# Challenging Stakeholder Questions

> Generate rigorous stakeholder challenge questions for proposal or meeting preparation.

- Skill: `itseffi/challenging-stakeholder-questions` (Agent Skill, multi-file: 2 files)
- Install (CLI): `npx skillmds@latest add itseffi/challenging-stakeholder-questions`
- Raw SKILL.md: https://api.skillmd.com/api/skills/itseffi/challenging-stakeholder-questions/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Product & Planning
- Author: itseffi (https://skillmd.com/u/itseffi)
- Updated: 2026-09-17
- Page: https://skillmd.com/skills/itseffi/challenging-stakeholder-questions

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# Challenging Stakeholder Questions

Generate probing questions that pressure-test a proposal.

## Instructions

### Step 1: Parse context
- Use goal/context and stakeholder details.
- State assumptions if details are missing.

### Step 2: Generate question set
- Produce at least 20 non-redundant questions.
- Cover: financials, resources, timeline, risks, market, competition, feasibility, UX, ethics, sustainability, team capability, performance history, strategic alignment, compliance, scalability.

### Step 3: Check quality
- Remove generic and repetitive questions.
- Ensure each question ties to provided context.

## Output

- Numbered question list (20+)

## When to Use

Use this skill when the task directly matches the workflow described above.

## When Not to Use

Do not use this skill when the request is unrelated, low-stakes, or better handled by a simpler direct response.