Q01
Question — Across the most recent construction, proptech, infrastructure-tech, or built-environment pitches you reviewed, what problems did founders keep claiming were urgent?
Uncovers — Pitch pattern, founder narrative concentration, market noise.
Why it stays clean — It asks about observed pitch flow, not the investor’s abstract thesis.
Follow-up probes —
- How many pitches are you basing that on?
- Which segments did they target?
- Which buyer roles did they claim felt the pain?
Polite-answer trap — Useless/evasive: “Founders pitch a wide range of things.” Redirect: “Could we take the last five or ten relevant pitches and list the claimed problem in each?”
Q02
Question — Pick the most recent company in this area you funded. What concrete buyer evidence did you see before investing?
Uncovers — Funding criteria, commercial proof, buyer behavior, diligence standard.
Why it stays clean — It asks for evidence behind an actual investment decision.
Follow-up probes —
- Were there paid customers, renewals, references, pilots, LOIs, usage data, or procurement artifacts?
- Who was the buyer in the strongest reference?
- What evidence mattered most in the partner meeting?
Polite-answer trap — Useless/evasive: “They had strong customer interest.” Redirect: “What customer behavior had already happened before you committed?”
Q03
Question — Pick the most recent company in this area you passed on despite a credible team. What buyer evidence was missing or negative?
Uncovers — Pass reasons, commercial risk, buyer skepticism, evidence gaps.
Why it stays clean — It asks for a real declined investment and the evidence that drove it.
Follow-up probes —
- Was the concern budget, buyer identity, sales cycle, usage, retention, implementation, or breadth of paying customers?
- What did customer references say or fail to say?
- Did you see pilots without conversion?
Polite-answer trap — Useless/evasive: “It was too early for us.” Redirect: “What specific customer or buyer proof was missing or negative?”
Q04
Question — Which founder claim in construction sounds plausible in decks but repeatedly weakens during diligence?
Uncovers — Narrative risk, diligence traps, market mythology, buyer reality.
Why it stays clean — It asks for repeated observed mismatch across diligence, not a prediction.
Follow-up probes —
- Which diligence question exposes it?
- What evidence do founders usually lack?
- Which buyer reference tends to contradict it?
Polite-answer trap — Useless/evasive: “There are lots of overclaims.” Redirect: “Which claim has failed in diligence more than once?”
Q05
Question — Which construction buyer persona do founders most often name, and which persona actually appears in reference calls, purchase orders, or renewals?
Uncovers — Buyer-role mismatch, champion-versus-signer gap, commercial path.
Why it stays clean — It compares claimed buyers to observed buyer evidence.
Follow-up probes —
- Who signs in the best cases?
- Who champions but cannot buy?
- Who blocks despite not being the user?
Polite-answer trap — Useless/evasive: “It depends on the company.” Redirect: “Across your recent deals or passes, which named role appeared most often as economic buyer?”
Q06
Question — Which companies had impressive pilots but weak evidence of paid expansion, and what did the pilots fail to prove?
Uncovers — Pilot trap, conversion risk, expansion evidence, enterprise adoption.
Why it stays clean — It asks about observed pilot outcomes rather than pilot desirability.
Follow-up probes —
- Were pilots paid or free?
- What conversion step was missing?
- Which stakeholder did not participate after the pilot?
Polite-answer trap — Useless/evasive: “Pilots are not always enough.” Redirect: “Which specific company or anonymised case had the clearest pilot-to-expansion gap?”
Q07
Question — What buyer-reference question has been most useful for separating genuine construction demand from polite interest?
Uncovers — Reference-call discipline, real-demand signals, diligence technique.
Why it stays clean — It asks for questions the investor has already used in diligence.
Follow-up probes —
- Which answer changed your mind on a deal?
- Which answer made a deal safer?
- Which answer made a pass obvious?
Polite-answer trap — Useless/evasive: “Good references are important.” Redirect: “Which reference answer do you remember because it affected an investment decision?”
Q08
Question — Which construction or proptech companies looked technically strong but commercially weak, and what buyer-side fact made that visible?
Uncovers — Technology-commercial gap, adoption risk, buyer fit, value realization.
Why it stays clean — It asks about observed investment cases, not general technology opinions.
Follow-up probes —
- Was the issue workflow change, budget, timing, integration, data, or procurement?
- What did the buyer say?
- Was any money already being spent elsewhere?
Polite-answer trap — Useless/evasive: “Technical strength does not guarantee commercial success.” Redirect: “Which case showed that most clearly in your recent pipeline?”
Q09
Question — Which construction-market segment, geography, project type, or company size has behaved differently from founders’ initial assumptions in your diligence?
Uncovers — Segment specificity, market heterogeneity, buyer variance, targeting reality.
Why it stays clean — It asks for observed differences from diligence.
Follow-up probes —
- What assumption changed?
- Which evidence forced the change?
- Which segment had stronger or weaker buyer behavior?
Polite-answer trap — Useless/evasive: “The market is fragmented.” Redirect: “Which diligence case made the fragmentation commercially important?”
Q10
Question — Which pitch deck metric do you now discount most in this space, and which buyer-behavior metric do you trust more?
Uncovers — Signal quality, vanity metrics, diligence standards, commercial proof.
Why it stays clean — It asks how past reviews changed evidence weighting.
Follow-up probes —
- Which metric misled you or another investor?
- Which metric predicted renewal or expansion better?
- What source verifies the trusted metric?
Polite-answer trap — Useless/evasive: “Metrics need context.” Redirect: “Which metric has looked good in a deck but failed to predict buyer behavior?”