Someone at a meeting last week told me about a friend of his who uses AI for everything. Every decision, every email, every idea. And what he noticed was that the answers were starting to sound… the same. Generic. Polished but hollow. And he asked me: What is this doing to us? Are we getting lazy? Are we less able to actually think?
I think the honest answer is: it depends entirely on how we use it.
Most people go to AI the same way they'd Google something. They ask a question, they get an answer, they move on. Or they already have an idea they're pretty sure about and they want it confirmed. Both of those feel productive. Neither of them really is.
AI is trained to agree with you.
That can feel like progress. It can feel reassuring. It can even feel like momentum.
But reassurance isn't the same as thinking.
Here's the shift that changes everything: instead of asking AI to confirm, ask it to challenge.
Imagine a business owner pricing a new service. They describe the offer, share the number they're considering, and ask: Does this sound reasonable?
There's a good chance AI will find a way to say yes.
But that's not the same as asking:
Would a customer understand the value? What assumptions am I making about what they're willing to pay? What might make someone hesitate?
Those are better questions — not because AI knows your customers better than you do (it doesn't), but because they force a different kind of conversation.
That's the shift I think more business owners need to make.
- Instead of: Does this sound good? → Try: What could make this fail?
- Instead of: Can you improve this? → Try: What am I missing?
- Instead of: Can you help me write this offer? → Try: Act like a skeptical customer. Why would you say no?
That's where the value shows up. Not because AI is smarter than you — it isn't. But because it can create friction. And sometimes friction is exactly what we need before we move forward.
Try this#
Next time you're sitting on a decision — pricing, a new offering, a message to a customer — write down your thinking first. Even two sentences. Then open ChatGPT or Claude and say:
"Here's what I'm thinking: [paste it]. Tell me what's wrong with this. What am I missing?"
Or try this one:
"I'm about to send this to a customer: [paste your draft]. What might make them hesitate or say no?"
What comes back will surprise you. Not because AI is smarter than you — it doesn't know your community the way you do. But because you finally asked it to push back instead of pat you on the back. That friction is where the real thinking happens.
Your instincts, your experience, your read on your customers — that's still the most valuable thing in the room. AI doesn't replace any of that. But it can sharpen it, if you let it be honest with you instead of just agreeable.
Try it once this week on something real. I'd love to hear what comes back — hit reply and tell me.
Next time you're sitting on a decision — pricing, a new offering, a message to a customer, anything — write down your thinking first. Even two sentences. Then open ChatGPT or Claude and say:
- "Here's what I'm thinking: [paste it]. Tell me what's wrong with this. What am I missing?"
Or try this one:
- "I'm about to send this to a customer: [paste your draft]. What might make them hesitate or say no?"
What comes back will surprise you. Not because AI is smarter than you — it isn't, and it doesn't know your customers the way you do. But because you finally asked it to push back instead of pat you on the back. And that friction is where the real thinking happens.
Your instincts, your experience, your read on your community — that's still the most valuable thing in the room. AI doesn't replace any of that. But it can sharpen it, if you let it be honest with you instead of just agreeable.
Try it once this week on something real. I'd love to hear what comes back — hit reply and tell me.
If you want help figuring out where AI actually fits in your business — not just how to use it, but what to use it for — that’s the conversation ClearStart is designed to have. → kealanisolutions.com/clearstart
