We spend so much time trying to have the right answers—for our pitch decks, our content, our audiences–that we’ve come to miss the point. The real leverage comes from asking the right questions.
A good question doesn’t just spark a conversation—it shapes the room, sets the tone, and opens a door that might’ve otherwise stayed locked.
So the question is: What makes a good question… good?
Most Questions Are Designed to Prove, Not Discover
If you’ve ever sat in a brainstorm that felt more like a debate team showdown—or watched a Q&A fall flat after someone asked a performative, status-signaling “question”—you’ve felt the problem.
Too many questions are veiled lectures, rhetorical traps, or insecure bids for validation. They’re not questions, they’re weapons. Or worse, empty calories.
And in that environment? Curiosity dies. Creativity dries up. And people stop sharing their best ideas.
Great Questions Are Invitations, Not Interrogations
The best questions don’t come from knowing the answer.
They come from wanting to.
They come from a place of genuine enrollment—where the person asking is on the same journey as the person answering. Not adversarial. Not performative. But aligned.
And they carry respect. Not deference or flattery, but a humble belief that the person you’re asking might know something that could make your work—or your thinking—better.
When you lead with curiosity and respect, something surprising happens: the person you’re asking often gives you more than an answer. They give you insight, candor, and sometimes… their best thinking.
The Questions That Shape Culture
- Podcast interviews that go viral don’t do so because the guest is famous. They hit because the host asked something no one else had the curiosity or courage to ask. Not “Tell me about your latest book,” but “When was the last time you doubted your own advice?”
- Great user research doesn’t ask “Would you use this?” It asks, “What did you do the last time you had this problem?”
- Legendary ad campaigns don’t start with “How do we sell more product?” They start with “What’s the emotional itch this product scratches that no one’s talking about?”
- Smart founders don’t ask investors, “Will you fund us?” They ask, “What red flags would keep you from funding someone like us?”
Each of these is a door opener. A trust builder. A permission slip for vulnerability, creativity, or truth.
Ask to Discover, Not to Display
Here’s the real work:
Don’t just try to look smart. Try to get smarter.
Don’t just ask questions that validate what you already believe. Ask the ones that might make you rethink it.
So here’s a challenge:
- Before your next pitch, interview, meeting, or collab—write down three questions that don’t have an obvious answer.
- Ask them from a position of enrollment and respect.
- See what opens up.
Because good questions don’t just get you better answers. They get you better conversations, better collaborators, and a better shot at building the thing you actually came here to build.
If you enjoyed this post, please consider sharing it with someone else–the buttons below can help.
Thank you!
