Risk & Concern Discovery

On first 8-10 discovery calls, explicitly ask: 'What concerns do you have about making this change?' and 'What could prevent this from being successful?'.

Create risk categories: Financial (budget, ROI, cost), Technical (integration, security, complexity), Organizational (change management, adoption, training), Timeline (urgency, competing priorities), Vendor (company stability, support, roadmap).

Use follow-up probes: 'What's the worst that could happen if this doesn't work?' and 'What would your CEO/board say if this failed?'.

Log all identified risks in Attio with severity rating (High/Medium/Low) and category; create mitigation plan for each high-severity risk.

Track PostHog events: risk_identified, high_severity_risk, mitigation_plan_created, risk_addressed.

Address risks immediately: provide proof points, case studies, guarantees, or commitments that mitigate specific concerns.

Create risk mitigation document: written plan showing how each identified risk will be addressed with specific actions and timelines.

Set pass threshold: Identify risks with ≥8 opportunities in 1 week with ≥70% having documented mitigation plans.

Measure impact: track how early risk discovery affects close rates, deal velocity, and objection frequency at proposal stage.

Document which risk discovery questions uncover most critical concerns; proceed to Baseline if threshold met.