In my last column, I talked about asking why. Asking cage-rattling questions.

So here are some questions . . . questions to ask inside your organization. With staff and committees and the board.

What questions would you add?

  • To what degree is your organization passionate about philanthropy and fund development, not just the mission? How can you nurture this passion?
  • Why is best practice best practice in the field of fund development? Which best practice is appropriate for your organization now—and why?
  • What’s the difference between a right and a wrong decision, and a preferred decision for this time in your organization?
  • What can be outsourced without compromising that which you and your organization should know?
  • What modifications of best practice would you propose for the sector, and why?
  • What do you anticipate as next practice for the sector, and why?
  • To what degree do your donors really want a relationship with your organization? Why?
  • How do we meet the multiple interests, emotions, motivations of our volunteers / donors over time and as they change?
  • How do we incorporate noble failure to build an adaptive, effective organization?
  • How and why would we use noble failure as a learning strategy?
  • Why are cage-rattling questions so scary?

To what degree / in what way are / can / should nonprofits be stabilizing forces of culture—while also questioning the status quo?

  • What is development’s role in change and leadership?
  • To what degree—why and why not—are we (as individuals and organizations) prepared to change? To what degree—why and why not—are we prepared for conflict, chaos, etc. to make change?
  • How do we change potential energy into action?
  • How do we create cultures of accountability?
  • How do we change dysfunctional politeness / cultures of congeniality?
  • What are the core beliefs of your organization? Why?
  • What assumptions do you, your colleagues, and your organizations make that stop you from changing?
  • What are the barriers to participating in fund development? Why? How will you overcome these?
  • How can you value all donors regardless of gift size?
  • What is your organization’s culture, its personality? How does your organization’s culture affect behaviors and interactions?
  • How can we ease people’s fears, anxieties, and discomforts about money?
  • What changes must happen—and why—to nurture conversation in your organization?

These are just a few questions. Even the “how” questions here start with a “why.” Why would we want to ask these questions? Why are these questions important? Of course, the key is to compose good questions. Questions that are truly meaningful to your organization, questions that matter to your fund development program. Good questions are open enough to kindle thinking and useful conversation. (And too many people don’t want thinking and conversation. Are you one of those “because I said so” people? Is your boss? Or can you build personal and organizational comfort to ask the most essential and cage-rattling questions?) Here are some tips for creating your questions:

  • Avoid questions with yes/no answers. That’s a real showstopper. Those kinds of questions shut down thinking and stop conversation.
  • Create open-ended questions. They stimulate thinking and produce more conversation. And people think you actually care for their thoughts!
  • Focus on strategic issues with significant implications. Don’t waste time with frivolous questions that don’t really matter.
  • Remove bias in your questions. I struggle with that. Sometimes my own assumptions are embedded in the question. Not good—another showstopper.
  • Aim for simplicity. Okay. I struggle with that, too. Overly complex questions distract people from the question and the conversation.

And one final thought: Asking meaningful questions is not a rhetorical exercise, where the questioner is attempting to make a point. Nor is it an attempt at sabotage or a test. Instead, the best questioning is stubbornly open-ended. The best questioning promotes conversation, learning, innovation, and change. And the truly essential questions take you to a new place entirely.