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Most nonprofits aren’t struggling to raise money because they lack passion or effort. They’re struggling because they’re building on sand.

A development director recently asked us a simple but incredibly important question:

“What does it actually look like to build a relationship with a foundation?”

Not in theory. Not in a textbook. But in real life.

Do you call them? Email them? Invite them for a tour? Wait until the application opens?

It’s a fair question, and one we hear often. For many organizations, foundation funding can feel transactional at best and mysterious at worst. You submit a proposal, hope it aligns, and wait for a decision.

We’ve all been there in life. Things are going great, cruising along, and we’re thinking “How did I get so lucky?” Then it happens: The Dip. It comes in many forms. An illness, a failure at work, the loss of a loved one…sometimes all in one week! The only thing in life we are assured of is tough times. Fundraising is no different.

Nonprofit leaders are known for wearing many hats—budget balancer, community builder, last-minute-slide-deck-finisher, professional schlepper—but the hat we too often leave on the shelf is the one labeled “curiosity captain”. Whether it's embracing AI, reimagining donor stewardship, or treating events as more than just logistical nightmares lifts with a side of lukewarm veggie trays and sweaty cheese cubes, we sometimes meet new ideas with hesitation or quiet resistance.

It’s time for a reset—not of our strategy, but of our attitude. Because—gulp—we might just be the problem. And that’s uncomfortable… but also incredibly fixable. What if we chose curiosity over fear, and open-minded exploration over the comfort of our preconceived notions? These shifts aren’t detours from our mission—they’re invitations to deepen and expand it. And spoiler: we don’t need to have all the answers to get started. We just need to be willing to ask better questions and create space for curiosity.

For many of us, planned giving seems intimidating—all those complex financial instruments and legal terminology. But here's the thing: the donors you need to reach, especially those born between 1965 and 1980, don't want to hear about charitable remainder trusts on your first conversation either. They want to know how they can make a real difference while being smart about their finances.

Gen X donors are hitting their peak earning years right now, and they will be the primary recipients of the Boomer estates. So, they’re thinking about legacy in ways that might surprise you. Let's break down how to reset your planned giving approach to connect with this unique generation.

As we move through the year, nonprofit leaders need to ask themselves: Are we where we hoped to be? These check-ins are about more than forecasting—they are a strategic opportunity.

These are opportunities to not just to evaluate results, but to ask deeper questions about direction, adaptability, and mission alignment. As Tod Bolsinger writes in Canoeing the Mountains, leadership today is no longer about mastering well-worn paths. It’s about stepping into the unknown, “off the map,” where the old tools don’t work, and the terrain requires new vision, vulnerability, and innovation.

Whether you’re ahead of pace or navigating unexpected challenges, this is your opportunity to drop the oars, stop paddling harder in the wrong direction and begin adapting to the real terrain ahead.

The Headwinds

Turmoil and uncertainty leave nonprofit volunteers and staff at a loss. Should we launch our campaign? Should we pause our campaign? What about our annual fund? Where do we go from here where “here” keeps shifting?

Is a capital expansion project included in your blueprint for growth? Whether a new facility, a refresh or update, or an addition, here are three early wins that should be considered now as the organization prepares for a capital campaign in the future.

If you're anything like me, you've probably found yourself staring at a blank document titled "Case for Support" more than once in your career. That moment when you need to distill your organization's entire heart and soul, its mission, impact, and vision, into something that resonates with potential supporters.  

I've been a part of a few conversations lately about navigating the changing landscape of nonprofit communications. One theme keeps emerging: many of us are cautiously exploring how new tools, including AI, might help with fundamental development work like crafting a case for support—without losing the authentic human connection that is at the core of what we do. 

We live in uncertain times, with constant social, political, and economic shifts. During the American War of Independence Lord Cornwallis surrendered to George Washington at Yorktown while the British band played the tune “the world turned upside down”. The most powerful army in the world had just been defeated by the American patriots. It must have indeed seemed like the world was upside down.

Today, nonprofit leaders may feel similarly challenged, as the funding and practices they have counted on in the past may no longer be available in the same ways. Whether you work in a nonprofit or volunteer as a board member, navigating uncertainty is part of the job description. Strategic management of resources is key to managing these uncertainties and ensuring your organization’s ability to fulfill its mission.