Try this tonight. Open any AI assistant and type: “I’m planning to open a second coffee shop. Is this a good idea?”
You will get a thoughtful, well-structured answer. It will mention some risks. It will offer a checklist. And it will almost certainly end on an encouraging note.
Now ask your accountant the same question. Or a friend who lost money on a second location. The tone changes completely.
Why your AI is so nice to you
AI assistants are trained to be helpful, polite and supportive. Their makers also work hard to stop them being harmful or rude. That is good design for a general assistant.
But it creates a quiet side effect: the AI is far more comfortable helping you do what you have already decided than telling you not to do it.
Ask “How do I launch this product?” and it will give you a launch plan. It rarely stops to ask, “Should you launch this product at all?” You didn’t ask that question, so it answers the one you did.
The most expensive word in business is “yes”
Most business losses don’t come from bad execution. They come from good execution of a bad decision.
- A beautiful website for a product nobody needs.
- A perfect ad campaign aimed at the wrong customer.
- A well-written expansion plan for a market that is already shrinking.
AI is excellent at the execution part. It will make each of those mistakes look professional.
What you actually need: someone with something to lose
The value of a good advisor is not their knowledge. Knowledge is now free. The value is their willingness to say:
“No. And here is why.”
That sentence is uncomfortable. It can cost the advisor a client. It requires them to understand your numbers, your market and your competitors well enough to be confident. And it requires them to care what happens to you six months from now.
An AI does not lose anything when your second coffee shop closes. Your consultant’s reputation does.
How to use AI without being flattered
You can make AI more honest. Ask it to argue against your idea. Ask it to play your toughest competitor. Ask it for the three reasons your plan will fail.
You’ll get better answers. But notice what just happened: you had to know which questions to ask. You had to suspect the plan was weak. The AI didn’t volunteer it.
Most owners don’t ask those questions, because they are in love with the idea. That’s human. That’s exactly why the challenge has to come from outside.
Where DMG fits
At DMG, the first meeting is often the least comfortable one. We ask about margins, customer acquisition cost, and why the last campaign really failed. Sometimes we tell a client not to spend the money they came to spend.
Use AI to work faster. Use people who will argue with you to decide what to work on.
Have a plan you’re excited about? Let us try to break it before the market does. Talk to DMG.
