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.

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.