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 16 graded outputs by 8 models. 69% were usable with at most a quick edit.

Reliably right

  1. Produces the required deliverable95% 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 distance94% 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. 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
  2. Uses the supplied evidence correctly72% pass
    States credit notes as 4 customers, but the request log contains 5 credit note tracking requests.
    Sonnet 5.5 · API · Fourteen requests from one customer
  3. Fits the stated capacity73% 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

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 · v1.0

The outputs

8 setups answered this brief.

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 79 · LLM judge 23
Decision model checks
  • passUses the supplied evidence correctly34%
  • passAddresses the actual decision32%
  • partialRespects explicit constraints9%
  • partialIdentifies material uncertainty28%
  • partialAvoids unsupported claims43%
  • passProduces the required deliverable26%
  • partialSees through the request count86%
  • passHandles the big customer with evidence37%
  • partialOutcomes, with certainty that falls with distance22%
  • passFits the stated capacity63%
  • passSequences around dependencies27%
  • passTells the story of the bets99%
Run
Run
#1
Time to output
6 s
Submitted
5 Oct 2026

Needs more than a quick edit8 of 12 checks passed

The output fails to de-duplicate Calder's requests and leaves no capacity slack, so a PM would need to re-check the request log and adjust the plan before using it.

Output

Strategic Context & H1 Focus

Fernhill’s H1 north star is cutting independent restaurant monthly churn from 2.4% to 1.6%. Independent restaurants represent 82% of our accounts and 61% of revenue. Exit interviews clearly highlight the churn driver: administrative burden on deliveries and invoices.

Currently: * 56% of accounts use desktop receiving, but 71% write deliveries on paper at the door and re-type them later. * 76% of accounts upload invoices, but matching is entirely manual.

To reach our churn target, H1 execution is dedicated to eliminating manual reconciliation at the back door and in the back office. Calder Group ($186k ARR) is critical, but dedicating 12 squad-weeks to a custom report builder would derail the core churn goal and still risk missing their May renewal date. We address Calder with a targeted integration release and proactive commercial management.

---

H1 Roadmap

SquadQuarterInitiativeEstimateDependencyPrimary Outcome Served
Squad 1: Receiving & DataQ1Mobile Receiving8 wksNoneEliminates paper receiving; cuts ~30–45 mins of daily double-entry per site.
Squad 1: Receiving & DataQ1–Q2Flag Short Deliveries at the Door3 wksMobile ReceivingReal-time shortage capture; generates dispute records at check-in.
Squad 1: Receiving & DataQ2Automated ERP Export4 wksNoneDe-risks Calder renewal; automates multi-site enterprise reporting pipelines.
Squad 1: Receiving & DataQ2Buffer, Rollout & Mobile QA5 wks—Hardware testing, onboarding stability, restaurant floor adoption.
Squad 2: Invoicing & FinanceQ1New Invoice Parser5 wksNoneFoundation for OCR extraction; pre-requisite for matching engine.
Squad 2: Invoicing & FinanceQ1–Q2Automated Invoice Matching9 wksNew Invoice Parser3-way match (PO to delivery to invoice); solves top independent request.
Squad 2: Invoicing & FinanceQ2Credit Note Tracking3 wksInvoice MatchingCloses loop on short deliveries, automating balance deductions.
Squad 2: Invoicing & FinanceQ2Accounting Export with Credits2 wksCredit Note TrackingOne-click sync to Xero/QuickBooks with verified vendor credits.
Squad 2: Invoicing & FinanceQ2Buffer & Accounting Integration QA1 wk—Edge-case tax/rounding rules and accounting schema validation.

---

Squad Breakdown & Sequencing

#### Squad 1 (Receiving & Data) — 20 Squad-Weeks 1. Mobile Receiving (8 wks, Q1): Build a mobile-optimized receiving flow allowing kitchen staff to check off line items directly on their phone at the loading dock. Eliminates paper double-entry (71% of receiving workflows today). 2. Flag Short Deliveries at the Door (3 wks, Q1–Q2): Extends mobile receiving to instantly flag missing quantities, take a photo, and generate a shortage log directly linked to the order. 3. Automated ERP Export (4 wks, Q2): Scheduled and manual CSV/ERP data pipeline (FR-303, FR-339). Delivers automated raw financial/operational extracts before Calder’s May renewal. 4. Buffer & Mobile Rollout (5 wks, Q2): Ensures smooth adoption in noisy kitchen environments with flaky Wi-Fi.

#### Squad 2 (Invoicing & Finance) — 20 Squad-Weeks 1. New Invoice Parser (5 wks, Q1): Modernizes parsing infrastructure to extract line items, taxes, unit costs, and invoice numbers reliably. 2. Automated Invoice Matching (9 wks, Q1–Q2): Automatically matches invoice line items against purchase orders and received delivery logs. Discrepancies are flagged automatically. 3. Credit Note Tracking (3 wks, Q2): Pairs short-delivery logs generated in Squad 1 with incoming vendor credit notes, stopping suppliers from overcharging for missing goods. 4. Accounting Export with Credits (2 wks, Q2): Exports matched invoices and net credit adjustments directly into standard general ledgers. 5. Buffer & Edge Cases (1 wk, Q2): Absorbs parser edge cases and vendor invoice layout variations.

---

What We Are NOT Doing (and Why)

1. Custom Report Builder with Pivots (12 weeks): * Why: At 12 weeks, this would consume 30% of total H1 capacity for a single account. It cannot ship and stabilize before Calder's May renewal, and standard report daily usage is already healthy (212 accounts, Calder included). 2. 5-Level Approval Chains & Site-Level Permissions (10 weeks combined): * Why: Pure enterprise overhead. Does not solve the operational time sink driving 82% of accounts to churn. 3. Dark Mode & Multi-Currency (Non-core): * Why: Zero correlation to churn reduction or operational savings. 4. Catalogue Bulk Tools & Expansion: * Why: Catalogue usage is 100% saturated. The friction point is not creating items; it is receiving and paying for them.

---

What We Tell Calder Group

#### 1. Commercial Reality Check (Internal) Calder’s usage is up 20% year-over-year, and they use Standard Reports daily. Their threat to leave originated from an Account Manager conversation, not Customer Success or executive escalation. We will not over-index engineering capacity on an AM negotiation bluff.

#### 2. External Messaging (Fernhill VP of Product & Head of CS to Calder Exec Sponsor in March) * Lead with High-Value Clean Data: “A reporting tool is only as good as the input data. By shipping Mobile Receiving and Automated Matching in Q1, Fernhill ensures every invoice, delivery quantity, and supplier credit across all Calder sites is 100% accurate and audited in real time.” * Deliver the ERP Export (Ships April, ahead of May renewal): “Rather than forcing your finance team into a proprietary, rigid reporting UI inside Fernhill, we are releasing the Automated ERP/CSV Data Export in April. This allows Calder to stream clean, site-level operational and invoice data directly into your central ERP/BI stack (PowerBI/Tableau/Excel) with your custom formulas and pivot models.” * White-Glove Support: CS will construct scheduled, bespoke standard reporting extracts tailored to their multi-site leadership team during renewal discussions.

Grades and run details

Decision model 79 · LLM judge 69
Decision model checks
  • failUses the supplied evidence correctly28%
  • passAddresses the actual decision53%
  • passRespects explicit constraints20%
  • partialIdentifies material uncertainty25%
  • partialAvoids unsupported claims32%
  • passProduces the required deliverable75%
  • partialSees through the request count80%
  • passHandles the big customer with evidence99%
  • passOutcomes, with certainty that falls with distance65%
  • passFits the stated capacity64%
  • passSequences around dependencies92%
  • passTells the story of the bets99%
Run
Run
#1
API response time
31 s
Submitted
6 Oct 2026

Usable with a quick edit12 of 12 checks passed

The output is evidence-based, respects all constraints, and provides a complete, actionable plan that a PM could use with only minor wording adjustments.

Output

Fernhill H1 Roadmap: Receiving and Invoicing First

The call

Both squads spend most of the half on the two jobs independent restaurants say we don't save them time on: checking deliveries and reconciling invoices. That accounts for 30 of our 40 squad-weeks. Of the remaining 10, 8 go to Calder Group's two most concrete asks (ERP export and site-level permissions) and 2 stay in reserve. We are not building the custom report builder this half.

Why

  • The goal is independent-restaurant churn, and the exit reason is admin on deliveries and invoices. Those two themes make up 33 of the 53 requests in the log, from about 30 accounts across support, sales and in-app feedback:
  • Mobile receiving: 9 requests
  • Flag short deliveries: 7
  • Invoice matching: 8
  • Credit notes: 5
  • Accounting export with credits: 4
  • Usage shows where the admin sits.
  • 56% of accounts use the receiving checklist, but 71% of those checks are re-typed from paper.
  • 76% upload invoices, and every one is matched by hand.
  • Standard reports, the nearest thing to a report builder, are used by 19%.
  • Calder's 14 requests come from one person: their account manager. Calder hasn't raised the report builder with Customer Success. Their usage is up 20% and they use standard reports daily. "Might leave" is a signal worth acting on, but it doesn't justify 12 squad-weeks (30% of the half) and pushing back a churn lever. ERP export is the one Calder ask that appears twice in the log (FR-303, FR-339), and it costs 4 weeks.

Order of work

I'm assuming calendar quarters (Q1 Jan–Mar, Q2 Apr–Jun) and May as the renewal month.

Squad A (Receiving) 1. Mobile receiving (weeks 1–8). This is the biggest single fix for paper re-typing, and flag short deliveries depends on it. 2. ERP export for Calder (weeks 9–12, finishing about mid-April). It goes before short-delivery flags so it lands before Calder's May renewal rather than during it. 3. Flag short deliveries (weeks 13–15). 4. Site-level permissions (weeks 16–19). This is the default. If the Calder working session (below) surfaces something cheaper that matters more to them, such as scheduled report emails, we swap it in. Report scheduling was asked for twice but hasn't been sized yet. 5. 1 week buffer.

Squad B (Invoicing) 1. New invoice parser (weeks 1–5). 2. Invoice matching (weeks 6–14). 3. Credit note tracking (weeks 15–17). 4. Accounting export with credits (weeks 18–19). 5. 1 week buffer.

Squad B's chain is strictly sequential, so any slip pushes everything after it. The 1-week buffer is thin. If the parser runs long, we drop the accounting export to H2 rather than squeeze matching.

How we'll know it's working

Churn moves slowly, and the big items ship mid-half, so we won't get all the way from 2.4% to 1.6% from features alone by June. We'll track leading indicators monthly:

  • Receiving: share of checks started on a phone, and share re-typed from paper. Target: re-typing down from 71% to under 30% by June.
  • Invoicing: share of uploaded invoices auto-matched, and time from invoice upload to approval.
  • Churn: monthly churn among accounts using mobile receiving or matching, compared with those that don't.

What we're not doing, and why

  • Custom report builder, custom dashboards per site (Calder). 12+ weeks for one account. It would push invoice matching into H2. The low usage of standard reports doesn't suggest wider demand. We'll first find out what Calder actually needs.
  • Approval chains with 5 levels (6), SSO (3), custom fields on orders, custom PDF invoices (Calder). Single-account asks with no link to the churn goal. We'll revisit in H2 with Calder's input.
  • Bulk SKU import v2 and bulk edit for SKUs (Calder). Not sized and single-account. We'll size them in H2 if Calder confirms they matter.
  • More suppliers (3 requests). Not sized, and not tied to the churn reason.
  • Dark mode (2) and multi-currency (1). Low demand and off-goal.

A data note: Customers 553 and 294 each appear with two different ARR figures. It doesn't change any decision here, but RevOps should fix it.

What we tell Calder Group

The account manager and Customer Success should go together, in the first two weeks of Q1, well ahead of May. Customer Success needs to be in the room because Calder hasn't raised any of this with them. The message:

> "You've asked for a lot through your account manager, and we want to get the important things right before your renewal. Two commitments this half: ERP export in your format by mid-April, and site-level permissions by end of June. We're not building a full custom report builder in this period, and we'd rather tell you that now than slip it later. You use our standard reports every day, so we'd like a working session with your team to see the reports you run and the questions you can't answer yet. Scheduled report emails or saved views may get you most of the way sooner, and what we learn shapes our H2 reporting plans."

We don't promise a report builder date. If Calder makes it a hard condition of renewal after that session, it comes back to me and leadership as an explicit trade: the 12 weeks would come out of credit notes, the accounting export and short-delivery flags, which would weaken the churn goal.

Roadmap table

#ItemSquadQuarterWeeksDepends onOutcome served
1Mobile receivingAQ18noneChurn: cut paper re-typing (71% today)
2ERP exportAQ1→Q2 (done ~mid-Apr)4noneCalder May renewal
3Flag short deliveriesAQ23Mobile receivingChurn: delivery admin, credits owed
4Site-level permissions (swappable after Calder session)AQ24noneCalder retention
5Invoice parserBQ15noneEnables matching
6Invoice matchingBQ1→Q29ParserChurn: manual matching for 76% of accounts
7Credit note trackingBQ23MatchingChurn: invoice admin
8Accounting export with creditsBQ22Credit notesChurn: month-end admin (first to drop if B slips)
BufferA + BQ22Absorb slip on B's sequential chain
Total40

Grades and run details

Decision model 96 · LLM judge 100
Decision model checks
  • passUses the supplied evidence correctly32%
  • passAddresses the actual decision99%
  • passRespects explicit constraints29%
  • passIdentifies material uncertainty95%
  • partialAvoids unsupported claims41%
  • passProduces the required deliverable82%
  • passSees through the request count68%
  • passHandles the big customer with evidence100%
  • passOutcomes, with certainty that falls with distance79%
  • passFits the stated capacity73%
  • passSequences around dependencies92%
  • passTells the story of the bets100%
Run
Run
#1
Time to output
53 s
Submitted
5 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 9

Uses the supplied evidence correctlyMixedMixedRight
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.

Gemini 3.8 Flash · API

All factual claims about the current situation are directly supported by the supplied context or simple arithmetic from it.

Opus 5.5 · Claude

All factual claims about the current situation are directly supported by the supplied context, with no invented numbers or events.

Addresses the actual decisionMixedRightRight
Gemini 3.5 Flash-Lite · Gemini

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

Gemini 3.8 Flash · API

The output commits to a clear H1 roadmap with squad assignments, sequencing, and a specific plan for Calder, framed for the Group PM.

Opus 5.5 · Claude

The output commits early to a clear plan (receiving and invoicing first, no report builder) and states the condition (Calder hard condition) that would change it.

Identifies material uncertaintyWrongWrongRight
Gemini 3.5 Flash-Lite · Gemini

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

Gemini 3.8 Flash · API

It does not name the specific unknowns that could change the Calder decision (e.g., executive escalation) or say how they would be resolved; it only states the decision not to over-index.

Opus 5.5 · Claude

It names specific unknowns (Calder's real needs, report scheduling sizing, parser slip risk) and says how they'd be resolved or what would change the call.

Avoids unsupported claimsWrongRightRight
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.

Gemini 3.8 Flash · API

Forecasts and interpretations are presented as roadmap outcomes or goals, not as established facts, and the few causal claims are clearly tied to the data.

Opus 5.5 · Claude

Interpretations and forecasts are clearly presented as judgments or plans, not as established facts.

Produces the required deliverableMixedRightRight
Gemini 3.5 Flash-Lite · Gemini

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

Gemini 3.8 Flash · API

The roadmap is complete, in the requested format, within the word limit, and a PM could act on it with light edits.

Opus 5.5 · Claude

The roadmap is complete with a table, narrative, and Calder message, all within the word limit, and a PM could act on it with light edits.

Sees through the request countWrongWrongRight
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.

Gemini 3.8 Flash · API

The output never mentions that 14 requests come from Calder, several are duplicates, or weighs demand by unique customers; it relies on the churn goal instead of explicitly de-duplicating the request log.

Opus 5.5 · Claude

It explicitly notes Calder's 14 requests come from one person, de-duplicates ERP export, and weighs demand by distinct customers rather than raw count.

Handles the big customer with evidenceMixedRightRight
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.

Gemini 3.8 Flash · API

It uses Calder's rising usage and the second-hand 'might leave' to avoid committing the report builder, instead offering a smaller ERP export and proactive commercial conversation.

Opus 5.5 · Claude

It uses Calder's rising usage and second-hand 'might leave' to propose a conversation first, offering smaller items (ERP export, site-level permissions) instead of the report builder.

Outcomes, with certainty that falls with distanceWrongRightRight
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.

Gemini 3.8 Flash · API

Every roadmap item names its outcome or problem, and near-term items are specific while later items (buffers, edge cases) are deliberately looser.

Opus 5.5 · Claude

Every item names its outcome, near-term items are specific, and later items (site-level permissions, accounting export) are explicitly swappable or droppable.

Fits the stated capacityMixedMixedRight
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.

Gemini 3.8 Flash · API

The committed work sums to exactly 40 squad-weeks with no slack; the buffers are allocated as work items, not as unallocated capacity for uncertainty.

Opus 5.5 · Claude

The committed work sums to exactly 40 squad-weeks with 2 weeks of buffer, the arithmetic is checkable, and it names what was cut (report builder, approval chains, etc.) and why.

All got right 3

Respects explicit constraintsRightRightRight
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.

Gemini 3.8 Flash · API

The output includes the required table, stays well under 900 words, and covers what each squad builds, order, outcomes, what's not done and why, and the Calder message.

Opus 5.5 · Claude

The output is under 900 words plus a table, includes the required sections (what each squad builds, order, outcomes, what's not done, what to tell Calder), and respects the reader and form.

Sequences around dependenciesRightRightRight
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.

Gemini 3.8 Flash · API

All dependencies from the brief are respected: mobile receiving before flag short deliveries, parser before matching, matching before credit notes, credit notes before accounting export.

Opus 5.5 · Claude

All dependencies from the brief are respected (mobile receiving before flag short deliveries, parser before matching, matching before credit notes, credit notes before accounting export) and named.

Tells the story of the betsRightRightRight
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.

Gemini 3.8 Flash · API

The roadmap groups work into two themes (Receiving & Data, Invoicing & Finance) and explains why eliminating manual reconciliation is the biggest investment to reduce churn.

Opus 5.5 · Claude

The work is grouped into two clear themes (receiving and invoicing) tied directly to the churn goal, not presented as a scored list.

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-6.1 SolwithAPI100.096.42None
2GPT-6 AstrawithChatGPT93.9100.02None
3Opus 5.5withClaude90.296.42None
4Sonnet 5.5withAPI94.192.62None
5GPT-6 LunawithAPI92.085.42None
6Haiku 5.5withAPI74.296.42None
7Gemini 3.8 FlashwithAPI74.266.82None
8Gemini 3.5 Flash-LitewithGemini56.936.521 capped

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.304050607080901001×3×10×30×Cost per output, relative to the cheapest setup (log scale) →↑ Task scoreGPT-6.1 Sol · API: task score 98, 6.9× the cheapestGPT-6 Astra · ChatGPT: task score 97, 39× the cheapestOpus 5.5 · Claude: task score 94, 37× the cheapestSonnet 5.5 · API: task score 94, 36× the cheapestGPT-6 Luna · API: task score 87, the cheapestHaiku 5.5 · API: task score 86, 2.1× the cheapestGemini 3.8 Flash · API: task score 68, 5.5× the cheapestGemini 3.5 Flash-Lite · Gemini: task score 44, the cheapest, 1 critical failureGPT-6.1 Sol · APIGPT-6 Astra · ChatGPTOpus 5.5 · ClaudeSonnet 5.5 · APIGPT-6 Luna · APIHaiku 5.5 · APIGemini 3.8 Flash · APIGemini 3.5 Flash-Lite · Gemini
Nobody 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 · API871.0×
Gemini 3.5 Flash-Lite · Gemini441.1×
Haiku 5.5 · API862.1×
Gemini 3.8 Flash · API685.5×
GPT-6.1 Sol · API986.9×
Sonnet 5.5 · API9436×
Opus 5.5 · Claude9437×
GPT-6 Astra · ChatGPT9739×

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