Tasks / Product Craft

Build a roadmap

Can the model sequence bets against capacity and dependencies, and explain the order?

Task type v1.0 · 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. 72% were usable with at most a quick edit.

Reliably right

  1. Produces the required deliverable96% pass
    The roadmap is complete, in the right form for a Group PM, within the word limit, and actionable without major gaps.
    GPT-6.1 Sol · API · Fourteen requests from one customer
  2. Outcomes, with certainty that falls with distance96% pass
    Every item names its outcome (e.g., reduce paper transcription, reduce manual reconciliation), and near-term items are specific while later ones are deliberately looser (e.g., '7 weeks for rollout, workflow improvement and contingency').
    GPT-6.1 Sol · API · Fourteen requests from one customer
  3. Handles the big customer with evidence94% pass
    It uses Calder's rising usage and the second-hand 'might leave' to propose a conversation first, not committing the report builder, and offers a bounded export if needed.
    GPT-6.1 Sol · API · Fourteen requests from one customer

Where it slips

  1. Fits the stated capacity53% pass
    Q3 Expenses row lacks squad-week allocation, so the committed plan cannot be fully checked against the 11-week capacity.
    Opus 5.5 · Claude · A year of spend management, with a hard deadline
  2. Tells the story of the bets54% pass
    The roadmap table is organized by squad, not grouped into a few themes, though the case provides thematic reasoning.
    Sonnet 5.5 · API · A year of spend management, with a hard deadline
  3. Sees through the request count72% pass
    The output never counts requests by requester, does not mention that 14 requests come from Calder or that several are duplicates, and does not compare themes by customer count.
    GPT-6 Luna · API · Fourteen requests from one customer

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. Outcomes, with certainty that falls with distance

    Does each roadmap item say the problem or outcome it serves, and does precision (dates, scope) decrease for later items?

    Passes when Every item names its outcome or problem. Near-term items are specific and later ones are deliberately looser.

  2. Fits the stated capacity

    Does the committed plan fit the team capacity the brief gives, with sums a reader could check, and does it say what was cut or deferred to make it fit?

    Passes when The committed work adds up to no more than the stated capacity, with some slack, the sums can be checked, and it names what was cut or pushed later and why.

  3. Tells the story of the bets

    Does the roadmap group the work into a few themes and explain why those are the biggest things to invest in now, rather than presenting a scored or ranked list of projects?

    Passes when A handful of themes, each with the reason it matters most now, and the items sit under them.

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 · Sequences around dependencies · 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

You're the Group PM at Fernhill. Build the roadmap for the next half (Q1 and Q2) for our two squads, in no more than 900 words plus a table: what each squad builds, in what order, the outcome each item serves, what we're not doing and why, and what we tell Calder Group. The request log, usage, capacity and goal are attached.

What the model was given5 items: About Fernhill, company_goal_h1.md, feature_requests_last_6_months.csv, feature_usage.md, capacity_and_estimates.md
About FernhillPurchasing and inventory software for restaurants and hotels: orders, deliveries, invoices and stock.
company_goal_h1.md5 lines · Download
# Company goal for the half

Cut churn among independent restaurants (82% of accounts, 61% of revenue) from 2.4% to 1.6% a month. Top churn reason in exit surveys: "too much admin; didn't save us time on deliveries and invoices".

Calder Group renews in May. Their account manager says they "might" leave without the report builder; they haven't raised it with Customer Success, and their usage is up 20% this year.
feature_requests_last_6_months.csv53 rows · Download
request,requester,requester_arr_usd,source,title,theme
FR-300,Customer 553,4353,Support ticket,Credit note tracking,Invoicing
FR-301,Customer 391,9773,Sales call,Match invoices to deliveries automatically,Invoicing
FR-302,Customer 341,4856,Support ticket,Match invoices to deliveries automatically,Invoicing
FR-303,Calder Group,186000,Account manager,ERP export (CSV variant),Integrations
FR-304,Customer 895,9595,Sales call,Mobile receiving (check deliveries on a phone),Receiving
FR-305,Calder Group,186000,Account manager,Report builder with pivots,Reporting
…
feature_usage.md8 lines · Download
# Usage of related features today (last 30 days, 1,140 accounts)

| Feature | Accounts using it | Note |
|---|---|---|
| Standard reports | 212 (19%) | Calder Group uses them daily |
| Receiving checklist (desktop only) | 640 (56%) | 71% of uses start on a desktop, then get re-typed from paper |
| Invoice upload | 870 (76%) | Matching is manual |
…
capacity_and_estimates.md5 lines · Download
# Capacity, Q1 to Q2

Two squads, about 10 squad-weeks of roadmap work each per quarter (40 in total over the half).

Estimates (squad-weeks): Mobile receiving 8. Flag short deliveries 3 (needs mobile receiving). Invoice matching 9 (needs the new invoice parser, 5). Credit note tracking 3 (needs invoice matching). Accounting export with credits 2 (needs credit note tracking). Custom report builder 12. ERP export 4. Approval chains 6. Site-level permissions 4. SSO 3.
What a strong answer doesThe answer key the graders mark against

Builds the half around the churn goal (independent restaurants, whose top exit reason is admin around deliveries and invoices), not the request count. The log has 53 requests, but 14 come from one customer, Calder Group, and several of theirs are the same thing under different names (report builder three times, ERP export twice, bulk SKU twice, scheduled reports twice); across everyone else, receiving and invoicing requests dominate (mobile receiving 9, invoice matching 8, flag short deliveries 7, credit notes 5, accounting export 4). Sequences the dependency chain: mobile receiving (8), then flag short deliveries (3); the invoice parser (5), then invoice matching (9), then credit note tracking (3), then the accounting export (2): about 30 squad-weeks, inside the 40 available with slack. Handles Calder with evidence: their usage is up 20% and they haven't raised leaving with Customer Success, so talk to them before committing the 12-week report builder; offer a smaller item (SSO, 3, or the ERP export, 4) if it fits. Says what's not being done (report builder, approval chains, dark mode, multi-currency) and why, with near-term items specific and later ones looser.

Critical failures (cap the score at 40)
  • Schedules an item before the item it depends on (for example invoice matching before the parser)
Task

Staff-level · v1.1

The outputs

9 setups answered this brief.

Usable with a quick edit8 of 12 checks passed

The sole factual slip (40 vs 39 requests) and the overconfident interpretation about the account manager can be corrected with a quick wording edit; the core reasoning and roadmap remain intact and do not need re-checking.

Output

Strategic Overview

Our H1 goal is to reduce independent restaurant churn from 2.4% to 1.6% per month. Independents represent 82% of our accounts and 61% of our revenue. Exit surveys point to one glaring issue: "too much admin; didn't save us time on deliveries and invoices."

Usage and request data confirm this friction: * Deliveries: 56% of accounts use the desktop receiving checklist, and 71% of those print it on paper and manually re-type it later. * Invoices: 76% of accounts upload invoices, but 100% of matching to orders/deliveries is manual. * Demand: Out of 40 feature requests from independent restaurants in the last six months, 33 are for Receiving and Invoicing workflow improvements.

We have 40 squad-weeks across two squads in H1. We will dedicate one squad to Invoicing Automation and the other to Mobile Receiving, with a small allocation in Q2 to protect the Calder Group renewal without derailing our core strategy.

---

H1 Roadmap Table

SquadQuarterInitiativeEstimateDependenciesOutcome Served
:---:---:---:---:---:---
Squad A (Invoicing)Q1New Invoice Parser5 wksNoneUnlocks automated line-item extraction to eliminate manual data entry.
Squad A (Invoicing)Q1–Q2Automated Invoice-to-Delivery Matching9 wksInvoice ParserEliminates manual invoice reconciliation (76% of accounts); directly attacks #1 churn driver.
Squad A (Invoicing)Q2Credit Note Tracking3 wksInvoice MatchingAutomates discrepancy resolution when deliveries are short or overcharged.
Squad A (Invoicing)Q2Accounting Export with Credits2 wksCredit Note TrackingCloses the loop with accounting software, removing final manual bookkeeping steps.
Squad A TotalH119 wks(1 wk buffer)
Squad B (Receiving)Q1Mobile Receiving8 wksNoneEliminates paper-to-desktop double entry (affects 71% of receiving users).
Squad B (Receiving)Q1–Q2Flag Short Deliveries at the Door3 wksMobile ReceivingCaptures delivery errors at the loading dock, feeding directly into Credit Note Tracking.
Squad B (Receiving)Q2ERP Export (CSV Variant)4 wksNoneSecures Calder Group renewal ($186k ARR) by getting their raw data into their BI/ERP tools.
Squad B (Receiving)Q2Adoption & UX Polish (Receiving/Invoicing)5 wksMobile ReceivingDrives adoption of new H1 workflows among at-risk independent accounts to ensure churn reduction.
Squad B TotalH120 wks

---

Execution Plan & Sequencing

#### Squad A: End-to-End Invoicing (19 of 20 weeks) Squad A will spend the entire half building a seamless, automated invoicing pipeline. 1. New Invoice Parser (Q1, Weeks 1–5): Required foundation. 2. Automated Invoice Matching (Q1 Week 6 – Q2 Week 4): Our second most-requested feature by independents (8 requests). Automatically reconciles uploaded invoices against delivery records. 3. Credit Note Tracking (Q2, Weeks 5–7): Requested 5 times. Ensures restaurants actually recover money when suppliers shortchange them. 4. Accounting Export with Credits (Q2, Weeks 8–9): Requested 4 times. Pushes clean, reconciled data into their accounting tools. Week 10 is reserved as buffer for edge-case supplier invoice formats.

#### Squad B: Receiving & Strategic Retention (20 of 20 weeks) Squad B will solve physical delivery admin first, then pivot to a targeted retention play. 1. Mobile Receiving (Q1, Weeks 1–8): Our #1 most-requested feature (9 requests). Lets kitchen staff check off deliveries on their phones at the back door, killing the clipboards-and-retyping workflow. 2. Flag Short Deliveries at the Door (Q1 Week 9 – Q2 Week 1): Requested 7 times. Allows staff to log missing items on their phone during check-in. (Bonus: This creates the exact data needed for Squad A’s Automated Invoice Matching and Credit Note Tracking). 3. ERP Export CSV Variant (Q2, Weeks 2–5): Delivered by early May ahead of Calder Group’s renewal. 4. Workflow Polish & Onboarding (Q2, Weeks 6–10): Shipping features doesn't lower churn unless customers use them. Squad B will spend the final 5 weeks removing friction from mobile/invoicing onboarding to ensure we hit the 1.6% churn target.

---

What We Are Not Doing (and Why)

  • Custom Report Builder (12 wks) & Reporting Add-ons: Only 19% of accounts use standard reports today. Spending 30% of our H1 capacity here starves our core receiving/invoicing workflows and guarantees we miss our churn goal.
  • Enterprise Admin (Approval chains - 6 wks, Site permissions - 4 wks, SSO - 3 wks): Zero independent restaurants asked for these. Building them turns us into bespoke enterprise software at the expense of 82% of our user base.
  • Catalogue Additions / Bulk SKU Tools: Catalogue already has 100% usage and isn't driving churn. Our Ops team can handle urgent supplier catalogue additions manually.
  • Dark Mode & Multi-Currency: Low request volume (3 total) and zero impact on admin time savings.

---

What We Tell Calder Group ($186k ARR)

The Reality: Calder’s usage is up 20% YoY, they use standard reports daily, and they haven't complained to CS. The renewal risk is likely an Account Manager hedging their bets. However, $186k is significant, so we shouldn't ignore them entirely.

The Pitch (Delivered jointly by Product, CS, and the AM): 1. Lead with Operational Value: Show them Mobile Receiving and Automated Invoice Matching shipping in Q1/early Q2. Across their multiple sites, eliminating paper receiving and manual invoice reconciliation will save their site managers hundreds of hours a month. 2. Solve the Underlying Reporting Need: Explain that we are not building a custom pivot-table builder inside Fernhill this half because we are focused on core operational automation. Instead, we are building their requested Custom ERP CSV Export in April (before their May renewal). This allows them to pull granular, site-level data directly into their existing ERP/BI tools (or Excel) to build whatever custom pivots and dashboards they need. 3. Bridge the Gap with CS: Have Customer Success set up a weekly manual email of their daily standard reports so they don't have to pull them manually.

Claims the judge couldn’t find in the brief

  • Out of 40 feature requests from independent restaurants in the last six months, 33 are for Receiving and Invoicing workflow improvements

Grades and run details

Decision model 63 · LLM judge 77
Decision model checks
  • failUses the supplied evidence correctly10%
  • partialAddresses the actual decision61%
  • partialRespects explicit constraints18%
  • partialIdentifies material uncertainty69%
  • partialAvoids unsupported claims62%
  • passProduces the required deliverable64%
  • partialSees through the request count40%
  • passHandles the big customer with evidence94%
  • passOutcomes, with certainty that falls with distance64%
  • failFits the stated capacity16%
  • passSequences around dependencies76%
  • passTells the story of the bets38%
Run
Run
#1
API response time
17 s
Submitted
13 Oct 2026

Needs more than a quick edit3 of 12 checks passed

The invoice matching estimate is incorrect, so the capacity plan is wrong and would need rework. A PM cannot use this without re-checking the evidence and recalculating.

Output

Fernhill H1 Product Roadmap (Q1–Q2)

Strategic Focus & Alignment

Our overriding company goal for H1 is to cut churn among independent restaurants (82% of accounts, 61% of revenue) from 2.4% to 1.6% a month. Exit surveys reveal the primary culprit: "too much admin; didn't save us time on deliveries and invoices."

Independent operators are drowning in manual paperwork at the back door and during invoice reconciliation. Therefore, both squads will be entirely laser-focused on automating receiving and invoice workflows in Q1 and Q2.

We have 40 total squad-weeks available (2 squads $\times$ 10 weeks per quarter). We are ruthlessly prioritizing features that directly target independent restaurant admin reduction, while deferring enterprise-heavy requests.

---

Squad 1: Receiving & Back-Door Ops

Squad 1 owns the physical receiving workflow, eliminating the friction of transcribing paper notes and catching vendor discrepancies at the door.

  • Q1 (Weeks 1–8): Mobile Receiving (8 squad-weeks)
  • Outcome: Enables staff to check deliveries directly on a phone or mobile device at the loading dock, eliminating the current clunky desktop-to-paper re-typing workflow used by 56% of accounts. Directly targets independent churn by saving hours of back-door admin.
  • Q1–Q2 (Overlap Weeks 9–10 & Q2 Weeks 1–3): Flag Short Deliveries at the Door (3 squad-weeks)
  • Outcome: Built immediately upon Mobile Receiving. Allows staff to instantly log missing or damaged items during the mobile check-in process, generating immediate vendor credit trails and saving reconciliation disputes.

---

Squad 2: Invoicing & Reconciliation

Squad 2 owns the financial workflow post-delivery, automating the tedious matching of paper/digital invoices against actual stock received.

  • Q1 (Weeks 1–9): Automated Invoice Matching (9 squad-weeks, including parser)
  • Outcome: Leverages the new invoice parser (5 weeks) alongside matching logic (4 weeks) to automatically reconcile uploaded invoices against verified deliveries. This attacks the second half of the independent churn bottleneck: manual invoice data entry.
  • Q2 (Weeks 1–4): Credit Note Tracking & Accounting Export (5 squad-weeks total)
  • Credit Note Tracking (3 wks): Tracks vendor credits resulting from short deliveries.
  • Accounting Export with Credits (2 wks): Seamlessly pushes reconciled invoices and credit notes to accounting software, removing end-of-month manual entry.

---

Roadmap Table

SquadQ1 InitiativeSquad-WeeksQ2 InitiativeSquad-WeeksPrimary Outcome
:---:---:---:---:---:---
Squad 1Mobile Receiving8Flag Short Deliveries3Eliminate paper re-typing at the back door; surface short deliveries instantly.
Squad 2Automated Invoice Matching9Credit Notes & Acct. Export5Automate invoice-to-delivery reconciliation and sync clean data to accounting.

---

What We Are Not Doing and Why

To hit our churn-reduction target, we are intentionally declining several high-visibility requests, notably from Calder Group (who accounts for $186k ARR, but whose account manager notes they "might" leave without the report builder).

1. Custom Report Builder (12 squad-weeks) & Calder’s Enterprise Requests (Approval chains, SSO, Site-level permissions, Custom PDF invoices): * Why: Building the Custom Report Builder would consume 30% of our entire company capacity for the half. While Calder Group represents significant ARR, their usage is actually up 20% this year, they have raised no complaints with Customer Success, and their renewal is in May. Diverting 12 weeks to appease an AM warning without CS validation while independent churn burns our revenue base is an unacceptable strategic risk. 2. More Suppliers / Catalogue Updates / Dark Mode / Multi-currency (FR-307, FR-315, FR-351, etc.): * Why: These are nice-to-haves that do not directly address the core operational admin burden cited in independent restaurant exit surveys.

---

What We Tell Calder Group

> "We value our partnership immensely and are thrilled to see your platform usage grow by 20% this year. For H1, our entire product and engineering organization is locked onto a company-wide mandate to eliminate back-office administrative overhead for operators—specifically delivering mobile receiving, short-delivery flagging, and automated invoice matching. > > Because these workflows directly accelerate daily operational efficiency, we aren't scheduling the Custom Report Builder or enterprise admin controls for Q1/Q2. However, your Account Manager and our Customer Success team are logging your specific reporting and export requirements so we can scope them for a future release cycle post-May renewal. We are fully committed to ensuring Fernhill continues to scale with Calder Group's operational needs."

Claims the judge couldn’t find in the brief

  • Automated Invoice Matching takes 9 squad-weeks including the parser (parser 5 weeks, matching logic 4 weeks).

Grades and run details

Decision model 83 · LLM judge 23
Decision model checks
  • passUses the supplied evidence correctly48%
  • partialAddresses the actual decision61%
  • passRespects explicit constraints16%
  • partialIdentifies material uncertainty23%
  • partialAvoids unsupported claims51%
  • passProduces the required deliverable30%
  • partialSees through the request count85%
  • passHandles the big customer with evidence40%
  • passOutcomes, with certainty that falls with distance27%
  • passFits the stated capacity48%
  • passSequences around dependencies27%
  • passTells the story of the bets48%
Run
Run
#1
Time to output
6 s
Submitted
5 Oct 2026

Usable with a quick edit11 of 12 checks passed

The output is a complete, evidence-based roadmap with a clear story, actionable table and Calder plan. A PM could use it with light edits and no need to re-verify facts or restructure the reasoning.

Output

Fernhill roadmap, Q1 and Q2

The call: Both squads go to the company goal: deliveries and invoices, the top reasons independents give for leaving. Calder gets a bounded share of capacity, not the roadmap. Calder's report builder can't ship before May, so we tell them that directly and commit to a scoped plan.

Why this split: - The receiving and invoice chains (30 of 40 squad-weeks) serve 32 different non-Calder accounts. Mobile receiving and flagging short deliveries touch 16 accounts. Invoice matching, credit notes and the accounting export touch 16. - Calder has 14 of the 53 requests, but they come from one account. Every Calder-only item totals 29 squad-weeks (report builder, ERP export, site permissions, SSO, approval chains). Taking all of it would consume 73% of the half. - Usage backs the sequence. 56% of accounts use the receiving checklist, but 71% of uses start on a desktop and get re-typed from paper, so mobile receiving removes that step. Invoice matching is manual for the 76% of accounts that upload invoices.

Capacity: 2 squads × 10 squad-weeks per quarter. The plan uses 40 of 40, with a 1-week spike per squad left at the end of Q2 for report builder scoping.

OrderSquadItemWeeksTimingOutcome it servesNotes
11Mobile receiving8Q1 wk 1–8Less time per delivery; ends paper re-typing9 requests, 9 accounts
22Invoice parser5Q1 wk 1–5Prerequisite for invoice matchingOnly item with no visible customer output; it gates the invoice chain
32Invoice matching9Q1 wk 6–10 to Q2 wk 4Less manual invoice admin8 accounts; biggest admin saving
41Flag short deliveries3Q1 wk 9–10 to Q2 wk 1Catch shortages at the door, not on the invoiceNeeds item 1; 7 accounts
51ERP export (CSV/ERP format)4Q2 wk 2–5Calder renewal; integrationCalder only; ships before May renewal
62Credit note tracking3Q2 wk 5–7Credits matched to invoicesNeeds item 3; 4 accounts
72Accounting export with credits2Q2 wk 8–9Invoices and credits reach accounting without re-keyingNeeds item 6; 4 accounts
81Site-level permissions4Q2 wk 6–9Calder multi-site accessCalder only; see below
91 + 2Report builder scoping spike1 eachQ2 wk 10Scoped plan and H2 date for CalderDesign only, no build

Dependencies are the risk. Item 2 gates the invoice chain. If the parser slips, items 3, 6 and 7 slip with it, and the invoice outcome misses the half. I'd rather flag that now than hide it inside the plan. If the parser runs over, the first move is to pull the Calder-only site permissions work (item 8) back into the buffer.

Measures: Time per delivery receipt and percentage of invoices auto-matched, tracked per cohort. Independent-restaurant churn (2.4% → 1.6% a month) is the outcome. We won't claim the roadmap alone moves it.

What we're not doing, and why

  • Full custom report builder (12 weeks). It's 60% of one squad's half, for one account, and the earliest it ships is around the May renewal with no slack. We do a scoping spike and commit to a decision date, not a build date.
  • SSO (3) and approval chains with 5 levels (6). Calder only, and the 5-level approvals request is a niche configuration. H2 candidates, to be revisited with Calder.
  • Custom PDF invoices, custom order fields, per-site dashboards, bulk SKU import v2 and bulk SKU edit. All Calder-only, none estimated. Not in H1.
  • Dark mode (2 accounts), multi-currency (1 account), more suppliers (3 accounts). Low demand, no estimates. Parked, not rejected.
  • Scheduled reports by email (Calder, 2 requests). Not estimated. It goes into the spike as a candidate for a smaller Calder deliverable.

What we tell Calder Group

  1. Customer Success calls them this week, not the account manager alone. They haven't raised the report builder with CS, and "might leave" is the kind of risk that surfaces too late.
  2. Be direct about the report builder: it's a substantial build, it won't land before May, and we won't promise a date we can't keep.
  3. What they get in H1: the ERP export in the format they asked for, shipping around early May, and site-level permissions by the end of June.
  4. The report builder: we scope it with them in June, and we commit to an H2 decision date by the end of June. We don't commit to a build date until the spike returns.
  5. Ask them two things: which reports they run daily (we know they use standard reports), and what minimum output would cover them until the full builder ships. Their answer decides whether scheduled email reports move up.

Asks for leadership: confirm Calder's renewal status and ARR before the CS call, and approve the spike's two squad-weeks. If Calder won't engage on the scoped plan, we should know before the roadmap is shared externally.

Grades and run details

Decision model 83 · LLM judge 100
Decision model checks
  • passUses the supplied evidence correctly7%
  • passAddresses the actual decision67%
  • passRespects explicit constraints25%
  • passIdentifies material uncertainty91%
  • partialAvoids unsupported claims51%
  • passProduces the required deliverable70%
  • passSees through the request count82%
  • passHandles the big customer with evidence95%
  • passOutcomes, with certainty that falls with distance82%
  • failFits the stated capacity28%
  • passSequences around dependencies74%
  • partialTells the story of the bets37%
Run
Run
#1
API response time
56 s
Submitted
8 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 8

Uses the supplied evidence correctlyWrongMixedRight
Gemini 4 Argon · API

The claim that there were '40 feature requests from independent restaurants' is false; 53 total minus 14 from Calder equals 39, so a statement about the current situation is not supported.

Gemini 3.5 Flash-Lite · Gemini

The output claims Automated Invoice Matching is 9 squad-weeks including the parser, but the supplied context indicates invoice matching is 9 weeks and the parser is a separate 5-week dependency, making the total 14.

Haiku 5.5 · API

Every statement about the current situation can be traced to the supplied context or is derived by clear arithmetic from it, with no invented facts.

Addresses the actual decisionRightWrongRight
Gemini 4 Argon · API

The output commits unambiguously to a roadmap split across two squads, addresses the churn goal, and specifies what to tell Calder Group.

Gemini 3.5 Flash-Lite · Gemini

The output does not state what result or condition would change the roadmap decision.

Haiku 5.5 · API

The roadmap commits unambiguously to investing in deliveries and invoices to address churn, with a clear call for Calder, and states what would change the plan (parser slippage).

Identifies material uncertaintyWrongWrongRight
Gemini 4 Argon · API

The output does not name specific unknowns that could change the plan, nor does it say how they would be resolved or what result would change the call.

Gemini 3.5 Flash-Lite · Gemini

The output does not name any unknowns that could change the decision or how they would be resolved.

Haiku 5.5 · API

It names the key dependency risk (invoice parser slip) and how it would be resolved (pull site permissions), and acknowledges the roadmap alone won't guarantee the churn outcome.

Avoids unsupported claimsWrongWrongRight
Gemini 4 Argon · API

It presents 'The renewal risk is likely an Account Manager hedging their bets' as a confident reality ('The Reality'), but this is an interpretation not established by the supplied evidence.

Gemini 3.5 Flash-Lite · Gemini

The output presents the invoice matching estimate (9 weeks including parser) as fact when the evidence does not support it.

Haiku 5.5 · API

Interpretations and forecasts (e.g., why mobile receiving reduces admin) are clearly linked to the data, and no claim is presented as fact that isn't supported.

Produces the required deliverableRightMixedRight
Gemini 4 Argon · API

The required roadmap table and narrative are present, within the length, and usable by the intended reader.

Gemini 3.5 Flash-Lite · Gemini

The capacity error makes the roadmap unusable without re-checking the evidence and redoing the capacity math.

Haiku 5.5 · API

The roadmap includes a detailed table, explicit not-doing list, and a specific Calder communication plan, all usable by a Group PM as-is.

Sees through the request countRightWrongRight
Gemini 4 Argon · API

The output separates Calder's 14 requests, de-duplicates their repeated asks, and weighs demand by number of independent customers asking (33 receiving/invoicing requests).

Gemini 3.5 Flash-Lite · Gemini

The output does not count requests by requester or de-duplicate Calder Group's multiple requests; it only notes Calder's requests are enterprise-heavy.

Haiku 5.5 · API

It explicitly notes Calder's 14 requests come from a single account, de-duplicates themes, and weights demand by distinct customer count rather than raw request volume.

Handles the big customer with evidenceRightMixedRight
Gemini 4 Argon · API

It uses Calder's rising usage and the second-hand 'might leave' to propose a smaller item (ERP CSV export) and a conversation, rather than committing the 12-week report builder by default.

Gemini 3.5 Flash-Lite · Gemini

The output does not offer Calder Group a smaller item (like SSO or ERP export) to address their concerns, only defers everything.

Haiku 5.5 · API

It uses Calder's rising usage and the second-hand 'might leave' to propose a direct CS conversation and a scoping spike, instead of committing the full report builder.

Outcomes, with certainty that falls with distanceRightMixedRight
Gemini 4 Argon · API

Every item names an outcome or problem; near-term items are specific (e.g., mobile receiving outcome) and later items (adoption polish) are deliberately looser.

Gemini 3.5 Flash-Lite · Gemini

Q2 items are given specific week ranges (e.g., 'Q2 Weeks 1-4') rather than deliberately looser precision for later items.

Haiku 5.5 · API

Every roadmap item states the outcome or problem it serves; early items have precise timing, and the later report-builder spike is deliberately scoped rather than committed.

All mixed 1

Fits the stated capacityMixedMixedMixed
Gemini 4 Argon · API

Committed work adds up to 39 squad-weeks with 1 week slack, sums are checkable, and the output names what was cut (report builder, enterprise admin, etc.) and why.

Gemini 3.5 Flash-Lite · Gemini

The committed plan sums to 25 squad-weeks based on an incorrect estimate; the actual required work (parser 5 + matching 9 + credit notes 3 + export 2 + mobile 8 + flag 3) totals 30, and the output's capacity claim is therefore invalid.

Haiku 5.5 · API

The committed work adds up to exactly 40 squad-weeks, the sums are verifiable, it names the items deferred (full report builder, SSO, approval chains, etc.), and includes a buffer/retreat plan.

All got right 3

Respects explicit constraintsRightRightRight
Gemini 4 Argon · API

The output stays within 900 words plus table, includes the required sections (what each squad builds, order, outcomes, what we're not doing, what we tell Calder), and frames the answer for the Group PM.

Gemini 3.5 Flash-Lite · Gemini

The output is under 900 words, includes a table, and covers what each squad builds, order, outcomes, what's not being done, and what to tell Calder Group.

Haiku 5.5 · API

The output is well under 900 words plus a table, includes the required elements (ordered items, outcomes, not-do list, Calder plan), and the proposed plan respects the squad and capacity limits.

Sequences around dependenciesRightRightRight
Gemini 4 Argon · API

The roadmap sequences invoice parser before matching, matching before credit notes, credit notes before accounting export, and mobile receiving before flag short deliveries, respecting all stated dependencies.

Gemini 3.5 Flash-Lite · Gemini

The roadmap places flag short deliveries after mobile receiving, and the invoice matching item includes the parser, implying the parser is done first.

Haiku 5.5 · API

All dependencies (flag short deliveries after mobile, invoice matching after parser, credit notes after matching, accounting export after credit notes) are respected and explicitly named.

Tells the story of the betsRightRightRight
Gemini 4 Argon · API

The work is grouped into two themes (Invoicing Automation and Mobile Receiving) tied directly to the churn reduction goal, and the narrative explains why those bets matter most now.

Gemini 3.5 Flash-Lite · Gemini

The work is grouped into two themes (Receiving & Back-Door Ops, Invoicing & Reconciliation) with clear reasons tied to the churn goal.

Haiku 5.5 · API

The roadmap groups work into the themes of deliveries, invoices, and Calder retention, and explains why each is the most important investment now to cut churn and manage the renewal.

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 79% of 150 checks.

#Model · HarnessTask scoreDecision modelLLM judgeRunsCritical failures
1GPT-6 AstrawithChatGPT88.0100.02None
2Opus 5.5withClaude88.396.42None
3GPT-6.1 SolwithAPI88.396.42None
4Sonnet 5.5withAPI90.292.62None
5Haiku 5.5withAPI74.496.42None
6GPT-6 LunawithAPI84.085.42None
7Gemini 4 ArgonwithAPI62.088.52None
8Gemini 3.8 FlashwithAPI58.366.82None
9Gemini 3.5 Flash-LitewithGemini57.136.521 capped

What you get for the cost

GPT-6.1 Sol · API scores within a point of GPT-6 Astra · ChatGPT at a sixth of the cost.

Task score against relative cost for each setup. The table below has the same figures.304050607080901001×3×10×30×Cost per output, relative to the cheapest setup (log scale) →↑ Task scoreGPT-6 Astra · ChatGPT: task score 94, 39× the cheapestOpus 5.5 · Claude: task score 93, 37× the cheapestGPT-6.1 Sol · API: task score 93, 6.9× the cheapestSonnet 5.5 · API: task score 92, 36× the cheapestHaiku 5.5 · API: task score 86, 2.1× the cheapestGPT-6 Luna · API: task score 84, the cheapestGemini 4 Argon · API: task score 77, 6.7× the cheapestGemini 3.8 Flash · API: task score 60, 5.5× the cheapestGemini 3.5 Flash-Lite · Gemini: task score 45, the cheapest, 1 critical failureGPT-6 Astra · ChatGPTOpus 5.5 · ClaudeGPT-6.1 Sol · APISonnet 5.5 · APIHaiku 5.5 · APIGPT-6 Luna · APIGemini 4 Argon · APIGemini 3.8 Flash · APIGemini 3.5 Flash-Lite · Gemini
Best valueNobody beats these on both score and costAt least one critical failure
Task score and relative cost by setup
SetupTask scoreRelative cost (cheapest = 1)
GPT-6 Luna · API841.0×
Gemini 3.5 Flash-Lite · Gemini451.1×
Haiku 5.5 · API862.1×
Gemini 3.8 Flash · API605.5×
Gemini 4 Argon · API776.7×
GPT-6.1 Sol · API936.9×
Sonnet 5.5 · API9236×
Opus 5.5 · Claude9337×
GPT-6 Astra · ChatGPT9439×

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

Turning strategy into a sequenced plan.

Why it matters

A roadmap is where strategy meets capacity. Dated feature lists turn guesses into promises.

What good looks like

  • Items are problems or outcomes, not just features
  • Sequencing reflects dependencies
  • Explicit trade-offs
  • Commitment falls with distance

Deliberately not measured

  • Gantt formatting
Capability tested

Sequencing under constraints

The failure we’re looking for

A dated wishlist sorted by excitement

Grading

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