Just Ask - Rethinking Development

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 planning, budgeting, cost control, risk management, and help navigate construction volatility and supply chain challenges.The real question isn’t just what they do: it’s whether your organization truly needs one.Greg breaks down:​What does an Owner’s Rep have responsibility for?​What is the opportunity cost of not hiring an Owner’s Rep?​Are they worth the money? Before you break ground, listen to this conversation.

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.If you’re planning a campaign, this is a conversation you don’t want to miss

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, take the test, or purchase the book at: https://www.workinggenius.comFind out more about Karyn and her work at supportingstars.com.

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.workinggenius.comFind out more about Karyn and her work at supportingstars.com.

Welcome to part two of a two part podcast series with our guest Stephanie Ballis, Director of Development for University of Idaho College of Law.Greg picks up where we left off, diving deeper into Stephanie’s journey and insights from her career in fundraising.