---
title: "Discovery Questions"
description: "Powerful questions organized by purpose. Draw from these throughout discovery sessions."
type: skill
canonical_url: https://claudary.paisolsolutions.com/skills/discovery-questions
source: "Claudary"
difficulty: intermediate
author: "Claude Code Knowledge Pack"
date: 2026-07-10T11:19:54.380Z
license: CC-BY-4.0
attribution: "Discovery Questions — Claudary (https://claudary.paisolsolutions.com/skills/discovery-questions)"
---

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

## Overview

# Discovery Questions

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

---

## 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?

---

## 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?

---

## 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?

---

## 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?

---

## 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]?

---

## 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?

---

## 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?

---

## 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?

---

## Question Selection Guide

| Situation                       | Question Category                         |
| ------------------------------- | ----------------------------------------- |
| User has lots of content        | Surface Hidden Content                    |
| User dismisses their expertise  | Reveal Tacit Expertise + Build Confidence |
| Evaluating a specific candidate | Test Ebook Potential                      |
| Candidate seems weak            | Challenge Weak Ideas                      |
| User in unique position         | Translation Bridges                       |
| Idea needs edge                 | Contrarian Angles                         |
| Transformation is unclear       | Spot Transformation                       |
| User lacks confidence           | Build Confidence                          |

---

## 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.

---

Source: [Claudary](https://claudary.paisolsolutions.com/skills/discovery-questions) · https://claudary.paisolsolutions.com