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.
Key Questions to Guide Your Strategy
1. Are we on pace to meet our fundraising and engagement goals?
Start with the data, but don’t stop there. In adaptive leadership, as Bolsinger explains, it’s not just about what is or isn’t working—it’s about why. What assumptions shaped your goals? Which of those assumptions still hold true?
2. What strategies are yielding strong results, and which are underperforming?
Instead of repeating what’s comfortable, be willing to abandon the “canoe”—the strategies that served you well on past terrain but aren’t equipped for the next leg of the journey. Embrace experimentation where old tactics fall flat.
3. Are we acquiring, retaining, and upgrading donors as planned?
Your donor base is also evolving. What do your results say about how donor expectations are shifting? Are you building trust and community, or just chasing metrics?
4. Are we using our data to drive decisions?
Data should be your compass, not your anchor. In uncharted territory, it can show you where you’ve been—but true leadership requires interpreting what data means and applying those insights courageously.
5. Are your board and staff aligned around development priorities?
Bolsinger reminds us that adaptive leadership is a shared endeavor. Is your team embracing the journey together? Are you equipping your board and staff to navigate ambiguity with clarity of mission and trust in each other?
Strategic Moves to Make Now
I believe a team is truly shaped by the decisions made in the distance between where they are and where they’re called to go. That journey is rarely linear—and it requires a different kind of leadership than what got you here.
Here are five adaptive strategies your organization should consider implementing today as you course-correct toward your goals:
1. Refresh your case for support.
Vision leaks. Recast. Recast. Recast.
In unfamiliar terrain, your case for support must do more than inform—it must inspire. Ensure your messaging speaks to the evolving landscape, reflects current community needs, and communicates a bold, compelling vision for the future.
2. Reforcast goals and reallocate resources as needed.
If the map has changed, so must your route. Now is the time to revise expectations, redirect resources toward what’s working, and let go of outdated plans. Course-correction is a sign of strength, not failure.
3. Prioritize donor retention and stewardship.
Extraordinary giving experiences create lasting loyalty. Build relational capital now through intentional stewardship—handwritten notes, thank-you calls, impact storytelling. In a rapidly changing world, donors crave connection more than ever.
4. Re-engage lapsed and LYBUNT donors.
Reach out with authenticity and transparency: “Here’s what your past gift made possible—and how we’re adapting to meet today’s challenges.” Donors want to be part of a movement that learns, grows, and endures.
5. Equip your leaders—board and staff—to lead adaptively.
Leadership is everything… never settle. Host a retreat or strategic session focused on fundraising alignment. Your board doesn’t need perfect scripts—they need a clear “why,” a strong invitation, and the confidence that their role in mission advancement matters.
In Canoeing the Mountains, Bolsinger writes, “The world in front of you is nothing like the world behind you.” This is especially true in the nonprofit sector today. And yet, while the terrain may be unfamiliar, your mission remains your true north.
Strategic thinking isn’t just about fixing what’s broken—it’s about becoming the kind of organization that can thrive in changing conditions. At DBD Group, we don’t just help nonprofits build plans—we help leaders build the courage, clarity, and capacity to lead off the map.
No matter the circumstances, you have the gift of insight—and the power to pivot. With adaptive leadership and intentional strategy, your organization can set a course not just to survive, but to flourish.
If your team would benefit from a mid-year planning session or a strategic partner to help navigate what’s next, let’s talk. DBD Group is here to walk alongside you—every step of the way.