Most discovery calls are boring. You ask about target audiences, pain points, and USPs. The client gives you the same sanitized answers they’ve given everyone else. You walk away with nothing you couldn’t have found on their website.
Here are better questions—the kind that surface real insight, uncover hidden stories, and give you material you can actually use.
Questions That Reveal Voice & Culture
1. What’s the last thing someone at your company got genuinely excited about that had nothing to do with closing a deal?
This tells you what they actually value versus what they say they value.
2. If your CEO had to explain what you do at a backyard BBQ, what would they say?
The gap between this and your official messaging is where your real voice lives.
3. What’s something your team argues about that customers would find boring but you find fascinating?
This is where your expertise—and your content differentiation—lives.
4. What do new hires always get wrong about your business in their first month?
Common misconceptions are content gold. They’re the gaps your content should fill.
5. What’s a question your sales team is tired of answering?
That’s your next blog series, video explainer, or FAQ page.
Questions That Uncover Real Differentiation
6. What do you do that your competitors think is a waste of time?
This often reveals your actual competitive advantage—the thing you believe in that others don’t.
7. What would you never outsource, even if it saved you money?
This tells you what’s sacred. What defines quality for them. What they’d lose their identity without.
8. If you could only keep three customers and had to fire the rest, who would you keep and why?
Forget personas. This tells you who they actually want to work with.
9. What’s the weirdest compliment a customer has ever given you?
Weird compliments often point to unexpected value. They reveal what you’re known for beyond your marketing.
10. What do your best customers understand that your worst customers don’t?
This is the insight gap your content needs to bridge.
Questions That Surface Stories
11. Tell me about a project that almost failed but ended up being your best work.
Struggle stories resonate. They’re more believable and more memorable than success porn.
12. What’s a mistake you made early on that you still think about?
Vulnerability builds trust. These stories make great founder content.
13. What’s something you built that nobody asked for but everyone ended up needing?
This is innovation narrative. It shows vision, not just execution.
14. Who’s a customer that changed how you think about your own product?
Customer stories are always better than product pitches.
15. What’s the smallest detail in your process that clients don’t notice but you obsess over?
Obsession = expertise. This is content that shows craftsmanship.
Questions That Expose Market Position
16. What do people assume about your industry that’s completely wrong?
Myth-busting content always performs. It’s contrarian without being clickbait.
17. What trend is everyone chasing that you think is overrated?
Taking a stance builds authority. Agreeing with everyone builds nothing.
18. What would your industry look like if you ran it for a year?
This reveals vision. It’s also great fodder for thought leadership.
19. Who in your space is doing something you respect, even if they’re not a direct competitor?
Generous perspectives build credibility. Plus, it surfaces adjacent content to study.
20. If you could uninvent one thing in your industry, what would it be?
This is your contrarian POV. Your “here’s what’s broken” platform.
Questions About Their Audience
21. What do your customers Google right before they find you?
This is SEO strategy, voice of customer research, and content calendar planning in one question.
22. What keeps your customers up at night that has nothing to do with your product?
Empathy starts here. Content that acknowledges the full picture earns trust.
23. What’s something your customers do after buying from you that surprises you?
Unexpected use cases = unexpected content angles.
24. What conversation happens in your customers’ world that you wish you were part of?
This reveals where the real authority is built—and where you’re not showing up yet.
25. If your customers had a secret Slack channel, what would they be complaining about?
This surfaces pain points they won’t say on a sales call but will respond to in content.
Questions That Reveal Content Gaps
26. What’s the last piece of content (yours or someone else’s) that made you say, “I wish we’d made that”?
Envy is a roadmap. It tells you what resonates and what’s missing.
27. What do your customers already know that you keep explaining anyway?
Stop wasting content on stuff they’ve already figured out. Move upstream.
28. What’s a question you want customers to ask but they never do?
If they’re not asking, it’s because you haven’t framed it right. Yet.
29. What internal document would your customers kill to read?
Turn internal knowledge into external content. It’s already written.
30. What industry publication or newsletter does your team read religiously?
Study what’s working in adjacent spaces. Borrow structure, not content.
The One Question That Changes Everything
31. If content marketing worked perfectly for you, what would change about your business in six months?
This isn’t about tactics. It’s about outcomes. And outcomes tell you what actually matters.
If they say “we’d get better leads,” dig deeper. Better how? From where? Saying what?
If they say “we’d be known for X,” now you have a positioning strategy, not just a content plan.
If they say “our sales team would stop explaining the same three things,” congratulations—you just found your content roadmap.
How to Use These Questions
Don’t ask all 31. Pick five that feel most relevant to the client and the engagement.
Ask them after the standard discovery stuff. Once the surface-level answers are out of the way, people relax. That’s when the good stuff comes out.
And here’s the key: Don’t just collect answers. Listen for patterns.
Most marketing discovery is about checking boxes. These questions are about finding the truth.
And the truth is always more interesting than the pitch deck.