How Soon Is Too Soon to Ask Again?

What can 4,000 major gift solicitations teach us about the human side of fundraising?In this episode of Just Ask, Greg reflects on a recent conference where he shared some of the most important lessons he’s learned from thousands of conversations with donors.But it’s a story from a recent visit with a billionaire that challenges some common assumptions about wealth, generosity, and the people behind the gifts.

Is your organization waiting until every detail is finalized before inviting donors into the vision?That might be a costly mistake.Major gifts don’t happen overnight. Neither do the relationships that make them possible.In this episode of Just Ask, Greg shares a conversation with a Southern California nonprofit that raises an important question: When does careful planning become a missed opportunity?The answer might surprise you.

A donor calls and tells you they’re redirecting their giving to another organization. What do you say?Do you graciously accept their decision? Ask a few more questions? Or is there a time and place to push back?And what happens when your organization’s success actually becomes a reason donors think you no longer need their support?In this episode of Just Ask, Greg and Bryan tackle a listener’s question about navigating these delicate conversations, understanding what motivates donors, and knowing when and how to make the case for continued support.

What happens when the biggest obstacle to a bold vision isn’t money, donors, or even the economy? What if, it’s the way we think?After a recent visit to the Theodore Roosevelt Presidential Library in Medora, Bryan had an uncomfortable realization: Even experienced fundraisers can fall into the trap of a small-minded attitude.In this episode of Just Ask, Bryan and Greg explore how small-minded thinking can quietly limit your mission’s potential. They’ll share how to recognize the attitude in yourself, break out of that mindset, and open yourself to approaching donors for your own big vision.

AI can write the email, draft the proposal, and build the follow-up. It might even tell you exactly what to say.But should it?We’re stepping back into the world of AI to talk about what happens when a tool designed to make development more efficient starts replacing the very thing that makes development work: human relationships.Where does AI help? Where does it hurt? And what might we lose when we put too much of fundraising on autopilot?

Should your school have a separate foundation?It can sound like a great way to strengthen fundraising, protect resources, and engage new leadership. But before you go and create a new organization, there’s a more important question to ask: Why?In this episode, Greg draws on years of experience working with Catholic schools and nonprofits to explore what happens when a foundation is created to solve one problem, but ends up creating entirely new ones.We talk about stewardship, trust, leadership, fundraising, and the questions every school should ask before deciding that a separate foundation is the answer.

Why does asking for a gift bring out so much fear?What if the very act of “asking” isn’t just about fundraising, but about becoming an instrument of what God wants to do in another person’s life… and your own?In this episode, Bryan and Greg explore The Healing Power of Asking.

We live in an age of shortcuts. AI can save time, automate tasks, and make almost any job easier. But some shortcuts cost you more than they save. In this episode, we explore one simple mindset that will make you a stronger fundraiser, and why sometimes the best thing you can do — is take the stairs.

What if strengthening your annual fund was the key to unlocking your long-term fundraising strategy? In this episode, Greg takes the lead to explore how a focused mini-campaign within your annual fund can secure major gifts for operational priorities, creating the financial stability needed to spend more time cultivating planned and endowment gifts. It’s a practical conversation about balancing today’s needs with tomorrow’s legacy.

The annual fund is often treated as the center of a fundraising program. But should it be? In this episode, Greg offers a thought-provoking perspective that may cause you to rethink where your development team’s time and energy are best spent.