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.

Usable with a quick edit12 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 92 · LLM judge 100
Decision model checks
  • passUses the supplied evidence correctly12%
  • passAddresses the actual decision98%
  • partialRespects explicit constraints27%
  • passIdentifies material uncertainty99%
  • partialAvoids unsupported claims38%
  • passProduces the required deliverable61%
  • passSees through the request count92%
  • passHandles the big customer with evidence100%
  • passOutcomes, with certainty that falls with distance66%
  • passFits the stated capacity56%
  • passSequences around dependencies76%
  • passTells the story of the bets99%
Run
Run
#1
Time to output
46 s
Submitted
5 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 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

Usable with a quick edit11 of 12 checks passed

The roadmap is clear, actionable, and covers all required elements. The credit note count error is minor and can be corrected with a quick edit without redoing the reasoning.

Output

Fernhill H1 roadmap (Q1–Q2)

The plan: 30 of our 40 squad-weeks go to the delivery-to-invoice workflow that exit surveys blame for churn. 4 go to Calder's ERP export, and 6 are held as buffer. We are not building the report builder.

Assumption: I've treated the invoice parser (5) as additional to invoice matching (9), so matching is 14 weeks in total. If the 9 already includes the parser, we gain 5 weeks of buffer and nothing else changes.

Roadmap

OrderSquadItemWeeksTimingOutcome servedDepends on
1AMobile receiving8Q1 W1–8Less admin on deliveries: 71% of checklist uses start on desktop and get re-typed from paper. Measure: share of receiving done on mobile.None
1BInvoice parser5Q1 W1–5Foundation for matchingNone
2BInvoice matching9Q1 W6 – Q2 W4Less admin on invoices: 870 accounts upload invoices and match them by hand. Measure: % of invoices auto-matched.Parser
2AERP export (Calder's format)4Q1 W9 – Q2 W2Protects the $186k Calder renewal in May. Needs format confirmed in January.None
3AFlag short deliveries3Q2 W3–5Catches shortages at the door, saving time recovering money laterMobile receiving
3BCredit note tracking3Q2 W5–7Less admin on creditsMatching
4BAccounting export with credits2Q2 W8–9Less bookkeeping reworkCredit notes
–A (5 wks), B (1 wk)Buffer6Q2Covers slippage on the new parser and matching, then the Calder reporting slice below–

Why this order

  • Outcome. The goal is churn among independent restaurants, and the top exit reason is admin on deliveries and invoices. Receiving and invoicing are exactly that workflow.
  • Demand. The request log is consistent with the usage data, though it shows who asks rather than who churns, so the exit survey and usage numbers carry more weight.
  • Mobile receiving: 9 customers, about $60k ARR.
  • Matching: 8 customers, about $45k.
  • Short deliveries: 7 customers, about $48k.
  • Credit notes: 4 customers.
  • Export with credits: 4 customers, about $28k.
  • Sequencing. The invoicing chain is strictly sequential, so it takes one squad for 19 of its 20 weeks. The receiving chain runs in parallel on the other squad.
  • ERP export before flagging. Calder's renewal has a hard date, and flagging doesn't. The export is two requests from Calder and the cheapest of their asks. It lands mid-April.
  • Timing risk. Mobile receiving ships around the end of March and matching around the end of April. Churn lags adoption, so I expect only partial movement toward 1.6% by June. I'd report leading indicators monthly (mobile share of receiving, auto-match rate) alongside churn, and set that expectation with the exec team now.

What we're not doing, and why

  • Custom report builder (12 weeks), plus dashboards, scheduling and custom PDFs.
  • Calder is the only requester of anything in the Reporting theme. Only 19% of accounts use standard reports at all.
  • The cost is 30% of H1 capacity. One squad would need all of Q1 plus two weeks of Q2, which pushes about 10 weeks of churn work out of H1.
  • The churn threat behind it is unverified (see below).
  • Approval chains (6), site-level permissions (4), SSO (3), custom fields, bulk SKU import v2 and bulk edit. These are all Calder-only. The three that have estimates total 13 weeks, with no independent-restaurant demand and no link to the churn reason.
  • More suppliers (3 customers), dark mode (2), multi-currency (1). They're unestimated and unconnected to the admin-time problem. I'll revisit them in the H2 planning.

The Calder rows are 14 of the 53 log entries (26%), but they come from one account via its account manager. Counted by customer, they are one voice. The log also has small inconsistencies, such as Customer 553 appearing twice with different ARR, so treat its figures as approximate.

Calder Group

What we know. Their account manager says they "might" leave without the report builder. They haven't said this to Customer Success, and their usage is up 20%, which looks like engagement rather than exit. It's a risk to test, not a requirement.

What we do internally 1. In the first two weeks of January, Customer Success and I meet Calder directly. We ask which decisions they need reports for, what standard reports lack, and whether the ERP export plus raw data in their own tools meets the need. 2. Ask the account manager to give us one ranked list from Calder instead of 14 separate asks. 3. Have engineering size a thin reporting slice (for example, scheduled standard reports). There's no estimate today. It can only be funded from the 6-week buffer, and only if the January conversation shows reporting is a real blocker. 4. Checkpoint at the end of February. If Calder confirms in writing that reporting decides the renewal, I bring the exec team a trade-off. The full builder means dropping the credit-note tail and the ERP export and running with zero buffer, and it still wouldn't ship by May.

What we tell Calder - "We've heard your reporting needs and want to understand them properly. We'd like an hour with your team in January." - "Your ERP export is on our roadmap and is due mid-April, ahead of your May renewal. We'll confirm the format with you first." - "The full report builder isn't in our plan for the first half. We'll tell you by the end of February whether a smaller reporting improvement is feasible."

We make no date commitment for the builder and no promise on SSO, permissions or approval chains. If the ERP export slips, Calder hears it from us before they find out themselves.

Risks to watch

  • Parser or matching slips. The buffer absorbs up to six weeks. Beyond that, credit notes and the accounting export move to H2, not receiving.
  • Calder's real blocker turns out to be reporting. That is the trade-off decision at the end-of-February checkpoint, made with real information instead of a "might".

Claims the judge couldn’t find in the brief

  • Credit notes: 4 customers

Grades and run details

Decision model 96 · LLM judge 92
Decision model checks
  • passUses the supplied evidence correctly4%
  • passAddresses the actual decision98%
  • partialRespects explicit constraints20%
  • passIdentifies material uncertainty100%
  • passAvoids unsupported claims37%
  • passProduces the required deliverable75%
  • passSees through the request count89%
  • passHandles the big customer with evidence100%
  • passOutcomes, with certainty that falls with distance76%
  • passFits the stated capacity60%
  • passSequences around dependencies79%
  • passTells the story of the bets95%
Run
Run
#1
API response time
81 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 9

Uses the supplied evidence correctlyRightMixedMixed
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.

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.

Sonnet 5.5 · API

States credit notes as 4 customers, but the request log contains 5 credit note tracking requests.

Addresses the actual decisionRightMixedRight
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.

Gemini 3.5 Flash-Lite · Gemini

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

Sonnet 5.5 · API

Commits to not building the report builder, offers a clear plan, and says what would change the call (Calder confirming reporting is a real blocker).

Identifies material uncertaintyRightWrongRight
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.

Gemini 3.5 Flash-Lite · Gemini

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

Sonnet 5.5 · API

Names the parser assumption, Calder's real blocker, and slippage risks, with resolution steps (January meeting, February checkpoint).

Avoids unsupported claimsRightWrongRight
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.

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.

Sonnet 5.5 · API

Interpretations are labelled as such; no confident claims are presented as fact without evidence.

Produces the required deliverableRightMixedRight
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.

Gemini 3.5 Flash-Lite · Gemini

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

Sonnet 5.5 · API

Provides a complete H1 roadmap with table, outcomes, cut items, and Calder messaging, usable by a Group PM.

Sees through the request countRightWrongRight
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.

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.

Sonnet 5.5 · API

Explicitly notes 14 Calder requests are from one customer, de-duplicates themes, and weighs demand by number of customers.

Handles the big customer with evidenceRightMixedRight
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.

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.

Sonnet 5.5 · API

Uses rising usage and second-hand 'might leave' to propose a conversation first, offers ERP export, and does not commit the report builder.

Outcomes, with certainty that falls with distanceRightWrongRight
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').

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.

Sonnet 5.5 · API

Every item names its outcome; later items (credit notes, accounting export) are explicitly contingent on buffer and may move to H2, making them deliberately looser.

Fits the stated capacityRightMixedRight
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.).

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.

Sonnet 5.5 · API

Committed work sums to 34 weeks plus 6 buffer = 40, matching capacity; cut items are named with reasons.

All got right 3

Respects explicit constraintsRightRightRight
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.

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.

Sonnet 5.5 · API

Stays within 900 words plus table, includes all required sections (table, what each squad builds, order, outcomes, what's not done, what to tell Calder).

Sequences around dependenciesRightRightRight
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.

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.

Sonnet 5.5 · API

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

Tells the story of the betsRightRightRight
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.

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.

Sonnet 5.5 · API

Groups work into the delivery-to-invoice workflow theme and Calder ERP export, explaining why these bets matter most for churn and 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-6.1 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