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Leadership scenario simulator

Generates 12 realistic leadership scenarios across 6 uncertainty-driven challenge types, each with role context, escalating decision points, stakeholder tensions, coaching debrief questions, and competency mapping to a…

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Purpose

Generate a set of realistic, decision-forcing leadership scenarios — grounded in a specific industry and seniority level — that put a manager into ambiguous, high-stakes situations and give the facilitator structured debrief questions to run a coaching conversation. Solves the problem of coaches and L&D teams reusing stale, generic case studies that don't produce real behavioral practice.

When to Use

Invoke this skill when the user asks to:

  • Create leadership practice scenarios or case studies for a workshop
  • Build role-play material for a coaching session or leadership program
  • Develop discussion scenarios for an MBA or executive education module
  • Generate "what would you do" situations for developing managers
  • Create material mapped to a leading-through-uncertainty or decision-making curriculum
  • Design simulation exercises for a leadership offsite or cohort program

Inputs Required

Before starting, collect:

  • Industry/context: The sector or business environment the scenarios should reflect
  • Seniority level: The leadership tier being developed (team lead, mid-level manager, director, etc.)
  • Program focus: The competency theme — defaults to leading through uncertainty if unspecified
  • Delivery format: Live coaching / group workshop / async self-study / MBA discussion
  • Team/org context: Team size, structure, or organizational realities to reflect
  • Difficulty calibration: Emerging leaders / experienced managers / mixed cohort
  • Competency framework: Any existing model to map against (optional — a default 6-competency model is used if none provided)

If program focus or competency framework is missing, default to leading through uncertainty mapped to the six competencies described in Step 1.

Instructions

Step 1: Anchor to the Competency Model

Map every scenario to one primary competency from this leading-through-uncertainty model (or the buyer's supplied framework):

  1. Deciding with incomplete information — acting before certainty is possible
  2. Communicating under ambiguity — being clear when the answer isn't
  3. Managing team morale through change — holding people through disruption
  4. Balancing competing stakeholder demands — no option satisfies everyone
  5. Adapting strategy when conditions shift — abandoning the plan without abandoning the direction
  6. Maintaining accountability under pressure — owning outcomes when it would be easy to deflect

Distribute the 12 scenarios so each competency is exercised at least once, with heavier weighting toward the buyer's stated program focus.

Step 2: Generate 12 Scenarios Across 6 Challenge Types

Produce 2 scenarios per challenge type. Each scenario must be industry-specific, seniority-calibrated, and free of any generic placeholder language.

Challenge Type 1 — The Incomplete-Information Decision (2 scenarios) A decision must be made now, but critical data is missing or unreliable.

  • Include a real time pressure and a cost to waiting
  • Present two plausible readings of the ambiguous situation

Challenge Type 2 — The Stakeholder Conflict (2 scenarios) Two or more parties with legitimate needs pull in opposite directions.

  • Give each stakeholder a defensible position — no obvious villain
  • Ensure the "compromise" option carries a real downside

Challenge Type 3 — The Team Morale Crisis (2 scenarios) A change, loss, or setback threatens team confidence and engagement.

  • Include at least one specific team member with a named reaction (resistance, disengagement, fear)
  • Make the emotional stakes as clear as the operational ones

Challenge Type 4 — The Strategy Pivot (2 scenarios) A previously committed direction is no longer viable and the leader must adjust.

  • Include sunk cost and the reputational risk of reversing course
  • Make the new direction uncertain, not a clean upgrade

Challenge Type 5 — The Accountability Moment (2 scenarios) Something went wrong and the leader must decide how to own it, upward and downward.

  • Include an easy deflection path that a weaker leader would take
  • Involve both a boss/board and the leader's own team

Challenge Type 6 — The Ethical or Values Tension (2 scenarios) A business-optimal move conflicts with stated values, fairness, or long-term trust.

  • Make the "wrong" choice genuinely tempting (profitable, fast, low-risk)
  • Keep it realistic — a gray-area dilemma, not a cartoon

Step 3: Build Each Scenario to a Fixed Structure

For every one of the 12 scenarios, include:

  1. Title — a short, evocative name for the situation
  2. Your role — who the participant is playing (title, tenure, mandate)
  3. The situation — 4–6 sentences of concrete setup with real names, numbers, and constraints
  4. The tension — one sentence naming the core conflict or trade-off
  5. Decision point 1 — the immediate call the leader must make
  6. Escalation — a curveball introduced after their first decision (new information, a stakeholder reaction, a deadline shift)
  7. Decision point 2 — the follow-up call forced by the escalation
  8. Primary competency — the mapped competency from Step 1
  9. Difficulty — Foundational / Stretch / Advanced

Step 4: Write the Coaching Debrief for Each Scenario

For every scenario, provide 4 debrief questions the facilitator can ask:

  • One that surfaces the participant's reasoning ("What information did you weigh most, and why?")
  • One that probes an unexamined assumption
  • One that connects the choice to the target competency
  • One that transfers the lesson to the participant's real work Also flag one common failure mode — the trap most participants fall into in this scenario.

Step 5: Add a Facilitator Guide

Close with a short facilitation section covering:

  • Suggested sequencing — which scenarios to run first for the stated difficulty calibration
  • Timing — recommended minutes per scenario for the chosen delivery format
  • Cohort adaptation — how to make any scenario harder or easier on the fly

Output Format

  • Structure: Competency model up front → 12 scenarios grouped by the 6 challenge types → facilitator guide
  • Length: 1,800–2,400 words
  • Format: Structured document — each scenario in a consistent labeled block; debrief questions as bullets
  • Sections: Competency Model → Challenge Type 1–6 (2 scenarios each) → Facilitator Guide
  • Tone: Grounded and realistic — the voice of an experienced facilitator; no melodrama, no easy answers, no hero narratives

Quality Checklist

Before delivering output, verify:

  • [ ] All 12 scenarios are present (2 per challenge type — count them)
  • [ ] Every competency from the model is exercised by at least one scenario
  • [ ] Each scenario has both Decision Point 1 and an escalation leading to Decision Point 2
  • [ ] Every scenario includes exactly 4 debrief questions plus a named common failure mode
  • [ ] Scenarios use specific names, numbers, and constraints — no bracketed placeholders or generic filler
  • [ ] Difficulty labels match the buyer's stated cohort calibration

Notes

  • The escalation step is what separates a simulation from a case study — a good curveball reveals whether the first decision was principled or lucky
  • Resist making any scenario have a clean "right answer"; the coaching value lives in the trade-off
  • For live coaching, reveal the escalation only after the participant commits to Decision Point 1 — do not show it up front
  • Ethical-tension scenarios generate the richest cohort discussion but are the easiest to write poorly; keep the tempting choice genuinely tempting

How to use this skill

This file is a Claude Code skill in Anthropic's standard format — markdown with YAML frontmatter at the top.

Installing in Claude Code:

  • ~/.claude/skills/<folder-name>/SKILL.md — auto-loads in every session anywhere on your machine (recommended for skills you'll use across multiple projects)
  • <your-project>/.claude/skills/<folder-name>/SKILL.md — auto-loads only when working in that project (recommended for project-specific skills)

Restart Claude Code or open a new session to register.

Using in Claude.ai, ChatGPT, Gemini, or other AI tools:

  1. Drag this file into a new chat, or copy and paste its contents
  2. Send your task or request as your next message — the AI will apply the skill where it fits

For Claude Code skill details: https://docs.anthropic.com/en/docs/claude-code/skills