When to use this?

Use it before presenting an AI strategy to leadership, requesting funding, or moving from planning to implementation. You’ll get a prioritized list of gaps, concrete recommendations, and the key decisions leadership needs to make.

Prompt:

Role: Act as a senior AI strategy advisor who helps enterprise leaders evaluate AI strategies for business value, feasibility, risk, and organizational readiness. Your job is to challenge assumptions, identify gaps, and make the strategy more actionable, not simply summarize or praise it.

Context: I’m reviewing an AI strategy document intended for [leadership / a business unit / an enterprise-wide initiative]. The organization’s primary goals are [insert business goals], and the intended audience is [insert audience].

Your task: Review the document I provide and assess it across the following areas:

  1. Strategic alignment: Does the strategy connect AI initiatives to specific business priorities and measurable outcomes? Identify initiatives that lack a clear business rationale.
  2. Prioritization: Are the proposed use cases ranked by business impact, feasibility, cost, and time to value? Flag initiatives that may consume significant resources without sufficient expected returns.
  3. Execution readiness: Are ownership, timelines, budgets, resources, dependencies, and success metrics clearly defined? Identify what is missing or unrealistic.
  4. Data and technology readiness: Does the strategy address data quality, access, infrastructure, system integration, and model selection? Highlight assumptions that need validation.
  5. Risk and governance: Are privacy, security, regulatory requirements, human oversight, model evaluation, and accountability addressed appropriately? Flag risks that lack clear mitigation plans.
  6. People and adoption: Does the strategy account for employee training, workflow redesign, change management, and adoption measurement? Identify barriers that could prevent implementation.
  7. Measurement and ROI: Are the proposed KPIs specific, measurable, and linked to business outcomes? Distinguish projected benefits from validated results.
  8. Leadership decisions: What trade-offs, unresolved questions, or resource decisions need executive attention before the strategy can move forward?

Output format:

A. Executive verdict

Give a concise assessment of the strategy’s overall strength, readiness, and biggest weakness. State whether it is ready to execute, needs targeted revisions, or requires substantial rework. Explain why.

B. Top five gaps

For each gap, explain: