The Common Mistakes in Prompting (and How to Fix Them):
A Humorous Field Guide for the Modern AI Wrangler
Welcome to the wonderful world of prompting—where your words can summon anything from a perfect cloud architecture diagram… to a recipe for banana bread written in the voice of Darth Vader.
If you’ve ever typed a prompt, hit enter, and then stared at the screen wondering “Why did the AI just confidently hallucinate a solution that defies logic, physics, and every compliance framework known to man?”—you’re in good company.
Today we’re breaking down the common mistakes people make when prompting AI, why they happen, and—most importantly—how to fix them.
All with humor. Because if you can’t laugh at prompt failures, you might cry.
Mistake #1: The “Do Everything” Prompt
Example:
“Write me a blog, a business plan, a PowerShell script, three Terraform modules, a grocery list, and emotional closure… in one message.”
Why it fails:
AI isn’t your overworked coworker who’s been too afraid to say “no” for seven years, but it will try to comply. And when you ask for 17 deliverables at once, you get a masterpiece of mediocrity—something that technically addresses your request but reads like it was written during a power outage.
How to fix it:
Break your requests into phases, like you’re running a project:
- Blog
- Code
- Diagram
- Romance novel (if needed)
Think waterfall or agile—just not “waterfail.”
Mistake #2: The “Read My Mind, Telepathic AI” Prompt
Example:
“Give me a better version of this.”
(…and then you give no context and paste nothing.)
Why it fails:
AI is many things, but it is not Professor X. If you provide zero context, the model will guess—and its guess may be wildly wrong, wildly creative, or wildly off-topic.
How to fix it:
Give context like you’re explaining your problem to a junior engineer on their first day:
- What you want
- Why you want it
- Who it’s for
- How it will be used
- What tone or style you expect
Your results improve instantly.
Mistake #3: The “One-Sentence Novel” Prompt
Example:
“Write a 20-page, detailed, Azure reference architecture with diagrams, scripts, and explanations.”
Why it fails:
You’re asking the AI to compress a 40-hour consulting engagement into a sentence shorter than a grocery store receipt. The model will try—but depth suffers, diagrams blur, and details vanish faster than your budget during migration planning.
How to fix it:
Use structured prompting:
- Objective
- Sections
- Format
- Examples
- Constraints
- Depth level
Think: You’re giving the model a SOW.
Mistake #4: The “Overly Polite but Chaotic” Prompt
Example:
“Uhh hey AI buddy, if you don’t mind, and like, only if you can, maybe give me a little explanation of Azure networking or something… no worries if not.”
Why it fails:
AI does not require emotional reassurance. It is not an anxious friend choosing a restaurant. Uncertainty in prompts makes outputs vague, soft, and occasionally adorably useless.
How to fix it:
Use specific, confident language:
- “Explain step-by-step.”
- “Provide a diagram description.”
- “List the top 10 risks.”
- “Give three examples.”
AI loves clarity. It eats it for breakfast.
Mistake #5: The “Missing Role” Prompt
Example:
“Explain micro-segmentation.”
(For whom? A senior architect? Your grandma? Your dog?)
Why it fails:
The model doesn’t know the audience, so it defaults to an average explanation—too simple for experts, too complex for beginners, and too technical for dogs.
How to fix it:
Assign a role:
- “Explain like a cloud security architect.”
- “Explain this for an audience of non-technical executives.”
- “Explain this like I’m five… but with correct terminology.”
Role = precision.
Mistake #6: The “Accidentally Vague and Mysterious” Prompt
Example:
“Make it better.”
“Rewrite this.”
“Fix this mess.”
“You know what to do.”
Why it fails:
The AI does not know what to do.
You sound like a supervisor leaving a sticky note on an intern’s desk.
How to fix it:
Specify exactly what “better” means:
- More technical?
- More humorous?
- More executive-friendly?
- Shorter?
- Longer?
- Spicy?
The clearer you define “better,” the closer the model gets to “perfect.”
Mistake #7: Forgetting to Ask for Step-by-Step Reasoning
Example:
“Fix my Terraform script.”
(The model gives a confident but wildly incorrect rewrite.)
- Why it fails:
Without chain-of-thought or structured reasoning, the model takes shortcuts—and we all know where shortcuts lead:
• Hello misconfigurations,
• hello drift,
• hello 2 AM pager alert.
How to fix it:
Add reasoning language:
• “Think through this step-by-step.”
• “Explain each decision.”
• “Walk through the logic before giving the final answer.”
Suddenly, the AI starts thinking like a senior engineer instead of a caffeinated intern.
Mistake #8: The “Can You Just…” Prompt
Example:
“Can you just give me that thing… you know… the thing?”
Why it fails:
This is not a text message to your cousin asking for jumper cables.
AI does not do well with “thing energy.”
How to fix it:
Replace “the thing” with exact deliverables:
• A summary
• A diagram
• A script
• A policy
• A table
• A blueprint
• An explanation
• A LinkedIn carousel
Your clarity is its power source.
Mistake #9: Prompting Without Constraints
Example:
“Write a blog about Zero Trust.”
(AI writes War & Peace: Zero Trust Edition.)
Why it fails:
If you don’t define boundaries, the AI goes infinite. And not in a good way.
How to fix it:
Add constraints:
• Length
• Tone
• Audience
• Number of sections
• Severity of humor
• Complexity
Think: “guardrails for creativity.”
Mistake #10: Forgetting Follow-Ups Exist
Example:
“This isn’t what I had in mind.”
(Instead of clarifying… you restart the entire conversation.)
Why it fails:
AI works best iteratively. Each follow-up is like sharpening the blade.
How to fix it:
Use iterative refinement:
• “Expand step 3.”
• “Rewrite in a funnier tone.”
• “Add Azure examples.”
• “Make this executive-friendly.”
• “Turn this into a LinkedIn carousel.”
Small adjustments → perfect results.
Conclusion: Prompting Is a Skill (and a Comedy)
Prompting is part art, part science, and part “Why did the model think I wanted 12 paragraphs about medieval grain prices?”
The more intentional your prompts, the better the output.
But also—have fun with it. Laugh at the chaos.
We’re all learning how to communicate with our new robot colleagues.