The Questions You Don’t Know to Ask: Why Fresh Eyes Reveal What Familiarity Hides in Nonprofit Fundraising
Early in my career in college athletic development, I watched leadership debate a familiar problem. The school reserved thousands of premium seats in both football and basketball venues for students, but student attendance rarely exceeded 50% of capacity. Meanwhile, donors sat on waiting lists for similar seats.
The debate seemed straightforward: should we open unused student seats to donors willing to pay a premium, or invest resources in boosting student attendance?
Both sides had compelling arguments. Both sides were asking the wrong question.
Instead of debating what we should do, we took a more straightforward approach: we asked the students themselves. “What would get you actually to attend games?”
We expected the usual answers: better marketing, different game times, and more giveaways. We were already offering plenty of incentives, including t-shirts, contest entries, and even free bacon, at early-arrival promotions.
What we heard instead stopped us in our tracks.
“We’d come if we could bring our parents to sit with us in the student section.”
College students wanted to sit with their parents. I’ll admit, none of us saw that coming. Not only did they want it, but they were also willing to pay full price for parent tickets to make it happen.
The request came from the sorority women on campus, one of the most organized and influential groups in the student body. When they made a decision as a group, other students followed. Including their parents wasn’t a fringe idea; it was a consensus from a community that understood their peers better than we ever could.
We implemented their suggestion. The results exceeded every metric we cared about:
Student sections went from half-empty to full. We generated significant revenue from parent ticket sales without cannibalizing donor seats. We built trust with influential student leaders who became partners in promoting big games. Season ticket holders reported in surveys that the energized atmosphere made the entire experience more enjoyable. Renewal rates increased across the board.
All of this happened because we were willing to ask a question we hadn’t thought to ask, to people we’d been making assumptions about.
That’s when I learned a truth that shaped my entire approach to nonprofit development: the people closest to the problem often hold the answer. But only if we’re humble enough to ask rather than assume.
The Proximity Paradox in Nonprofit Organizations
When you work closely with a nonprofit organization, you develop something invaluable: deep knowledge of its history, its people, its mission, and its community. You understand the nuances that outsiders miss. You know why specific fundraising approaches failed in the past and which board members champion which priorities.
While this institutional knowledge is an invaluable resource, if not counterbalanced with new or creative perspectives, it can lead to significant blind spots.
The closer you are to the work, the more assumptions become invisible. That donation form everyone complains about? It’s been that way for six years, so it fades into the background. The major donor segment you stopped cultivating? Someone tried that approach once, and “it didn’t work,” so it became organizational truth. The board meeting structure that eats three hours but produces little direction? That’s how board meetings go.
These aren’t failures of leadership or intelligence. They’re the natural result of proximity. When you see something every day, you stop noticing it altogether.
The Echo Chamber
Even highly effective nonprofit organizations with successful results can find themselves trapped in echo chambers. Your board and staff comprise dedicated and passionate individuals who care deeply about the mission. However, if they all come from similar professional backgrounds, live in similar communities, or share similar experiences with your organization, their collective wisdom has its limitations. These limits become less obvious and more challenging to address the longer they are allowed to proceed as standard operating procedure.
I’ve sat in meetings where everyone nodded along to strategic plans that contained fundamental flaws, nobody questioning them. Not because the attendees weren’t smart or engaged, but because they all shared the same assumptions about what was possible, what donors wanted, or how programs should operate.
“We all agree” is a phrase that should raise an immediate red flag, and “that’s how we’ve always done things” is exactly why you should explore a new approach.
Why Outsiders Ask Different Questions About Your Fundraising Strategy
Fresh eyes don’t just see differently; they question differently.
An outsider may not know what’s been tried before, so they ask about approaches your team dismissed years ago. They don’t understand your industry’s constraints, so they suggest ideas borrowed from other sectors. They notice the confusing language on your website that you stopped reading ages ago. They wonder why you’re not talking to that obvious donor segment.
Sometimes, these questions reveal that your old assumptions are no longer valid. Perhaps you attempted peer-to-peer fundraising eight years ago with disappointing results, but donor behaviors and digital tools have undergone significant changes. Maybe your major donor cultivation cycle made sense when you had different staffing, but now it’s creating bottlenecks nobody acknowledges.
At other times, outsiders ask questions that prompt you to articulate the “why” behind decisions that have become automatic. This articulation itself is valuable. Either you discover your reasoning is sound and feel more confident in your approach, or you realize the original reason no longer applies.
The most powerful outside questions aren’t challenges to your expertise. They’re invitations to examine what you’ve stopped examining yourself.
The Questions That Change Everything in Nonprofit Development
Over my years in development, I’ve noticed certain types of questions that fresh perspectives tend to ask:
“Why do you do it that way?” This simple question about routine processes can uncover inefficiencies that drain time and resources. Why does every gift over $50,000 require a signed pledge agreement? Why do you only reach out to major donors twice a year? Often, the answer is “because we’ve always done it that way,” which isn’t really an answer at all.
“What if you stopped doing that entirely?” Organizations accumulate programs, events, and initiatives like barnacles on a ship. An outsider might ask what would happen if you eliminated that annual event that everyone dreads planning, or that report nobody reads. Sometimes the answer is “nothing bad,” which frees up capacity for higher-impact work.
“Who have you not asked?” When you’re close to an organization, you develop mental models of who cares about your work and who doesn’t. Fresh eyes question these models. What about lapsed donors who gave consistently for years and then stopped? What about board members who rolled off five years ago? What about the community members your programs serve who’ve never been invited to give?
“What’s working better than you think?” Organizations naturally focus on problems to solve. Outsiders sometimes notice that you’ve stopped celebrating success. That volunteer retention rate you consider “okay” might be exceptional compared to peer organizations. That small program generating modest revenue might have extraordinary growth potential. Fresh eyes can help you see your own strengths more clearly.
When Nonprofits Most Need Outside Perspective
Not every challenge requires external input. But certain situations practically beg for fresh eyes:
When effort isn’t translating to results. You’re working harder than ever, implementing best practices, executing campaigns, and the numbers stay flat. This doesn’t mean you stopped growing. This effort was necessary to get this far. You determined your most important priority and executed it successfully. It may be challenging to decide on how to maintain your new baseline while still having the capacity to implement what is now the latest and most important priority. The best advice I’ve received at a time like this is to stop evaluating what tasks were accomplished and start evaluating how you spent your time. You’ve checked off your to-do list. But what larger goal did this time accomplish?
When “we’ve tried everything” feels true. This phrase usually means “we’ve tried everything we can think of,” which is different. An outsider’s framework might suggest approaches that literally haven’t occurred to your team.
During major transitions. New leadership, strategic planning, and capital campaigns. These pivotal moments deserve questions from people who don’t have a vested interest in past decisions or current politics. New staff will inherently bring new perspectives. What better time to gather as many new ideas as possible?
When success mystifies you. Sometimes organizations stumble into something that works brilliantly but can’t articulate why. Fresh eyes can help identify the factors driving success so you can replicate it intentionally. Pure luck is rare. Be prepared to be lucky, then convert that luck to procedure.
Where to Find Fresh Perspectives for Your Nonprofit
The good news is that an outside perspective doesn’t require hiring expensive consultants (though I obviously think consultants can be valuable). Here are sources of fresh eyes that might already be within reach:
Lapsed supporters. Former donors and board members who’ve moved on are goldmines of honest feedback. They cared enough to be involved once, but no longer have political capital to protect. Ask them what they saw when they were close to your work.
People your programs serve. If you run a food bank, when’s the last time someone who uses your services gave input on your fundraising strategy? They understand your impact in ways your board never will.
For-profit equivalent professionals. Corporate structures bring efficiency frameworks. Entrepreneurs bring risk tolerance. Working artists bring creative approaches to funding challenges. Each individual has something to teach the others.
Strategic consultants and advisors. Yes, I’m obviously biased here. However, there’s value in working with someone whose entire job is asking questions, free from organizational politics, whose experience spans multiple organizations and contexts, and who has no vested interest in maintaining the status quo.
The key isn’t just finding diverse perspectives; it’s creating space for them to be honest. If people feel that their input will be dismissed or that honesty carries social costs, they’ll tell you what you want to hear rather than what you need to know.
The Courage to Not Know: Humility in Nonprofit Leadership
Here’s what seeking outside perspective really requires: the humility to admit you might not see everything.
This is harder than it sounds, especially for leaders who built the organization or development professionals who’ve generated millions in revenue. Success can make us confident that we understand what works. Expertise can give us confidence that we’ve considered every angle. Proximity can make us feel like we know our organizations better than anyone possibly could.
All of that can be true, and an outside perspective can still reveal critical blind spots.
A donor once told me, “The kindest thing you can do for another person is to ask them for help.” This quote stuck with me. The day before, I had been volunteering at a youth center where a teen asked for my help with homework. Providing that help brought me immeasurable joy. Reflecting on that joy and the donor’s quote made me realize something. If it is kind to ask for help, it is selfish not to ask for help when it is available.
Seeking fresh eyes isn’t an admission that outsiders have “better” answers. It’s recognition that they have different questions, and other questions unlock what you already know but haven’t been able to access.
An Invitation to Look Differently at Your Nonprofit Development Strategy
Throughout my career in development, I’ve found that the most transformative insights don’t come from importing someone else’s playbook. They come from asking questions that help organizations see themselves clearly, free from the assumptions that familiarity creates.
If your organization feels stuck, or if you’re working hard without corresponding results, or if everyone on your team agrees about everything, you might benefit from someone asking the questions you don’t know to ask.
This is precisely why I named my practice Ask the Turtle. Sometimes the turtle approaching the road knows exactly where it’s going. And sometimes the turtle needs someone to ask, “Where are you trying to go?” not to redirect its journey, but to help it identify and address potential hazards on the way towards its destination.
I’d welcome the opportunity to be those fresh eyes for your organization. Not to tell you what other nonprofits are doing or to prescribe predetermined solutions, but to ask the questions that help you see what proximity has hidden.
Whether you’re considering working with a nonprofit consultant or want to talk through your development challenges with someone outside your organization’s daily operations, I’m here to listen first and question second.
Because the most powerful solutions don’t come from outside expertise, they come from helping you see what’s been there all along.
Schedule a complimentary listening conversation to explore how a fresh perspective might benefit your organization.
Nate Warren is the founder of Ask the Turtle LLC, providing nonprofit development consulting services to organizations throughout New England and beyond. Connect with him at nate@asktheturtle.com or schedule a complimentary listening conversation through asktheturtle.com.