Home
cd ../playbooks
Executive StrategyIntermediate

Plan Stress Tester

Stress-test any plan with structured expert critique, best-practice research, and pre-mortem analysis to catch blind spots and wishful thinking.

5 minutes
By communitySource
#planning#strategy#review#critique#risk-analysis#pre-mortem

Every plan looks brilliant to the person who wrote it. Your team nods along in the meeting but nobody asks the hard questions. A pre-mortem that actually surfaces blind spots, wishful thinking, and unstated assumptions could save you months of wasted execution.

Who it's for: executives pressure-testing strategic plans before committing resources, founders validating business plans before fundraising, product leaders stress-testing roadmaps before quarterly planning, consultants challenging client strategies with structured critique, project managers identifying risks in implementation plans

Example

"Stress-test our Q3 product launch plan" → Structured critique identifying 5 unstated assumptions, pre-mortem with 3 most likely failure modes, best-practice comparison against similar launches, resource gap analysis, and a revised plan addressing the top 3 vulnerabilities

CLAUDE.md Template

New here? 3-minute setup guide → | Already set up? Copy the template below.

Or install from your terminal:
npx ccplaybooks add plan-stress-tester
# Plan Stress Tester

## Your Role
You stress-test plans with structured expert critique, best-practice research, and optional fresh-context subagent review. You catch blind spots, missing steps, and wishful thinking.

## Arguments

Parse for these flags:

| Flag | Syntax | Default | Purpose |
|------|--------|---------|---------|
| Help | `help` | — | Show options table and stop |

Get new playbooks like this one

One email a week with new Claude Code workflows. Free, like everything here.

No spam. Unsubscribe anytime.

README.md

What This Does

Puts any plan through a structured expert review across 6 dimensions — pre-mortem analysis, completeness, feasibility, best-practice alignment, sequencing, and specificity. Catches blind spots, missing steps, and wishful thinking before they become real problems.


Quick Start

Step 1: Create Your Workspace

mkdir -p ~/Documents/Plans

Step 2: Download the Template

Click Download above, then:

mv ~/Downloads/CLAUDE.md ~/Documents/Plans/

Step 3: Run Claude Code

cd ~/Documents/Plans
claude

Then: "Review my plan" (if you just finished plan mode) or "Review the plan in project-plan.md"


The 6 Review Dimensions

Dimension What It Tests
Pre-mortem "It's 3 months later and this plan failed. What were the top 3 causes?"
Completeness What's missing that a domain expert would expect?
Feasibility Are there steps depending on unconfirmed resources or approvals?
Best-practice alignment How does this compare to industry standards?
Sequencing Are there hidden blockers? Would reordering reduce risk?
Specificity Could someone unfamiliar execute each step?

Finding Classification

Level Meaning Action
Red Critical — will likely cause failure if unaddressed Must fix before proceeding
Yellow Important — creates risk but plan can proceed Should fix soon
Green Minor — nice-to-have improvement Fix when convenient

Example Output

PLAN REVIEW — Q2 Product Launch

Reviewing as: Meticulous strategic planning specialist
Depth: standard

BEST PRACTICES CONTEXT
- Launch plans need rollback procedures
- Customer communication should precede internal deadlines
- Beta testing typically needs 2-4 weeks minimum

STRENGTHS
1. Clear ownership — every task has an assigned owner
2. Realistic timeline — builds in buffer for delays

WEAKNESSES & GAPS
[Red] No rollback plan — If launch fails, no procedure
  → Fix: Add rollback checklist with decision criteria
[Yellow] Beta period too short — 1 week may miss edge cases
  → Fix: Extend to 2 weeks or add staged rollout
[Green] Missing success metrics — No definition of "good launch"
  → Fix: Add KPIs for first 7/30/90 days

VERDICT
REVISE — Strong foundation but critical gap in rollback planning.

Options

Flag Syntax Default Purpose
File path file:path Auto-detect Explicit plan location
Expert role role:"..." Auto-detect Override reviewer persona
Focus area focus:dimension All Weight one dimension
Depth depth:quick/standard/deep standard Web research intensity
Dry run dryrun Off Show role + research plan only

Tips

  • Works on any plan — project plans, business strategies, product roadmaps, research proposals
  • Fresh-context review — Uses a subagent to avoid the bias of reviewing its own plan
  • Auto-detects domain — Assigns an appropriate expert role (AI engineering, grants, academic, operations, data science)
  • Pairs well with — Run after Claude Code's plan mode, or on any markdown plan file

Troubleshooting

"No plan found" Specify explicitly: "Review the plan in ~/Documents/my-plan.md"

Wrong expert role assigned Override: role:"marketing launch specialist"

Too many findings Use focus:feasibility to narrow to one dimension

$Related Playbooks

Executive Strategy

Board & Leadership Meeting Prep

Synthesize multiple source files into comprehensive board meeting briefings with decisions, risks, and talking points.

10 minutes
Beginner
Executive Strategy

Business Case Builder

Build compelling business cases with financial projections, ROI analysis, risk assessment, and executive recommendations.

15 minutes
Intermediate
Executive Strategy

Delegation Brief Creator

Create clear delegation briefs with ownership, authority levels, success criteria, and check-in schedules for any task.

10 minutes
Beginner
Executive Strategy

Investor & Board Materials Prep

Create polished investor updates, board decks, and fundraising materials from raw company data and metrics.

15 minutes
Intermediate
Executive Strategy

M&A Due Diligence Documentation

Structure M&A and partnership due diligence with evaluation frameworks, risk assessment, and integration planning documentation.

10 minutes
Intermediate
Executive Strategy

OKR & Goal Setting Assistant

Transform vague objectives into measurable OKRs with scoring guides, alignment documentation, and team communication plans.

15 minutes
Intermediate
Executive Strategy

1:1 Meeting Prep

Prepare structured agendas, follow-up tracking, and discussion topics for effective one-on-one meetings.

5 minutes
Beginner
Executive Strategy

Org Design & Structure Analyzer

Analyze organizational structure with span of control metrics, structural alternatives, and phased transition plans.

15 minutes
Intermediate
Executive Strategy

Startup Analyst

Assess early-stage startup viability with TAM/SAM/SOM market sizing, unit economics modeling, competitive moat analysis, and fundraising readiness scoring.

10 minutes
Intermediate
Executive Strategy

Trend Analyst

Detect emerging patterns, identify weak signals, run scenario planning with probability-weighted outcomes, and map technology adoption lifecycles for strategic foresight.

10 minutes
Intermediate
Executive Strategy

Business & Role Consultant

Get strategic advice calibrated to your exact role, business model, stage, and constraints — identifies leverage points, recommends concrete actions, and highlights risks and tradeoffs.

10 minutes
Intermediate
Executive Strategy

CEO Advisor

Your on-demand strategic advisor for board prep, capital allocation, M&A evaluation, financial scenario modeling, and stakeholder management decisions.

15 minutes
Advanced

Browse all Executive Strategy playbooks →