Ask about the last ten leads, not opinions about software.

Opening

• “I’m not trying to sell you software yet. I’m trying to understand how quote requests actually move through your business.”
• “Think about the last 10 leads or quote requests you received. I want the real workflow, not the ideal one.”

Lead flow and response

• “How many quote requests or leads did you get last week?”
• “Where did they come from: website, phone, Google LSA, Google Ads, Facebook, Angi/Thumbtack/HomeAdvisor, referrals, yard signs, repeat customers?”
• “How fast did you respond to the last 10?”
• “How many went unanswered for more than an hour? More than a day?”
• “How often do homeowners tell you they already got another bid or booked someone else?”
• “Do you track lead source, close rate, and missed leads anywhere?”

Quote workflow

• “What information do you need before you can give a useful preliminary price?”
• “What can be estimated from address/satellite/homeowner inputs?”
• “What always requires a site visit?”
• “How do you measure today?”
• “How do you price: per foot, materials, gates, height, style, demo, minimums, travel, margin rules?”
• “Show me, if you can, a recent quote and how it was built.”
• “How long from first contact to quote sent?”
• “Where do quotes get stuck?”

Current software and process

• “What tools do you use now: ArcSite, QuoteIQ, Jobber, Housecall Pro, Houzz Pro, Buildertrend, JobNimbus, ServiceTitan, Fence Cloud, Builder Prime, ProDBX, Elite Technique, QuickBooks, spreadsheets, paper?”
• “What do you like and hate about that stack?”
• “Does anything already send automatic follow-ups?”
• “Does anyone check whether quotes were followed up?”
• “Who owns this process: owner, office manager, estimator, salesperson, crew lead?”

Pain and economics

• “What is an average job worth for you by fence type?”
• “What gross margin do you target?”
• “How many extra jobs per month would make a quoting/follow-up tool obviously worth it?”
• “What is one missed lead worth?”
• “Do you pay for leads or ads? Roughly how much per month?”
• “If this helped you book one incremental job per month (hypothesis to validate), what would it be worth?”
• “Would you rather pay monthly software, a setup fee, per qualified quote, or a managed monthly retainer?”

Trust boundaries

• “Would you let software send an instant preliminary range to a homeowner?”
• “Would you let a managed quote desk respond to leads using approved scripts?”
• “What must you personally approve before it goes to the homeowner?”
• “What would make this untrustworthy?”
• “What is a quote mistake that would actually cost you money?”

Pilot close

• “If we set this up with your real pricing rules and approval gates, would you run a 30-day pilot with real leads?”
• “What would the pilot need to prove for you to keep paying?”
• “Who else would need to approve?”
• “Can we review five historical leads and generate sample quote packets together?”

Adjacent vertical variant

• Replace fence-specific questions with the unit of scope:
• Landscaping/lawn: turf sq ft, beds, mulch, route density, recurring contract value.
• Concrete: sq ft, thickness, demo, base, access, slope/drainage, reinforcement.
• Exterior painting/siding/windows: wall area, windows/doors, surface condition, prep, product choice.
• Decks/outdoor living: deck size, material, footing, railings, stairs, permits, design complexity.

Business preference questions

• Do you want to run a service-heavy company for the first 6–12 months if it teaches the product and creates revenue?
• Would you personally do onboarding calls, price-book setup, and quote review with the first 5–10 contractors?
• Are you comfortable with FenceQuote touching homeowner communication, or should it stay contractor-internal?
• Do you want a low-touch SaaS business even if it grows more slowly, or a messier service business that may learn faster?
• What would make this business worth it to you: subscriptions, revenue share, agency-like cash flow, eventual SaaS multiple, or trade-specific operating company?

Customer validation questions

Ask fence contractors:

• How many quote requests/leads do you get per week?
• Where do they come from: website, phone, Google LSA, Angi/Thumbtack, referrals, yard signs?
• How fast do you usually respond?
• How many leads go unanswered or delayed because you are on a job?
• How long does it take to send a quote after first contact?
• How often do homeowners ask for a quote before an onsite visit?
• How many bids do you think homeowners are comparing you against?
• What software do you already use?
• What happens after you send a quote? Do you follow up systematically?
• If someone could set up your quote flow and handle first response/follow-up with your approval, what would that be worth?

Disqualifying answers

Bad signs for Path B:

• “We already respond instantly and follow up every quote.”
• “Our pricing is too custom to estimate from satellite/inputs.”
• “We would never let anyone else message homeowners.”
• “We only want software under $50/mo.”
• “Lead volume is low; this is not a real pain.”

Bad signs for Path A:

• “Can you set it up for me?” from almost everyone.
• “I do not know how to price that in the system.”
• “My web guy would have to do it.”
• “We tried CRMs; no one kept up with them.”
• “We get leads, but I forget to follow up.”