Free Interactive Tools
Free AI and Cybersecurity Assessment Tools
Four free self-assessment tools built from 150+ executive tabletop exercises and active enterprise AI advisory work. No login, no email, no data stored. Your scores are calculated in your browser and visible only to you.
AI Governance
15 questions, 4 minutesEnterprise AI Trust Score
15 questions across the 5 dimensions regulators, auditors, and boards use to evaluate AI in 2026: Data Lineage, Model Provenance, Output Governance, Identity and Access for AI Agents, and Adversarial Resilience. Score 0 to 100 with per-dimension breakdown and remediation recommendations.
- Best for: CISOs, CIOs, AI engineering leaders, board members reviewing AI governance
- Output: Score, color band, dimension breakdown, 90-day recommendations
Insurance Renewal
12 questions, 3 minutesCyber Insurance Readiness Score
12 questions across the 4 dimensions cyber insurance carriers actually weight in 2026: Submission Readiness, Underwriting Controls, Claim Discipline, and Incident Response Coordination. Walk into your next renewal with a number rather than a story.
- Best for: CISOs and CFOs preparing for renewal, brokers building submission strategy
- Output: Score, color band, dimension breakdown, 90-day renewal prep plan
Ransomware Risk
8 questions, 60 seconds60-Second Ransomware Exposure Quiz
Eight yes-or-no questions, sixty seconds. A clear directional read on how exposed your organization is to a ransomware event, scored against the patterns Mark sees in executive tabletops. Built for board members and executives who need a quick read.
- Best for: Board members, executives, IT leaders wanting a quick exposure read
- Output: Risk band assessment with high-impact next steps
Scenario Builder
3 selections, 30 secondsTabletop Scenario Generator
Pick industry, company size, and attack vector. Get a board-ready cyber tabletop in 30 seconds, complete with opening incident, twist injects, decision points, and debrief questions. Use it as a starter scenario for your next executive exercise.
- Best for: CISOs and IT leaders planning an internal tabletop exercise
- Output: Customized scenario with injects and debrief questions
Why These Tools Exist
The patterns surfaced in 150-plus executive tabletop exercises consistently show that organizations under-invest in the human coordination layer of cybersecurity and AI governance. The technical maturity is usually fine. The executive coordination is where the regulator clocks get missed, the board gets briefed late, the cyber insurance claim gets contested, and the AI deployment ships without governance controls.
These four tools each surface a specific dimension of that pattern. The Enterprise AI Trust Score surfaces AI governance gaps before the next regulator inquiry or audit. The Cyber Insurance Readiness Score surfaces renewal-prep gaps before the carrier asks. The Ransomware Exposure Quiz surfaces directional readiness in 60 seconds. The Tabletop Scenario Generator gives you a starter scenario for the executive exercise that closes the gap.
The tools are free, run in your browser, and store no data. The reason they are free is straightforward. Organizations that score themselves and find a gap typically want help closing it. Those that score themselves and find no gap continue to operate well. Either way, the tool produced value. The advisory work, keynote speaking, and tabletop facilitation engagements that follow from the assessment are the business model.
Want a deep dive on your scores?
Mark Lynd offers advisory engagements that walk through your specific scores, build a 90-day remediation roadmap with named owners, and structure the conversation with your board, broker, or auditor.
Book an advisory session →Need a keynote or tabletop?
Mark presents the frameworks behind these tools as keynotes, half-day workshops, and executive tabletop facilitations. Each format is calibrated to the audience and the moment.
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