Tasks / Strategy

Challenge an idea

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

Task type v1.2 · 2 tasksLast changed 6 Oct 2026 · ChangelogDifficulty

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

From 18 graded outputs by 9 models. 44% were usable with at most a quick edit.

Reliably right

Finds the load-bearing assumption100% pass
The critique targets the assumption that agencies' growth is limited by a shortage of new leads, using referral, abandoned-outbound, and capacity evidence.
GPT-6.1 Sol · API · An AI SDR for small agencies
Uses the interviews faithfully100% pass
All quotes are accurately taken from the transcripts and correctly attributed to A05, A04, and A08.
GPT-6.1 Sol · API · An AI SDR for small agencies
Finds the timeline that sinks it100% pass
Cites 9-month build and concludes Q1 launch is unsupported.
GPT-6 Astra · ChatGPT · Five billion dollars, on paper

Where it slips

Uses the supplied evidence correctly50% pass
Claims that local taxes and multi-state operations affect eligibility are not supported by the supplied context, which only mentions state-by-state tax rules.
GPT-6 Astra · ChatGPT · Five billion dollars, on paper
Avoids unsupported claims56% pass
Presents the existence of local taxes and multi-state complexity as fact without support from the context.
GPT-6 Astra · ChatGPT · Five billion dollars, on paper
Finds the need behind the idea71% pass
It mentions A05's past-client reminder idea but does not state the underlying need or offer a full alternative with its cost and what it displaces.
GPT-6 Astra · ChatGPT · An AI SDR for small agencies

How it’s graded

Each check is built on how world-class product and growth leaders do this work, as they’ve described it on Lenny’s Podcast, and names the leader it comes from.

Finds the need behind the idea
Does the critique identify the underlying need the idea is meant to serve, and offer at least one other way to meet that need, at a different cost, saying what would have to be dropped for it?
Passes when States the need behind the proposal, and gives an alternative way to meet it with its cost and what it displaces.
Gokul RajaramLenny’s Podcast

Plus our standard checks

Uses the supplied evidence correctly · Addresses the actual decision · Respects explicit constraints · Identifies material uncertainty · Avoids unsupported claims · Produces the required deliverable · Tigers, not paper tigers · and 4 written for each task, which you’ll see in the tasks below.

The tasks

Read the brief, then compare up to three outputs, 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.

What the model was given7 items: Scenario, Founders' hypothesis (from our planning doc), Interview summary (14 agencies, 5–20 staff, last six weeks), Interview log, interview-A05-content-agency.md, interview-A04-shopify-agency.md, interview-A08-packaging-studio.md

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 doesThe answer key the graders mark against

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 at 40)

Invents interview quotes or attributes a quote to the wrong agency
Treats the founders' feast-or-famine hypothesis as confirmed by the interviews

Task

Staff-level · v1.16

The outputs

9 setups answered this brief.

GPT-6.1 SolAPI100Usable with a quick edit Haiku 5.5API100Usable with a quick edit GPT-6 LunaAPI98Usable with a quick edit Gemini 4 ArgonAPI90Usable with a quick edit Sonnet 5.5API83Needs more work GPT-6 AstraChatGPT81Needs more work Gemini 3.8 FlashAPI40Critical failure Opus 5.5Claude40Critical failure Gemini 3.5 Flash-LiteGemini40Critical failure

Gemini 4 ArgonAPI

Usable with a quick edit11 of 12 checks passed

The output is well-structured, evidence-backed, and almost ready to use. A quick edit to make the test measure an early signal (e.g., qualified meetings) would align it fully.

Output

The Core Reason This Fails

Cold outbound does not work for small agencies without a human to work the leads—and our target market lacks that human.

Our hypothesis assumes small agencies lack pipeline because founders are too busy to send emails. The interviews show that even when emails are sent for them, cold leads don't close because agency services are high-trust purchases. Closing a cold lead requires intensive, bespoke follow-up (custom audits, nurturing, and qualifying calls) that busy agency founders still do not have time to do. If we sell a $600/month autonomous emailer, agencies will either reject it out of fear for their reputation, or churn within six months when the meetings fail to convert into revenue.

The Evidence

Cold leads don’t convert without trust: 11 of 14 agencies get an average of 86% of revenue from referrals and repeat work. Of the 9 that tried outbound (including outsourced agencies and contract SDRs doing the work for them), 7 quit within six months with zero closed deals. As A05 put it: "Content is a trust purchase... They booked meetings, I'll give them that, maybe six or seven a month. But the people on those calls had no idea who we were... We didn't close anything." (See also A01, A10).
Email is only 10% of the job: A04 (one of only two agencies succeeding at outbound) explicitly warned us: "It works because of the follow-up, not the first email... What wins deals is that I then send them a teardown of their site, a short video, and I'm on the phone with them within a week... Most agencies our size don't have someone like me. The owner does sales on the side. They don't have the time to follow up, and the follow-up is the job."
Automation threatens their real pipeline: Because reputation drives referrals, founders fear automated outreach. Both A04 and A05 refused to let AI send unread emails ("I'm not letting anything send in our name unread"). Past automation burned A11 ("domain ended up on a spam list") and A02 ("LinkedIn shut our founder's account down. That's our best referral network").
Shrinking addressable market: 3 of 14 agencies (A08, A12, A14) are capacity-constrained, not lead-constrained. A08 noted: "I don't need more leads, I need another designer... [An AI SDR] would make my problem worse."

Where the Evidence Cuts the Other Way

Commoditized/technical niches can work: The two successful outbound users (A04 Shopify, A07 SEO) sell technical services where need can be spotted externally (e.g., outdated tech stacks) rather than pure creative trust. A07 converts 1 in 10 meetings using outsourced lead-gen.
A04 will buy a research copilot: A04 would pay $600/month if we replace their research stack (Apollo/Clay) and save three hours a day—provided they approve every email.
The problem is real, the channel is wrong: 6 of 14 agencies do suffer feast-or-famine swings. A05 solved a famine in 30 days by emailing past clients and offered to pay $200/month "tomorrow" for an AI tool that nurtures warm contacts and referral partners.

What We Need to See to Be Proved Wrong

Founder-led agencies (5–15 staff, no dedicated BD) must convert cold AI-sourced emails into signed deals (not just booked meetings) within a 10-week sales cycle, without spending more than two hours a week on manual follow-up.

The Cheapest Test

A 10-week "Wizard of Oz" concierge test. Recruit 5 founder-led agencies (exclude those with BD staff) to pay $300/month. Using off-the-shelf tools (Apollo, Clay, Claude), we manually research prospects and draft personalized emails for founder approval. Pass criteria: At least 2 of the 5 agencies close a paying client within 10 weeks and renew at $600/month. Cost: ~$500 in software and our time; zero code written.

Grades and run details

Decision model 88 · LLM judge 92

Decision model checks

partialUses the supplied evidence correctly9%
passAddresses the actual decision98%
passRespects explicit constraints55%
passIdentifies material uncertainty98%
partialAvoids unsupported claims38%
passProduces the required deliverable83%
passFinds the load-bearing assumption79%
passUses the interviews faithfully33%
passEngages the counter-evidence82%
partialA cheap test that can actually read out91%
passTigers, not paper tigers89%
passFinds the need behind the idea37%

Run

Run: #1
API response time: 11 s
Submitted: 13 Oct 2026

Gemini 3.5 Flash-LiteGemini

Needs more than a quick edit7 of 12 checks passed

Contains an invented statistic about A07 and proposes a test for a different product, so a PM would need to re-check evidence and redesign the test.

Output

Why an AI SDR for Small Agencies Will Fail: Pre-Mortem Analysis

For: Founding Team (£800k runway, 20 months remaining) Product: AI Sales-Development Rep ($600/month) targeting agencies with 5–20 staff

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1. The One Reason It Fails

Small agencies do not suffer from a lack of prospecting volume; they suffer from a lack of trust and execution capacity. Cold outbound is fundamentally the wrong tool for their business model. Because creative and professional services are "trust purchases," agencies rely overwhelmingly on referrals and repeat clients. Automated cold emails damage their reputation rather than building a reliable pipeline.

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2. The Evidence (Interview Quotes)

Trust & Referrals Outweigh Cold Acquisition

“Content is a trust purchase: you're letting someone write in your company's voice… When the CFO introduced us, the first call was about scope, not about whether we were any good.” — A05 (Content Agency)
“Every client we have came from someone vouching for us.” — A03 (PR Boutique)

Cold Outbound Fails Small Agencies

“The replies were mostly people asking us to take them off the list.” — A09 (Paid Social Agency)
“Our domain ended up on a spam list. Took weeks to fix.” — A11 (WordPress Agency)
“It cost us about £400 for every meeting, and the meetings didn't close.” — A10 (B2B Marketing Agency)

The Real Bottleneck is Capacity and Follow-Up, Not Leads

“If you sent me ten more leads in October I'd have to say no to nine of them.” — A08 (Packaging Design Studio)
“The AI could save me the research hours, sure. It can't do the call... and the follow-up is the job.” — A04 (Shopify Development Agency)

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3. Where the Evidence Cuts the Other Way

The Pain is Real: Six of the 14 interviewed agencies explicitly described painful "feast-or-famine" revenue swings, validating the founders' premise that pipeline stability is a major issue.²
Outbound Can Work: Two agencies (A04 and A07) successfully use outbound to drive 30% to over 50% of new revenue⁴, proving that agency outbound can function under specific circumstances.³

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4. What We Would Need to See to Be Proved Wrong

To believe this product can succeed at $600/month for 5–20 staff agencies, we would need to see empirical proof that small agencies without a dedicated in-house business development lead can: 1. Generate positive ROI from cold AI outreach without harming their domain reputation. 2. Convert cold prospects into high-trust creative/professional services contracts without a human-led multi-channel follow-up loop.

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5. The Cheapest Test

Run a targeted messaging experiment to 50 agencies with 5–20 staff. Pivot the pitch away from a cold-outbound AI SDR toward what A05 actually requested: an automated relationship assistant that tracks past clients and referral networks, drafting warm check-in notes.

If agencies will not engage with or pre-order a warm-relationship retention tool at $200–$600/month, they will certainly reject a cold AI prospecting tool.¹

What a PM had to fix

1Test or gate too weakTighten the testSubstantial rework
What we’d changeTest the reason the memo gives: whether agencies without a BD person can turn AI-sent cold email into deals. Demand for a different product doesn't settle that.
2Hypothesis stated as factReframe it as a hypothesisTargeted repair
Source: Founders' hypothesis (from our planning doc)Small agencies live feast or famine.
What we’d changeSix of 14 is some agencies, not validation of the founders' premise. Say that.
3Contradiction missedSurface the contradictionTargeted repair
What we’d changeSay what sets A04 and A07 apart: a dedicated BD person doing the follow-up. That's the evidence for the memo's own reason, and it's left unused.
4Invented evidenceVerify or remove the claimQuick edit
What we’d changeRemove 'over 50%': A07's share of new revenue from outbound isn't given anywhere.

Claims the judge couldn’t find in the brief

Two agencies (A04 and A07) successfully use outbound to drive 30% to over 50% of new revenue.

Grades and run details

Decision model 79 · LLM judge 54

Decision model checks

passUses the supplied evidence correctly18%
passAddresses the actual decision82%
partialRespects explicit constraints27%
passIdentifies material uncertainty31%
partialAvoids unsupported claims27%
partialProduces the required deliverable51%
passFinds the load-bearing assumption94%
passUses the interviews faithfully76%
partialEngages the counter-evidence86%
partialA cheap test that can actually read out86%
passTigers, not paper tigers66%
passFinds the need behind the idea33%

Run

Run: #1
Time to output: 7 s
Submitted: 25 Sept 2026

Check by check

Where the outputs differ comes first. Open a check to read the judge’s reasons. “Mixed” means the two graders disagreed.

Where they differ 4

Uses the supplied evidence correctlyRightMixed

Gemini 4 Argon · API

All factual claims about the current situation are drawn accurately from the supplied brief, interview summary, logs, and transcripts.