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Better Questions
What makes a good question?
Jaime Solis
19 Sep
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“Judge a man by his questions rather than his answers.” — Voltaire
The Red Thread This Week
Better Questions
If you’re anything like me, you’ve spent a lot of time trying to have the right answers for people.
Trying hard to deliver “right” in slides and presentations, in content, and on behalf of audiences and customers.
But in the push to deliver right answers, I know I’ve been guilty of completely ignoring a key part of actually being valuable:
Real value, and 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.
For example, “must listen” podcast episodes don't go viral ONLY because the guest is famous.
More often than not, they spread because they ask questions no one else had the curiosity or courage to ask.
Not "Tell me about your latest project," but "When was the last time you doubted your own advice?"
But beware…we have a tendency to treat questions like weapons instead of invitations.
If you've ever sat in a brainstorm that felt more like a debate team showdown, or seen a Q&A take an uncomfortable turn after someone asked a performative "question," you've felt the problem.
Too often, questions are veiled lectures, rhetorical traps, or insecure bids for validation.
In that environment, curiosity dies. Creativity dries up. People stop sharing their best.
This week's Red Thread is about the art of asking better questions.
The kind that build trust, spark insight, and open doors you didn't even know existed.
~ Jaime
🔑 The Unlock
How to Ask Better Questions
A great question is a generous, precise tool to help move your work forward. Here's how to shift your approach:
1️⃣ In the Moment, Drink the Kool-Aid
Great questions come from a place of genuine curiosity, where you're on the same journey as the person answering. Not trying to trap them or show how smart you are.
Instead of: "Don't you think this approach is pretty risky?"
Try: "What risks are you most concerned about with this approach?"
2️⃣ Ask for Stories, Not Opinions
Stories reveal nuance and truth. Opinions reveal bias.
Instead of: "Would you use this product?"
Try: "What did you do the last time you had this problem?"
3️⃣ Question Your Own Assumptions
The most powerful questions challenge what you think you already know.
Instead of: "How do we convince more people that our product works?"
Try: "What emotional itch does our product actually scratch for people?"
4️⃣ Give Permission for Vulnerability
The questions that go viral, build trust, and spark breakthrough thinking give people permission to be honest.
Instead of: "Tell me about your success."
Try: "Has there ever been a time where you might have felt like a fraud?"
📌 Remember: Better questions don’t just collect information. They give you a better shot at building the thing you actually came here to build.
💡 Creative Edge
Questions Shape Culture
The questions that make an impact, build relationships, and change companies all share one thing: they give people the air cover to say something they’ve never said before.
Podcast interviews that stand out don’t ask, “Tell me about your new book.” They ask, “What part of your creative process feels really scary, or unreliable?”
Smart 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?” They start with, “How sure are we of the desires, hopes, and fears of our customers?”
When someone asks you a question and you think, “No one’s ever asked me that before,” something shifts.
You feel seen. Safe enough to share your real answer, not your safest answer.
Great builders and leaders do this on purpose.
📌 Mindset shift: Good questions are permission slips for vulnerability. They create conditions for people to share even more value than you may have expected.
🎲 Prompt Playground
Your Question Upgrade System
Use this prompt to prep for your next important conversation:
Copy + paste the prompt below into your AI tool of choice (ChatGPT, Claude, Gemini, etc.) and fill in the blanks.
Prompt:
I have an important conversation coming up and I want to ask better questions. Ones that discover rather than prove, and invite rather than interrogate.
My situation:
Type of conversation: [meeting, interview, pitch, etc.]
Who I'm talking to: [describe the person/people]
What I'm hoping to accomplish: [your real goal, not just the surface one]
What I think I already know: [your assumptions about the situation]
Questions I was planning to ask: [list your current questions]
Help me upgrade my approach:
First, rewrite 3 of my weakest questions to be more curious and inviting.
Second, suggest 3 completely new questions that might challenge my assumptions or give the other person permission to be more honest.
Third, create one "game-changing question" that could shift the entire conversation from competition to collaboration.
Finally, give me one "door opener" question. Something unexpected that could reveal possibilities neither of us has considered.
Make sure all questions come from a place of genuine enrollment and respect, not interrogation.
✅ Bonus Prompt:
"What question am I afraid to ask in this conversation, and how could I ask it in a way that builds trust rather than creates defensiveness?"
📡 Industry Pulse
Snap's "Crucible Moment" – CEO’s 14-year letter admits being squeezed between tech giants and nimble startups — Snap Newsroom
YouTube's Creator Evolution – New report on how emerging creators reshape content — YouTube Trends
Human Connection Beats AI Marketing – Relationship marketing becomes the new competitive moat — Forbes
Coda Music Ditches Algorithms – New streaming service chooses human curation over AI — Music Business Worldwide
Marketers from Sephora, Duolingo, and more share how they’re adjusting their approach for 2026 — Marketing Brew
🛠️ Creator Tools
Summate.io — Summarize the content you follow; newsletters, YT channels, RSS, in to a beautiful daily digest.
Elsa AI — AI-powered marketing platform for rich ICPs, strategy, and content.
Hedy — Your personal conversation coach helping you think faster and communicate better, in real time.
💼 Open Opportunities
Head of Business Development – EVEN (remote) View Role →
Video & Sound Engineer/Post Production Manager – Quill (remote) View Role →
Your next move in Music
Explore the MBW Job Board →
Crack into Podcasting
Check out the Sounds Profitable Job Board →
📌 Know someone looking? Forward this to them!
⚡ Your Next Move
JMedia is my creative strategy shop, where I help leaders and creators turn their ideas into media that builds audience.
Here are a few ways we can work together when you’re ready:
🗓️ Get 1:1 Support from Me: Need a thought partner to help shape what's next for your project or team? Let’s talk.
🎙️ Audit Your Podcast: Get pro-level eyes on your podcast without hiring a full-time producer.
🚀 Speaking Engagements & Workshops: Looking for a speaker for your next live (or virtual) event? Or someone to lead your next strategic workshop? Drop me a note.
Thanks for spending time with Red Threads this week, I’m glad you’re here :)
~ Jaime