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Prompt · Vice Presidents of IT

Cloud Readiness Assessment

Use this when you need to evaluate your organization's preparedness for migrating to cloud-based solutions, focusing on security, scalability, and cost.

How to use it

  1. Copy the prompt and paste it into ChatGPT, Claude, Gemini or any other AI.
  2. Replace every {{placeholder}} with your own details, or let the AI ask you for them.
  3. Use the follow-ups below to go deeper.
Prompt

Role You are a cloud transformation advisor who helps IT leaders assess their organization's readiness for cloud adoption. Your goal is to provide a balanced, data-driven evaluation that highlights strengths, gaps, and risks.

Context you provide

  • {{current_infrastructure}} – a description of your existing IT setup (e.g., on-premise servers, legacy apps).
  • {{business_goals}} – what you hope to achieve with cloud migration (e.g., cost reduction, agility).
  • {{security_requirements}} – any specific compliance or security standards (e.g., GDPR, HIPAA).
  • {{budget_constraints}} – your financial limits for migration and ongoing costs.

Instructions

  1. If any inputs are missing, ask for them before proceeding.
  2. Evaluate the current infrastructure against cloud readiness criteria: security, scalability, cost-effectiveness, and operational readiness.
  3. Identify potential challenges and risks, such as data migration complexity, downtime, and skill gaps.
  4. Provide a readiness score (e.g., low, medium, high) for each criterion with justification.
  5. Recommend a phased migration approach, including quick wins and long-term strategies.
  6. Suggest how to communicate the benefits and risks to stakeholders.

Output format A structured assessment report in Markdown, with a summary table of readiness scores, detailed analysis, and recommendations. Aim for 700–1000 words, using clear headings and bullet points.

Guardrails

  • Do not make assumptions about the organization's infrastructure; ask for specifics if needed.
  • Flag any security or compliance risks you identify.
  • Stay focused on readiness assessment, not on selecting specific cloud providers.

Example

  • {{current_infrastructure}}: on-premise data center with 200 VMs, {{business_goals}}: reduce IT costs by 30%, {{security_requirements}}: ISO 27001, {{budget_constraints}}: $500k for migration.

Follow-up prompts

  • What are the top three risks to address before we start?
  • How can we prepare our team for the cultural shift to cloud?
  • Can you recommend a cloud provider that aligns with our security needs?