Exercise 2 Prompts

AI-Driven Business Innovation Masterclass

Exercise 2: AI-Assisted Strategic Analysis

Prompt Templates & Examples

Use these prompts during Exercise 2 to practice the three AI strategic analysis techniques.

Recommended AI Tools: - Google Gemini (free, no login required) - ChatGPT (free tier available) - Claude (via claude.ai)

Pro Tip: Upload the RetailFlow Company Overview to your AI tool first to give it context about the case study.

TECHNIQUE 1: RISK DEEP-DIVE

Use AI to find threats and blind spots you might have overlooked

Basic Template:

I'm planning to [describe AI initiative]. What are 3-5 risks I might have overlooked?

Example Prompts:

Chatbot Risk Analysis:

I'm planning to deploy AI chatbots for customer service in retail.
What are 3 risks I might have overlooked?

Dynamic Pricing Risks:

We're implementing dynamic pricing AI in our retail stores.
What could go wrong that I haven't considered?

Using RetailFlow Context:

[Upload RetailFlow Company Overview first]

RetailFlow is considering AI inventory optimization ($1.1M investment).
What are 5 risks specific to a mid-sized retailer like RetailFlow that
might not be obvious from the ROI projections?

TECHNIQUE 2: REVERSE PROMPTING

Let AI interview YOU to reveal gaps in your thinking

Basic Template:

I'm evaluating [AI initiative]. Ask me [5-10] critical questions I should answer before investing.

Example Prompts:

General AI Investment Questions:

I need to evaluate an AI project for my organisation.
Ask me 5 critical questions I should answer before investing.

Specific Initiative Questions:

I'm considering AI inventory optimization for a retail chain.
What questions should I be asking before making this investment?

Using RetailFlow Context:

[Upload RetailFlow Company Overview first]

I'm the CEO of RetailFlow evaluating 4 AI investments: chatbots ($525K),
dynamic pricing ($1.3M), inventory optimization ($1.25M), and fraud detection ($1.05M).

Ask me 10 questions to determine which should be our priority, considering our
$2M budget constraint.

TECHNIQUE 3: AI DEBATE

Create a strategic debate to see multiple perspectives

VERSION A: Single AI, Both Sides (Easiest)

Basic Template:

Facilitate a strategic debate about [decision]:

**Role 1 (PRO):** Argues for [option A]. Present 3 compelling arguments.
**Role 2 (CON):** Argues for [option B]. Present 3 compelling arguments.

After presenting both sides, have each side rebut the other's strongest argument.

Example: Investment Decision

Facilitate a strategic debate about RetailFlow's AI investment decision:

**Chief Innovation Officer (PRO):**
Argues we should invest $850K in AI dynamic pricing NOW.
Present 3 compelling arguments for immediate action.

**Chief Financial Officer (CON):**
Argues we should wait 18 months before investing.
Present 3 compelling arguments for delaying investment.

After presenting both sides, have each executive rebut the other's strongest argument.

Example: Scale vs Kill Decision

Debate: Should we scale our AI chatbot pilot or kill the project?

**VP Customer Service (SCALE):**
The pilot showed 65% automation. Argue for full rollout. 3 reasons.

**CFO (KILL):**
ROI is only 119% over 3 years. Argue for killing it. 3 reasons.

Each side rebuts the other's top concern.

VERSION B: Two AIs Cross-Critique (Most Interactive)

Requires two different AI tools (e.g., ChatGPT + Claude)

Step 1 - Ask BOTH AIs the same question:

Should RetailFlow invest $1.3M in AI dynamic pricing now, or wait 18 months?
Present your recommendation with 3 supporting arguments.

Step 2 - Copy AI #1’s answer, paste into AI #2:

Another AI strategist gave this recommendation:

[PASTE AI #1's FULL ANSWER HERE]

Critique this recommendation. What are the 3 weakest points in their argument?

Step 3 (Optional) - Copy AI #2’s critique, paste into AI #1:

Another strategist critiqued my recommendation with these points:

[PASTE AI #2's CRITIQUE HERE]

Respond to these criticisms. Where is their critique wrong or incomplete?

VERSION C: Two AIs, Assigned Sides

AI #1 (ChatGPT) - PRO side:

Argue FOR investing $1.3M in AI dynamic pricing NOW.
Give 3 strong arguments supporting immediate investment.

AI #2 (Claude) - CON side:

Argue AGAINST investing in AI dynamic pricing now. Recommend waiting 18 months.
Give 3 strong arguments for delaying investment.

Then Cross-Critique (paste AI #1’s answer into AI #2):

Another strategist argued FOR immediate investment:

[PASTE AI #1's ANSWER]

Critique their arguments. What are the 3 weakest points?

RETAILFLOW-SPECIFIC PROMPTS

Use these with the RetailFlow case study context

Risk Deep-Dive for RetailFlow:

[Upload RetailFlow Company Overview]

RetailFlow (500 employees, $500M revenue, 75 stores) is considering AI chatbots
for customer service ($525K investment, 119% ROI).

What are 3-5 risks specific to mid-sized retail that we might overlook?

Reverse Prompting for RetailFlow:

[Upload RetailFlow Company Overview]

I'm the Investment Committee Chair at RetailFlow. We must allocate $2M across
4 AI projects: Chatbot (119% ROI, low risk), Pricing (150% ROI, ethical risk),
Inventory (163% ROI, exceeds budget), Fraud (169% ROI, 6-mo delay).

Ask me 7 questions to determine the optimal portfolio allocation.

AI Debate for RetailFlow:

[Upload RetailFlow Company Overview]

RetailFlow Investment Committee is split on AI fraud detection ($1.05M, 169% ROI):

**CIO (PRO):**
Argues fraud detection is critical despite 6-month data prep delay. 3 arguments.

**Chief Ethics Officer (CON):**
Argues ethical risks (bias) are too high. 3 arguments.

Each rebuts the other's top concern.

TIPS FOR EFFECTIVE PROMPTING

1. Provide Context

Upload the RetailFlow Company Overview or paste key facts: - Company size: 500 employees, $500M revenue, 75 stores - Budget constraint: $2M total for AI investments - Strategic priorities: Growth + operational efficiency

2. Be Specific

❌ “What about AI?” ✅ “What are 3 risks of deploying AI chatbots for customer service in retail?”

3. Ask for Structure

  • “Give me 3-5 examples”
  • “Present this as a pros/cons table”
  • “Rank these by priority”

4. Iterate

  • Start with a broad question
  • Follow up: “Elaborate on point #2”
  • Challenge: “What if our budget is cut in half?”

5. Use Multiple AIs

  • Different AIs have different “personalities”
  • ChatGPT: Balanced, comprehensive
  • Claude: Detail-oriented, cautious
  • Gemini: Creative, sometimes contrarian

EXERCISE WORKFLOW

During Exercise 2 (70 minutes):

  1. Individual Brainstorm (10 min):
    • Identify threats and opportunities for RetailFlow
    • Use your experience and intuition
  2. AI-Assisted Analysis (40 min):
    • Risk Deep-Dive (15 min): Find blind spots
    • Reverse Prompting (15 min): Let AI question your assumptions
    • AI Debate (10 min): See multiple perspectives
  3. Synthesis (10 min):
    • What did AI reveal that you missed?
    • What did you catch that AI missed?
    • How would you use AI + human judgment together?
  4. Group Discussion (10 min):
    • Share insights with your table
    • Discuss: When is AI helpful? When is human judgment critical?

KEY LEARNING

AI as Augmentation (not replacement): - ✅ AI finds blind spots you missed - ✅ AI generates alternatives quickly - ✅ AI challenges your assumptions

But: - ❌ AI doesn’t understand your organisation’s culture - ❌ AI lacks context about stakeholder politics - ❌ AI can’t make the final decision (you must)

Best practice: Human expertise + AI analysis = Better strategic decisions

ADDITIONAL RESOURCES

Questions during the exercise? Ask your facilitator or experiment with different prompt variations!