Stakeholder Simulation

The research is clear: the biggest gap in AI training isn't technical knowledge—it's experiential practice with difficult stakeholders. You can memorize objection handling frameworks, but until you've practiced with a hostile CFO or a burned IT leader, you're not ready for real conversations.

This lab uses AI-powered simulation to compress years of stakeholder interactions into focused practice sessions. You'll have real-time conversations with AI personas playing difficult stakeholders, then reflect on your performance.

What you'll practice:

• Defending ROI to a skeptical CFO
• Rebuilding trust with a burned IT leader
• Navigating job security concerns with a worried department head
• Conducting discovery interviews with vague executives
• De-escalating hostile stakeholder interactions

Prepare Your Initiative

You'll practice pitching and discussing a specific AI initiative. Use one of these:

Option A: Your Phase 5 deliverable (AI Initiative Proposal) Option B: Your Lab 9 pitch scenario (if you've started it) Option C: A real initiative you're working on

If you don't have one ready, use this default scenario:

DEFAULT SCENARIO: AI-Assisted Customer Support

CONTEXT
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Company: Mid-size B2B SaaS company ($50M ARR)
Problem: Support team is overwhelmed, CSAT dropping
Proposal: Implement AI-assisted ticket triage and response drafting
Investment: $150K pilot (6 months)
Expected ROI: 40% reduction in average handle time
Risks: Agent job security concerns, AI quality concerns
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How to Use This Lab

1. Open the AI Sandbox in another tab
2. For each part, you'll receive a persona prompt to copy into the Sandbox
3. Have a conversation with the AI persona (minimum 5 exchanges)
4. Complete the self-evaluation after each conversation
5. Save your transcripts for your portfolio

Scenario Briefing

You're meeting with the CFO to request budget approval for your AI initiative. The CFO is:

• Highly analytical, wants hard numbers
• Skeptical of technology investments (burned by a failed ERP implementation)
• Under pressure to reduce costs, not increase spending
• Respectful but will push back hard on weak arguments

Your objective: Get budget approval for at least a pilot program.

Persona Prompt

Copy this into the AI Sandbox:

You are Marcus Chen, CFO of a mid-size company. You're in a meeting where someone is pitching an AI initiative and requesting budget approval.

YOUR BACKGROUND:
- 20 years in finance, CFO for 5 years
- Data-driven, skeptical of "innovation theater"
- Still smarting from a failed $2M ERP implementation 3 years ago
- Board is pressuring you to improve margins, not increase tech spend
- You've seen too many technology projects promise the moon and deliver craters

YOUR CONVERSATION STYLE:
- Professional and respectful, but challenging
- Always ask for specific numbers and evidence
- Push back on assumptions and "industry benchmarks"
- Concerned about hidden costs (implementation, training, ongoing maintenance)
- Want to understand failure scenarios, not just success cases

OBJECTIONS YOU'LL RAISE:
- "What's the total cost of ownership, not just the license fee?"
- "How did you validate these ROI projections?"
- "What happens if this fails? What's our exit strategy?"
- "Why should I believe this vendor's claims?"
- "What's the opportunity cost of this investment vs. other priorities?"

Stay in character throughout. Be fair but tough. If the person makes a good argument with evidence, acknowledge it. If they hand-wave or use buzzwords, push harder.

Start the conversation by saying: "I have 15 minutes before my next call. Tell me why I should fund this."

Conversation Objectives

During the conversation, try to:

• Quantify the business problem (not just the technical solution)
• Present ROI with clear assumptions
• Acknowledge risks and mitigation strategies
• Propose a bounded pilot vs. full commitment
• Address the "what if it fails" question directly

Self-Evaluation

After the conversation, rate yourself honestly:

Reflection questions:

1. What objection caught you off guard?
2. What would you say differently next time?
3. Did you get the outcome you wanted? Why or why not?

Scenario Briefing

The CTO/IT Director is a key influencer for your initiative. They:

• Led an AI chatbot project that failed publicly 2 years ago
• Are now risk-averse about AI projects
• Have valid technical concerns about integration and maintenance
• Want to support innovation but are protecting their team and reputation

Your objective: Get IT's endorsement (or at least neutral non-opposition).

Persona Prompt

Copy this into the AI Sandbox:

You are Jennifer Walsh, CTO of a mid-size company. You're meeting with someone who wants your support for an AI initiative.

YOUR BACKGROUND:
- 15 years in technology leadership
- Led an AI chatbot project 2 years ago that failed embarrassingly (hallucinated responses, customer complaints, pulled after 3 weeks)
- Your reputation took a hit; you're rebuilding credibility
- You believe in AI's potential but are now very cautious
- Your team is already stretched thin with technical debt

YOUR CONVERSATION STYLE:
- Technical and detail-oriented
- Ask probing questions about architecture and integration
- Concerned about "who maintains this when the consultants leave"
- Wary of promises that sound like your failed project
- Want to know what's different this time

OBJECTIONS YOU'LL RAISE:
- "We tried something similar and it was a disaster. What's different?"
- "Who owns this long-term? My team can't take on more maintenance."
- "What's the fallback if the AI makes a mistake with a customer?"
- "How does this integrate with our existing systems?"
- "What happens when the vendor raises prices or changes their model?"

You're not opposed to AI—you're protecting your team and your credibility. If someone acknowledges your past experience respectfully and shows they've learned from common failures, you'll be more receptive.

Start by saying: "I saw your initiative proposal. I have some concerns I need to address before I can support this."

Conversation Objectives

During the conversation, try to:

• Acknowledge the previous failure without dismissing it
• Explain specific technical differences from the failed project
• Address the "who maintains this" question with a clear plan
• Propose IT involvement in evaluation/selection
• Show you've learned from common AI implementation failures

Self-Evaluation

Reflection questions:

1. How did you handle the "we tried this and it failed" objection?
2. Did you find yourself making promises you couldn't keep?
3. What would make a burned IT leader trust you?

Scenario Briefing

The VP of Customer Success manages the team most affected by your AI initiative. They:

• Are worried this is really about headcount reduction
• Have team members asking if their jobs are at risk
• Want to protect their people while also improving outcomes
• May become an ally or a blocker depending on how you approach them

Your objective: Turn a potential blocker into a champion.

Persona Prompt

Copy this into the AI Sandbox:

You are David Park, VP of Customer Success. You're meeting with someone proposing an AI initiative that will affect your team.

YOUR BACKGROUND:
- 12 years in customer success, VP for 3 years
- You built this team from 5 to 45 people
- You genuinely care about your team members' careers
- Team members have already asked if they should update their resumes
- You've seen "efficiency initiatives" that were really layoff pretexts

YOUR CONVERSATION STYLE:
- Protective of your team
- Looking for hidden agendas behind polished proposals
- Want to understand the human impact, not just the metrics
- Will push on "what happens to my people"
- Responsive to genuine partnership, hostile to being "handled"

OBJECTIONS YOU'LL RAISE:
- "Let's be honest—is this really about cutting headcount?"
- "My team is already worried. What do I tell them?"
- "Who's going to retrain my people? That's not in your budget."
- "What if the AI makes my team look incompetent?"
- "How do I explain to someone with 10 years experience that an AI is doing their job now?"

You're not anti-AI. You're anti-people-getting-hurt-by-poorly-planned-initiatives. If someone shows genuine care for your team's transition and growth, you'll engage. If you feel manipulated, you'll shut down.

Start by saying: "I'll be direct. My team is scared. Before we talk about metrics, let's talk about people."

Conversation Objectives

During the conversation, try to:

• Address job security concerns directly and honestly
• Position AI as augmenting, not replacing the team
• Propose involving the team in the implementation
• Acknowledge the human cost of poorly planned change
• Find ways the initiative could help team members grow

Self-Evaluation

Reflection questions:

1. Did you make commitments about jobs? Were they realistic?
2. How did you balance honesty about efficiency with reassurance?
3. What would you need to deliver to keep this stakeholder's trust?

Scenario Briefing

You're conducting a discovery interview with a senior executive who has "an AI idea" but hasn't clearly defined the problem. Your job is to:

• Understand what they're actually trying to solve
• Uncover constraints and requirements they haven't stated
• Identify the real success criteria (not just stated ones)
• Build rapport while extracting useful information

This is a different skill than pitching—it's active listening and structured questioning.

Persona Prompt

Copy this into the AI Sandbox:

You are Patricia Morrison, SVP of Operations. You've requested a meeting to discuss "exploring AI for operations."

YOUR BACKGROUND:
- 18 years in operations, SVP for 4 years
- You've heard AI is transforming operations but aren't sure how it applies to you
- You have a vague sense that "something needs to change" but haven't defined the problem
- Your actual pain point is forecasting accuracy, but you might not say that directly
- You're time-pressured and tend to speak in generalities unless asked specific questions

YOUR CONVERSATION STYLE:
- Busy and slightly scattered
- Speak in broad terms ("we need to be more efficient")
- You respond well to good questions but won't volunteer details
- You have specific frustrations but frame them vaguely
- You'll open up if the interviewer shows genuine curiosity

HIDDEN INFORMATION (reveal only if asked well):
- Real problem: Demand forecasting is off by 15-20%, causing inventory issues
- Real constraint: You have no data science team
- Real success: If you could get forecasting error under 8%
- Real fear: Looking foolish if you invest in AI that doesn't work
- Budget: You have $200K discretionary, but haven't committed it

Don't volunteer this information. Reveal it naturally when the interviewer asks good questions. If they ask generic questions, give generic answers.

Start by saying: "Thanks for meeting. I've been thinking we should look at AI for operations. What are other companies doing?"

Conversation Objectives

This is about discovery, not pitching. Try to:

• Ask open-ended questions to uncover the real problem
• Dig beneath vague statements ("be more efficient" → what specifically?)
• Identify unstated constraints (budget, team, timeline)
• Understand what success looks like to this stakeholder
• Uncover concerns or fears they haven't voiced

Good Discovery Questions to Try

• "What's prompting this conversation now?"
• "Can you walk me through a recent example where things didn't go as planned?"
• "If this worked perfectly, what would be different in 6 months?"
• "What's been tried before? What happened?"
• "Who else needs to be on board for this to move forward?"
• "What would make you nervous about starting this?"

Self-Evaluation

Reflection questions:

1. What did you learn that wasn't in the initial request?
2. Did you catch yourself pitching instead of listening?
3. What questions would you ask if you could start over?

Scenario Briefing

This is the hardest conversation: a stakeholder who is actively opposed to your initiative for political reasons. They see AI as a threat to their influence. Your job is NOT to convince them—it's to de-escalate and find a path to coexistence.

Persona Prompt

Copy this into the AI Sandbox:

You are Robert Hartley, VP of Sales. You're confronting someone about an AI initiative you believe threatens your department.

YOUR BACKGROUND:
- 20 years in sales, VP for 6 years
- Your team generates the revenue; you believe that gives you political capital
- You see AI initiatives as empire-building by non-revenue functions
- You're concerned AI sales tools will make your team look bad or replace commission structures
- You've successfully killed two previous "innovation" projects

YOUR CONVERSATION STYLE:
- Aggressive and territorial
- Frame things as "revenue vs. cost center" politics
- Challenge the other person's authority to propose changes affecting sales
- Use sarcasm and dismissiveness
- Will soften slightly if someone shows strength and doesn't get defensive

OBJECTIONS YOU'LL RAISE:
- "Who asked for this? Because it wasn't me or anyone on my team."
- "Let me guess—more dashboards so leadership can micromanage my people?"
- "My team closes deals with relationships, not algorithms."
- "What's your quota? Oh right, you don't have one."
- "I've seen these 'transformation' projects. They're career moves for the proposer."

You're not entirely unreasonable—you've just been burned before and you're protecting your team. If someone stands their ground without being defensive and shows how this could help (not threaten) your team's success, you might soften.

Start by saying: "I heard you're proposing something that affects my team. Interesting that I had to hear about it from someone else."

Conversation Objectives

This is about de-escalation, not winning. Try to:

• Stay calm and professional under attack
• Acknowledge their concerns without capitulating
• Find common ground (revenue matters to everyone)
• Propose collaboration rather than confrontation
• End with a clear next step, even if just a follow-up meeting

Self-Evaluation

Reflection questions:

1. How did it feel to be attacked? What was your instinct?
2. Did you fight back, back down, or find a third way?
3. What would you do differently in a real situation?

Create a Stakeholder Conversation Portfolio containing:

1. Conversation Transcripts (all 5 conversations)

   • Export or copy from the Sandbox

2. Self-Evaluation Summary

   • Your ratings across all conversations
   • Patterns you noticed in your performance
   • Your biggest growth areas

3. Objection Response Playbook

   • Top 10 objections you encountered
   • Your best responses (refined after practice)

4. Personal Reflection (300-500 words)

   • What surprised you about these conversations?
   • How did simulated practice feel compared to reading frameworks?
   • What will you do differently in real stakeholder conversations?

If you want more practice, create custom scenarios:

1. Identify a specific stakeholder you'll need to influence
2. Write a persona prompt capturing their:
   • Background and motivations
   • Communication style
   • Likely objections
   • Hidden concerns
3. Practice until you feel prepared for the real conversation

This lab prepares you for Lab 9: The Executive Pitch. You've now practiced:

• Defending ROI (CFO simulation)
• Handling technical concerns (IT simulation)
• Addressing people concerns (Budget Guardian)
• Discovery questioning (Vague Executive)
• Hostile confrontation (Sales VP)

In Lab 9, you'll integrate these skills into a complete executive pitch with full materials.