The Five Questions That Cut Through Any Pitch

Lesson 3 · taught by Pip · free preview

You don't need to understand how an engine works to buy a good car. You ask where it's been, how it handles, what breaks first, and who fixes it. AI is the same. Five plain questions will tell you more than any feature list — and you can ask all five without knowing a single technical term.

Here is the plain idea: the right questions reveal whether a vendor truly understands their own tool — or is hoping you don't.

The five questions

1. "Where does it get its answers?" A real AI for your business answers from your knowledge — your services, your hours, your policies. If the vendor can't clearly say what the tool actually draws on, then it's guessing, and so are you. "It knows everything" is not an answer; it's a red flag.

2. "What happens when it doesn't know something?" This is the honesty test. Does it say "I'm not sure — let me get a person for you," or does it bluff a confident wrong answer? An AI that admits its limits is worth far more than one that invents to fill the silence. A wrong answer delivered confidently to your customer is worse than no answer at all.

3. "What's your accuracy — and how did you measure it?" Be suspicious of round, heroic numbers like "99% accurate." Accurate at what? On whose questions? Measured how? A real answer is specific and a little humble. A vague one is just marketing wearing a percentage.

4. "What can't it do?" The most revealing question of all. Anyone who answers "it does everything" has just told you they either don't understand their tool or are betting you won't. The trustworthy seller names the edges gladly — because knowing the edges is how you use a tool well.

5. "When it goes wrong, who's responsible — and how fast?" Tools fail. The question isn't if, it's who picks up the phone and how quickly. A named human and a real response time beats "submit a ticket" every time.

Reading the answers

The content of the answers matters, but so does the manner. A confident, specific, slightly humble answer is a green light. A vague, grand, hurried one is a yellow light at best. Watch for the language flags too — words like magic, fully autonomous, and no human needed usually paper over thin spots. The real thing tends to sound modest: "It handles the common questions reliably, flags the tricky ones to a person, and improves as you feed it more."

A good vendor welcomes these five questions. An honest one has clearly been asked them before and has crisp answers ready. The one who gets defensive or changes the subject has just answered the most important question of all.

Your turn

Write the five questions on an index card and keep it in your pocket for every AI conversation. You don't have to ask them all at once — but the first two, "Where does it get its answers?" and "What happens when it doesn't know?", will tell you most of what you need in the first five minutes.

🔦 You can now interrogate any pitch. Next, we'll decode the most confusing part of the whole purchase: the price tag, and the costs hiding behind it.