learn-asking-right-questions-as-ai-with-phoebe / Session 3 of 6
Learn Asking the Right Questions as an AI Developer with Phoebe · Session 3 of 6

The AI developer's questions, and the bench

Sessions 1 and 2 argued that what you ask decides what you learn. Tonight the argument is replaced by a count. Adeline Tan sits in this page with a fact sheet you cannot see: 24 things that are true about Harbourline and its supplier WhatsApps, worth 69 points, eight of which she will only say once she trusts you, and one of which needs a lot of trust. You have 45 minutes and a bank of 37 questions, sorted into five kinds. The page runs the same meeting five ways in front of you: the technical opener most developers were trained to give, a shuffle, the Six Doors in printed order, the doors tuned for an AI developer, and the fast yes-or-no interview that looks like the best meeting in the room. Then it hands you the chair.

🔴 Bench night Bring your door sheet from session 1 No code tonight, all clicking 45 min
0-3 · Welcome 3-17 · Five kinds of question 17-40 · The bench, then your own meeting 40-45 · Q&A
Part 0

Where we start

A bench is a fixed person and a fixed clock, so that when two ways of asking get two different results the only thing that differed was the asking. The person is constructed: Harbourline is invented and so is Adeline, and every fact on her sheet, every minute cost and every trust gate is printed in a file you can open and change. What the bench claims is not a number about pharmacies or chatbots. It is a mechanism, shown as an ordering you can reproduce: jargon costs twice, leading questions record beliefs that are wrong, and the facts that matter most only come out once trust exists. The corridor the doors come from is stated once, in full, here; tonight uses door 3, the current way, as the widest.

🎫 Clear all three quiz questions to stamp your passport counted = computed from the printed bank, in your browser constructed = the company, the person, the sheet

★ What you walk out with tonight. Your own question bank sorted into the five kinds, the counted answer to "what is the framework worth against a shuffle" (54 against 30, on this sheet), the honest reason tuning the order buys only one point for an AI developer, why the kind of question matters far more than its place, and one run of the meeting in your own hands with a score beside the presets.

Part 1 · covers the five kinds, and the AI developer's door

Five kinds of question, one of which earns trust

7 min live

Every question in the bank is one of five kinds, and Adeline answers each kind differently. The kinds are not about wording. They are about what comes back: a fact, nothing, a generic, a request to explain yourself, or an agreement with something you assumed. The AI developer's door, the current way, has the highest-value fact on the sheet behind it, and it is opened by one kind only.

FIVE KINDS, AND WHAT COMES BACK the kind is not the wording; it is what she can do with it OPEN "Show me one thread from yesterday, start to finish." 40 threads a day 3-language orders trust, one notch up CLOSED "Is it three area managers?" "yes" one fact at most, nothing you did not ask VAGUE "What would you like AI to do for you?" "a chatbot?" a generic, and three minutes gone JARGON "What is your tolerance for hallucination rate?" ? "sorry, what do you mean?" and a notch lost five minutes, not three LEADING "So the assistant should reply to the suppliers itself?" "I suppose so." "replies on its own" is now in your notes. It is wrong. Only the first kind moves the trust meter up, and eight of the 24 facts on the sheet are behind that meter.
🔍 Click to zoom - the two right-hand cards cost more than they look: one in minutes and trust, one in a build that goes wrong later
LiveWhat each kind gets back, and what it costs3 min▶

Open. About the past or the present, answerable by anyone who runs the shop. "Show me one thread from yesterday, start to finish." It costs three to five minutes, it uncovers the facts behind its door, and it earns a point of trust, which is the currency the sensitive facts are priced in. Every open question in the bank carries a teach-back line.

Closed. Yes or no. "Is it three area managers?" One or two minutes, one fact at most, and only the fact you already had the shape of. Cheap, and useful for confirming, but a meeting made of them learns nothing you did not walk in expecting.

Vague. "What would you like AI to do for you?" It sounds open. It is not, because it hands her your job, and what comes back is a generic: the board wants AI on a slide. Three minutes for a sentence you could have guessed.

Jargon. "What is your tolerance for hallucination rate?" She has to ask what you mean, so it costs the question plus an explanation, five minutes rather than three, and she is a little less sure you understand her business. On the bench that is a point of trust lost, and it is the only kind that loses one.

Leading. "So the assistant should reply to the suppliers automatically?" She says "I suppose so", because the question told her the expected answer and she is being polite. Nothing true came back. Something false went into your notes, and it costs later, when you build a bot that says yes on its own. On the bench a leading question records a belief with a cost attached, and the fast interview records five of them.

LiveThe AI developer's door is the current way, and here is its bank3 min▶

An AI developer's output replaces or assists a human step. The facts that decide whether it is safe are the thread as it happens today, which replies are lookups and which are decisions, how often the person catches an error, and who checks the output. On Adeline's sheet the single most valuable fact, worth 5 of 69, is one real thread end to end: the supplier sends a confirmation, the area manager checks it against the outlet's order in a different WhatsApp group, and replies OK or queries; about forty threads a day per manager, and about four in five end in a plain OK. Right behind it, and only once she trusts you a little: about one confirmation in twenty has a wrong price or a substitute in it. And from the decision door: only the area manager may accept a substitute or a price change, and a wrong substitution is a compliance problem, not a customer-service one.

The four open questions that open those facts are the first four in the AI-developer-tuned order on the bench, each with its teach-back line:

  • "Show me one thread from yesterday, start to finish. What did you do at each message?" Teach-back: "The workflow as it happens today is the spec. I cannot automate a step I have not watched a person do."
  • "How often is a confirmation wrong, and how do you catch it?" Teach-back: "The error rate today is the bar any assistant has to beat, and how you catch errors is the part the assistant has to keep."
  • "In a thread, which replies need a person to decide, and which are just looking something up?" Teach-back: "I split every workflow into lookups and decisions. Assistants do lookups, people keep decisions, and the line between them is yours to draw."
  • "What is the worst thing that happens if a reply is wrong?" Teach-back: "The worst case sets how much checking the assistant needs. A wrong delivery time and a wrong drug are not the same mistake."

Asked first, they put 23 points in your notes by minute 17 and take trust to 4, past the level the sheet's most sensitive fact is priced at.

Self-studyThe whole bank, by kind3 min▶

Thirty-seven questions: twenty open (two to five per door, five of them behind the current way), four vague, five jargon, five leading, three closed. The open ones are the sheet you built in session 1 with Adeline's answers already attached. The others are there because they are what gets asked in real meetings, and the bench needs them to show what they cost. Every one is printed with its kind, its minute cost and the facts it reaches in the bank file the page loads; the widget below draws its buttons from that file, so what you click is what it counts.

KindIn the bankMinutesWhat comes backTrust
Open203 to 5The facts behind its door, when trust is high enough for them+1
Closed31 to 2One fact at most0
Vague43 to 4A generic; at most one low-value fact0
Jargon55"Sorry, what do you mean?"-1
Leading51 to 2"I suppose so", and a false belief with a cost of 2 to 40
Real world

The chatbot she already switched off. A constructed case, Harbourline, with a familiar shape. Last year the POS vendor's chatbot answered a customer's prescription question wrongly, and Adeline switched it off within a week. She will not mention it if you open with model choices; she mentions it when you ask what she has tried before. It is the reason the words "replies on its own" make her wary, and the reason the lookups-versus-decisions question is the one that earns her trust fastest.

Build-along · the bench

Five ways of asking, counted in front of you

★ 23 min · the main event

Work down the five presets in order. For each, read the verdict line, then the counters, then the transcript underneath: what you asked, what she said, what it was worth, and where trust stood. Say out loud what changed before moving to the next. The last preset is the anti-lever, the interview that looks most efficient, and the bench shows what it costs. Then the lower half of the widget gives you the chair: same person, same 45 minutes, your choice of questions, scored beside the presets.

Read it in this order. Net value, then false beliefs, then doors opened, then the "after 20 minutes" counter. Net value is what you can build on. False beliefs are what you will build wrong, and for an assistant that talks to suppliers a wrong belief ships as behaviour. Doors opened is whether you can write a brief at all. The 20-minute counter is what is in your notes if she gets called away, which happens.

Part 2 · covers what the bench finds

Same person, five answers

5 min live

The bench above computes these live; the numbers here are the ones it produces on the printed bank, written down so they can be argued with after class. Change a value in the bank file and they move. The ordering does not. One of the findings is smaller than you might hope, and it is stated as it is.

NET VALUE OUT OF 69, FIVE WAYS OF ASKING THE SAME PERSON wide bar = net value after 45 minutes · thin bar = what was in your notes after 20 · scale: 8 px per point, from x = 230 The efficient interview 21 5 false beliefs · after 20 min: -4 The technical opener 11 4 facts, 2 doors · after 20 min: 0 Any order at all 30 mean of 200 · range -1 to 52 after 20 min: 14 Six Doors, in order 54 after 20 min: 22 Tuned for an AI developer 55 after 20 min: 23 the ceiling, 63 an optimizer that can read her sheet Same person, same clock. The kind of question, far more than its place, decided 11 points or 54.
🔍 Click to zoom - the bottom two bars are one point apart; the gap that matters is between the top two and the bottom two
Way of askingNet valueAfter 20 minFactsDoorsFalse beliefs
The efficient interview (leading and closed first)21-41265
The technical opener (five jargon questions first)110420
Any order at all (mean of 200 shuffles)30.114.312.85.42.5
Six Doors, door by door54221860
Six Doors, tuned for an AI developer (current way widest)55231860
Ceiling: an optimizer that can read the sheet6332

All counted from the printed bank. Random is a mean over 200 seeded shuffles; its best single draw is 52 and its worst is -1.

LiveFinding 1: tuning buys one point here, and that is the honest number2 min▶

Six Doors in printed order gets 54 of 69 with no false beliefs and every door opened. Tuning the order for an AI developer, current way first, gets 55, and 23 in your notes by minute 20 instead of 22. One point. It is small for a plain reason: Adeline's request is already about the current way, so the printed order gets there early anyway. By minute 12 it has already asked which replies are lookups and which are decisions, and by minute 16 the next question has brought back the one-in-twenty error rate that sits behind the current-way door. There is not much left for a better order to win.

The ceiling is 63, from a search that is allowed to read the fact sheet, and here it does something worth noticing: it opens with the lookups-versus-decisions question, which a real interviewer could ask first with no sheet at all. For this role the framework and the optimizer agree on the opener and differ on what follows; the extra eight points come from knowing which later question reaches which hidden fact, and nobody in a real meeting knows that. The framework is the thing you can do on Tuesday, blind, and get 54.

LiveFinding 2: a shuffle is not neutral, it is a spread2 min▶

Two hundred shuffles of the same bank average 30.1 and range from -1 to 52. The average is the meeting most people run when they have a good list and no order: some of the jargon lands early and costs trust, a leading question or two gets recorded, and a door stays shut. The spread is the argument for an order at all. A method that scores 54 every time is worth more than one that scores 52 on a good day and -1 on a bad one, and for an assistant that will talk to 36 suppliers, the bad days are the ones that reach a shelf.

Self-studyFinding 3: the kind matters far more than the order2 min▶

Put the numbers side by side: the technical opener 11, the efficient interview 21, the Six Doors 54. The order of the good questions moved the score by one point; the kind of question moved it by more than forty. That is the lesson of the bench for an AI developer.

The technical opener shows why. Five questions in a row about fine-tuning, hallucination tolerance, eval sets, vector stores and guardrails spend 25 of the 45 minutes and take trust to -3. The obvious cost is the minutes. The one that matters is what happens next: by the time an open question about the product list is asked, trust is still below zero, so when the question that could have surfaced Kenneth's January exit comes, she holds it back. The meeting ends with four facts and two doors, and the thread itself, the current way, was never opened. Every one of those five is a question you will need answered, most of them by yourself in week three. They were asked of the wrong person, first.

Part 3 · covers the anti-lever

The efficient interview records five things that are wrong

4 min live

Sixteen questions in 43 minutes, eight answers in the first ten. It feels like the best-run meeting in the building. On the bench it finds twelve true facts worth 37 and opens all six doors, and it still ends at 21, because five of the things in your notes are things she agreed to rather than things that are true, and those five cost 16. At minute 20 it is the only preset below zero.

ONE LEADING QUESTION, SIX WEEKS LATER LEADING "So the assistant should reply to the suppliers automatically?" "I suppose so." thread notes bot replies itself week six: an auto-reply bot approves a substitute -4 and a compliance problem WHAT WAS TRUE, ON HER SHEET only an area manager may accept a substitute or price change, and a substitution needs a record by law. Last year the vendor's chatbot was switched off in a week. THE OPEN VERSION, 4 MINUTES "In a thread, which replies need a person to decide, and which are just looking something up?" gets the split: lookups to draft, decisions kept by her She was not lying. The question carried the answer you wanted, and she is polite. The cost lands later.
🔍 Click to zoom - the red line in the notebook is the only thing the fast interview produces quickly
LiveWhy "I suppose so" is worse than silence2 min▶

A closed question that gets a "no" has taught you something. A leading question almost never gets a "no", because it carries its expected answer and the person across the table is being courteous, busy, or both. Fitzpatrick's rule for customer conversations applies without change: people will say yes to be polite. What comes back is not information about her business; it is information about how agreeable she is, filed as if it were the first thing.

The bench prices each false belief at what building on it wastes. "The assistant replies to suppliers on its own" costs 4: a bot that says yes to a substitute nobody checked, when only the area manager may accept one and each needs a record by law. "The orders are in English" costs 3: a matcher that cannot read Malay, Chinese or the outlets' product nicknames. "There is an order table to match against" costs 4: there is none, only another WhatsApp group. "Mistakes are rare and cheap" costs 3: about one in twenty is wrong, and a wrong drug is not cheap. "The managers will use a separate app" costs 2: they live in WhatsApp, in a van. Five leading questions in six minutes, and the meeting stands at minus 16 before the first true fact.

Self-studyThe honest nuance: when a closed question is right2 min▶

Closed questions are not the villain; leading ones are. "Is it three area managers?" is closed and gets a real fact for one minute, and the bench scores it so. The rule is about sequence: confirm with a closed question after an open one has shown you the shape of the answer, never before. And the anti-lever carries its own limit: it is not the lowest score on the bench. The technical opener, at 11, is lower, because jargon wastes more minutes than leading questions do. What makes the efficient interview the anti-lever is not its total but what its total hides: 21 looks like a middling meeting, and five of the lines behind it are wrong, the costliest being the one that becomes the product. The bench does not pretend that speed is the sin. Assuming is.

Real world

The demo that went well. A constructed case with a familiar shape. A developer runs a tight session with an operations lead, sixteen questions, every one answered, and demos a bot a fortnight later that drafts and sends OK to forty supplier confirmations in a minute. It is impressive until the first confirmation with a substitute in it gets an OK too. The lead, asked why she agreed the bot should reply on its own, says what people say: "You seemed to know what you wanted. I assumed you knew." The fix costs nothing but the sequence: ask which replies are lookups and which are decisions before you build anything that replies.

Homework

Before session 4

30 min
  1. Run your own meeting twice in the lower half of the bench: once with your session 1 sheet in your hand, once without. Write down the two scores and which doors you left shut the second time.
  2. Sort your last real requirements call. Take the notes from a meeting where someone asked you for an AI feature and mark each question you asked with its kind. Count the jargon and the leading ones. Each leading one is a belief in your spec that nobody checked.
  3. Change one number in the bank file and re-run. Double the cost of every false belief, or halve the minute cost of jargon. Write one sentence on what moved and what did not; the ordering should survive, and if it does not, you have found the assumption the bench rests on.
  4. Bring the teach-back lines from your sheet, especially the four for the current way. Session 4 rewrites them for a person who has never heard the word model, and picks the one concept per meeting worth explaining properly.
Check yourself

Three questions

Clear all three and session 3 gets stamped in your passport.

1 · The efficient interview finds 12 true facts worth 37 and opens all six doors. Why does it end at 21, and at minus 4 after 20 minutes?

37 minus 16 is 21. The costliest belief, that the assistant replies to suppliers on its own, is the one that turns into the product, and the truth on her sheet is that only an area manager may accept a substitute and each one needs a record. Speed is not the defect. Assuming out loud is.

2 · Tuning the order for an AI developer scores 55 against 54 for the printed order, and the ceiling, 63, opens with the lookups-versus-decisions question. What is the honest reading?

A one-point gain is reported as one point. The lesson for this role sits elsewhere: the kind of question moved the score from 11 and 21 to 54, and the order of good questions moved it by one.

3 · The technical opener asks five sensible AI questions first, fine-tuning, hallucination tolerance, eval sets, vector stores, guardrails, and ends with four facts and two doors. What went wrong?

Five jargon questions spend 25 minutes and take trust to -3, the floor. The questions about the product list come after, at trust below zero, so Kenneth's January exit stays unsaid. The plain versions, which system holds the product list and who can log in, open the data door without costing trust.

Sources covered

What this session teaches, and where it came from

✓Every count on the benchComputed in the browser from the printed bank file, and verified headlessly in node before any page quoted a number; the two agree to the point
✓People say yes to be polite; ask about the past, not the futureRob Fitzpatrick, The Mom Test, 2013; the leading-question mechanism on the bench is his observation made countable
◐Harbourline, Adeline Tan, and every value on her sheetConstructed to be typical, including the one-in-twenty error rate, the substitution record and the switched-off chatbot. The bench claims the ordering and the mechanism, never the numbers as facts about any real business; change the bank and re-run
◐The one-point gain from tuningReported as counted. It is small because this request already points at the current way; a request that did not would leave more for tuning to win, and that is not claimed here

Every fact on this page, and its verification tier, is recorded in the course's source map.

Session 3 cheat sheet · pin this

Five kindsOpen, closed, vague, jargon, leading. Only open earns trust; only jargon loses it; only leading records a lie.
The bench, on this sheetJargon 11 · fast 21 · shuffle 30.1 (-1 to 52) · Six Doors 54 · AI-developer-tuned 55 · ceiling 63.
Kind beats orderThe order of good questions moved the score by one point. The kind of question moved it by more than forty.
Open the thread firstOne real thread end to end, how often it is wrong, which replies are lookups and which are decisions. 23 in your notes by minute 17.
Open first, confirm secondA closed question after an open one is cheap and true. Before one, it is a guess with a yes attached.
Nothing replies on its ownA substitute needs a person and a record. Ask where that line sits before you build anything that answers.