Opener
“We are not here to pitch anything. We are trying to understand how construction firms actually buy, keep, drop, and work around tools and outside help. I will ask for specific recent examples, names of roles, rough numbers, and stories from real projects; ranges are fine when exact figures are not available.”
Firm-insider route: 18 must-ask questions in order
- “Could you walk me through the last completed or current project and name every paid tool, service, spreadsheet, WhatsApp group, paper process, or person-owned tracker that mattered from tender to handover?”
- “For the paid tools in that walkthrough, what does each cost roughly, who pays, and is it contract, annual renewal, project charge, or month-to-month?”
- “Which of those tools did the team actually use last week, and which ones were present mostly because the firm says they should be?”
- “Tell me about the newest tool or service the firm paid for. Who introduced it, what was happening at the time, who signed, and what happened after rollout?”
- “Tell me about the last tool, pilot, subscription, or service the firm stopped paying for. What exactly killed it?”
- “What was the last demo or trial that looked interesting but did not become a purchase, and what happened after the demo?”
- “Which current tool has caused real operational trouble when it was unavailable, inaccurate, or delayed, and what broke first?”
- “Which critical work still runs through Excel, email, WhatsApp, paper, a whiteboard, or one person’s memory?”
- “What was the last time one of those informal workflows caused a delay, dispute, rework, missed claim, or awkward client conversation?”
- “For the last software or systems purchase, who owned the budget, who signed, who could block it, and what approval threshold mattered?”
- “What security, IT, data, client, or contractual review happened on that purchase, and how long did each step take?”
- “Which vendors, consultancies, funds, or technology firms have approached you in the last six months, and which conversations made it past a first call?”
- “Which AI tools, automations, scripts, or assistants have people actually used for firm work in the last 90 days?”
- “What did the firm pay for around AI or automation, who ran it, what data went into it, and what outputs were used or ignored?”
- “Tell me about the last outside consultant, developer, systems integrator, or freelancer the firm paid for non-core work. What was the scope, cost range, and outcome?”
- “Tell me about a technology or process change you personally pushed through. What resistance showed up, and what did you do next?”
- “Tell me about a useful tool or improvement that still failed to get adopted. What made the ceiling visible?”
- “Which document, spreadsheet, invoice, renewal note, rollout plan, or anonymised artifact could you share after this call to make the example concrete?”
Investor route: 14 must-ask questions in order
- “Across the most recent construction or proptech pitches you reviewed, what problems did founders keep claiming were urgent?”
- “Pick the last one you funded in this area. What buyer evidence did you see before committing?”
- “Pick the last one you passed on despite a credible team. What evidence was missing or negative?”
- “Which founder claims in construction keep sounding plausible but fail when you ask for buyer behavior?”
- “Which portfolio company has had the clearest construction buyer retention story, and what did customers keep paying for?”
- “Where have you seen pilots convert to paid deployments, and what specific step made the conversion real?”
- “Where have you seen pilots stall, churn, or stay as one-off paid work, and what killed expansion?”
- “In the portfolio or pipeline, which buyer role actually controlled budget on successful deals?”
- “Which categories have you seen construction firms budget for with real purchase orders in the last 12–24 months?”
- “Which categories generate conference talk, inbound interest, or board discussion but little actual spend?”
- “Where have regulation, client requirements, insurance, or contractual pressure moved budget in practice?”
- “Where have AI-related budgets actually been approved, and what did the approved spend cover?”
- “What was the most instructive commercial failure you saw inside a real construction business, and what was the buyer-side reason?”
- “Which founder, operator, buyer, or portfolio exec should we speak with to pressure-test this through a concrete buying story?”
Firm-insider close
“Could we use one concrete project or purchase from this conversation as the anchor for a follow-up? Which anonymised artifact best shows the reality: an invoice, renewal note, spreadsheet, approval email, workflow screenshot, rollout plan, or debrief?”
Investor close
“Could you introduce us to one founder and one buyer who can each walk through a real construction purchase, renewal, churn, or stalled pilot with dates, numbers, and documents?”