The difference between getting generic fluff and genuinely useful insights usually comes down to one thing: how you ask the question. Here's how to get the most out of your AI conversations.
The Big Secret: Context Changes Everything
AI doesn't know anything about you until you tell it. The biggest mistake people make is asking questions like they're typing into Google:
Bad: "How do I increase revenue?"
You'll get generic advice that could apply to literally any business. Try this instead:
Better: "I run a State Farm agency with $2.1M in premium. My auto retention is 83% but life production is lagging. What are three ways I could grow life sales given my current book?"
The more context you provide, the more useful the answer.
A Simple Framework: CRAFT
When you need something specific, think through these five things:
- Context — Background about your situation
- Role — Who you want the AI to act as (advisor, analyst, devil's advocate)
- Ask — Your specific question or request
- Format — How you want the answer (bullets, table, step-by-step)
- Tone — Professional? Casual? Detailed? Concise?
Example Using CRAFT
"I'm a State Farm agent [Context] and I need you to act as my financial advisor [Role]. My team member just asked for a raise. Here's our current comp structure and production numbers [upload document]. Help me think through whether it makes sense financially [Ask]. Give me a pros/cons table and a recommendation [Format], and be direct about it [Tone]."
It's a Conversation, Not a Form
One of AI's superpowers is the ability to go back and forth. Don't treat it like you're filling out a form—treat it like you're talking to a smart colleague who happens to be available 24/7.
Start with your question, then follow up:
- "Can you say that in simpler terms?"
- "What's the risk if I go that route?"
- "How does this change if production goes up 20%?"
- "What am I missing here?"
- "Play devil's advocate—poke holes in this."
Each follow-up sharpens the conversation and gets you closer to something actually useful.
Upload Your Documents
You don't have to type everything out. Upload documents and reference them:
- "Here's my comp recap from last quarter. What should I be paying attention to?"
- "I attached my lease agreement. What are the key terms I need to understand?"
- "Look at this vendor proposal. What questions should I ask before I sign?"
AI can read and analyze documents way faster than you can summarize them. Use that.
Real Examples You Can Steal
Here are some prompts you can adapt for your own conversations:
For Financial Analysis
"Here's my P&L from last month. Compare it to the previous three months and flag anything that changed by more than 10%."
For Decision Support
"I'm thinking about adding a part-time CSR at $20/hour for 20 hours a week. Walk me through the financial impact and help me decide if it makes sense right now."
For Drafting Communications
"Write a professional email turning down a software vendor. I want to be clear it's a no for now, but leave the door open. Keep it under 100 words."
For Strategic Thinking
"I want to grow my book by $500K in premium next year. Given my mix of auto, home, and life, what's the most realistic path? Factor in my retention rates and close rates."
For Problem Solving
"My auto retention dropped from 87% to 83% this quarter. Help me brainstorm what might be causing it and give me a checklist to investigate."
Getting Better Over Time
The more you use AI, the better you'll get at asking the right questions. Pay attention to what works and what doesn't:
- Answer too generic? Add more context about your specific situation.
- Answer too long? Ask for a summary or bullet points.
- Missing the point? Clarify what you're really trying to solve.
- Too complicated? Ask for an explanation a non-expert would understand.
Save the prompts that work well for you. Build your own go-to library.
The Bottom Line
Talking to AI effectively is a skill—but it's a learnable one. Give context, be specific about what you need, and treat it as a conversation rather than a one-shot query.
The business owners getting the most value from AI aren't the most tech-savvy. They're the ones who know how to ask good questions and aren't afraid to keep pushing until they get something useful.