Project retrospective writer

Create LESSONS.md files that capture institutional knowledge, especially failures. Think like a journalist writing about your own project—be specific, be honest, name the actual mistakes.

When to use

• After completing an investigation or project
• When shutting down or pausing a publication
• Post-mortem for events
• Handing off a project to someone else
• Annual review of ongoing initiatives

The critical section: "The real problem"

This is the most valuable part of any retrospective. It answers:

"What did we THINK we were building vs. what was ACTUALLY needed?"

Good example:

We built a comprehensive tagging system when users just needed full-text search. Three weeks on features no one used.

Bad example (too generic):

We learned the importance of user research.

Template structure

# LESSONS.md

## Project
- **Name:** [Project name]
- **Dates:** [Start - End]
- **Status:** [Completed / Abandoned / Ongoing]
- **Author:** [Your name]

## Summary
[One paragraph: what it did, what impact it had, why it matters]

## What worked

### Technical wins
- [Specific decision and WHY it worked]
- [Tool/pattern that saved time]

### Process wins
- [Methodology that helped]
- [Communication pattern that worked]

## What didn't work

### Critical failures
- [Thing that blocked progress - be specific]
- [Wrong assumption and its cost]

### Technical debt
- [Shortcut that hurt later]
- [Complexity that wasn't needed]

### External factors
- [Things outside your control that impacted project]

## The real problem
[This is the most important section]

What we thought: [Initial assumption]
What was actually needed: [Reality]
The gap cost us: [Time/effort/money wasted]

## Recommendations

### If continuing this project
1. [First priority]
2. [Second priority]
3. [Third priority]

### If starting fresh
- [What to do differently]
- [What to skip entirely]

### Tech stack verdict
- **Keep:** [Tools that worked well]
- **Replace:** [Tools that caused problems]
- **Add:** [Tools you wished you had]

## Reusable artifacts

| Component | Why it's valuable |
|-----------|------------------|
| [Name] | [Specific reuse potential] |
| [Name] | [Why someone else should use this] |

## Questions for next time
- [Unanswered questions worth investigating]
- [Things you'd research before starting]

Voice guidelines

• Honest, specific, slightly self-deprecating
• Like explaining to a friend why the project took twice as long
• No corporate speak or blame-shifting
• Name specific mistakes, not vague "challenges"

What to include vs exclude

The specificity test

For each item in "What didn't work," ask:

• Can I name the specific decision?
• Can I quantify the impact?
• Would this help someone avoid the same mistake?

If no to any → Be more specific.

Examples of good vs bad entries

Bad - too vague:

• Communication could have been better
• We underestimated the complexity
• Testing was insufficient

Good - specific and actionable:

• Skipped schema validation on data files. Cost: 3 hours debugging a typo that caused silent failures.
• Built custom date picker when browser native input would have worked. 2 days wasted.
• No error messages when data fails to load—users just see blank screen.

"The real problem" examples

Weak:

We learned that requirements can change.

Strong:

We built an admin dashboard for editors when they actually needed a Slack bot. They live in Slack—forcing them to open a web app was friction they'd never accept. The dashboard has 2 monthly active users; the Slack bot prototype we built in a day has 47.

Red flags in your writing

If you find yourself writing these, stop and be more specific:

• "Communication is key"
• "We learned the importance of..."
• "Going forward, we should..."
• "Challenges included..."
• "There were some issues with..."

These are placeholders for real insights. Replace them.

Journalism-specific templates

Templates are in the templates/ directory:

Template selection

What kind of project?
├── Investigation/analysis → research-project.md
├── Conference/workshop → event.md
├── Newsletter/podcast → publication.md
└── Newsroom tool → editorial-tool.md

The best retrospectives are written by people who got burned and want to save others from the same fate.