Just Ask - Rethinking Development

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 to...

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.

How soon can you ask for another gift? It’s one of the biggest fears in fundraising: asking again too quickly. But is there actually a “right” timeline? In this episode of Just Ask, we talk donor psychology, stewardship, timing, and why fundraisers often overthink the second ask.

Every fundraiser has a white whale. The donor you just know could come through… someday. Is it discipline to keep going, or denial? Let’s talk about when to walk away.

If your development team feels like a revolving door, it’s not just a hiring problem: it’s a strategy problem. In this episode, we dig into why talented fundraisers walk, what it’s actually costing your organization, and how smarter compensation and creativity can change the game.

For years, endowments have lived in the “we’ll get there” category. But the reality is shifting. If long-term sustainability matters, building your endowment is no longer optional: it’s essential. In this episode, we break down why now is the moment to start (or finally take seriously) your endowment effort.

AI is everywhere right now, but what actually matters for fundraisers? Bryan and Greg discuss how AI is showing up in fundraising, the tasks it can take off your plate, and the judgment call every fundraiser has to make: what do you hand off, and what do you hold onto?

What if you could build the perfect fundraiser? What qualities would they have? Stronger asks? Better scripts? More confidence? Maybe. But the real superpower might be something far simpler: listening. In this episode of Just Ask – Rethinking Development, we explore why the best fundraisers don’t just talk: they listen.

You’re launching a capital campaign. The vision is clear. The excitement is building. But who’s protecting the owner? In this episode of Just Ask – Rethinking Development, Greg tackles a question many nonprofits overlook: Should you hire an Owner’s Representative for your building project? What does an Owner’s Rep actually do? They represent the owner, not the architect or contractor. They oversee...

Have you ever experienced the frustration of a campaign goal increasing after your feasibility study was complete? What went wrong? In this episode, Greg shares the single most important estimate that determines whether your feasibility study will be accurate or woefully misleading. He also explains the common missing elements that cause organizations to get this number wrong in the first place. I...

Some development leaders wait for direction. Others go the extra mile. What makes the difference? In this episode, Bryan and Greg explore a mindset shift that changes how development leaders approach their work — and why the most effective fundraisers don’t think like employees at all.

Do fundraisers really care about donors—or just the donation? Bryan challenges a common assumption that fundraisers are driven by need, not stewardship—and explains why that mindset gets philanthropy wrong.

Ever wish you could go back and give your younger fundraising self a few pointers? Greg and Bryan unpack the insights, the pitfalls, and the practical advice they’d offer any new fundraiser stepping into the field.

Behind every transformational gift is a donor wondering whether the vision is real and their investment will matter. In this episode, we unpack the simple questions that build confidence—and keep campaigns from stalling.

Fundraising is full of familiar phrases—but some might be past their prime. In this episode, Bryan and Greg swap stories, share mild rants, and explore the words and clichés that feel tired, stale, or overused in nonprofit fundraising.

What’s the single most important factor that determines a major gift? It’s not your case statement, your campaign, or your vision. It’s something more personal. Greg explains the surprising key behind every major gift—and how leaders can build the kind of trust that moves generosity.

Before you book the caterer or send the invites, stop and ask: why are you holding an event in the first place? In this episode, Bryan leads a candid conversation with Greg on what truly makes a fundraising banquet worth doing — and what the key steps are for a successful event.

Who are the donors most likely to make the ultimate gift—and what keeps your nonprofit in their will? Dr. Russell James returns to Just Ask to share the top three insights every fundraiser needs to understand bequest giving.

Dr. Russell James of Texas Tech joins Greg today to share insights from decades of charitable giving research—and why three words, “identity, challenge, and hero”, can reshape how you connect with donors.

If you think the top reasons a campaign fails are because of money, messaging, or motivation—you’d be wrong. The real killers are much simpler—and far more common. Last time, we uncovered the #1 reason campaigns fail. This week, Greg pulls back the curtain on reason #2, and it’s one that might be hiding in plain sight.

The last place any nonprofit wants to end up is in a stalled—or worse, failing—capital campaign. But what’s the real cause when that happens? With more than 30 years of experience leading campaigns for Catholic schools and institutions, Greg reveals the number one reason campaigns fail—and what you should be doing to avoid it.

What’s the difference between good and great? Bryan makes the case today for why “hustle” is one of the key ingredients for fundraising success today, and yet, many nonprofits lack it.

What happens when you ask for too much? Bryan is back with Greg to unpack a recent visit—one that led to one of the worst reactions to an ask he’s ever seen. It raises the age-old fundraising question: Can you really ask for too much? Bryan says yes... but the story doesn’t end there. Tune in to hear why.

Welcome to part two of Greg’s conversation with Karyn Macfarlane, founder of Supporting Stars and certified Working Genius Certified Facilitator. How does the Working Genius apply to a development teams of one? Together Greg and Karyn go through the 6 Types of Working Genius by Patrick Lencioni and why knowing them can enhance your fundraising potential. You can learn more about the Working Genius...

Greg sits down today for part one of a conversation with Karyn Macfarlane, founder of Supporting Stars and certified Working Genius Certified Facilitator. Together they go through the 6 Types of Working Genius by Patrick Lencioni and why knowing them can enhance your fundraising potential. You can learn more about the Working Genius, take the test, or purchase the book at: https://www.workinggeniu...