Discovery Question Generator

Uncover the real problems businesses are willing to pay $15K+ to solve.

What This Skill Does

You input a business type (dentist, gym, contractor, restaurant, etc.), and this skill generates 30-50 strategic discovery questions organized by category to help you:

✅ Uncover Hidden Pain Points - Find problems they didn't know could be solved ✅ Understand Current Workflows - Map their actual daily operations ✅ Identify Tech Stack Gaps - Discover what tools they're struggling with ✅ Quantify Cost of Problem - Calculate hours wasted, revenue lost ✅ Qualify Budget & Authority - Ensure they can afford and approve $15K+ ✅ Build Trust & Credibility - Sound like an expert who understands their business

Who This Is For

Software Tailors who need to:

• Conduct effective discovery calls with potential clients
• Find the $15K opportunities hidden in "we need help with scheduling"
• Ask questions that reveal the real problem, not surface symptoms
• Qualify whether a lead is worth pursuing
• Position themselves as strategic advisors, not just code monkeys

How To Use This Skill

Input Format

Simply provide:

1. Business Type - Industry or niche (e.g., "fire inspection company", "personal training gym", "dental practice")
2. Optional Context - Any specific pain points you already know about

Example Input:

Business Type: Fire inspection company
Context: They mentioned they're using Excel to track inspections and losing track of which buildings are due for reinspection.

Output Format

The skill generates organized question sets like this:

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Discovery Questions for: Fire Inspection Company

Category 1: Current Workflow & Pain Points (10-12 questions)

Purpose: Understand their day-to-day operations and identify friction points

1. Walk me through a typical day for one of your inspectors from start to finish.

   • Why this works: Gets them narrating their workflow naturally, revealing inefficiencies they've normalized

2. How do you currently assign inspections to your field team?

   • Listen for: Manual processes, phone calls, group chats, spreadsheet updates

3. What happens when an inspector arrives on-site? What's their first step?

   • Listen for: Paper forms, tablet confusion, missing information

4. How long does it typically take an inspector to complete an inspection report after finishing on-site?

   • Listen for: "2-3 hours of paperwork", "they do it at home after dinner"

5. Tell me about the last time something went wrong with an inspection - what happened?

   • Listen for: Missed inspections, lost paperwork, angry clients

6. How do you know which buildings are due for their next inspection?

   • Listen for: "We check Excel every Monday", "Sometimes we forget and clients call us"

7. What's your process when a client calls asking for their inspection report?

   • Listen for: Time wasted searching files, inconsistent report formats

8. How many hours per week would you estimate your team spends on paperwork vs. actual inspections?

   • Listen for: Shocking ratios like 30% admin work

9. What do your inspectors complain about most?

   • Listen for: Real frustrations from the people doing the work

10. If you could wave a magic wand and fix one thing about how inspections are managed, what would it be?

    • Listen for: Their dream solution - often reveals the highest-value feature

Category 2: Data & Documentation (8-10 questions)

Purpose: Understand how they store, access, and share information

11. Where do you currently store completed inspection reports?

    • Listen for: Dropbox folders, email attachments, physical filing cabinets

12. How do clients receive their inspection reports?

    • Listen for: Email PDFs manually, clients have to call and request them

13. Can you pull up a report from 6 months ago in less than 2 minutes right now?

    • Listen for: "Uh, probably not" = pain point

14. Do you track inspection history for each building? How?

    • Listen for: Excel, handwritten notes, "we try to remember"

15. What information do you need to reference from past inspections when scheduling new ones?

    • Listen for: Data relationships they need but don't have

16. How do you handle photos from inspections?

    • Listen for: Inspector cell phones, lost photos, inconsistent formats

17. Have you ever had a compliance audit? How hard was it to pull together the required documentation?

    • Listen for: Panic, scrambling, "took us 3 days"

18. Do multiple people need access to the same inspection data?

    • Listen for: Collaboration needs, permission requirements

Category 3: Scheduling & Operations (8-10 questions)

Purpose: Identify bottlenecks in planning and coordination

19. How far in advance do you typically schedule inspections?

    • Listen for: Chaos vs. planning, reactive vs. proactive

20. What happens when an inspector calls in sick and has 5 inspections scheduled?

    • Listen for: Panic, manual rescheduling nightmare

21. How do you balance emergency inspections vs. routine scheduled ones?

    • Listen for: Prioritization chaos

22. Do you ever have inspectors driving across town multiple times because inspections weren't grouped by location?

    • Listen for: Wasted drive time, fuel costs

23. How much time does your office staff spend on the phone scheduling and rescheduling inspections?

    • Listen for: Quantifiable hours = cost savings justification

24. Can your inspectors see their schedule from their phone?

    • Listen for: "No, we text them every morning" = opportunity

25. How do you know if an inspection is running late or was completed early?

    • Listen for: Lack of real-time visibility

26. What's your process for annual re-inspections? How do you remember which buildings need them?

    • Listen for: Manual tracking, missed revenue opportunities

Category 4: Client Communication (6-8 questions)

Purpose: Discover customer service pain points

27. How often do clients call asking about inspection status or reports?

    • Listen for: Frequent interruptions = opportunity for client portal

28. What do clients complain about most regarding your service?

    • Listen for: Slow reports, lack of transparency, hard to schedule

29. How do you notify clients when their inspection is complete?

    • Listen for: Manual phone calls/emails = automation opportunity

30. Do clients ever need to reschedule? How does that process work?

    • Listen for: Back-and-forth phone tag

31. Have you ever lost a client because of administrative issues (not the quality of inspections)?

    • Listen for: Revenue lost due to poor process = ROI justification

Category 5: Growth & Scalability (6-8 questions)

Purpose: Understand if current process blocks growth

32. How many inspections do you currently handle per month?

    • Listen for: Baseline volume

33. If you wanted to double your inspection volume, what would break first in your current system?

    • Listen for: Scalability concerns

34. Have you turned down work because you couldn't handle the volume?

    • Listen for: Lost revenue = massive opportunity cost

35. How many inspectors do you have? Do you plan to hire more?

    • Listen for: Growth plans = urgent need for better systems

36. What prevents you from taking on more clients right now?

    • Listen for: Administrative bottlenecks, not inspection capacity

37. If you had better systems, how much more revenue could you realistically generate per year?

    • Listen for: ROI numbers for your pitch

Category 6: Budget & Decision Making (5-7 questions)

Purpose: Qualify if they can afford and approve $15K+ solution

38. What's your annual revenue, roughly?

    • Listen for: Size of business = ability to invest

39. Have you invested in custom software or tools for your business before?

    • Listen for: Comfort with technology investment

40. What do you currently spend on software/tools per month?

    • Listen for: Existing budget for solutions

41. If I could show you a solution that saves your team 15 hours per week, what would that be worth to you?

    • Listen for: Value-based thinking vs. cost-based thinking

42. Who else would need to approve a decision like this?

    • Listen for: Decision-making authority, multiple stakeholders

43. What would need to be true for you to invest in a custom solution in the next 30-60 days?

    • Listen for: Urgency, readiness to buy

44. If you don't fix this problem, what happens in 6 months?

    • Listen for: Cost of inaction = urgency

Category 7: Technical Environment (4-6 questions)

Purpose: Understand their current tech stack and constraints

45. What devices do your inspectors use in the field? (iPhones, Android, tablets?)

    • Listen for: Technical requirements

46. Do you have a company website? Who manages it?

    • Listen for: Technical comfort level

47. Are there any systems you need this to integrate with? (QuickBooks, Stripe, etc.)

    • Listen for: Integration requirements

48. How tech-savvy is your team? Do they pick up new tools easily?

    • Listen for: User experience priorities

49. Do you have any compliance requirements for data storage or security?

    • Listen for: Regulatory constraints

Category 8: Vision & Desired Outcomes (3-5 questions)

Purpose: Understand their ideal future state

50. If we build this perfectly, what does success look like 6 months from now?

    • Listen for: Concrete metrics (hours saved, revenue increased)

51. What would your inspectors say if this worked exactly as you hoped?

    • Listen for: User satisfaction goals

52. What's the one metric you'd track to know this was worth the investment?

    • Listen for: How they'll measure ROI

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How to Use These Questions

During the Discovery Call

Don't ask all 50 questions - That's overwhelming. Instead:

1. Start with Workflow questions (Category 1) to get them talking naturally
2. Follow the conversation - Let their answers guide which categories to explore
3. Dig deeper when they mention pain points: "Tell me more about that", "How often does that happen?"
4. Listen for emotion - Frustration, anger, stress = expensive problems they'll pay to solve
5. Quantify everything - "How many hours?", "How much does that cost?", "How often?"

Red Flags (Questions that disqualify prospects)

• Annual revenue under $500K → Likely can't afford $15K
• "We need this to be under $2K" → Wrong budget expectation
• "I need to think about it for a few months" → No urgency
• "We're just exploring options" → Tire-kicker, not ready to buy

Green Flags (Questions that indicate ready buyers)

• "How soon can you start?" → Urgency
• "What if we wanted to add [feature]?" → Thinking about expansion
• "We're currently wasting 20 hours a week on this" → Quantified pain
• "I can make this decision myself" → Authority

Question Frameworks

The Time Waste Question

"How many hours per week does your team spend on [manual process]?"

• Reveals cost of problem
• Creates urgency
• Builds ROI justification

The Magic Wand Question

"If you could wave a magic wand and fix one thing, what would it be?"

• Gets to core desire
• Reveals highest-value feature
• Opens up dream scenario conversation

The Failure Story Question

"Tell me about the last time [process] went wrong. What happened?"

• Gets emotional response
• Reveals real-world consequences
• Creates fear of inaction

The Growth Blocker Question

"If you wanted to double your business, what would break first?"

• Reveals scalability needs
• Creates vision of future growth
• Justifies investment now

The Cost of Inaction Question

"If you don't solve this problem, what happens in 6 months?"

• Creates urgency
• Reveals true cost
• Motivates decision

Adapting Questions to Different Industries

This skill generates industry-specific questions, but the underlying frameworks apply across all businesses:

Service Businesses (HVAC, Plumbing, Inspections)

• Focus on: Scheduling, dispatch, route optimization, client communication

Retail/Inventory (Shops, Warehouses)

• Focus on: Inventory tracking, supplier management, sales reporting

Professional Services (Law, Accounting, Consulting)

• Focus on: Client management, time tracking, document organization

Healthcare (Clinics, Physical Therapy)

• Focus on: Patient scheduling, records management, billing

Construction/Trades (Contractors, Builders)

• Focus on: Job tracking, material management, crew scheduling

Best Practices

DO:

• ✅ Ask open-ended questions that get them talking
• ✅ Listen more than you talk (80/20 rule)
• ✅ Take detailed notes on pain points
• ✅ Quantify everything in hours and dollars
• ✅ Ask "Why?" and "Tell me more" to dig deeper
• ✅ Let silence happen - don't fill every pause

DON'T:

• ❌ Pitch solutions before understanding the problem
• ❌ Ask yes/no questions - they shut down conversation
• ❌ Lead the witness ("Wouldn't it be great if...")
• ❌ Skip budget qualification questions
• ❌ Assume you understand without asking

After the Discovery Call

Synthesize Findings

1. List top 3-5 pain points they mentioned
2. Calculate cost of problems (hours × hourly rate)
3. Identify must-have features vs. nice-to-haves
4. Draft software blueprint using the Business Problem to Blueprint skill
5. Prepare proposal with ROI calculation

Follow-Up

Send a summary email:

• Thank them for their time
• Recap the problems you heard
• Preview your solution approach
• Schedule next call to present proposal

Remember

The goal of discovery questions isn't to interrogate - it's to understand their world deeply so you can build software that solves their real problems. The best software tailors ask questions that make prospects say: "Wow, you really get our business."

Good questions lead to great software. Great software gets $15K+ price tags.