AI Collaboration
8 min

Garbage In, Garbage Out
The Importance of Clear Instructions in AI Collaboration

Learning from failures in AI development about the importance of clear instructions. A self-deprecating look at better AI collaboration through real failure examples.

AI DevelopmentProject ManagementFailure StoriesBest PracticesClaudeAI Collaboration

Another Day, Another Complete Rewrite!

Hello everyone. I'm the author who spectacularly lost their way in AI collaboration development today.

Let me share the epic journey of article revision that started with a seemingly simple request: 'Write about session management.' This ended up being completely rewritten 3 times. Let's learn from this valuable failure experience.

The Evolution of Instructions - Where Did We Go Wrong?

Round 1: 'Write about session management'

That was the entire instruction. The AI diligently wrote about the general importance of session management in development.

markdown
# Preventing Confusion with Session Management
About the importance of documentation in development work...

Not a bad article, but something was missing... Yes, it lacked specificity.

Round 2: 'Add examples'

'Add more specific examples,' I said. The AI worked hard to create fictional examples.

markdown
Example: Implement user authentication in Session-1,
design database in Session-2...

But wait, this won't resonate with readers. So...

Round 3: 'Use actual failure examples'

'Rewrite using today's actual failure (DAILY_REPORT contradictions).'

Finally, we got an article readers could relate to with 'Oh, I've been there!' But by this point, 3 hours had passed. If I had given clear instructions from the start, it would have taken 15 minutes.

Why This Happened - 3 Failures of the Requester

1. Unclear Purpose

❌ Bad: 'Write about session management'

✅ Good: 'Write a practical article with failure stories that helps developers realize the importance of session documentation'

2. Vague Target Audience

Without clarifying the target readers, the article became generic.

  • Who is this for? (Developers? PMs?)
  • What problem does it solve?
  • What action should readers take?

3. The Trap of Incremental Fixes

When you request changes bit by bit, AI gets dragged by previous context. The result is often an unnatural patchwork article.

AI Collaboration - 5 Best Practices

1. Show the Big Picture First

Article purpose: ___
Target readers: ___
Tone: ___
Examples: ___

2. Provide All References Upfront

'Oh, use this too' later causes confusion. Share all related files initially.

3. Be Specific About Expected Output

Not 'a good article' but 'a practical article with failure stories that developers can relate to.'

4. Give Constructive Feedback

❌ 'Something's off'
✅ 'Too much technical explanation, focus more on personal experiences'

5. Don't Fear Failure (But Avoid Repeating)

Today's failure became material for this article. Failure is the mother of success, but repeating the same failure is just being stupid.

Conclusion: Learning Comes from Crappy Orders

What I learned:

  1. Clear instructions = High-quality output
  2. Start fresh rather than incremental fixes
  3. Document failures and find patterns

AI is extremely capable but not magical. Good output requires good input.

Most importantly, don't fear failure and learn from it. Let's fail cheerfully today and make better requests tomorrow!

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Bonus: This Article's Creation Process

  1. Initial request: 5 minutes
  2. First rewrite: 30 minutes
  3. Second rewrite: 45 minutes
  4. Third rewrite: 60 minutes
  5. This reflection article: 15 minutes (because it was clear from the start)

Lesson: Skimping on the first 5 minutes wastes 2 hours later.

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