When Answers Are Free, Questions Become Priceless
Why most teams give up on AI (and how better questions creates better leaders)
As more companies incorporate AI tools into their daily work, a typical pattern emerges:
Excitement about AI's potential → disappointment → Back to business as usual
The teams seeing value from AI aren't necessarily using better tools—they're asking better questions. The problem isn't the AI. It's that most people don't know how to ask good questions.
Why This Matters
Most people treat AI like Google with a personality- they make vague requests, expect detailed responses, then get disappointed when answers are generic.
I like to think of AI like hiring a brilliant intern who knows everything but has zero context about your business. Give them vague instructions, get useless work. Give them clear direction, and they'll amaze you.
The difference isn't the AI—it's the quality of the question.
Compare these two approaches:
Bad: "How do I increase sales?"
Result: Generic tips about customer service and pricing
Good: "I run a local restaurant. Our lunch rush is slow because office workers don't know we exist. What are three low-cost ways to attract nearby office workers during lunch?"
Result: Actionable ideas—lunch specials, office delivery partnerships, targeted local ads
A Framework for Better Questions
Instead of throwing vague “google-like” search requests at AI and hoping for the best, here's a simple framework that consistently delivers better results:
1. Start with What You Already Know
The best AI interactions happen when you already understand the domain. Share your existing knowledge, your hypothesis, or what you think the answer should look like.
When you know what good looks like, you can guide the AI toward better answers and immediately spot when it's heading in the wrong direction.
Instead of: "How do we improve customer retention?"
Try this: "I think our customers cancel in month 2 because they never complete our setup process. Help me design a 90-day plan to fix this specific problem."
2. Be Ruthlessly Specific
AI takes your questions literally - it responds to what you ask, not what you meant to ask. Include key details like audience, goals, constraints, and context.
Vague: "Write a marketing email"
Specific: "Write an email to customers who bought our software last year. Tell them about the new mobile app feature and include a 20% upgrade discount."
3. Create Context Before Content
Begin by explaining relevant background information. What does the AI need to know to give you a useful answer?
Basic: "Fix this email"
With context: "I'm responding to a 5-year customer who spends $2,000 annually. They're upset about a shipping delay. Help me write an apologetic response that offers a 10% discount."
4. Break Down Complex Questions
AI works best with clear, focused questions. When you have extremely long content or complex reasoning across multiple ideas, break it down. Give AI smaller, more manageable chunks instead.
For complicated tasks, guide the AI through step-by-step reasoning. Ask it to "think out loud" or create a plan before giving you an answer. The logic behind a recommendation is often more valuable than the recommendation itself.
Too broad: "What's our growth strategy?"
Step-by-step: "Let's build a growth strategy. First, help me identify our top 3 competitive advantages. Then, which customer segments would value these most?"
5. Iterate and Refine
Don't expect perfection on the first try. If the AI's response isn't quite what you needed, clarify or adjust your question. Often a single sentence of clarification can completely transform the quality of the response.
First attempt: "Analyze our customer churn"
Refining: "Looking at that churn analysis again, I need you to focus specifically on customers who left after less than 3 months and identify patterns in their usage before cancellation"
The Unexpected Leadership Benefit
In "Generative AI: Working Faster, But Are We Thinking Less?" , we discussed the worry that AI might make us lazy thinkers. But I believe the opposite is happening. Learning to ask AI better questions makes you better at managing people.
The same skills that get better AI results, also make you a better leader:
Explaining exactly what you want
Providing clear context upfront
Defining success before starting
Breaking complex problems into steps
If you can get an AI to deliver useful work, you can do the same with your team.
The discipline of good questioning trains your brain to think more systematically about problems and solutions- making you a better manager, strategist, and communicator with your human colleagues.
Your Next Move
Pick one task you normally give to AI. Rewrite your prompt using this framework. Compare the results.
In a world where everyone has AI tools, the most valuable skill isn't knowing the answers—it's knowing what to ask.
Every company will have ChatGPT. The winners will be those whose people know how to think with it.