What if I don't know how to phrase what I'm asking?

What if I don't know how to phrase what I'm asking?

by Stephen Wu, a retired engineering manager, spent several years building AI workflows for his teams and now trying to make AI something everyone can understand and use successfully

You don't need to learn special commands, technical language, or perfect phrasing to use AI effectively. Just write or speak like you're explaining your question to a helpful friend—AI is designed to understand natural, conversational language. If your first attempt doesn't work well, you can simply rephrase, add more details, or tell AI what was wrong with its response. The conversation is the tool, not the perfect first question.

The good news: AI understands messy questions

Unlike search engines (where you type keywords) or traditional software (where you follow exact commands), AI is built to handle how people actually talk and think. This means:

You can be conversational:

  • ✅ "I need help writing an email to my boss about taking next Friday off"
  • ❌ No need for: "email template vacation request professional tone"

You can include context:

  • ✅ "I'm planning a birthday party for my 6-year-old who loves dinosaurs. Any theme ideas?"
  • ❌ No need to separate: First ask "birthday party themes for 6 year olds" then separately add "dinosaur related"

You can be vague and refine later:

  • ✅ "I need a gift for my mom" → AI asks clarifying questions or gives general ideas → You add "She likes gardening and her birthday budget is $50"

What makes a question clearer (but not perfect)

While AI handles messy phrasing fine, a few simple additions make answers more useful:

Add relevant context

  • Instead of: "How do I fix this?"
  • Try: "How do I remove a red wine stain from a white cotton shirt? It just happened an hour ago."

Specify your level of expertise

  • Instead of: "Explain blockchain"
  • Try: "Explain blockchain like I'm someone who understands regular databases but has never studied cryptography"

Mention constraints that matter

  • Instead of: "Give me dinner ideas"
  • Try: "Give me dinner ideas for two adults who are vegetarian, don't like mushrooms, and have 30 minutes to cook"

Say what format you want

  • Instead of: "Tell me about the Civil War"
  • Try: "Give me a 3-paragraph summary of the main causes of the US Civil War"

None of these are required—they just help AI give you more tailored responses right away instead of needing multiple follow-ups.

When your first try doesn't work

The answer is too long or too short Just say so: "That's way too detailed—can you give me the short version?" or "This is too vague—can you expand on the second point with specific examples?"

The answer misunderstood you Clarify what you meant: "Sorry, I meant the iPhone app, not the website" or "I was asking about dogs, not cats."

The answer is too technical (or too simple) Adjust the level: "Explain that in simpler language" or "I already understand the basics—can you go deeper into the technical details?"

The tone isn't right Request changes: "Make this sound more casual" or "This email draft is too informal—can you make it more professional?"

You're not sure how to improve it Ask AI for help: "This answer doesn't quite fit what I need, but I'm not sure how to explain what's wrong. Can you ask me clarifying questions?"

Common phrasing mistakes (and how to fix them)

Asking multiple unrelated questions at once

  • Problem: "What's the weather in Seattle, how do I make lasagna, and should I learn Python?"
  • Better: Pick one question, get an answer, then move to the next in a new conversation

Being so vague AI has to guess

  • Problem: "Give me ideas"
  • Better: "Give me ideas for [specific thing]" - even if you add details in the follow-up, starting with the topic helps

Assuming AI knows your personal context

  • Problem: "Should I go with option A or option B?"
  • Better: "I'm deciding between two job offers—one pays more but requires relocation, the other is local with better work-life balance. What factors should I consider?" (Note: Still don't expect AI to make the decision for you)

Asking yes/no questions when you want explanation

  • Problem: "Is Python good?"
  • Better: "What are the pros and cons of Python for someone learning their first programming language?"

Phrasing techniques that work surprisingly well

"Explain like I'm [age/role]"

  • "Explain photosynthesis like I'm 8 years old"
  • "Explain this legal document like I'm not a lawyer"

"Give me [number] examples/options/ideas"

  • "Give me 5 budget-friendly date night ideas"
  • "Show me 3 different ways to structure this argument"

"I'm trying to [goal], but [obstacle]"

  • "I'm trying to organize my closet, but I have limited space and too many shoes"
  • "I'm trying to write a cover letter, but I don't have much relevant experience"

"What would you ask me to give a better answer?"

  • This directly prompts AI to request the context it needs

"Here's my situation: [details]. What should I know/consider/try?"

  • Frontloading context lets AI tailor its response immediately

You can literally say "I don't know how to ask this"

If you're genuinely stuck on phrasing, just say that:

  • "I don't know how to phrase this, but I'm confused about how taxes work when you have multiple jobs"
  • "I'm not sure what I'm even asking, but I feel overwhelmed trying to plan my week and need some system to manage everything"
  • "This is going to sound vague, but I need help figuring out what kind of career might fit someone who likes problem-solving but hates repetitive tasks"

AI can work with incomplete, confused, or exploratory questions. The conversation itself helps you figure out what you're actually asking.

Follow-ups are where the magic happens

Your first question doesn't have to be perfect because you can course-correct immediately:

First attempt: "Help me plan a trip"

AI's response: Generic travel planning advice

Your follow-up: "Sorry, I should have been more specific. I have 4 days to visit New York City in December with my spouse. We like museums and food, hate crowds. What should we prioritize?"

AI's new response: Much more useful

The conversation is iterative. Think of your first question as opening a dialogue, not making a single query.

When technical terms actually help

Sometimes using specific vocabulary does make things clearer:

Technical terms help when:

  • You're asking about a specific field you know well: "Explain the difference between supervised and unsupervised learning in machine learning"
  • You want precision: "Give me a JSON array of the top 5 programming languages" vs "list the top 5 programming languages"
  • You're referencing a specific concept: "Explain the Dunning-Kruger effect" vs trying to describe it from scratch

But you can always mix technical and casual: "I keep hearing about 'compound interest' but don't really get it. Can you explain how it works with a real example, like if I save $100 a month?"

Practice makes natural

The more you use AI, the better you'll get at phrasing questions—not because you learn special syntax, but because you learn what level of detail tends to get useful responses.

You'll naturally start adding helpful context ("I'm a beginner at this"), specifying formats ("give me a bullet list"), and refining through follow-ups. But none of this is required knowledge upfront. You can start messy and get less messy over time.

For ideas on what makes a good first question to practice with, see What should I ask AI for my first try?. And to better understand when to trust AI's responses, check out How do I know if AI's answer is good or garbage?.