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Skills from A Smart Bear

Interview Questions: Test your hypotheses without leading the witness

Turn each hypothesis into an open-ended, unbiased interview question — a miniature experiment that uncovers what customers actually think, not what you hope to hear. Adapted from Chapter 10 of Hidden Multipliers: A multiplier of one's own.

Input
A HYPOTHESES.md file — or a single hypothesis you want to test in an interview.
Output
A QUESTIONS.md of numbered questions in interview order, each mapped to the hypotheses it tests (single-hypothesis mode: the final question, in chat).

What this is about

Ask a customer "Blogs get hacked all the time and it's devastating, right? Would you like extra security?" and everyone says yes — they'd look foolish otherwise. You led the witness to the answer you wanted to hear, and now you'll never know the answer you needed to hear. Most customer interviews fail exactly here: not in who you talk to, but in questions that quietly telegraph the hoped-for answer and harvest polite agreement dressed up as validation.

This is the third step of the interview method that runs goals → hypotheses → questions. Because every question is anchored to a hypothesis, writing good ones stops being guesswork: each question is a miniature experiment, held to four criteria from the book — it must be able to confirm or negate the hypothesis, hint at no particular answer, elicit specifics rather than sentiment, and invite information you didn't know to ask for. The skill drafts candidates, grills every version — including yours — with a polite-stranger test, phrases everything in your customers' own vocabulary, and refuses outright to finalize a question that violates the criteria, because a leading question doesn't just weaken an interview; it manufactures false evidence. The one sanctioned exception, straight from the source: near the end of an interview you may float a specific price, because the visceral reaction to a real number is itself the data.

Give it your whole HYPOTHESES.md and it walks the list — grouping related hypotheses so the set fits a real conversation, ordering the result like an interview plan, and maintaining QUESTIONS.md as a live file from the first settled question so a long session (or a resumed one) never loses work. Or give it a single hypothesis and it simply works that one question into shape with you and hands it back in chat — no files, no ceremony.

Example invocation

You can invoke the skill like this:

/asb-interview-questions Here's my HYPOTHESES.md from the hypotheses
exercise — turn these into the questions I'll actually ask.

The session works through your hypotheses one at a time, drafting and attacking each question until it's genuinely open-ended, then writes QUESTIONS.md as a ready-to-use interview plan.

Or bring one hypothesis with no file at all:

/asb-interview-questions My hypothesis: gym owners spend at least 2
hours a week chasing failed membership payments. How do I ask about
this without planting the answer?

In single-question mode, the skill works one phrasing into shape with you and hands back the final question in chat.

One practical note: say where you're working. Name a directory (or point at your existing files) when you invoke, and the skill keeps the method's files together there — if you don't, it asks before creating anything.

From the source

Two sources form the foundation of this skill:

  • As in Chapter 10 of Hidden Multipliers: A multiplier of one's own (section "Questions: What to Ask During the Interview") — hiddenmultipliers.com — the questions step itself: the four criteria, the leading-the-witness failure and its security-question example, and the bad-versus-good question table this skill's grilling is built on.
  • The Iterative-Hypothesis customer development method — the published article version of the method, including the price-quoting exception, the value-testing question pattern, and the follow-up probes for chasing surprises.

Supporting articles each supply a piece of the mechanism: