Tasks / Strategy

Develop product strategy

Can the model make a coherent choice grounded in the evidence, rather than list aspirations?

Task type v1.1 · 2 tasksLast changed 6 Oct 2026 · ChangelogDifficulty

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

From 16 graded outputs by 8 models. 38% were usable with at most a quick edit.

Reliably right

  1. Produces the required deliverable100% pass
    Complete strategy document in the requested form, length, and for the named reader; the board could act on it.
    GPT-6 Astra · ChatGPT · Supply or demand for a stalled marketplace
  2. Diagnosis before prescription100% pass
    Diagnosis: students can't find the right tutor; actions (intake, recommendations, rematch, manual matching) directly address it.
    GPT-6 Astra · ChatGPT · Supply or demand for a stalled marketplace
  3. Tells the CEO plainly100% pass
    It clearly states the enterprise-first plan is wrong for next year, backs it with numbers, and presents the alternative.
    GPT-6 Astra · ChatGPT · Enterprise, says the CEO

Where it slips

  1. Names an advantage that's hard to copy11% pass
    Does not name a benefit and a barrier that a well-funded competitor couldn't copy; no moat is identified.
    GPT-6 Astra · ChatGPT · Supply or demand for a stalled marketplace
  2. Proposes tests that could fail42% pass
    The SMB pilot lacks a numeric threshold for success; while the payback guardrail has a threshold and action, not every proposed test/gate meets the full requirement.
    GPT-6 Astra · ChatGPT · Enterprise, says the CEO
  3. Avoids unsupported claims44% pass
    Presents 'root cause: we've let the loudest requests set the roadmap' and 'SMB remains our top-of-funnel' as facts without labelling them as hypotheses or citing evidence.
    Haiku 5.5 · API · Enterprise, says the CEO

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.

  1. Diagnosis before prescription

    Does the strategy name the crux, the specific obstacle or opportunity the evidence points to, and do the proposed actions follow from that diagnosis?

    Passes when States one crux grounded in the supplied evidence, and each major action visibly addresses it.

  2. Names an advantage that's hard to copy

    Does the strategy say what will make its position hard for an informed, well-funded competitor to copy (a benefit customers value plus a barrier to copying it), rather than relying on being first, on features, or on funding?

    Passes when Names the benefit and the barrier, and why a capable competitor couldn't simply replicate it.

  3. Says what it gives up

    Does the strategy name what the company will stop doing, or deliberately not do, in order to pursue it?

    Passes when Names at least one real thing being dropped or declined, with the reason it loses out.

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 · Proposes tests that could fail · and 2 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

Our tutoring marketplace has stalled at about 4,000 bookings a month. Write a one-page strategy for the next 12 months (about 500 words) for our CEO to take to the board. We can fund one major bet.

What the model was given4 items: Scenario, Metrics, Research, Board view
ScenarioTutorly connects secondary-school students with independent tutors for online lessons at £30–45 an hour; we take a 20% commission. There are 6,500 active tutors and 11,000 active students. We have 18 months of runway and about £1.2m to put behind the one bet.
MetricsTutor supply up 60% year on year; bookings up 8%. 70% of tutors get zero bookings in a typical month. Repeat booking rate is 64% for students who book twice.
ResearchStudents cite 'finding the right tutor' as their top problem. Tutors cite 'not enough students'.
Board viewThe board believes paid acquisition of students is the answer.
What a strong answer doesThe answer key the graders mark against

Recognise the contradiction: supply is abundant but matching fails, so buying demand into a broken match pours water into a leaky bucket. Choose matching quality and say what is given up.

Critical failures (cap the score at 40)
  • Recommends paid demand acquisition without addressing matching
Task

Staff-level · v1.12

The outputs

8 setups answered this brief.

Usable with a quick edit8 of 12 checks passed

The strategy is actionable, evidence-based, and framed for the board; a PM could add a numeric threshold to the Month 3 gate and a brief moat argument with a quick edit without redoing any reasoning.

Output

Tutorly: 12-Month Strategy Board paper, for decision

The problem Bookings have grown 8% while tutor supply grew 60%. We are not short of tutors or students. We are failing to connect them. Students say their top problem is finding the right tutor. Tutors say they lack students, and 70% get no bookings in a typical month. Once a student books twice, 64% keep booking, so the product works when a match happens. The leak is in the first match.

Why not paid student acquisition The board's instinct is to buy more students. I recommend against it for now: - Paid students would arrive at the same broken search and matching flow that already frustrates them. We would be paying to acquire customers we are likely to lose before their second booking. - Our tutor base is already larger than our demand. More students would mainly bring more tutors into the same competition for the few bookings available. - Acquisition spend scales with cost. Matching improvements scale with use.

The bet: fix first-match conversion (£1.2m) Over 12 months we will build a guided matching system and test it against the current search:

  1. Structured intake (Months 1–4). Students give subject, exam board, year group, goals, budget, and availability. Required before search.
  2. Curated shortlists (Months 2–6). Within one hour, students receive three ranked tutors with a free 15-minute intro call. A small concierge team handles hard cases such as niche subjects and last-minute exam prep.
  3. Ranking that rewards fit and responsiveness (Months 3–8). Ranking weighs subject expertise, response time, and student outcomes. New tutors get guaranteed early exposure so that supply does not stall at the bottom.
  4. Tutor activation (Months 4–12). Tutors with zero bookings in 30 days receive coaching on profile quality and availability, plus targeted introductions.

Budget (£1.2m) - Product and engineering: £600k - Concierge matching team: £300k - Tutor activation and targeted student tests: £200k - Measurement and contingency: £100k

Targets (12 months) - Bookings: 4,000 → 5,500 per month - Students with a first booking within 7 days of intake: baseline in Month 1, target +50% - Share of tutors with at least one booking per month: ~30% → 45% - Repeat rate (second booking): hold at or above 64%

Decision gates - Month 3: Intake and shortlist live for a test cohort. Confirm the conversion baseline and the uplift. - Month 6: If first-match conversion has not improved by at least 20% against control, stop further build and move remaining funds to a small, controlled paid-acquisition test. If it has, scale the concierge model and begin targeted acquisition in segments where our supply is deepest. - Month 9: Review unit economics. Each booking should contribute enough commission to cover concierge cost.

Runway This plan spends £1.2m over 12 months and leaves about six months of runway for the gates above. If the Month 6 gate fails, we retain the option to pivot without running out of cash.

What we are asking the board to approve 1. Fund the £1.2m matching-led plan. 2. Approve the Month 6 gate and the reallocation rule if it fails. 3. Defer paid student acquisition until conversion data supports it.

The board's instinct is right that growth needs more students. But we already have more tutors than we can match, and the evidence points to the match as the bottleneck. Fixing that first makes every future pound of acquisition work harder.

Grades and run details

Decision model 71 · LLM judge 85
Decision model checks
  • failUses the supplied evidence correctly18%
  • passAddresses the actual decision100%
  • passRespects explicit constraints35%
  • passIdentifies material uncertainty100%
  • failAvoids unsupported claims34%
  • passProduces the required deliverable89%
  • passSurfaces the central contradiction100%
  • passMakes a clear choice100%
  • passDiagnosis before prescription100%
  • partialProposes tests that could fail48%
  • failNames an advantage that's hard to copy46%
  • passSays what it gives up100%
Run
Run
#1
API response time
16 s
Submitted
8 Oct 2026

Needs more than a quick edit6 of 12 checks passed

The output contains an unsupported claim about the current model and lacks testable gates, so a PM would need to re-check evidence and add kill criteria.

Output

MEMORANDUM

TO: Board of Directors, Tutorly FROM: Chief Executive Officer DATE: October 2023 SUBJECT: 12-Month Strategic Plan: Unlocking Growth via Managed Matching

---

Executive Summary: Diagnosing the Growth Plateau

Our marketplace has stalled at 4,000 bookings/month (~£30k monthly net revenue) despite healthy user numbers (11k students, 6.5k tutors).

The Board’s instinct to deploy our £1.2m reserve into paid student acquisition is understandable, but premature. The data reveals a liquidity and conversion bottleneck, not an awareness problem: * Supply is bloated and disengaged: Tutor supply grew 60% YoY, yet 70% receive zero bookings monthly. * Friction kills discovery: Students cite “finding the right tutor” as their primary obstacle. Our open-directory model forces parents to sift through 6,500 profiles, causing decision paralysis and drop-off. * Underlying product-market fit is proven: When students reach a second booking, 64% retain.

Pouring paid traffic into an unguided directory will burn our £1.2m on high CAC and low conversion. Our single bet for the next 12 months is transitioning from an open directory to an intelligent, Managed Matching Engine.

---

The Single Bet: "The Perfect Match" Engine

Instead of browsing endless profiles, parents will complete a 60-second diagnostic intake (curriculum tier, personality, learning barriers, availability). Our matching engine pairs them with the single best tutor—backed by a 100% “First Lesson Satisfaction Guarantee” (rebooked free if not a fit).

By actively directing demand to a curated, high-performing top quartile of our supply (~1,500 tutors), we solve both sides of the marketplace: students find immediate trust, and active tutors earn dependable income.

#### Allocation of the £1.2m Capital: 1. Product & Matching Tech (£500k): Algorithmic intake flow, automated calendar sync, and in-app instant booking to eliminate messaging back-and-forth. 2. Onboarding & Operations (£300k): Quality vetting, tiering supply, and a proactive concierge team to manually rescue failed first sessions. 3. Targeted Performance Marketing (£400k): Phased acquisition deployed only once the match-to-book conversion rate improves.

---

12-Month Execution Roadmap

  • Q1–Q2 (Fix the Engine):
  • Replace public browse with the guided diagnostic matching flow.
  • Restrict active routing to the top 25% highest-rated tutors to concentrate liquidity.
  • Launch the "Fit Guarantee" to de-risk the first booking.
  • Q3 (Solve the 2nd Booking):
  • Automate recurring weekly reservation slots right after lesson one (optimizing for the 64% retention threshold).
  • Introduce 4-lesson starter packs to mathematically guarantee lesson two.
  • Q4 (Scale What Works):
  • Deploy the remaining £400k into intent-driven paid channels (Google Search for GCSE/A-Level revision), scaling into a proven, high-converting funnel.

---

Targets & Milestones

MetricCurrent12-Month Target
:---:---:---
Monthly Bookings4,00010,000+
Search-to-First-Booking CVRBaseline+40%
% Tutors with ≥1 Booking/mo30%65% (of active tier)
Annualized Net Revenue (20%)£360k£900k+

Conclusion: Fixing search friction activates the high-retention engine we already possess. By funding matching instead of brute-force acquisition, we reach sustainable unit economics and double our run-rate within our existing 18-month runway.

Claims the judge couldn’t find in the brief

  • Our open-directory model forces parents to sift through 6,500 profiles, causing decision paralysis and drop-off

Grades and run details

Decision model 67 · LLM judge 46
Decision model checks
  • failUses the supplied evidence correctly77%
  • passAddresses the actual decision73%
  • passRespects explicit constraints41%
  • partialIdentifies material uncertainty45%
  • failAvoids unsupported claims89%
  • passProduces the required deliverable66%
  • passSurfaces the central contradiction100%
  • passMakes a clear choice93%
  • passDiagnosis before prescription100%
  • failProposes tests that could fail37%
  • partialNames an advantage that's hard to copy41%
  • passSays what it gives up99%
Run
Run
#1
API response time
16 s
Submitted
1 Oct 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 correctlyMixedWrong
Haiku 5.5 · API

All factual statements about the current situation appear in the brief or context, or follow from the supplied numbers.

Gemini 3.8 Flash · API

The output invents that the current model is an open directory and that it causes decision paralysis, which is not in the supplied context.

Addresses the actual decisionRightMixed
Haiku 5.5 · API

Commits early to matching as the one bet, defers paid acquisition, and names the Month 6 conversion improvement condition that would change the answer.

Gemini 3.8 Flash · API

The output commits to one bet but never states what result or condition would change that decision.

Identifies material uncertaintyRightWrong
Haiku 5.5 · API

Month 6 gate sets a clear numeric threshold and action; the plan acknowledges the risk and a pivot option if the bet fails.

Gemini 3.8 Flash · API

No material unknowns are named, nor how they would be resolved or what would change the call.

Avoids unsupported claimsMixedWrong
Haiku 5.5 · API

Interpretations like 'not short of students' and 'leak is in the first match' are grounded in the supplied evidence and not presented as unsupported assertions.

Gemini 3.8 Flash · API

The output presents the interpretation that an open-directory model causes decision paralysis as an established fact, without labelling it as a hypothesis.

All got wrong 2

Proposes tests that could failWrongWrong
Haiku 5.5 · API

The Month 3 gate lacks a numeric threshold, does not specify what result would stop or continue, and thus doesn't fully meet the 'test that could fail' requirement.

Gemini 3.8 Flash · API

The roadmap lists targets but no explicit test gates with numeric thresholds, measurement windows, and the actions each outcome triggers.

Names an advantage that's hard to copyWrongWrong
Haiku 5.5 · API

Does not name a benefit customers value plus a barrier that would make the position hard for a well-funded competitor to copy.

Gemini 3.8 Flash · API

The strategy does not name any benefit-plus-barrier that would make the position hard for a well-funded competitor to copy.

All got right 6

Respects explicit constraintsRightRight
Haiku 5.5 · API

Delivers a ~500-word one-page board paper that respects the single-bet budget and runway.

Gemini 3.8 Flash · API

The output is a one-page memo (~500 words) for the board, proposes one major bet, and does not recommend all options in parallel.

Produces the required deliverableRightRight
Haiku 5.5 · API

Output is a complete board-ready paper within the length, formatted for the CEO to take to the board and act upon.

Gemini 3.8 Flash · API

The memo is the right form for the board, within the word limit, and could be acted on with light edits.

Surfaces the central contradictionRightRight
Haiku 5.5 · API

Explicitly states that supply grew 60% while bookings grew only 8%, highlighting the disconnect that the matching bet addresses.

Gemini 3.8 Flash · API

It surfaces the contradiction that tutor supply grew 60% but 70% get zero bookings, and students can't find the right tutor.

Makes a clear choiceRightRight
Haiku 5.5 · API

Chooses the matching bet and clearly defers paid student acquisition, naming what is given up.

Gemini 3.8 Flash · API

It chooses the Managed Matching Engine as the single bet and clearly forgoes the board's immediate paid acquisition approach.

Diagnosis before prescriptionRightRight
Haiku 5.5 · API

Diagnoses the first-match conversion as the crux and then proposes structured intake, curated shortlists, ranking, and tutor activation that all address it.

Gemini 3.8 Flash · API

It diagnoses a matching bottleneck as the crux, and the proposed actions (matching engine, curated supply) directly address it.

Says what it gives upRightRight
Haiku 5.5 · API

Explicitly defers paid student acquisition, naming the sacrificed growth lever and the reason (conversion data needed first).

Gemini 3.8 Flash · API

It declines the board's plan to pour £1.2m into immediate paid acquisition, explaining it would burn cash on high CAC and low conversion.

Results

Every setup we’ve tested on this task type, across all its tasks and repeats, graded on the current checklist. Calibrated. Where our PM checked the graders by hand, they agreed on 84% of 76 checks.

#Model · HarnessTask scoreDecision modelLLM judgeRunsCritical failures
1GPT-6 AstrawithChatGPT83.388.52None
2Haiku 5.5withAPI77.180.82None
3Sonnet 5.5withAPI77.180.82None
4GPT-6.1 SolwithAPI79.276.92None
5GPT-6 LunawithAPI77.176.92None
6Opus 5.5withClaude83.365.42None
7Gemini 3.8 FlashwithAPI68.857.72None
8Gemini 3.5 Flash-LitewithGemini60.442.32None

What you get for the cost

No setup scores within 5 points of the leader at half its cost or less here, so the leader is also the best value.

Task score against relative cost for each setup. The table below has the same figures.4050607080901001×3×10×30×100×Cost per output, relative to the cheapest setup (log scale) →↑ Task scoreGPT-6 Astra · ChatGPT: task score 87, 84× the cheapest (1 of 2 outputs estimated)Haiku 5.5 · API: task score 80, 1.7× the cheapestSonnet 5.5 · API: task score 78, 27× the cheapestGPT-6.1 Sol · API: task score 77, 12× the cheapestGPT-6 Luna · API: task score 74, the cheapestOpus 5.5 · Claude: task score 71, 68× the cheapest (1 of 2 outputs estimated)Gemini 3.8 Flash · API: task score 61, 8.1× the cheapestGemini 3.5 Flash-Lite · Gemini: task score 49, 3.1× the cheapest (1 of 2 outputs estimated)GPT-6 Astra · ChatGPTHaiku 5.5 · APISonnet 5.5 · APIGPT-6.1 Sol · APIGPT-6 Luna · APIOpus 5.5 · ClaudeGemini 3.8 Flash · APIGemini 3.5 Flash-Lite · Gemini
Nobody beats these on both score and costCost partly estimated (app runs with no usage meter)
Task score and relative cost by setup
SetupTask scoreRelative cost (cheapest = 1)
GPT-6 Luna · API741.0×
Haiku 5.5 · API801.7×
Gemini 3.5 Flash-Lite · Gemini493.1× (partly estimated)
Gemini 3.8 Flash · API618.1×
GPT-6.1 Sol · API7712×
Sonnet 5.5 · API7827×
Opus 5.5 · Claude7168× (partly estimated)
GPT-6 Astra · ChatGPT8784× (partly estimated)

Cost is each output’s tokens at the model’s list price, shown relative to the cheapest setup. Runs done in an app have no usage meter, so theirs are estimated from the same setup’s measured runs. How we compare cost

About the task

The PM job

Writing a strategy memo that leadership can act on.

Why it matters

Strategy that doesn't choose isn't strategy. Models write fluent strategic prose easily; making a choice the evidence supports and naming what it gives up is harder.

What good looks like

  • Diagnoses the one obstacle that matters before prescribing
  • Makes one clear choice and names what is sacrificed
  • Grounds the choice in the supplied evidence
  • Surfaces the tension or contradiction in the data
  • Defines how we would know it is working

Deliberately not measured

  • Market sizing accuracy beyond the supplied data
  • Financial modelling
Capability tested

Choosing where to play and what not to do, from supplied evidence

The failure we’re looking for

Strategic-sounding aspirations without a diagnosis or a choice

Grading

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