, urgency can quietly shape the conversation. Leaders may feel pressure to close a gap or secure a major gift quickly. But donors can often sense that pressure, even when it isn’t explicitly stated.

Financial Clarity Creates Donor Confidence

One insight from the conversation stood out clearly: donor confidence is often tied to financial clarity.

When nonprofit leaders understand their runway, their reserves, and their long-term financial strategy, they enter major gift conversations from a much more grounded place.

That steadiness changes the tone entirely.

Instead of sounding reactive or anxious, leaders communicate thoughtful stewardship and long-term vision. And that confidence often invites deeper partnership from supporters.

From Pressure to Partnership

Another important theme was language. Joanna often encourages leaders to shift their thinking away from transactional language like “donors” and toward the idea of giving partners.

This subtle shift reflects a much bigger mindset change.

Major gift conversations shouldn’t feel like moments of pressure or persuasion. Instead, they can become invitations into partnership, which is an opportunity for supporters to help shape the future of a mission they care about.

Leadership Decisions Drive Strong Conversations

Ultimately, the strongest major gift conversations don’t start in the meeting itself.

They start earlier, with leadership decisions about financial clarity, strategic priorities, and long-term sustainability.

When nonprofit leaders slow down long enough to make those decisions first, they show up in donor conversations with a steadiness that supporters can feel.

And in high-stakes moments, that steadiness can make all the difference. We're here to help, so schedule a time to connect with our team of nonprofit fiduciary partners to learn more.

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