Tasks / Define

Build a roadmap

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

Measures the modelTask v1.0 · 2 casesDifficulty

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

From 14 graded outputs by 7 models. 36% were usable with at most a quick edit.

Reliably right

Outcomes, with certainty that falls with distance95% pass
Every item names the outcome or problem it serves; near-term items have specific targets (mid-December, January) while later items are looser (trigger-based, contract-dependent).
Sonnet 5.5 · API · Two squads, eight asks, one half
Sequences around dependencies89% pass
Messaging service is built before SMS reminders and waitlist auto-fill, reminders before waitlist, and deposits are placed after the contract can be signed; the key dependencies are named.
Sonnet 5.5 · API · Two squads, eight asks, one half
Plans on the squads we actually have89% pass
It explicitly excludes the two new squads from committed critical-path work and treats their capacity as upside after observed ramp.
GPT-6 Astra · ChatGPT · A year of spend management, with a hard deadline

Where it slips

Makes the call on procurement50% pass
It correctly challenges the $6M claim but proposes only time-bounded validation without a threshold that would justify the full procurement build.
GPT-6 Luna · API · A year of spend management, with a hard deadline
Produces the required deliverable50% pass
The roadmap and case are present, but the case is too long and the roadmap has capacity conflicts that would require major rework.
GPT-6.1 Sol · API · A year of spend management, with a hard deadline
Uses the supplied evidence correctly61% pass
Most numbers and quotes are correct, but the output presents 'undermines booking reliability' as a current fact when the supplied context only says calendar sync failures cause 38% of support tickets.
GPT-6 Astra · ChatGPT · Two squads, eight asks, one half

Case viewer

Read the brief, then put up to three outputs side by side, each with the LLM judge’s verdict on every check. Highlights mark what a PM had to fix.

The brief

You're the PM for Tidewell's booking product. Write the roadmap for the next two quarters (Q4 2026 and Q1 2027) and what comes after, for Dana Okafor, our CPO, and the two squad leads. It will also be shared with Sales and Design, so it needs to say what we're not doing and why. Keep it under 800 words. Everything we know is below.

What the model was given7 items: About Tidewell, Goals for the next two quarters (set by the CEO), Data, Capacity, Candidate work (estimates in squad-weeks, from the squad leads), Sales note, FitPhysio's evaluation notes (shared by their operations director)

About TidewellOnline booking and scheduling for independent physiotherapy clinics. 1,450 clinics, $3.9M ARR.

Goals for the next two quarters (set by the CEO)1. Cut no-shows for our clinics: it's the main thing we promise them. 2. Cut churn among multi-site clinics.

DataNo-shows average 11% of appointments across all clinics. The 40 clinics that text their own patients a reminder the day before average 6%. Multi-site clinics are 16% of clinics and 38% of ARR; their monthly logo churn is 2.9%, against 1.3% for single-site clinics. In exit surveys, 23 of the 31 multi-site clinics that left in the last year cited 'can't see all our locations in one place'. Booking page: 64% of visits end in a booking. In 18 customer interviews this quarter, nobody mentioned the booking page.

CapacityTwo squads. Each has 13 weeks a quarter, but about a quarter of each squad's time goes on support and bugs, so we plan on 10 squad-weeks of roadmap work per squad per quarter.

Candidate work (estimates in squad-weeks, from the squad leads)1. Calendar sync fix, 5. Calendar sync failures cause 38% of support tickets; engineering expects fixing them to free about 3 squad-weeks a quarter of support time, starting the quarter after it ships. 2. Messaging service (SMS provider, patient consent records, templates), 8. Nothing patient-facing on its own. 3. SMS reminders with confirm or cancel, 6. Needs the messaging service. 4. Multi-site dashboard (every location's bookings and utilisation in one view), 10. 5. Waitlist auto-fill: texts waitlisted patients when a slot frees up, 7. Needs the messaging service. It only fills slots cancelled with some notice, which is rare today: patients don't cancel, they just don't turn up. 6. Deposits at booking, 14. Needs a payments partner contract; Legal says the earliest it can be signed is mid-February 2027. 7. Booking page redesign, 9. Requested by the Head of Design. 8. Physitrack integration (sends patients' exercise plans to the Physitrack app), 8. See the Sales note.

Sales noteFrom Jordan, Head of Sales: “FitPhysio Group (30 sites, $64,800 ARR) is our biggest deal this year. I told them Physitrack would be live by Christmas. It's what closes the deal.”

FitPhysio's evaluation notes (shared by their operations director)“Must have: see all 30 sites' bookings and utilisation in one place. Nice to have: Physitrack integration.”

What a strong answer doesThe answer key the graders mark against

A two-quarter roadmap that fits about 40 squad-weeks (10 per squad per quarter), with items framed as the outcome they serve. Puts the calendar sync fix first because it frees capacity for Q1, builds the messaging service before reminders and the waitlist, and sequences reminders before the waitlist since slots only free up once patients can cancel. Commits the multi-site dashboard in the half: it serves the churn goal and is FitPhysio's own must-have, so it tells Sales to lead with the dashboard rather than promising Physitrack by Christmas. Leaves deposits for after the contract (it can't be built in the half once signing is mid-February) and doesn't commit the booking page redesign without evidence. A committed plan of about 36 squad-weeks (sync 5, messaging 8, dashboard 10, reminders 6, waitlist 7) leaves a little slack; Physitrack only fits if something else goes. Near-term items are specific, later ones looser, and it names what's not being done and why.

Critical failures (cap the score at 40)

Schedules an item before something it depends on: SMS reminders or waitlist auto-fill before the messaging service, or deposits shipping in the half
Commits clearly more than about 40 squad-weeks of work to the two quarters

Case

Mid-level · v1.1 · synthetic · B2B SaaS, healthcare, capacity, sales promise

The outputs

7 setups answered this brief. Pick up to three to read side by side.

Sonnet 5.5API100Usable with a quick edit GPT-6.1 SolAPI100Usable with a quick edit Opus 5.5Claude88Usable with a quick edit GPT-6 AstraChatGPT83Needs more work GPT-6 LunaAPI83Needs more work Gemini 3.8 FlashAPI63Needs more work Gemini 3.5 Flash-LiteGemini23Critical failure

GPT-6 LunaAPI

Needs more than a quick edit9 of 11 checks passed

A PM could use most of it, but the Q1 calendar sync placement undermines the capacity logic and would need resequencing before it is fully decision-ready.

Output

Tidewell Booking Roadmap | Q4 2026–Q1 2027

For: Dana Okafor, CPO; squad leads; Sales and Design North star: Reduce clinic no-shows and multi-site churn. We have 20 roadmap squad-weeks per quarter across two squads; support and bugs are planned separately.

Q4 2026 — Build the multi-site view and messaging foundation

Multi-site dashboard — 10 squad-weeks. Show bookings and utilisation across every location in one view. This directly addresses the most-cited multi-site exit reason (23 of 31 surveyed departures) and FitPhysio’s stated must-have.
Messaging service — 8 squad-weeks. Build the SMS provider, patient consent records and templates needed for reminders. This is foundational work, not a patient-facing launch; reminders follow in Q1.

Capacity: One squad takes the dashboard; the other builds messaging, with two squad-weeks uncommitted.

Sales: Jordan’s Christmas commitment for Physitrack is not in this roadmap. FitPhysio called it “nice to have,” while the multi-site view is a must-have. Please correct the commitment with FitPhysio now; do not sell a Christmas delivery date.

Q1 2027 — Launch reminders and fix calendar sync

SMS reminders with confirm/cancel — 6 squad-weeks. Launch using the Q4 messaging foundation, with rollout and measurement. Forty clinics that send their own day-before texts average 6% no-shows versus 11% overall. That’s a promising signal, not proof of causation; measure results against a comparison group and track cancellations as well as no-shows.
Calendar sync fix — 5 squad-weeks. Address a cause of 38% of support tickets. Engineering expects it to free about three squad-weeks of support time per quarter, starting Q2.

The remaining Q1 roadmap capacity is reserved for rollout learning and iteration rather than adding another large commitment.

Success measures: No-show rate for reminder-enabled appointments versus comparison; reminder delivery, confirmations and cancellations; dashboard adoption across multi-site locations; and multi-site support and churn trends.

After Q1 — Reassess before committing

Waitlist auto-fill: Revisit once reminders give patients a way to cancel and we know whether cancellations happen with enough notice. Today, patients mostly don’t cancel, so auto-fill has few openings to act on.
Deposits: Reassess after the payments contract can be signed (earliest mid-February) and we have evidence on reminder impact and clinic appetite. The 14-week estimate and partner dependency make it unsuitable for this committed plan.
Physitrack: Reassess against customer evidence and capacity; it is not committed for Q4 or Q1.
Booking page redesign: Revisit if research identifies a meaningful problem. Booking-page conversion is 64%, and nobody in 18 recent interviews raised it; it is not the best use of capacity against current goals.

Explicitly not doing now

We are not building the booking redesign, waitlist auto-fill, deposits or Physitrack in these two quarters. This is a focus decision: prioritize the evidenced churn driver and test the clearest no-show intervention before investing in lower-evidence or dependency-heavy work.

Grades and run details

Decision model 91 · LLM judge 10 of 12 checks

Decision model checks

passUses the supplied evidence correctly27%
passAddresses the actual decision81%
failRespects explicit constraints11%
passIdentifies material uncertainty80%
passAvoids unsupported claims53%
passProduces the required deliverable15%
passEvery commitment serves the goals91%
passHandles the Sales promise with evidence100%
passOutcomes, with certainty that falls with distance85%
passFits the stated capacity32%
passSequences around dependencies81%

Run

Run: #1
API response time: 31 s
Submitted: 1 Oct 2026

Check by check

Open a check to read the judge’s reasons. “Mixed” means the two graders disagreed.

Mixed 2

Respects explicit constraintsMixed

It is under 800 words, addressed to the named readers, includes what is not being done and why, and respects the stated capacity and dependencies.

Every commitment serves the goalsMixed

The calendar sync fix is committed in Q1 but only frees support capacity starting Q2, so it does not serve the two-quarter goals or free capacity within the half as required.

Got right 9

Uses the supplied evidence correctlyRight

The output uses the supplied numbers, dates, customer statements, and capacity facts correctly, and its few inferences follow from the context.

Addresses the actual decisionRight

It commits to a clear two-quarter roadmap for the named readers and states conditions that would change later decisions, though it could be stronger on what would change the committed plan itself.

Identifies material uncertaintyRight

It names material unknowns such as reminder causation, cancellation notice, contract timing, and booking-page evidence, and says how they would be resolved.

Avoids unsupported claimsRight

It labels the 6% versus 11% signal as not proof of causation and frames later items as reassessments rather than committed facts.

Produces the required deliverableRight

It is a usable roadmap for the CPO, squad leads, Sales, and Design, with committed work, deferred work, success measures, and a sales message.

Handles the Sales promise with evidenceRight

It uses FitPhysio's own must-have/nice-to-have notes to tell Sales to correct the Christmas Physitrack promise and lead with the committed dashboard.

Outcomes, with certainty that falls with distanceRight

Each item names the problem or outcome it serves, and later items are deliberately looser than near-term commitments.

Fits the stated capacityRight

The committed work totals 29 squad-weeks against 40 available, with explicit slack and deferrals to make it fit.

Sequences around dependenciesRight

It places reminders after the messaging service, defers waitlist until reminders create cancellations, and defers deposits until the contract can be signed.

Results

Every setup we’ve tested on this task, across all cases and repeats, graded on the current checklist. Calibrated: the graders match our PM on 89% of checks.

#	Model · Harness	Decision model	LLM judge	Runs	Critical failures
1	Sonnet 5.5withAPI	89.6	100.0	2	None
2	GPT-6 AstrawithChatGPT	91.7	87.5	2	None
3	GPT-6.1 SolwithAPI	91.7	84.6	2	None
4	GPT-6 LunawithAPI	85.0	76.3	2	None
5	Opus 5.5withClaude	80.5	65.1	2	None
6	Gemini 3.8 FlashwithAPI	70.1	51.9	2	None
7	Gemini 3.5 Flash-LitewithGemini	28.4	8.3	2	2 capped

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