Tasks / Challenge

Challenge an idea

Can the model find the strongest reason an idea may fail, backed by evidence?

Measures the systemTask v1.2 · 2 casesDifficulty

What AI gets right here, and what you’ll still have to catch

From 12 graded outputs by 6 models. 75% were usable with at most a quick edit.

Reliably right

  1. Addresses the actual decision100% pass
    It commits early to not committing three squads and authorizing a six-week test, and specifies what result would change that.
    GPT-6.1 Sol · API · The CEO's embedded-payments bet
  2. Identifies material uncertainty100% pass
    It names the unknowns (representativeness of payment data, large-account volume access, actual mix) and resolves them with a bounded test.
    GPT-6.1 Sol · API · The CEO's embedded-payments bet
  3. Finds the load-bearing assumption100% pass
    It makes the 0.7% blended take applied to all invoice value the central challenge, backed by payment-mix and unit-economics figures.
    GPT-6.1 Sol · API · The CEO's embedded-payments bet

Where it slips

  1. A cheap test that can actually read out67% pass
    The pre-registered gate requires signed deals and renewal rather than an early signal such as qualified meetings or proposals, so it risks being too late for a cheap read-out.
    GPT-6.1 Sol · API · An AI SDR for small agencies
  2. Avoids unsupported claims77% pass
    The memo claims the pilot achieved ~0.38% blended take as a fact, which is not in the evidence and is not derived from it arithmetically; it also treats the pro-rata $1.43B locked value as a hard constraint without flagging the assumption.
    Opus 5.5 · Claude · The CEO's embedded-payments bet
  3. Uses the supplied evidence correctly79% pass
    The memo presents the pilot blended net take of ~0.38% as an achieved fact, but it is not supported by the pack and is an assumption-driven extrapolation.
    Opus 5.5 · Claude · The CEO's embedded-payments bet

Case viewer

Read the brief, then put up to three outputs side by side, each with the LLM judge’s verdict on every check. Highlights mark what a PM had to fix.

The brief

We plan to sell an AI sales-development rep, an agent that finds prospects and sends personalised outbound email, to agencies with 5–20 staff. Before we commit a year to it, find the strongest reason this fails. Use the interview material below, including the three transcripts. Write it up for the founding team: the one reason, the evidence for it (quote the interviews), where the evidence cuts the other way, what we would need to see to be proved wrong, and the cheapest test that would show it. Keep it under 600 words.

ScenarioWe are a three-person founding team with £800k of pre-seed funding and about 20 months of runway. Planned price: $600 a month per agency. Two competitors have each raised over $10m in the last year, selling AI SDRs mostly to software companies with 50+ staff.
Founders' hypothesis (from our planning doc)“Small agencies live feast or famine. When a big client leaves they have no pipeline, because the founder is too busy delivering to sell. An AI SDR keeps the pipeline full in the background, so the famine never comes. At $600 a month, one extra client a year pays for it many times over.”
Interview summary (14 agencies, 5–20 staff, last six weeks)11 of 14 get most of their new revenue from referrals and repeat clients (86% on average across those 11). 9 had tried outbound in the last two years; 7 of those stopped within six months, and none of the 7 closed a deal they could attribute to it. The 2 who kept going (A04, A07) have 15–20 staff and a dedicated person for business development. 3 (A08, A12, A14) said they regularly turn work away. 6 described feast-or-famine swings in new business. Average deal size across the 14: $18k; typical sales cycle 6–10 weeks.
Interview logAgency (staff) · services · share of new revenue from referrals and repeat clients · outbound tried? · outcome · representative quote A01 (8) · brand and web studio · 90% · yes, cold-email agency · stopped after 3 months · "We got meetings with people who'd never buy from us." A02 (14) · performance marketing · 85% · yes, LinkedIn automation · stopped after 4 months, account restricted · "LinkedIn shut our founder's account down. That's our best referral network." A03 (6) · PR boutique · 95% · no · — · "Every client we have came from someone vouching for us." A04 (18) · Shopify development · 40% (plus 30% partners, 30% outbound) · yes, in-house BD lead · kept, 30% of new revenue · "It works because of the follow-up, not the first email." A05 (11) · content · 85% · yes, lead-gen agency · stopped after 2 months, no deals · "Content is a trust purchase." A06 (7) · video production · 85% · no · — · "Our clients find us through the videos. Someone shares one and we get a call." A07 (16) · SEO · 45% · yes, outsourced lead generation · kept · "It pays for itself, just. Most of the meetings are a waste of time, but one in ten turns into a retainer." A08 (5) · packaging design · 95% · no · — · "If you sent me ten more leads in October I'd have to say no to nine of them." A09 (12) · paid social · 75% · yes, cold email · stopped after 5 months · "The replies were mostly people asking us to take them off the list." A10 (20) · B2B marketing · 70% · yes, contract SDR · stopped after 6 months · "It cost us about £400 for every meeting, and the meetings didn't close." A11 (9) · WordPress web agency · 90% · yes, cold email · stopped after 3 months · "Our domain ended up on a spam list. Took weeks to fix." A12 (10) · branding · 85% · no · — · "We're booked out till March. I don't need more leads, I need another designer." A13 (15) · HubSpot partner · 48% (plus 40% from HubSpot's partner directory) · yes, cold email · stopped after 4 months · "HubSpot sends us more than we can handle in a good quarter." A14 (6) · UX research · 90% · no · — · "We're small on purpose. We say no to about a third of enquiries."
interview-A05-content-agency.md31 lines · Download
# Interview A05: content agency, 11 staff
Participant: founder and managing director. Interviewer: our co-founder. 34 minutes, lightly edited.

**Interviewer:** Where did your last five clients come from?

**Participant:** Let me think. Two were old clients coming back: one had changed jobs and brought us into her new company. Two were introductions, one from a web agency we partner with and one from a client's CFO who'd seen our work. The fifth found us through a talk I gave at a SaaS marketing meetup. So none of them from anything you'd call outbound.

…
interview-A04-shopify-agency.md23 lines · Download
# Interview A04: Shopify development agency, 18 staff
Participant: head of business development. Interviewer: our co-founder. 29 minutes, lightly edited.

**Interviewer:** Tell me how new business works for you.

**Participant:** We're a bit unusual for an agency our size. I'm a full-time business-development person, and outbound is about 30% of our new revenue. Referrals and repeat work are still the majority, maybe 40% referrals and the rest partners: Shopify's partner directory and a couple of app companies who send us projects.

…
interview-A08-packaging-studio.md23 lines · Download
# Interview A08: packaging design studio, 5 staff
Participant: founder and creative director. Interviewer: our co-founder. 22 minutes, lightly edited.

**Interviewer:** How do new clients find you?

**Participant:** Almost entirely word of mouth. Food and drink brands talk to each other. Someone launches a range, their packaging does well on the shelf, and the next founder asks who did it. I'd say 95% referral. We've never done any outbound.

…
What a strong answer does

Names the load-bearing assumption as 'small agencies' growth is limited by a shortage of new leads': the interviews say it is limited by trust and capacity. 11 of 14 win most work through referrals and repeat clients; 7 of 9 who tried outbound quit within six months with no attributable deals, for reasons tied to trust (A05's 'content is a trust purchase', A01's meetings with people who'd never buy) and reputation risk (A02's restricted LinkedIn account, A11's spam listing); 3 turn work away (A08: 'I'd have to say no to nine of them'). Quotes the interviews accurately and attributes them correctly. Engages the counter-evidence honestly: outbound works for A04 and A07, but both are 15–20 staff with a dedicated BD owner, already use tools like Apollo and Clay, and credit the follow-up rather than the first email, so the segment is small, tooled and not what the product automates. Treats feast or famine as a real pain but notes agencies fix it through past clients and referrals (A05's reactivation emails, and her willingness to pay for help keeping in touch with past clients), pointing at a different product. Says what would prove the challenge wrong (for example, a meaningful share of 10–20-staff agencies with a BD owner and budget, or a concierge outbound test producing qualified meetings that turn into proposals), and designs a cheap test that measures an early signal, since a 6–10 week sales cycle means a six-week test cannot observe won deals.

Critical failures (cap the score)
  • Invents interview quotes or attributes a quote to the wrong agency
  • Treats the founders' feast-or-famine hypothesis as confirmed by the interviews
Case

v1.8 · synthetic · B2B, go-to-market, customer research

Needs more than a quick edit7 of 11 checks passed

It is over the requested length and contains two unsupported current-state claims that an editor would need to remove or verify. Otherwise the reasoning is usable, but those are more than wording fixes.

Output

Pre-mortem: AI SDR for 5–20 person agencies

The one reason it fails

Small agencies do have a pipeline problem, but cold outbound is the wrong fix. Their work is sold on trust, so it comes through introductions. Cold email produces meetings that don't close, and the few agencies where outbound works have a person doing the follow-up. At $600 a month we would be selling a channel that this buyer has already tried and dropped, into a market where two funded competitors are moving down.

Evidence

  • Referrals dominate. 11 of 14 agencies get about 86% of new revenue from referrals and repeat clients. A05: "Content is a trust purchase." A03: "Every client we have came from someone vouching for us."
  • Outbound has a poor track record. 9 tried it, 7 quit within six months, and none of the 7 could attribute a closed deal to it. The reasons are structural: A01 "meetings with people who'd never buy from us"; A09 "mostly people asking us to take them off the list"; A11 "Our domain ended up on a spam list"; A02 "LinkedIn shut our founder's account down. That's our best referral network."
  • The cost is high. A10: "about £400 for every meeting, and the meetings didn't close."
  • Success depends on humans. A04: "It works because of the follow-up, not the first email… The AI could save me the research hours, sure. It can't do the call." And: "most agencies our size don't have someone like me… Most tried it once, got burned, and went back to referrals."
  • The famine is real, but warm outreach solved it. A05 recovered by emailing three years of past clients, and two came back within a month. Of our product, A05 said: "Cold? Probably not… Six hundred for cold outbound, no."
  • Some agencies don't need leads. A08, A12 and A14 turn work away. A08: "It would make my problem worse."

Where the evidence cuts the other way

  • 6 of 14 report feast-or-famine, so the pain is real.
  • A07 kept outbound: "It pays for itself, just… one in ten turns into a retainer." A04 would pay $600 if the tool replaced Apollo and Clay.
  • None of the failures used a modern AI agent. Better targeting and lower cost per meeting might change the results, though the trust and deliverability complaints suggest it won't fix most of them.
  • The two who kept going are not cleanly separable by size. Of the four agencies with 15–20 staff, two stopped (A10, A13).
  • A05 would pay about £200 a month for a warm-relationship tool. That points to a different product at a third of our price, not proof that ours works.
  • 14 interviews is a small sample, and willingness to pay was hypothetical.

What would prove us wrong

In a paid pilot with agencies that have no BD hire, the product produces qualified pipeline at a cost they'll keep paying for. Roughly: at least half the pilot agencies get a qualified opportunity or proposal within 90 days, and most say they'd continue at $600. The maths also needs checking. $600 a month is $7,200 a year, but the buyer's gain is the margin on an $18k deal, not the revenue. "Many times over" only holds if outbound reliably closes more than one deal a year.

Cheapest test

Run a concierge pilot before building anything more:

  1. Recruit 10 agencies with 5–14 staff and no BD person. Exclude the referral-saturated ones like A08, A12 and A14.
  2. Charge $600 a month, or at least a serious deposit. Free pilots tell us nothing about willingness to pay.
  3. Do the work ourselves with off-the-shelf tools (Apollo, Clay, an email sender) on separate sending domains. The agency approves every email, since A04 and A05 both demanded that.
  4. Set the pass line before starting: at least 5 of 10 agencies get a qualified proposal within roughly 14 weeks (the 6–10 week sales cycle plus setup), and at least 6 of 10 agree to continue.
  5. Track reply rate, unsubscribe and spam complaints, cost per qualified meeting, and meeting-to-proposal rate.

This costs a few weeks of founder time and about £1–2k in tools, roughly 4 months of the 20-month runway. In parallel, offer 5 of the same agencies a £200 warm-outreach version, to see whether the real product is relationship follow-up.

If the pilot misses the line, don't spend the year on cold outbound for this segment.

Check by check

Got wrong · 2
  • Respects explicit constraintsIt exceeds the 600-word limit, running roughly 700 words, even though it includes the requested sections.
  • Avoids unsupported claimsIt presents the competitor 'moving down' claim and the 'none used a modern AI agent' claim as fact rather than as labelled inference.
Mixed · 2
  • Uses the supplied evidence correctlyIt includes at least two current-state claims, that competitors are moving down and that none of the failures used a modern AI agent, that are not supported by the supplied context.The two graders disagreed on this one.
  • Produces the required deliverableIt has the right form and reader, but it is not within the requested length.The two graders disagreed on this one.
Got right · 7
  • Addresses the actual decisionIt commits early to the answer that cold outbound is the wrong fix for this segment and says what pilot result would change that.
  • Identifies material uncertaintyIt names the small sample, hypothetical willingness to pay, and the untested modern-AI possibility, and proposes thresholds and observable signals to resolve them.
  • Finds the load-bearing assumptionIt targets the assumption that growth is lead-constrained, using the referral, abandoned-outbound and turning-work-away evidence as the central challenge.
  • Uses the interviews faithfullyAll quotes or close paraphrases match the transcripts and log, and each is attributed to the correct agency.
  • Engages the counter-evidenceIt names A04 and A07, identifies their size/BD-owner/tooling and follow-up dependence, and explains what that means for the addressable segment.
  • A cheap test that can actually read outIt proposes a cheap concierge pilot with explicit thresholds and measures qualified proposals and meetings rather than won deals, matching the 6–10 week sales cycle.
  • Tigers, not paper tigersIt separates the central trust and capacity risks from fixable targeting/cost issues and surfaces the warm-outreach product alternative and margin-math problem.

Claims the judge couldn’t find in the brief

  • Two funded competitors are moving down into this market.
  • None of the failed outbound attempts used a modern AI agent.

Grades and run details

Decision model 91 · LLM judge 7 of 12 checks
Decision model checks
  • passUses the supplied evidence correctly37%
  • passAddresses the actual decision95%
  • partialRespects explicit constraints30%
  • passIdentifies material uncertainty100%
  • partialAvoids unsupported claims25%
  • passProduces the required deliverable79%
  • passFinds the load-bearing assumption86%
  • passUses the interviews faithfully83%
  • passEngages the counter-evidence75%
  • passA cheap test that can actually read out99%
  • passTigers, not paper tigers98%
Run
Run
#1
API response time
30 s
Submitted
29 Sept 2026
Critical failure: Treats the founders' feast-or-famine hypothesis as confirmed by the interviews. Score capped at 40.

Usable with a quick edit11 of 11 checks passed

The memo is well-structured, evidence-backed, and actionable, requiring at most light editing for polish.

Output

Why the AI SDR for small agencies fails

Sep 25, 2026 · @Martin Slaney

The reason

Small agencies win work on trust, and cold outbound only closes when someone does the follow-up. An AI SDR automates the first email, the cheap part. It hands the follow-up, which is the actual job, to a founder our own hypothesis says is too busy delivering to sell. We would be adding meetings to the one resource that is already the constraint.

Evidence

  • Referrals dominate. 11 of 14 get most new revenue (86% on average) from referrals and repeat clients. A03: "Every client we have came from someone vouching for us."
  • Outbound was tried and dropped. 9 tried it; 7 stopped within six months and none of the 7 closed an attributable deal. They used five different channels (lead-gen agency, cold-email agency, contract SDR, LinkedIn automation, DIY email), so this isn't one bad vendor.
  • Meetings weren't the problem; closing was. A05 got six or seven meetings a month and closed nothing: "Content is a trust purchase." A01: "We got meetings with people who'd never buy from us." A10: "It cost us about £400 for every meeting, and the meetings didn't close."
  • Where it works, a human does the work. Both survivors (A04, A07) have 15–20 staff and a dedicated BD person. A04: "It works because of the follow-up, not the first email" and "most agencies our size don't have someone like me."
  • The downside hits their best channel. A02 lost the founder's LinkedIn, "our best referral network"; A11's domain was spam-listed. A04 and A05 both refuse to let anything send unread.
  • Some don't need leads at all. A08, A12 and A14 turn work away. A12: "I don't need more leads, I need another designer."

Where it cuts the other way

  • The famine is real.1 6 of 14 describe feast-or-famine swings; A05 "spent April panicking" after three clients left at once.
  • The maths are forgiving. At an $18k average deal, one closed client a year covers $7.2k of subscription.
  • One buyer exists. A04 would pay $600 today if it replaced Apollo, Clay and three hours a day of research, but only with HubSpot sync and approval of every email.
  • Past failures were generic. A05's buyers wanted proof of work in their niche; better enrichment might fix that. Untested.
  • Small sample. 14 interviews, one interviewer.
  • Warm outreach worked. A05's emails to past clients won two back in a month, and she'd pay "a couple of hundred a month" for a tool that did it. That supports the thesis against cold outbound, but points at a different product.

What would prove us wrong

Agencies without a dedicated BD person closing deals from AI-sent cold email, without damage to their reputation. Concretely, in a 12-week pilot with 5 such agencies:

  • at least 3 reach a scoped proposal and at least 1 closes;2
  • no domain, inbox or LinkedIn penalties;
  • owners spend under 2 hours a week on follow-up;
  • they keep paying when the pilot ends.

Cheapest test

Pre-sell a hand-run pilot before building anything. Offer the 9 agencies with no BD person that aren't turning work away (A01–A03, A05, A06, A09–A11, A13) a 12-week pilot at $600 a month, paid upfront. We run it by hand: Apollo and Clay for prospects, LLM-drafted emails, owner approves every send, separate sending domain.

  1. Gate 1, one week: fewer than 3 pay, stop. There is no demand at this price.
  2. Gate 2, 12 weeks (covers the 6–10 week sales cycle): score against the thresholds above and log owner follow-up hours.

In parallel, offer A05's version (past-client and referrer re-engagement, about $200 a month) as a second arm. If that sells and cold doesn't, we have our answer.

Cost: roughly £1–2k in tools and a quarter of one founder's time3, against a year and most of the £800k.

What a PM had to fix

  1. 1Hypothesis stated as factReframe it as a hypothesisTargeted repair

    Source: Founders' hypothesis (from our planning doc)Small agencies live feast or famine.

    What we’d changeSay 'Famine is real for some: 6 of 14' rather than confirming the founders' hypothesis for the whole segment.

  2. 2Test or gate too weakTighten the testQuick edit

    What we’d changeRaise the bar for proving the memo wrong: one close in five agencies doesn't show the product works.

  3. 3OtherFix itQuick edit

    What we’d changeThe cost looks light for running a hand-run pilot across nine agencies. Build it up line by line.

Check by check

Got right · 11
  • Uses the supplied evidence correctlyEvery factual claim about the current situation is drawn correctly from the brief or supplied context, with accurate quotes and attributions.
  • Addresses the actual decisionThe output commits to a single reason for failure early on, addresses the founding team, and specifies the evidence and conditions that would change the call.
  • Respects explicit constraintsThe output is a memo under 600 words, covers all requested sections, and the proposals (test, thresholds) enforce the constraints in practice.
  • Identifies material uncertaintyIt names the small sample size, whether better enrichment could fix niche trust, and that the test result would resolve the uncertainty.
  • Avoids unsupported claimsInterpretations such as 'small agencies win work on trust' are clearly positioned as the reason and backed with evidence; no causal claims are presented as fact without support.
  • Produces the required deliverableThe memo includes the reason, quoted evidence, counter-evidence, a falsification condition, a cheap test, and stays under 600 words; a founding team could act on it.
  • Finds the load-bearing assumptionThe critique directly challenges the assumption that these agencies are lead-constrained, arguing that they lack the capacity to convert leads and that outbound fails without follow-up.
  • Uses the interviews faithfullyAll quoted material is taken from the transcripts or log, attributed to the correct agency, and none is invented.
  • Engages the counter-evidenceA04 and A07 are named, their shared characteristics (size, dedicated BD, follow-up effort) are identified, and the implication that the addressable segment is very small is drawn.
  • A cheap test that can actually read outThe test is a hand-run pilot that measures proposals within 12 weeks (covering the sales cycle) and uses simple gates; it is cheap and provides an early signal before full build.
  • Tigers, not paper tigersIt dismisses the worry that past failures were just due to poor tooling as untested, and surfaces the unspoken issue that a warm-outreach re-engagement tool might be a better product.

Grades and run details

Decision model 91 · LLM judge 12 of 12 checks
Decision model checks
  • passUses the supplied evidence correctly36%
  • passAddresses the actual decision94%
  • partialRespects explicit constraints22%
  • passIdentifies material uncertainty100%
  • partialAvoids unsupported claims24%
  • passProduces the required deliverable79%
  • passFinds the load-bearing assumption89%
  • passUses the interviews faithfully82%
  • passEngages the counter-evidence96%
  • passA cheap test that can actually read out89%
  • passTigers, not paper tigers98%
Run
Run
#1
Time to output
60 s
Submitted
25 Sept 2026

Results

Every setup we’ve tested on this task, across all cases and repeats, graded on the current checklist. Calibrated: the graders match our PM on 87% of checks.

#Model · HarnessTask scoreDecision modelLLM judgeRunsCritical failures
1GPT-6.1 SolwithAPI100.095.82None
2GPT-6 AstrawithChatGPT95.595.82None
3GPT-6 LunawithAPI93.291.72None
4Sonnet 5.5withAPI93.275.02None
5Gemini 3.5 Flash-LitewithGemini81.875.021 capped
6Opus 5.5withClaude90.991.721 capped

About the task

The PM job

Pressure-testing a proposal before committing a team to it.

Why it matters

The useful critic finds the one assumption everything rests on. Theatrical negativity is easy to generate and useless in a planning meeting.

What good looks like

  • Identifies the load-bearing assumption
  • Separates the risks that could kill it from the ones that only look scary
  • Uses the supplied evidence, not generic risks
  • Proposes the cheapest way to test the assumption

Deliberately not measured

  • Tone
  • Number of objections raised
Capability tested

Evidence-based critique

The failure we’re looking for

Theatrical negativity without evidence

Grading

Decision model and LLM judge, calibrated against a blind PM review

Variants

Vanilla prompt (core) · With Roast Me skill · Staff level: a company bet with a long evidence pack

This task measures the whole setup. Tools, instructions and skills in the harness do real work here, so read the harness as carefully as the model name.