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

Usable with a quick edit11 of 12 checks passed

The output is complete, evidence-based, and clearly structured. A PM could use it with minor wording tweaks, without re-checking facts or redoing the reasoning.

Output

H1 decision: remove delivery-to-invoice admin

Prioritise the independent-restaurant workflow: receive once, capture shortages, match invoices, track credits, export without rework. The company outcome is monthly churn falling from 2.4% to 1.6% in the segment representing 82% of accounts and 61% of revenue.

The evidence supports this over enterprise reporting: - Receiving has 640 active accounts; 71% of uses involve desktop entry followed by retyping from paper. - Invoice upload reaches 870 accounts, but matching remains manual. - These workflow requests account for 33 log entries from 32 distinct non-Calder customers. That shows breadth, although we must verify which are independent restaurants. - Calder’s 14 entries represent one $186k account, not 14 independent demand signals. Duplicate requests and inconsistent ARR entries must not inflate priority.

Roadmap and capacity

Assign stable ownership: Squad A—Receiving & Integrations; Squad B—Invoice Automation. Dates are planning targets, subject to initial technical validation.

Squad / quarterBuild order and scopeSquad-weeksOutcome / release target
---------:---
A — Q11. Mobile receiving: phone-based delivery checks and saved received quantities8Eliminate paper-to-desktop re-entry. Pilot, then release by March.
A — Q1Instrumentation, restaurant onboarding, pilot fixes2Establish baseline admin time and turn release into repeated use.
B — Q11. New invoice parser, then 2. invoice matching, first tranche5 + 5Establish dependable invoice data and build matching. No promise of completed matching in Q1.
A — Q22. Flag short deliveries, after mobile receiving3Capture discrepancies at the door rather than reconstructing them later. Target April.
A — Q23. ERP export, conditional on the Calder discovery gate below4 heldRemove a verified export workaround; potentially support renewal without building a reporting platform.
A — Q2Receiving rollout, reliability, adoption experiments3Reduce failed/incomplete receiving sessions and expand sustained restaurant adoption.
B — Q22. Finish invoice matching → 3. credit note tracking → 4. accounting export with credits4 → 3 → 2Target April matching, May credits, June export. Reduce reconciliation, credit chasing and duplicate accounting entry.
B — Q2Quality and rollout contingency1Resolve matching/export issues without cutting correctness safeguards.

Capacity: each squad uses 10 weeks per quarter; total 40. This comprises 30 weeks of core feature work, four conditionally held for ERP export, and six for instrumentation, adoption and contingency. No hidden third squad or assumed spare engineering capacity.

Matching should start with high-confidence suggestions and explicit review of exceptions—not unattended financial decisions. Credit tracking follows completed matching; accounting export follows credits. Mobile receiving precedes shortage capture. The squads should agree shared delivery/invoice identifiers early, without inventing an additional prerequisite for matching.

Outcomes and decision gates

In January, baseline independent-restaurant admin time, receiving completion, matching effort and cohort churn. Recruit restaurants doing significant delivery/invoice work, including recently disengaged accounts—not just enthusiastic requesters.

Proposed release-success thresholds, to validate against those baselines: - Receiving: at least 30% less median time per delivery, including subsequent re-entry. - Invoices: at least 30% less manual reconciliation time, with no increase in material errors. - Adoption: at least half of pilot accounts repeatedly use the relevant workflow within four weeks.

Use a staggered rollout with comparable restaurant cohorts to assess improvement, rather than attributing every churn change to launches. Review workflow outcomes monthly and segment churn throughout H1; June churn alone may not capture the full effect of later releases.

If matching or mobile receiving slips, protect the core sequence: release the conditional ERP allocation first, then move later scope rather than bypassing quality checks.

ERP gate: by end-January, PM, CS and the account manager meet Calder’s actual users and renewal decision-maker. Confirm the job, current workaround, required fields, renewal significance and whether the four-week estimate covers acceptance criteria. Commit only if this is a valuable, bounded export—not a disguised report builder. Otherwise redirect those four weeks to core-workflow quality and adoption.

What we are not doing

  • Custom report builder, pivots, site dashboards, scheduling and custom PDFs: insufficient breadth and weaker connection to the churn goal. The builder alone costs 12 weeks; it cannot fit alongside the core programme even if all ten non-core weeks were reclaimed.
  • Approval chains, permissions, SSO and custom order fields: defer pending demonstrated retention, security or contractual necessity; none is established here.
  • Catalogue expansion, bulk SKU tools, dark mode and multi-currency: defer. Catalogue’s universal usage does not establish that these additions reduce admin-related churn. Unestimated requests are not free extras.

What we tell Calder Group

“You’re important to Fernhill, and we want to understand what reporting prevents you from doing today. We are not committing to a custom report builder before your May renewal. Our H1 investment is delivery and invoice automation. We will assess whether a bounded ERP export or existing standard reports can meet your immediate need, and return with a written scope and credible timing.”

CS owns the renewal plan, with a January discovery meeting and an April executive checkpoint. Daily report usage and 20% overall usage growth do not prove safety—but an unverified “might leave” does not justify displacing the company’s retention strategy.

Grades and run details

Decision model 88 · LLM judge 100
Decision model checks
  • passUses the supplied evidence correctly28%
  • passAddresses the actual decision88%
  • passRespects explicit constraints18%
  • passIdentifies material uncertainty98%
  • passAvoids unsupported claims33%
  • passProduces the required deliverable62%
  • passSees through the request count88%
  • passHandles the big customer with evidence100%
  • passOutcomes, with certainty that falls with distance69%
  • failFits the stated capacity14%
  • passSequences around dependencies70%
  • partialTells the story of the bets38%
Run
Run
#1
Time to output
46 s
Submitted
5 Oct 2026

Usable with a quick edit10 of 12 checks passed

The roadmap is complete, evidence-based, and directly usable; a PM could adopt it with minor wording tweaks and no re-checking of facts or logic.

Output

H1 roadmap

Priority: reduce admin that contributes to independent-restaurant churn. We’ll automate the invoice-to-credit workflow and make receiving work where deliveries happen. That addresses the stated churn reason and repeated requests across customers. Calder’s renewal matters, but the report-builder risk is unconfirmed, so we’ll validate it before committing 12 squad-weeks to a bespoke capability.

OrderSquad / timingWhat we buildOutcome served
1Squad A · Q1 (8 weeks)Mobile receivingLets staff check deliveries on a phone instead of re-typing paper checklists. Desktop-to-paper re-entry is a clear source of admin.
2Squad B · Q1 (5 weeks)Invoice parserPrerequisite for matching; prepares invoice data for automation.
3Squad B · Q1–Q2 (9 weeks total: 5 in Q1, 4 in Q2)Match invoices to deliveriesReduces manual reconciliation, directly addressing “too much admin”; invoice upload is already used by 76% of accounts. Starts after the parser.
4Squad A · Q2 (3 weeks)Flag short deliveriesSurfaces discrepancies at receiving, before they become invoice errors. Starts after mobile receiving.
5Squad B · Q2 (3 weeks)Credit note trackingExtends the automated invoice workflow to credits; starts after matching.
6Squad B · Q2 (2 weeks)Accounting export with creditsMakes the completed invoice-and-credit workflow easier to carry into accounting; starts after credit tracking.
—Squad A · Q1 (2 weeks); Squad A · Q2 (7 weeks)Field validation, rollout, adoption and measurement for the aboveValidate the receiving workflow with restaurants, help teams adopt it, and measure whether it reduces re-entry and invoice admin. Include direct Calder discovery in Q1.
—Squad B · Q2 (1 week)Hardening and release bufferProtects quality across the dependent invoice workflow before broad rollout.

This uses the 40 available squad-weeks: 20 per quarter. The invoice sequence is parser → matching → credit tracking → accounting export; receiving is mobile receiving → short-delivery flags.

Not doing this half

  • Custom report builder, dashboards and scheduled reports: 12 weeks, with the reported renewal risk coming from the account manager rather than Calder’s CS team; Calder’s usage is up 20% and it uses standard reports daily. We’ll validate the specific reporting job and whether it is truly a renewal blocker before reallocating capacity. A bespoke builder is not currently the best fit for the independent-restaurant churn goal.
  • ERP export, SSO, site permissions, approval chains, custom fields, catalogue work and other Calder requests: several are substantial or bespoke, and none has stronger evidence against the stated churn driver than the selected workflow improvements. We won’t imply these are committed.
  • More suppliers and dark mode: lower priority than reducing delivery and invoice admin.

What we tell Calder Group

“We’ve heard that reporting may affect your May renewal. We’re not committing to a custom report builder yet: your teams use standard reports daily, usage is growing, and we haven’t confirmed with you which reporting tasks are blocked. We’d like to meet with your reporting users and Customer Success early in Q1 to understand the must-have use cases and renewal criteria. We’ll come back with a clear proposal; meanwhile, we’ll be investing in reducing delivery and invoice admin across Fernhill.”

If that conversation confirms custom reporting is a hard renewal condition, we’ll bring the trade-off back for an explicit roadmap decision rather than promise a feature we haven’t scoped or prioritized.

Grades and run details

Decision model 83 · LLM judge 92
Decision model checks
  • passUses the supplied evidence correctly56%
  • passAddresses the actual decision83%
  • passRespects explicit constraints46%
  • passIdentifies material uncertainty98%
  • passAvoids unsupported claims38%
  • passProduces the required deliverable58%
  • partialSees through the request count66%
  • passHandles the big customer with evidence97%
  • passOutcomes, with certainty that falls with distance67%
  • failFits the stated capacity23%
  • passSequences around dependencies89%
  • partialTells the story of the bets48%
Run
Run
#1
API response time
58 s
Submitted
6 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 correctlyWrongRightRight
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.

GPT-6 Astra · ChatGPT

All factual claims about the current situation are directly from the supplied context or derived by arithmetic from it, with no invented facts.

GPT-6 Luna · API

All factual claims about the current situation are directly supported by the supplied context.

Identifies material uncertaintyWrongRightRight
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.

GPT-6 Astra · ChatGPT

It names specific unknowns (whether requesters are independent restaurants, whether Calder's ERP export is truly needed, risk of slips) and describes how they will be resolved or what would change the plan.

GPT-6 Luna · API

Identifies the unconfirmed report-builder risk and states that a conversation with Calder will resolve it and could change the plan.

Avoids unsupported claimsWrongRightRight
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.

GPT-6 Astra · ChatGPT

Interpretations and forecasts are clearly labelled as such (e.g., 'we must verify', 'subject to initial technical validation'), and no unsupported causal claims are presented as fact.

GPT-6 Luna · API

Interpretations like 'desktop-to-paper re-entry is a clear source of admin' are grounded in the usage data; no unsupported confident claims are made.

Sees through the request countRightRightWrong
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).

GPT-6 Astra · ChatGPT

The output explicitly notes Calder's 14 entries are one account, counts distinct non-Calder customers, and weighs demand by breadth rather than raw count.

GPT-6 Luna · API

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.

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.

GPT-6 Astra · ChatGPT

The committed work sums to 40 squad-weeks with slack (30 core, 4 conditional, 6 instrumentation/adoption/contingency), and the output names what was cut (report builder, approval chains, etc.).

GPT-6 Luna · API

The committed work sums to 40 squad-weeks (30 for features + 9 for validation/rollout + 1 buffer), and the output names what was cut and why.

All got right 7

Addresses the actual decisionRightRightRight
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.

GPT-6 Astra · ChatGPT

The output commits to a clear roadmap decision (delivery-to-invoice admin focus) and includes a conditional gate for Calder that says what would change the call.

GPT-6 Luna · API

Commits to a clear roadmap (receiving and invoicing automation) and says the Calder conversation would change the call if reporting is a hard renewal condition.

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.

GPT-6 Astra · ChatGPT

The output is well under 900 words plus a table, includes all requested elements (squad builds, order, outcomes, what's not done and why, what to tell Calder), and the plan would enforce the constraints.

GPT-6 Luna · API

The output is under 900 words plus a table, includes the required sections, and addresses the Group PM reader.

Produces the required deliverableRightRightRight
Gemini 4 Argon · API

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

GPT-6 Astra · ChatGPT

The roadmap table, not-doing list, and Calder message are all present, within the word limit, and usable by a product manager with light edits.

GPT-6 Luna · API

Provides a complete roadmap table with order, squad, timing, outcomes, a not-doing list with reasons, and a Calder message; a PM could act on it with light edits.

Handles the big customer with evidenceRightRightRight
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.

GPT-6 Astra · ChatGPT

It uses Calder's rising usage and the second-hand 'might leave' to propose a discovery meeting and a conditional ERP export, not the report builder, and explains the reasoning.

GPT-6 Luna · API

Uses Calder's rising usage and the second-hand 'might leave' to propose a discovery conversation instead of committing the report builder; no small item fits the full capacity, so omission is acceptable.

Outcomes, with certainty that falls with distanceRightRightRight
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.

GPT-6 Astra · ChatGPT

Every roadmap item names its outcome or problem, and later items have less precise dates and scope (e.g., 'Target April', 'conditional on the Calder discovery gate').

GPT-6 Luna · API

Every item names its outcome; near-term items are specific and later items (rollout, hardening) are deliberately looser.

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.

GPT-6 Astra · ChatGPT

All dependencies from the brief are respected (parser before matching, mobile receiving before flag short, matching before credits, credits before accounting export) and the order is explained.

GPT-6 Luna · API

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

GPT-6 Astra · ChatGPT

The roadmap groups work into two themes (Receiving & Integrations, Invoice Automation) under the overarching bet of removing delivery-to-invoice admin to reduce churn, with clear rationale.

GPT-6 Luna · API

Groups work into two themes (invoice-to-credit automation and mobile receiving) tied directly to the churn reason.

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