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:

• Business Type - Industry or niche (e.g., "fire inspection company", "personal training gym", "dental practice")

• 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

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

How do you currently assign inspections to your field team?

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

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

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

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"

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

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

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"

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

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

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

• Listen for: Shocking ratios like 30% admin work

What do your inspectors complain about most?

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

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

Where do you currently store completed inspection reports?

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

How do clients receive their inspection reports?

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

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

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

Do you track inspection history for each building? How?

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

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

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

How do you handle photos from inspections?

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

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"

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

How far in advance do you typically schedule inspections?

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

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

• Listen for: Panic, manual rescheduling nightmare

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

• Listen for: Prioritization chaos

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

• Listen for: Wasted drive time, fuel costs

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

• Listen for: Quantifiable hours = cost savings justification

Can your inspectors see their schedule from their phone?

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

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

• Listen for: Lack of real-time visibility

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

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

• Listen for: Frequent interruptions = opportunity for client portal

What do clients complain about most regarding your service?

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

How do you notify clients when their inspection is complete?

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

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

• Listen for: Back-and-forth phone tag

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

How many inspections do you currently handle per month?

• Listen for: Baseline volume

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

• Listen for: Scalability concerns

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

• Listen for: Lost revenue = massive opportunity cost

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

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

What prevents you from taking on more clients right now?

• Listen for: Administrative bottlenecks, not inspection capacity

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

What's your annual revenue, roughly?

• Listen for: Size of business = ability to invest

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

• Listen for: Comfort with technology investment

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

• Listen for: Existing budget for solutions

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

Who else would need to approve a decision like this?

• Listen for: Decision-making authority, multiple stakeholders

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

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

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

• Listen for: Technical requirements

Do you have a company website? Who manages it?

• Listen for: Technical comfort level

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

• Listen for: Integration requirements

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

• Listen for: User experience priorities

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

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

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

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

• Listen for: User satisfaction goals

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:

• Start with Workflow questions (Category 1) to get them talking naturally

• Follow the conversation - Let their answers guide which categories to explore

• Dig deeper when they mention pain points: "Tell me more about that", "How often does that happen?"

• Listen for emotion - Frustration, anger, stress = expensive problems they'll pay to solve

• 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

• List top 3-5 pain points they mentioned

• Calculate cost of problems (hours × hourly rate)

• Identify must-have features vs. nice-to-haves

• Draft software blueprint using the Business Problem to Blueprint skill

• 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.