--- name: discovery-question-generator description: Generate 30-50 deep discovery questions for any business type to uncover hidden pain points, workflow bottlenecks, and $15K+ software opportunities during client conversations. --- # 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: --- ## 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 --- ## 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.