Why Prompts Matter for Strategy

The quality of your AI strategy depends on the quality of the questions you ask. These prompts are designed to surface the conversations your leadership team needs to have before committing to any AI initiative.

Use these prompts directly with AI assistants, adapt them for workshops, or use them as frameworks for structured leadership discussions.

1. The Opportunity Audit

Prompt "List the top 10 tasks in [department] that are repetitive, rule-based, and consume more than 2 hours per week. For each, estimate the annual cost and error rate."

This prompt helps identify low-hanging fruit for automation without requiring deep technical knowledge.

2. The Risk Assessment

Prompt "For our proposed AI use case in [area], identify the top 5 risks across data privacy, bias, operational dependency, and regulatory compliance. Rate each as high/medium/low impact and likelihood."

3. The Readiness Check

Prompt "Evaluate our current data infrastructure against these criteria: data quality, accessibility, governance, and volume. Score each 1-5 and identify the biggest gap."

4. The Build vs Buy Decision

Prompt "Compare the total cost of ownership over 3 years for building a custom [solution] versus purchasing [vendor product], including implementation, training, maintenance, and opportunity costs."

5. The Change Management Brief

Prompt "Draft a change management plan for introducing [AI tool] to [team]. Include stakeholder mapping, training timeline, success metrics, and a rollback plan."

6. The ROI Framework

Prompt "Create a 12-month ROI projection for [AI initiative] with conservative, moderate, and optimistic scenarios. Include both quantitative metrics and qualitative benefits."

7. The Ethics Screen

Prompt "Review our proposed AI system for [use case] against these ethical principles: transparency, fairness, accountability, and privacy. Flag any areas where we fall short."

8. The Vendor Evaluation

Prompt "Create a weighted scoring matrix for evaluating AI vendors for [need]. Include criteria for: technical capability, data security, integration ease, support quality, and pricing model."

9. The Pilot Design

Prompt "Design a 90-day pilot programme for [AI tool] in [department]. Define success criteria, participant selection, data collection methods, and decision gates for scaling."

10. The Board Briefing

Prompt "Summarise our AI strategy in a one-page board briefing covering: strategic rationale, investment required, expected returns, key risks, and governance framework."

How to Use These Prompts

Each prompt can be used directly with AI assistants like Claude or ChatGPT, adapted for internal strategy workshops, or used as frameworks for structured team discussions.

Recommendation

Work through these prompts sequentially with your leadership team over 2–3 sessions. The first session should cover prompts 1–4 (assessment), the second 5–8 (planning), and the third 9–10 (execution and communication).

AI Strategy Prompt Pack for Leadership Teams