The eraser hurtled directly toward me.
I had just asked my favorite professor if he could explain the concept one more time. It was a summer statistics course during the final stretch of my undergraduate degree. I was struggling to grasp the concepts, and he was clearly running out of patience.
I stopped breathing for a few seconds, gathered my books, and hurried out of the classroom. I found refuge in the student center, only to discover the rest of the class following behind me, offering encouragement. Their question was simple:
Why did that happen?
Apparently, I had asked one question too many.
Throughout college, I operated under one assumption: if I had a question, someone else in the room probably had the same one but wasn’t willing to ask it. So I did.
At that stage of my life, I never considered what my questions felt like to the person answering them. It was all about satisfying my curiosity.
Today, I still ask questions. It’s how I learn. Some people call it a gift. Others might call it a curse. I suppose it depends on which side of the conversation you’re standing on.
One summer, I spent a great deal of time with a young woman preparing to leave for her first year of college. She tagged along with me on several nonprofit site visits. One of her favorite questions was beautifully simple:
Why?
I answered her questions as best I could and checked to see whether my explanations made sense. Then one day I watched her ask someone else, Why? While touring a nonprofit daycare, she posed a question, and I realized the person answering it didn’t fully appreciate its value.
It was the kind of question that had no simple answer, the kind worth talking through with other staff, volunteers, and board members. It was the kind of question that carried the possibility of new opportunities.
Her question wasn’t a challenge. It was an invitation to go deeper and better understand the challenges the nonprofit faced.
She wanted to know why the organization operated the way it did, why a program existed, why a process mattered, and why the mission was being carried out in that way.
Her generation often viewed organizations through a different lens, and their questions revealed assumptions that the rest of us no longer noticed.
Our attachment to the question why starts early, usually right after we master the word no. For experienced questioners, like many donors I know, why questions are powerful tools.
They get to root causes and core motivations. They challenge assumptions, and the answers make us both better informed and wiser.
Nonprofit leaders, board members, and donors all ask why questions to understand reasons, causes, and purpose. But the most effective leaders know the first why is rarely enough.
Real understanding comes from layering questions. One of the most effective strategic planning tools I’ve used is the Five Whys, a problem-solving technique developed by Toyota to uncover the root cause of an issue. The premise is deceptively simple: ask Why? Then ask Why? again. By the fourth or fifth answer, you’ve usually moved beyond symptoms to the real challenge.
Consider the kinds of questions nonprofit leaders, board members, and donors ask every day.
For program effectiveness:
- Why is participation in this program declining?
- Why are families not completing the program?
- Why are referrals from our community partners decreasing?
For fundraising:
- Why aren’t more first-time donors becoming recurring donors?
- Why did this donor choose to support us?
- Why are we relying so heavily on one funding source?
For mission and strategy:
- Why are we the right organization to solve this problem?
- Why is this work still needed?
- Why do we offer this program instead of partnering with another organization?
How it works
Imagine a donor asking, “Why are you expanding your food pantry?”
The first answer might be, “Because demand has increased.”
Why has demand increased?
“Because more working families are seeking assistance.”
Why are more working families struggling?
“Because housing and childcare costs have risen faster than wages.”
Why does that matter to our mission?
“Because our mission is family stability, not simply food distribution.”
Why does that change our approach?
“Because it tells us we need to expand financial coaching and strengthen community partnerships in addition to providing food.”
What we learned from the simple why
The conversation began with a larger food pantry. It ended with a clearer understanding of the community’s changing needs. That’s the power of layering questions. Each answer leads naturally to the next why, uncovering assumptions, testing strategy, and revealing opportunities that might otherwise remain hidden.
I’ve learned that organizations willing to engage in these deeper conversations often discover insights they had never thought about. Sometimes they uncover strengths they had overlooked. Other times they identify gaps that had been hidden beneath years of “that’s the way we’ve always done it.”
Whether the questions come from a first-time donor, a new board member, a college student, or a consultant, they deserve more than a quick answer. They deserve thoughtful reflection.
So the next time someone asks, “Why” don’t rush to respond.
Write the question down.
Sit with it.
Then ask the next question.
You may discover that the conversation changes not only their understanding of your organization-but yours as well.
And yes, my professor did apologize. He arrived at the student center only moments after the rest of the class. He remains one of my all-time favorite professors.
Apparently, I recovered.
But I never stopped asking questions. I just learned that the most valuable answers often come from the question that follows the first one.
Read it. Share it. Pass it on.
If you have a question or a topic you would like to see explored in future posts, please reach out to me.
The Gift of Giving by Dawn Franks is a practical, inspiring guide to living with purpose through generosity. Filled with real-world wisdom, it encourages readers to make a meaningful difference and leave a lasting legacy. Click to learn more about The Gift of Giving.
Website: www.dawnfranks.com
Email: dawn@dawnfranks.com
Facebook: https://www.facebook.com/dawfranks/
LinkedIn: www.linkedin.com/in/dawn-franks-strategicsolutions/
