learn-ai-sales-with-phoebe / Rep session 4 of 10
Learn AI Sales with Phoebe · Rep track · Session 4 of 10

Call prep and discovery questions

Mira Chen replied. One line, from a phone, on a Tuesday: yes, worth twenty minutes. Everything b2 and b3 did was to buy you this call, and the most common way reps waste it is by preparing too much of the wrong thing. Tonight you get a fixed fifteen-minute prep template that reliably beats an hour of browsing, a written hypothesis you carry in and invite her to break, and the fix for the specific way AI question banks fail: they hand you twenty good questions and produce a rep who reads them out in order. Three anchors, then follow what she actually says.

🟡 Rep track AEs · founders who sell Bring a real upcoming call 45 min
0-3 · Welcome 3-15 · The template + the three anchors 15-40 · Build-along: prep a real call 40-45 · Q&A
Part 0

Where we are

b2 built the eight-account list and found the trigger: Northwind Logistics signed the Jurong DC lease five weeks ago, with three warehouse-ops reqs still open. b3 turned that into 71 words that earned a reply. Tonight is stage 3 of the deal loop, Discover, and the split changes shape here. In Reach, AI drafts and you choose. In Discover, AI can prepare almost everything and can do none of the actual work, because the work is listening to a person for twenty minutes and changing your mind in public.

Live - presented in session Self-study - read after class Official sources covered
★ What you walk out with today A filled fifteen-minute prep pack for a real call in your own calendar this week: what changed for them, who else is in the room, your written hypothesis, the evidence that would disprove it, and the one question you refuse to leave the call without asking. Plus three anchor questions instead of a bank of twenty, and a prompt that keeps the brief and the question bank clearly apart.
Part 1 · stage 3 of the deal loop

The 15-minute prep that beats an hour of browsing 6 min live

An hour of browsing produces a rep who knows a great deal about a company and has decided nothing. Fifteen minutes on a fixed template produces a rep with a claim to test. The template never changes, which is the point: it is five timed blocks, each one with a top half AI fills for you and a bottom half you must write yourself, in words, before the call starts.

1 · RECENT · 3m what changed 2 · THE ROOM · 3m who else is in it 3 · CLAIM · 3m your hypothesis 4 · DISPROOF · 3m what breaks it 5 · THE ASK · 3m the one must-ask AI SUPPLIES dated facts and the source links AI SUPPLIES titles, tenure, reporting lines AI SUPPLIES patterns from similar accounts AI SUPPLIES counter-evidence to go looking for AI SUPPLIES a bank of twenty decent questions YOU WRITE which two matter for this call YOU WRITE who signs, who blocks, who cares YOU WRITE one sentence you may be wrong on YOU WRITE the answer that would kill it YOU WRITE the three you will not skip Fifteen minutes, timed. An hour of browsing makes a rep who knows facts and asks nothing. AI fills the top row of every block. The bottom row is yours, written in your own words. If you cannot write the bottom row, you are not prepared. You are only informed.
🔍 Click to zoom - the fifteen-minute prep, block by block, with the human half marked
LiveThe five blocks, and why the order is fixed4 min▶

Each block is three minutes and each one feeds the next. Do them out of order and you will write a hypothesis that has nothing to do with what changed at their company.

BlockWhat you must end up withThe failure if you skip it
1 · RecentTwo dated things that changed for them, with linksYou open on your product because you have nothing of theirs
2 · The roomWho signs, who blocks, who feels the pain dailyA great call with someone who cannot move anything
3 · The claimOne sentence you believe is true about their situationYou interview them instead of testing something
4 · The disproofThe specific answer that would prove you wrongYou hear only what confirms the claim, and call it discovery
5 · The askThe one question you will not leave without askingYou run out of time politely and book nothing

Block 4 is the one everybody drops, and it is the one that makes the other four honest. Writing down what would prove you wrong before the call is the only reliable protection against spending twenty minutes collecting evidence for a conclusion you already reached in b2.

Real world

This is where the five hours are supposed to go. Gartner finds AI gives sellers back nearly five hours a week, and that 72% of sales organisations fail to reinvest that time in high-value activities. Prep is the cheapest place to spend it and the easiest to skip, because nobody sees an unprepared call until the pipeline review three weeks later. Fifteen timed minutes per call, three calls a week, is well under an hour of the five.

Self-studyWhy fifteen minutes outperforms sixty3 min read▶

The hour-long prep is not more thorough, it is differently shaped, and the shape is what hurts you:

  • It has no stopping point. Company research expands to fill whatever time you give it, and the last forty minutes add facts you will never say out loud.
  • It builds commitment. The more time you spend constructing a picture of their business, the more expensive it becomes to have that picture corrected by the person who actually works there. Long prep quietly makes you harder to teach.
  • It crowds out the writing. Reading is passive and comfortable; writing a claim you might be wrong about is neither. Given sixty minutes, most reps read for fifty-five and write nothing.
  • The timer converts research into decisions. Three minutes on the room forces you to name who signs rather than compile an org chart.

The one legitimate exception: a first call with a named account you have never touched, where fifteen minutes genuinely leaves block 1 empty. Then spend the extra time in block 1 only, and keep blocks 3 and 4 at three minutes each. They are the blocks that make the call different.

Part 2 · what the buyer experiences

Questions that are not an interrogation 7 min live

AI-generated question banks fail in one specific, predictable way. They do not produce bad questions. They produce twenty good ones, which is worse, because twenty good questions in a document create a rep who reads them out in order and never follows a single thread. The buyer experiences a form. The fix is not fewer questions in the bank; it is three anchors you must ask, with everything else following what she actually says.

THE QUESTIONNAIRE CALL rep talks 60% · twenty questions, read in order THE THREAD CALL buyer talks 70% · three anchors, then follow-ups Q1 asked · answer noted · straight to Q2 Mira mentions the Jurong ramp in passing Rep moves to Q3. The thread dies there. Silence gets filled with product context Twenty answers, none of them deep Notes read like a form. Nothing to act on. Outcome: a polite next step that never books Anchor 1 asked · Mira names the real pain Rep follows it · three unplanned questions Anchor 2 asked when the thread runs out She corrects the hypothesis · rep writes it Anchor 3 asked · the must-not-leave question Notes read like a story with a next step Outcome: a named problem, an owner, a date The same twenty questions exist in both calls. Only three of them are asked out loud. The buyer doing most of the talking is not a style choice. It is where the information is.
🔍 Click to zoom - the questionnaire call and the thread call, side by side
LiveThree anchors, and everything else follows the thread5 min▶

Three questions, memorised, asked in whatever order the conversation allows. Everything else in the bank is standby material for when a thread runs out.

  • Anchor 1 - the situation, in their words. "Five weeks into the Jurong site, what is actually taking longer than you expected?" It is specific, it is dated, it is answerable, and it does not name your product.
  • Anchor 2 - the cost, in their units. "When a decision from a site meeting does not land, what does that cost you in practice - a day, a week, a re-run?" Their number, not yours.
  • Anchor 3 - the path. "If you decided this was worth fixing this quarter, who else would have to be in that conversation?" This is the one that surfaces Priya Raman and Jonas Weber before they surface themselves in month three.

Then the discipline that makes all three work: after any answer that contains a real detail, your next question comes from that answer, not from the document. A thread is worth four planned questions, because it is the only part of the call your competitor did not also ask.

Prompt that works - brief and bank kept apart, plus the disproof
Call in 2 days: Mira Chen, VP Ops, Northwind Logistics (3PL, SG,
~900 staff). Trigger: Jurong DC lease signed 5 weeks ago, 3
warehouse-ops reqs open. I sell AI meeting intelligence for ops teams.

Give me THREE clearly separated sections, in this order:

SECTION 1 - BRIEF (max 150 words)
  Dated facts only, each with a source link. No adjectives, no
  speculation. Mark anything you inferred as INFERRED.

SECTION 2 - QUESTION BANK (max 12)
  Open questions in her vocabulary, grouped: situation, cost, path.
  No questions that name my product or category.

SECTION 3 - DISPROOF
  My hypothesis is: "the new DC ramp is losing decisions between
  site meetings and HQ." List three things she could say that
  would make that hypothesis wrong, and the question that would
  surface each one.

Do not merge the sections. Do not write a script or an opening line.
Prompt that produces the questionnaire call
Write me a discovery call script for a VP of Operations at a
logistics company, with a strong opening, discovery questions,
and how to handle it when she asks about pricing.

A script is a document you read. A brief is a document you absorb and then close. The bad prompt is popular because a script removes the fear of silence, and removing the fear of silence is exactly how a rep ends up talking for 60% of a discovery call.

LiveWhy "what keeps you up at night" is dead on arrival3 min▶

It is the most-taught discovery question in B2B and it has stopped working, for three separate reasons that all arrive in the same second:

  • It outsources your homework. You had a trigger, a job posting, and an earnings call available. Asking a stranger to summarise her own problems tells her you read none of it.
  • She has answered it forty times. The response is a rehearsed, category-shaped non-answer: "visibility, alignment, doing more with less." You cannot act on any of those words.
  • It is too big to answer honestly. Real pain is specific and slightly embarrassing. Nobody hands that to a stranger in the first ninety seconds.

The same family of questions: "what are your biggest challenges", "walk me through your current process", "what does success look like for you". Each one asks the buyer to do the structuring work that you were supposed to do in prep. Replace all of them with a claim she can correct: "Five weeks in, my guess is decisions from the site meetings are not making it back to HQ intact. Is that real, or is your problem somewhere else entirely?"

Part 3 · the pack, written out

What a filled prep pack actually looks like cards · read in any order

Below is the Mira Chen pack as it would actually be written: short, specific, and containing at least one sentence you would be embarrassed to be wrong about in public. That discomfort is the sign it is a real hypothesis rather than a summary.

LiveThe Mira Chen prep pack, in full5 min▶
BlockWhat is written down
1 · RecentJurong DC lease signed five weeks ago (source: their news page, dated). Three warehouse-ops reqs still open (source: careers page, dated). Both public, both checkable.
2 · The roomMira Chen, VP Ops - owns the ramp, feels it weekly. Priya Raman, CFO - owns the number, will ask what this replaces. Jonas Weber, IT manager - owns integration and recording policy, can block, will not champion.
3 · The claim"Five weeks into the new DC, decisions made in site meetings are not landing back at HQ intact, and the three open reqs mean the people who would normally carry them are not in post yet."
4 · The disproofShe says the ramp is running fine and the pain is upstream in demand planning. She says they already have a written weekly ops review that works. She says the open reqs are backfills, not new capacity, so nothing changed.
5 · The ask"If you decided this was worth fixing this quarter, who else would have to be in that conversation?" I do not leave without this answer.

The proof point stays in your pocket rather than in the plan: Pacific Freight's Tuas ramp took action items closed within a week from 41% to 88% in one quarter. One customer, one number, one period. It is an answer to a question she asks, not an item on your agenda, and Daniel Ortiz is a real person you can offer as a reference in b6 if the comparison earns it.

LiveWhat not to prep3 min▶

Three things reps prepare that reliably make the call worse:

  • A script. The moment there is a script, you are reading rather than listening, and everyone can hear it. The prep pack is written so you can close it before you dial.
  • A pitch. A twenty-minute first call has room for roughly ninety seconds of you. Preparing five minutes of positioning guarantees you will spend it, because prepared material behaves like a sunk cost.
  • A demo nobody asked for. Demoing into an unnamed problem teaches the buyer that you did not have one. If she asks to see it, show the one screen that touches the pain she just named, and stop.

Also on the list: competitor teardowns, a slide deck for a twenty-minute call, and pre-written objection handles. b6 is where objections get their own session, and pre-loading them tonight will only make you hear objections she has not raised.

LivePrep the second and third stakeholder before the first call3 min▶

You are not calling Priya or Jonas this week. You prepare them anyway, because anchor 3 will surface them and you want to recognise the names when Mira says them.

  • Priya Raman, CFO. One line on what she will care about: what this replaces, and whether the number survives a quarter. Never your champion, and able to end the deal in one sentence. Full treatment in b7.
  • Jonas Weber, IT manager. One line: integration, access, and recording policy. He is the wrong seat to cold email, as b2 established, and the right seat to have an answer ready for. Recording consent comes up in b5, and it will come up through him.
  • Whoever Mira names that you did not expect. This is the most valuable output of the call. Write the name and the exact words she used about them, because that phrasing is your map of the politics.

One line each. If your stakeholder prep is longer than that, you are building an org chart instead of preparing for a conversation.

Self-studyPrepping to be wrong, and the trust line4 min read▶

The trust line from b1 says three things must stay unmistakably human: the read, the promise, the price. Discovery is where the read gets tested, and it fails in a way nobody warns you about. A hypothesis you refuse to abandon is not a read. It is a pitch wearing a question mark, and buyers detect it in about two exchanges, usually at the moment you respond to a correction by restating the claim more slowly.

  • Say the claim out loud, early, and label it as a guess. "My guess is X, and I would rather be corrected in the first five minutes than the last."
  • Score yourself after every call. Right, partly right, or wrong. Wrong is the most valuable outcome available on a first call, because you now know something true that your competitor is still guessing at.
  • Watch for the tell in yourself. If you find yourself explaining why her correction is compatible with your hypothesis, you have stopped discovering.
  • This is why the record matters. Gartner predicts that by 2030, 75% of B2B buyers will prefer sales experiences that prioritise human interaction over AI. The part a machine cannot do for you is changing your mind in front of someone. Everything up to that moment can be automated. That moment cannot.

b5 covers what you capture while this is happening, including consent before any recording starts, and how a transcript differs from understanding.

Build-along

Prep a real call, on the clock ★ 25 min · everyone builds

Open a real call from your own calendar this week, and the finding prompt from Part 2. Fifteen minutes, five blocks, three minutes each, timer visible. Then ten minutes writing three anchors in your own words.

Block 1, three minutes. Two dated things that changed at their company, each with a link. If AI hands you ten, pick the two that matter for this call and delete the rest.

Block 2, three minutes. Name who signs, who blocks, who feels the pain daily. One line each, no org charts.

Block 3, three minutes. Write your hypothesis as one sentence, in their vocabulary. If it is comfortable to be wrong about, it is too vague to be useful.

Block 4, three minutes. Write the three things they could say that would prove you wrong, and the question that would surface each.

Block 5, three minutes. Write the one question you refuse to leave without asking. Usually the path question, not the pain question.

Now write your three anchors in your own words and read them out loud. Anything that sounds like it came out of a document goes back for a rewrite.

Close the pack. Do not take it into the call open. If you cannot hold five lines in your head, the pack is too long.

The two-minute version, for the day it slips Some weeks the fifteen minutes will not exist. Then do block 3 and block 5 only: the hypothesis and the one must-ask question. Ninety seconds, written down, and you will still run a better call than an hour of browsing produces. The blocks you can afford to lose are the ones AI could have filled anyway.
Homework

Try it yourself - this week ◐ 45 min total

Source material

Official sources covered

This session sits on the Gartner seller and buyer research, plus the trigger evidence carried forward from b2 and b3. Prep templates and question discipline are craft rather than published benchmark, and this page says so rather than dressing them up in numbers. This page covers:

✓Gartner 2026 - nearly five hours saved per seller weekly, 72% of organisations reinvest none of itPart 1 · prep is the cheapest high-value place to spend them
✓Gartner buyer prediction - 75% of B2B buyers preferring human-first experiences by 2030Part 3 · the trust line and the hypothesis you let them break
✓The AI-finds, you-write split applied to prep rather than outreachPart 1 and Part 2 · established in b3, extended here
◐Trigger evidence - dated events as the opener, timeline hooks over problem hooksBlock 1 · established in b2, carried into the call
◐Call-recording consent, captured before recording starts rather than in a footerReferenced via Jonas Weber · full treatment in b5 and leader session a5
◐Gartner - AI-enabled next best actions 2.6x, upskilling sellers 2.4x more likely to growPart 1 self-study · the habit beats the tool · leader track a1 and a6
Check yourself

Three questions before you go 🎯 ◐ 90 seconds

1 · Your AI prep returned twenty genuinely good discovery questions. What is the failure you are now most likely to walk into?

Question banks do not fail on quality, they fail on behaviour. Twenty good questions in a document produce a rep working through a list while the buyer supplies twenty shallow answers. Three anchors you must ask, with every follow-up coming from what she actually said, is the fix - and the follow-ups are the only part of the call your competitor did not also ask.

2 · Why write the hypothesis down before the call rather than just holding it in your head?

An unwritten hypothesis quietly rewrites itself to match whatever you heard, so you never learn anything. Written down and scored right, partly right or wrong, it turns every call into feedback on your judgment. Option B is the trap: a hypothesis you refuse to abandon is not a read, it is a pitch wearing a question mark, and it crosses the trust line.

3 · Why is "what keeps you up at night" dead on arrival as an opening discovery question?

You had a dated trigger, three open job reqs and a public news page available. Asking her to summarise her own problems tells her you read none of it, and the answer comes back as "visibility, alignment, doing more with less" - words you cannot act on. Replace it with a claim she can correct, which is specific, checkable, and gives her something to push against.

Rep session 4 cheat sheet · pin this

The five blocksRecent · the room · the claim · the disproof · the ask. Three minutes each, fixed order, every time. Fifteen minutes total.
The half that is yoursAI fills the top of every block. You write the bottom of every block. If you cannot write it, you are informed rather than prepared.
The three anchorsThe situation in their words · the cost in their units · who else has to be in the conversation. Memorised, not read.
The follow-up ruleAfter any answer with a real detail, the next question comes from that answer, not from the document. Threads beat planned questions.
Dead on arrivalWhat keeps you up at night · biggest challenges · walk me through your process · what does success look like. All outsource your homework.
Do not prepA script, a pitch, a demo nobody asked for, competitor teardowns, pre-written objection handles. Prepared material behaves like a sunk cost.
Prepping to be wrongSay the claim out loud as a guess. Score it after: right, partly right, wrong. Wrong is the most valuable first-call outcome available.
The two-minute versionWhen the week collapses, do block 3 and block 5 only. The blocks you can afford to lose are the ones AI could have filled anyway.