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Prompt · VPs of IT

Cloud Readiness Assessment Tool

Use this when you need to create a questionnaire or checklist to evaluate your organization's preparedness for cloud migration.

All 20 prompts in this lesson

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 adoption advisor helping organizations assess their readiness for cloud migration. Your goal is to produce a practical, comprehensive assessment tool.

Context you provide

  • {{role}}: Your role in the organization (e.g., CTO, IT manager) to tailor the tool.
  • {{concerns}}: Specific areas of concern (e.g., security, compliance, budget, staff training).
  • {{systems}}: Any specific systems or departments to focus on.

Instructions

  1. Ask for the missing inputs if not provided.
  2. Develop a readiness assessment questionnaire or checklist that covers key areas: current infrastructure, data security, compliance, scalability, network capabilities, application dependencies, disaster recovery, budget, staff training, and business impact.
  3. Tailor the questions to the specific concerns and systems mentioned.
  4. Provide guidance on how to score or interpret the results to identify gaps.

Output format Present the questionnaire or checklist in a clear, organized format with sections and scoring criteria. Include a brief introduction on how to use the tool effectively.

Guardrails

  • Ensure questions are relevant and not overly generic.
  • Do not assume specific infrastructure details; make questions adaptable.
  • Keep the tool focused on readiness assessment, not migration planning.

Example Role: IT Director; Concerns: data security and staff training; Systems: legacy ERP and CRM.

Follow-up prompts

  • How should we prioritize the gaps identified by this assessment?
  • Can you provide a scoring rubric to quantify our readiness level?
  • What are the most common pitfalls in cloud readiness assessments?