I’ve come to believe that strategic planning isn’t about following a step-by-step process; it’s about asking the right questions. If you don’t ask the best questions, the answers, ideas, and plans that emerge won’t address what’s truly needed to propel your organization forward. Unfortunately, many strategic planning processes at nonprofits focus more on checking boxes in a generic process than on identifying the most important questions to ask.
Here are three powerful questions I’ve encountered that can transform a nonprofit’s strategic planning efforts.
The Question for New Ideas: “What Would Have to Be True for This to Work?”
At some point, every organization will consider doing something new—a new program, market, structure, or delivery method. The idea might be exciting, but it’s easy to get bogged down in debates about feasibility. I often hear people ask, “How can we prove that this idea will work?” But let’s be honest: it’s impossible to prove an untested idea. The scientific method itself is based on testing hypotheses, not proving them in advance.
Still, people often stall, wanting all the data before moving forward. This guarantees they’ll never move forward because there will always be unknowns. That’s why I love this question from Dr. Roger L. Martin:
“What would have to be true for this to work?”
Notice the question doesn’t ask, “What is true?” because we don’t always know what’s true, and we can argue endlessly about which data points matter most. Instead, “What would have to be true?” opens up room to imagine the ideal conditions for success. Then, you can compare those conditions to what you know about the world and start identifying gaps. This question unlocks possibilities where barriers previously stood, allowing teams to move forward even in the face of uncertainty.
The Question for Purpose: “Are We the Right Ones to Meet This Need?”
Nonprofits are guided by the needs of their communities, and that’s a good thing. But sometimes, focusing solely on community needs—without considering the organization’s capabilities—leads to mission creep, overstretching resources, failed programs, and subpar service delivery. It’s one thing to observe a problem; it’s another to be equipped to solve it.
I’ve seen well-meaning nonprofits launch programs they weren’t prepared to run simply because they saw a need and wanted to help. But as Dr. Michael Stone asks in his book on nonprofit strategic planning:
“Are we the right ones to meet this need?”
The question isn’t whether there’s a need. Of course, there is. Observing a need doesn’t require expertise. The real question is whether your organization has the capabilities, resources, and expertise to address it effectively. Too often, nonprofits think, “No one else is meeting this need, so it’s up to us.” But why should the default response be you doing something instead of inspiring others to act?
Ideas that scale usually do so through larger, better-resourced entities like governments—not by nonprofits stretching their limited resources to the breaking point. So, take it a step further: “Given our capabilities and resources, are we the right ones to meet this need?”
The Question for Unique Value: “If Our Organization Disappeared, Would We Be Easy to Replace?”
The term “value proposition” is common in business. It refers to what makes a company’s product or service unique in the market. Nonprofits need to understand their value propositions, too. There’s a community value proposition (why your services matter) and a donor value proposition (why donors should fund you).
Most nonprofits can articulate their community value proposition—it’s usually embedded in the mission statement. But what about the donor value proposition? Why should donors, foundations, or funders support you over another nonprofit doing similar work? This is where the next question comes in:
“If our organization disappeared, would we be easy to replace?”
If the answer is yes, then your organization may lack a unique advantage—something that sets you apart and makes you irreplaceable. If donors see you as interchangeable with another nonprofit, why wouldn’t they fund the one that’s cheaper, faster, or closer to their priorities? This question pushes you to identify your unique capabilities—whether it’s your team, your network, your relationships, or your institutional knowledge—and leverage them in your donor value proposition.
Asking the Right Questions
These three questions—“What would have to be true for this to work?”, “Are we the right ones to meet this need?”, and “If our organization disappeared, would we be easy to replicate?”—aren’t just thought exercises. They’re practical, strategic tools that help nonprofits make critical decisions.
By asking these questions, you ensure your strategic planning isn’t just a rote process but a meaningful exploration of clarity, purpose, and value. Because when you ask the right questions, you position your organization to move forward with confidence and impact.
