Strategic Decision Post-Mortem

VerifiedSafe

Run an honest retrospective on an executed decision, scored against pre-committed success and kill criteria, revisiting preserved dissent and assumptions.

Sby Skills Guide Bot
ProductivityIntermediate
11/3/2026
Claude Code
#post-mortem#decision-review#retrospective#strategic-planning#governance

Recommended for

Automated summary

Closes the strategic sprint loop by scoring an executed decision against pre-committed success and kill criteria and revisiting preserved dissent.

Strengths

  • Scores outcomes against success and kill criteria committed before the decision, reducing retroactive justification
  • Revisits preserved dissent and original assumptions with explicit yes/no/partial scoring
  • Outputs a structured post-mortem record with forward actions and routing to follow-up commands
  • Builds calibration over time through 90-day checkpoints and quarterly reviews

Limitations

  • Requires prior decision and execution artifacts plus actual outcome data supplied by the user
  • Value is capped by how well the original success and kill criteria were defined
  • Tied to the cs command chain, so it is less useful as a standalone skill
When to use it

Use it when an executed decision hits its 90-day checkpoint, a kill criterion triggers, or a quarterly review of past decisions is due.

When not to use it

Avoid it when no pre-committed criteria or decision record exists, or while the decision is still being executed.

Security analysis

Safe
Quality score82/100

This is a pure instructional prompt/markdown template for running a decision post-mortem. It declares no tools and contains no executable commands, network calls, file deletions, or credential handling. The only filesystem reference is a documented output path (~/.claude/postmortems/) that the agent's own tooling would write to, which is benign and expected for a note-taking workflow. No prompt-injection or obfuscation attempts were observed.

No concerns found

How this analysis is made

Examples

90-day pricing review
/cs:post-mortem decisions/2025-03-pricing-change.md — run the 90-day review against the success and kill criteria we committed to before launch.
Revisit boardroom dissent
Score last quarter's enterprise tier launch against its original metrics and revisit the dissent preserved from the boardroom memo.
Quarterly decision audit
Run a post-mortem on all decisions executed this quarter and flag any kill criteria that were triggered.

name: "post-mortem" description: "/cs:post-mortem <decision> — Honest retrospective on an executed decision, scored against original assumptions and dissent. Closes the strategic sprint loop. Use when a decision hits its 90-day review checkpoint or its kill criteria trigger — e.g. scoring last quarter's pricing change against its pre-committed success metrics."

/cs:post-mortem — Honest Retrospective

Command: /cs:post-mortem <decision-path>

Closes the strategic sprint loop. Scores a decision against the success and kill criteria written before the decision (not retro-fitted) and revisits the preserved dissent. This is the rigor that compounds over time.

Pipeline Position

/cs:office-hours  →  /cs:brief  →  /cs:boardroom  →  /cs:decide  →  /cs:execute  →  /cs:post-mortem
                                                                                       ↑ you are here

When to Run

  • At the 90-day checkpoint (auto-scheduled by /cs:decide)
  • When a kill criterion triggers
  • After a major decision is reversed
  • Quarterly on all decisions of the past quarter

Inputs

  • The decision record (output of /cs:decide)
  • The execution plan (output of /cs:execute)
  • Actual outcomes (metrics, events, customer signals)

Output: Post-Mortem Record

Saved to ~/.claude/postmortems/YYYY-MM-DD-<slug>.md:

# Post-Mortem: <decision title>
**Decision date:** YYYY-MM-DD
**Post-mortem date:** YYYY-MM-DD
**Status:** WIN / PARTIAL / LOSS / MIXED

## Outcome Scoring (against pre-committed criteria)

| Success Criterion | Threshold | Actual | Met? |
|---|---|---|---|
| <metric 1> | <threshold> | <actual> | ✅ / ❌ |
| <metric 2> | <threshold> | <actual> | ✅ / ❌ |

| Kill Criterion | Threshold | Actual | Triggered? |
|---|---|---|---|
| <metric> | <threshold> | <actual> | ✅ / ❌ |

**Overall:** WIN / PARTIAL / LOSS / MIXED

## What We Got Right
- <factor 1>
- <factor 2>

## What We Got Wrong
- <factor 1>
- <factor 2>

## Preserved Dissent — Revisited
[Original dissent from the boardroom memo, scored:]

- **<dissenter>:** <original concern>
  - **Did it materialize?** YES / NO / PARTIAL
  - **Cost if YES:** <quantified impact>
  - **Lesson:** <one sentence>

## Assumption Audit
[Original brief's assumptions, scored:]

- **Assumption 1:** <text>
  - **Held?** YES / NO / PARTIAL
  - **Why:** <explanation>

## Process Lessons
- **Phase 2 isolation worked?** YES / NO
- **Devil's advocate concerns played out?** YES / NO / PARTIAL
- **Cadence was right?** YES / TOO LOOSE / TOO TIGHT

## Forward Actions
- [ ] <change to operating system or routing logic>
- [ ] <new decision to make based on this learning>
- [ ] <update company-context.md>

## Status
- WIN → archive, log lesson
- LOSS → schedule follow-up boardroom: `/cs:brief` for the next call

Why Pre-Committed Criteria Matter

The biggest temptation in post-mortems is retroactive justification: "we always knew X, that's why we did Y." Pre-committed criteria, signed at /cs:decide time, eliminate that move. The numbers either matched or they didn't.

Why Revisit Dissent

The dissent column from /cs:boardroom is the single most useful piece of organizational memory. Most of the time, the dissenter was directionally right. Revisiting and scoring it builds calibration over years.

Routing

  • /cs:brief — if the post-mortem surfaces a new decision
  • /cs:freeze — if the post-mortem reveals a process gap that needs cooldown enforcement
  • Updates to company-context.md via cs-onboard

Related


Version: 1.0.0

From the file to a first result

The download contains exactly the content displayed on this page. This copy may differ from the latest version in the source repository.

View the source and supporting files

This download contains SKILL.md only. Any scripts, references, templates and dependencies are not included. Get the required files from the source, preserving their directory structure, before continuing.

1. Download the file

Download SKILL.md

From the root of a test project, save the file as .skill-downloads/strategic-decision-post-mortem-mvg6txge/SKILL.md, or use the command below. This folder is for inspecting the skill before installation.

Command for macOS/Linux or WSL: requires a POSIX shell and curl. On Windows without WSL, use the download button and create the folder manually.

mkdir -p '.skill-downloads/strategic-decision-post-mortem-mvg6txge' && curl --fail --show-error --location 'https://skills-guides.com/api/skills/strategic-decision-post-mortem-mvg6txge/download' --output '.skill-downloads/strategic-decision-post-mortem-mvg6txge/SKILL.md.part' && mv '.skill-downloads/strategic-decision-post-mortem-mvg6txge/SKILL.md.part' '.skill-downloads/strategic-decision-post-mortem-mvg6txge/SKILL.md'

2. Check prerequisites

Read SKILL.md before using it. If it references scripts or external services, inspect them and prepare the required access in your test environment.

No recognized prerequisites section in this file. This does not mean it is self-contained: libraries, tools and access requirements may be mentioned elsewhere in the content or source repository.

The platforms on this page are catalog indications. The paths below follow tool documentation; they do not prove this skill has been run in those tools. No minimum tool version is confirmed for this listing.

3. Load the skill

After inspection, copy the complete folder into your project using one of the commands below, then open a new tool session. The command stops if a folder with the same name already exists: compare the files before replacing it.

Claude Code
test -f '.skill-downloads/strategic-decision-post-mortem-mvg6txge/SKILL.md' && test -s '.skill-downloads/strategic-decision-post-mortem-mvg6txge/SKILL.md' && mkdir -p '.claude/skills' && test ! -e '.claude/skills/post-mortem' && cp -R '.skill-downloads/strategic-decision-post-mortem-mvg6txge' '.claude/skills/post-mortem'

OpenSkills

OpenSkills must already be installed. The local install/read procedure is checked with OpenSkills 1.5.0, which requires Node.js ≥ 20.6.0. Catalog slugs are not resolved automatically.

Official OpenSkills installation
openskills install './.skill-downloads/strategic-decision-post-mortem-mvg6txge'

openskills read 'strategic-decision-post-mortem-mvg6txge'

Reading should display the installed file content and its base directory. It does not run the skill or install its dependencies.

For an agent that reads AGENTS.md, then sync the index. This command changes AGENTS.md: review the diff before using it.

openskills sync

Manual method or another tool: attach SKILL.md to a conversation, or open it in an agent that can read files. Include any required supporting resources. No universal folder is recognized by every tool.

4. Try a first task

Use a short, synthetic input: an API endpoint, a small document or an interface brief. In a new conversation, attach the file or give the agent its path, then adapt this request:

Read .skill-downloads/strategic-decision-post-mortem-mvg6txge/SKILL.md and apply its instructions to this example: [describe a test input]. Identify any missing files, dependencies or access. Produce the result requested by the skill without inventing data or running unreviewed scripts.

Expected result: output matching the skill instructions, or a precise list of missing prerequisites. A read confirmation alone does not validate a first use. If an external resource is unavailable, that path remains untested.

Related skills