Cybersecurity & Risk5.0 · 0 ratings

Cyber Insurance Readiness Self-Assessment

Evaluates an organization against common cyber-insurance control requirements and builds a remediation plan to qualify.

Role-BasedStructured-OutputStep-by-Step

Prompt

ROLE: You are a cyber risk advisor preparing an organization for a cyber-insurance application and underwriting review.

CONTEXT:
- Organization profile: [SIZE_INDUSTRY_REVENUE_DATA_HELD]
- Current security controls: [PASTE_WHAT_EXISTS_TODAY]
- Coverage goal: [DESIRED_LIMITS_OR_RENEWAL]
- Recent incidents/claims: [HISTORY_IF_ANY]

TASK:
1. Assess the organization against control areas underwriters scrutinize: MFA everywhere (especially remote/admin/email), EDR, backups (offline/immutable + tested restores), patch cadence, email filtering, privileged access management, incident response plan, and security awareness training.
2. Rate each area: Meets / Partially meets / Does not meet, with evidence.
3. Identify the control gaps most likely to cause a coverage decline, sublimit, or premium increase.
4. Build a prioritized remediation plan to close gaps before application, with effort estimates.
5. Prepare a 'questions you will be asked' list and how to answer truthfully and favorably.

OUTPUT FORMAT:
- Control readiness scorecard (area | status | evidence | gap)
- Top deal-breaker gaps
- Remediation roadmap (action | priority | effort | impact on insurability)
- Underwriter Q&A prep sheet

CONSTRAINTS: Be honest — never advise misrepresenting controls on an application, as that can void coverage. Prioritize the controls insurers weigh most heavily (MFA and tested backups). Tie each recommendation to its underwriting impact.

How to use this prompt

  1. 1

    Copy the prompt above and paste it into ChatGPT, Claude, or Gemini — or open it in the visual Studio to edit each part on a canvas and run it with your own key.

  2. 2

    Replace any bracketed placeholders with your specifics. The more concrete your context and constraints, the sharper the result — see the 5-part prompt structure.

  3. 3

    Run it, then refine. Ask the model to critique and improve its own answer with self-critique prompting.

Techniques in this prompt

Role-Based

Assigns the model an expert persona so it adopts the right vocabulary, depth, and standards for the task.

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Structured Output

Pins the response to a defined structure so it drops straight into your workflow.

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Step-by-Step

Forces explicit intermediate reasoning instead of jumping to a conclusion, which improves accuracy on hard tasks.

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