Discovery Questions

Powerful questions organized by purpose. Draw from these throughout discovery sessions.

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Questions That Surface Hidden Content

Use when mining existing content for ebook candidates.

Finding patterns:

• What topics keep appearing across your content?
• Looking at your last 20 posts, what themes emerge?
• What content have you created multiple times in different forms?
• Where do you find yourself going deeper than others?

Finding performance signals:

• What content performed surprisingly well? Why do you think?
• What generated the most comments or questions?
• What do people share most often?
• What content brought new audience members?

Finding gaps:

• What did you start but never finish?
• What series did you plan but never complete?
• What questions in comments have you not fully addressed?
• What topic do you reference without fully explaining?

Finding gold in the archive:

• What old content still gets traffic?
• What would you write differently now?
• What evergreen content could be expanded?
• What content are you most proud of?

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Questions That Reveal Tacit Expertise

Use when helping users see knowledge they don't recognize as valuable.

The obvious flip:

• What do you know that feels so obvious you'd never think to teach it?
• What do you take for granted that beginners struggle with?
• What can you do without thinking that others find hard?
• What's intuitive to you that requires explanation for others?

The teaching lens:

• What do you find yourself explaining over and over?
• What questions do people bring you?
• What do people thank you for helping them understand?
• If someone shadowed you for a week, what would surprise them about how you work?

The journey lens:

• What do you know now that you wish you knew when you started?
• What was the hardest thing to learn in your field?
• What breakthrough changed how you thought about your work?
• What would you tell your younger self?

The frustration lens:

• What do people consistently get wrong in your field?
• What advice frustrates you when you hear it repeated?
• What do beginners waste time on that you've learned to skip?
• What "common wisdom" is actually wrong?

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Questions That Test Ebook Potential

Use when evaluating whether an idea is ebook-worthy.

The scope test:

• How many chapters does this naturally have?
• Can you describe it in one sentence?
• What's in and what's out?
• Could this be covered in a blog post, or is it genuinely bigger?

The transformation test:

• What can someone DO after reading this that they couldn't before?
• What's the before state? What's the after state?
• How would you know the ebook worked?
• What problem does this solve?

The reader test:

• Who specifically is this for?
• Can you picture one person who would buy this?
• What would they search for that would lead them here?
• Why would they care?

The viability test:

• Would someone pay $15 for this?
• What's the alternative if this ebook doesn't exist?
• What makes your take unique?
• Does this exist already? How would yours be different?

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Questions That Find Contrarian Angles

Use when exploring unconventional perspectives.

Direct contrarian questions:

• What do you believe that most people in your field get wrong?
• What conventional wisdom do you push back against?
• Where do you disagree with respected voices?
• What would your controversial take be?

The enemy frame:

• What bad advice is widely repeated?
• What common practice actually hurts people?
• What "best practice" isn't actually best?
• What trend concerns you?

The experience frame:

• What have you learned through experience that contradicts the books?
• What works for you that "shouldn't" work according to experts?
• What failure taught you something the mainstream misses?
• What do you do differently than you're "supposed to"?

The "actually" frame:

• What's actually true about your field that people don't realize?
• What looks simple but is actually complex (or vice versa)?
• What matters that people ignore?
• What doesn't matter that people obsess over?

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Questions That Uncover Translation Bridges

Use when exploring unique intersections.

The worlds question:

• What different worlds do you inhabit?
• What communities are you part of that don't normally overlap?
• What seemingly unrelated areas of expertise do you have?
• What unusual combination of experiences do you bring?

The translation question:

• What do you find yourself explaining to one group about another?
• What do [Group A] not understand about [Group B] that you could bridge?
• What insight from one field applies to another?
• What language do you translate between domains?

The intersection question:

• What unique perspective comes from your combination of experiences?
• What do you see that others in just one field would miss?
• What patterns do you notice across domains?
• What would [Field A] learn from [Field B]?

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Questions That Spot Transformation

Use when clarifying what changes for the reader.

Before/after questions:

• Where is your reader when they start?
• Where do you want them to be when they finish?
• What's different after reading this?
• What can they do, think, or feel differently?

The observable change question:

• If I watched your reader for a week after finishing, what would I see differently?
• What behavior changes?
• What decisions would they make differently?
• What would they stop doing? Start doing?

The "so what" question:

• Why does this matter?
• What happens if they don't learn this?
• What does this enable for them?
• What's the cost of not knowing this?

The achievable change question:

• Is this transformation realistic from an ebook?
• Can someone really get there from 10-20K words?
• What's the smallest meaningful transformation?
• What transformation is ebook-sized?

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Questions That Challenge Weak Ideas

Use when pressure-testing candidates.

The hard questions:

• Why would someone pay for this?
• What makes you qualified to write this?
• Who else has written about this, and how is yours different?
• Is this genuinely ebook-sized, or are you forcing the format?

The audience reality check:

• Where will readers find this?
• Who is actually searching for this?
• What problem are they actively trying to solve?
• Is there evidence of demand, or just assumption?

The honesty questions:

• What's the weakest part of this idea?
• What would make you abandon this candidate?
• What would need to be true for this to succeed?
• Are you excited about this, or do you feel like you should be?

The alternatives question:

• What if this isn't an ebook? What else could it be?
• Is there a better format for this idea?
• Could this be smaller (blog post)? Bigger (book)? Different (course)?
• Are you wedded to ebook format for the right reasons?

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Questions That Build Confidence

Use when users doubt their value.

External validation questions:

• What do people come to you for advice on?
• What have colleagues asked you to teach them?
• What have you been thanked for helping with?
• What problems do people bring you?

Expertise reframe questions:

• How long have you been doing this?
• How many times have you done this?
• What do you know after 5 years that you didn't know day one?
• What's the learning curve you've already climbed?

Value reframe questions:

• If you could save someone 6 months of struggle, what would you teach them?
• What mistake did you make that others could avoid?
• What took you years to learn that you could shortcut for someone?
• What do you wish someone had told you?

Permission questions:

• Who else is writing about this who doesn't know more than you?
• What makes someone "qualified" to write an ebook?
• What would it take for you to feel ready?
• What if you're already ready and just don't know it?

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Question Selection Guide

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Using Questions Effectively

One at a time: Never barrage with multiple questions. Ask one, listen, follow up.

Listen for signals: The answer often contains the next question. Follow the energy.

Go deeper: Surface answers need follow-up. "Tell me more about that." "What specifically?"

Circle back: Early answers often become relevant later. "Earlier you mentioned... how does that connect?"

Productive silence: After asking, wait. Don't rush to fill silence.