Are We Asking the Right Questions?

Last week, during a strategy session with a client and their board, I leaned back and said, “Wait, what if we’re solving for the wrong problem?”

That one question shifted the entire conversation.

In social impact work, we often focus on answers — the grant deadline, the fundraising target, the program we’re trying to design. But the quality of our answers will always depend on the quality of the questions we ask first.

Think about it:

• Instead of asking “How do we raise more money?” try “Why do people give to us in the first place?”

• Instead of “How do we get volunteers?” try “What would make someone proud to show up for us?”

• Instead of “How do we keep our board engaged?” try “What unique gifts does each board member want to bring to the table?”

• Instead of “How do we make this grant fit?” try “Does this grant truly fit us?”

Curiosity isn’t a distraction from strategy. It is a strategy.

Here’s a simple practice I use with clients (and myself when working on my own organizations): whenever you feel stuck, reframe your question with one of these starters:

• What if…

• Why does this matter…

• How might we…

• Who else could…

These aren’t tricks — they’re invitations to think differently. And when we think differently, we often find clarity, alignment, and energy we didn’t realize we had.

So the next time you feel pressure to deliver the “right” answer, pause. Ask: Am I asking the right question?

Because sometimes, the future of your strategy depends not on what you know — but on what you’re curious enough to ask.

I’d love to know: What’s one powerful question you’re holding right now? Drop me a note here to share, and I’ll get back to you with my thoughts.

Here’s to asking curious (and challenging) questions!