Tasks / Growth

Activation & onboarding review

Can the model find the friction that matters most and prioritise the fixes?

Task type v1.1 · 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. Respects explicit constraints100% pass
    The output is a review addressed to Omar, well under 800 words, and respects the requested form.
    GPT-6 Luna · API · The checklist isn't the moment
  2. Produces the required deliverable100% pass
    The review covers activation definition, evidence, changes, design proposal, and goal, is addressed to Omar, within length, and is actionable.
    GPT-6 Luna · API · The checklist isn't the moment
  3. Activation defined by what predicts retention100% pass
    Activation is defined by the behaviour that predicts retention (bank+cat 10+), and fixes are judged by their effect on that event.
    GPT-6 Luna · API · The checklist isn't the moment

Where it slips

  1. Uses the supplied evidence correctly44% pass
    The output states 'we have no step-level data for screens 2–8', 'a blank builder is hard for non-analysts', and 'people invite colleagues to something useful, not to a setup screen' as facts, none of which appear in the brief or follow from arithmetic.
    Opus 5.5 · Claude · Analytics tool losing users at setup
  2. Avoids unsupported claims55% pass
    It presents 'a blank builder is hard for non-analysts' and 'people invite colleagues to something useful, not to a setup screen' as established facts without labelling them as hypotheses.
    Opus 5.5 · Claude · Analytics tool losing users at setup
  3. Addresses the actual decision56% pass
    The output commits to a ranked order but does not state what result or condition would change that order, as required.
    GPT-6 Astra · ChatGPT · Analytics tool losing users at setup

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. Activation defined by what predicts retention

    Does the review define (or question) the activation event by whether it predicts retention, and judge fixes by their effect on that event rather than on step completion?

    Passes when Names the activation behaviour and its link to retention (from the supplied data, or as an explicit assumption to verify), and ranks fixes by their effect on it.

  2. Gets people to value sooner

    Do the recommended fixes shorten the path to the first moment of value, by removing or deferring steps before it or starting people with templates or sample data, rather than adding tours, tooltips or extra steps?

    Passes when The main fixes cut or defer steps before first value, or give a warm start, and say which steps go.

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 · Gets the base of every number right · 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 PM for onboarding at Tidepool. Omar, our Head of Product, has asked for a review of onboarding (his note is below). Write it in no more than 800 words: what activation should mean for us, the evidence, what to change in onboarding, and what to make of the design team's proposal and next quarter's goal. The files are attached.

What the model was given4 items: About Tidepool, omar_note.md, onboarding_today.md, first_week_behaviour.csv (August sign-ups: how many who did each thing in their first week were still active at day 60)
About TidepoolA personal finance app: connect your bank, see where your money goes, and budget.
omar_note.md1 lines · Download
From Omar (Head of Product): "Activation is flat at 61%. Review our onboarding and tell me what to fix. The design team has proposed a celebration screen and a progress bar for the checklist."
onboarding_today.md8 lines · Download
# Onboarding today (for 4,000 sign-ups in August)

1. Sign up (100%)
2. Setup checklist: name your account, pick a theme, set a savings goal, enable notifications (61% complete it)
3. Connect a bank (50%)
4. Categorise transactions (34% reach 10)

…
first_week_behaviour.csv (August sign-ups: how many who did each thing in their first week were still active at day 60)first_week_behaviour,retained_at_day_60,churned_by_day_60 All sign-ups,1120,2880 Completed the setup checklist,742,1696 Connected a bank account,964,1036 Categorised 10+ transactions,891,489 Connected a bank AND categorised 10+ transactions,842,238 Created a budget,410,820 Opened the app 4+ days,870,1310
What a strong answer doesThe answer key the graders mark against

Works out retention for each first-week behaviour from the file: all sign-ups 28% (1,120 of 4,000); completed the checklist about 30% (barely better than average); connected a bank about 48%; categorised 10+ transactions about 65%; connected a bank and categorised 10+ about 78%, and that group is about three-quarters of everyone retained (842 of 1,120). So the checklist isn't activation and raising its completion to 75% would do little; activation should be connecting a bank and categorising ten transactions in week one. Recommends cutting or deferring checklist steps that sit before that (theme, notifications, savings goal) and getting people to connect a bank and categorise sooner (for example suggested categories to confirm), and resets the goal to the new activation rate (about 27% today, 1,080 of 4,000). Treats the celebration screen and progress bar as polishing the wrong step. Notes that the data shows correlation and proposes a test to confirm that driving the behaviour improves retention.

Critical failures (cap the score at 40)
  • Recommends raising checklist completion as the main goal
Task

Staff-level · v1.0

The outputs

8 setups answered this brief.

Needs more than a quick edit8 of 11 checks passed

Unsupported claims about the value of naming/theme and the visibility of bank-connection drop-off would need correction or removal before use.

Output

Onboarding review: what activation should mean

To: Omar | From: Onboarding PM | Data: August cohort (4,000 sign-ups), day-60 retention

Summary

Activation is flat because we are measuring the wrong thing. Finishing the setup checklist barely predicts whether someone stays. Connecting a bank and categorising 10+ transactions in week one does predict it strongly. I recommend we redefine activation around that, rebuild onboarding to get people there faster, and replace next quarter's checklist goal.

What activation should mean

Activated = connected a bank AND categorised 10+ transactions in the first week.

This is the moment Tidepool delivers its core promise: seeing where your money goes. Only 27% of August sign-ups reached it, so our real activation rate is less than half the 61% we report.

The evidence

Day-60 retention by first-week behaviour (baseline: 28% of all sign-ups retained):

First-week behaviourUsersRetained if did itRetained if didn't
Completed setup checklist2,438 (61%)30%24%
Created a budget1,230 (31%)33%26%
Opened app 4+ days2,180 (55%)40%14%
Connected a bank2,000 (50%)48%8%
Categorised 10+ transactions1,380 (35%)65%9%
Bank + 10+ categorised1,080 (27%)78%10%

Five things stand out:

  1. The checklist is a weak signal. Completers retain at 30% versus 24% for non-completers, close to the 28% baseline. 1,696 people completed it and still churned.
  2. Bank plus categorisation is the strongest signal. Users who did both retain at 78%. They make up 27% of sign-ups but 75% of everyone retained at day 60.
  3. Each half is weak on its own. About 920 people connected a bank without categorising, and they retained at 13%. About 300 categorised without a bank, and they retained at 16%. The value comes from real transactions that the user has made sense of.
  4. The biggest leaks are at the steps that matter. Half of sign-ups never connect a bank. Of those who do, 46% never reach 10 categorised transactions.
  5. Budget creation isn't a good activation metric. Its retention lift is small and only 31% do it. That is worth investigating separately for a budgeting app.

Caveats: this is one cohort and the data is correlational. Motivated users may simply do more of everything. The gaps are large enough to act on, but we should confirm cause with experiments rather than assume it.

What to change in onboarding

  1. Put bank connection first. Today it comes after a four-item checklist that we lose 39% of users on. Naming the account and picking a theme add no value at signup and can move to settings. Ask for notifications later, once there is something worth notifying about, such as a first spending summary. The savings goal becomes optional after categorisation.
  2. Make connecting a bank feel safe and fast. Address security concerns at the moment of asking, with plain-language reassurance about read-only access. Offer the most popular banks up front. Instrument the drop-off between starting and finishing the connection, which we can't currently see.
  3. Guide the first 10 categorisations straight after connecting. Show recent transactions with suggested categories so each one is a one-tap confirm. End with an immediate payoff: "Here's where your money went this month."
  4. Recover people who stall. Send a reminder to anyone who connected but hasn't categorised within 48 hours. That group is about 920 people a month retaining at 13%.

Each change should ship as an A/B test with day-60 retention as the outcome. That is how we confirm the relationship is causal.

The design team's proposal

A celebration screen and a progress bar are reasonable patterns, but aimed at the checklist they would polish a step that doesn't drive retention. I'd ask design to point the same ideas at the new milestone:

  • A progress bar for "connect bank, then categorise 10 transactions."
  • A celebration on the 10th categorisation, paired with the first spending insight.

That is a small redirect of their work, not a rejection of it.

Next quarter's goal

I recommend we retire the 61% → 75% checklist goal. Even if we hit it, and every extra completer gained the full 6-point retention gap (which is generous), that would mean roughly 30–35 more retained users per 4,000 sign-ups.

Compare moving just 10% of sign-ups (400 people) into the bank-plus-categorised group. If even a fraction of that 68-point retention gap is causal, the payoff is several times larger.

Proposed goal: raise week-one bank connection plus 10+ categorised transactions from 27% to 35%, with day-60 retention as the guardrail metric. We should set the final target once the first experiment shows how much the metric moves.

Next steps

  • This week: confirm the new activation definition with you and analytics, and backfill it for June and July to check it holds across cohorts.
  • Weeks 2–4: run an A/B test of bank-first onboarding with the checklist deferred, and add instrumentation to the bank connection flow.
  • Weeks 4–8: test the guided categorisation flow and the redirected progress bar and celebration screen.

Claims the judge couldn’t find in the brief

  • Naming the account and picking a theme add no value at signup.
  • We can't currently see drop-off between starting and finishing the bank connection.

Grades and run details

Decision model 82 · LLM judge 75
Decision model checks
  • failUses the supplied evidence correctly74%
  • passAddresses the actual decision93%
  • passRespects explicit constraints39%
  • passIdentifies material uncertainty80%
  • passAvoids unsupported claims30%
  • passProduces the required deliverable62%
  • passComputes retention by behaviour36%
  • passTests before trusting the correlation100%
  • passActivation defined by what predicts retention100%
  • failGets the base of every number right70%
  • passGets people to value sooner81%
Run
Run
#1
Time to output
32 s
Submitted
5 Oct 2026

Needs more than a quick edit6 of 11 checks passed

The output lacks a causation caveat and test proposal, and makes unsupported causal claims; a PM would need to add those before using it.

Output

To: Omar, Head of Product From: PM, Onboarding Subject: Onboarding Review & Activation Strategy

---

Executive Summary

Our current activation rate (61%) is flat because we are measuring and optimizing the wrong milestone. Completing our setup checklist barely moves the needle on long-term retention.

To drive retention, we must redefine activation around core product value—connecting a bank and categorising transactions—and reorient our onboarding funnel and quarterly goals to support it.

---

1. What Activation Should Mean (and the Evidence)

Activation should represent the “Aha!” moment: the point where a user experiences Tidepool’s core value proposition and forms a lasting habit.

Currently, we define activation as completing the setup checklist (name account, pick theme, set savings goal, enable notifications). The data shows this is a vanity metric:

  • Baseline Day 60 Retention: 28.0% (1,120 / 4,000 sign-ups)
  • Checklist Completion: 30.4% Day 60 retention (742 / 2,438) — a negligible +2.4 percentage point lift over baseline.

By contrast, actions tied to our core utility (seeing where money goes) dramatically predict retention: * Connected a bank account: 48.2% Day 60 retention (964 / 2,000) * Categorised 10+ transactions: 64.6% Day 60 retention (891 / 1,380) * Connected bank AND categorised 10+ transactions: 78.0% Day 60 retention (842 / 1,080)

Users who complete both core actions retain at nearly triple the baseline rate. In fact, this group accounts for 75.2% of all retained users at Day 60 (842 of 1,120), despite representing only 27% of initial sign-ups.

New Activation Metric: > A user connects a bank account and categorises at least 10 transactions within their first 7 days.

---

2. Design Proposal & Next Quarter’s Goal

#### The Design Proposal (Celebration Screen & Progress Bar) The design team’s proposal is solving the wrong problem. Adding progress bars and celebration screens to cosmetic tasks (picking themes, naming accounts) creates artificial friction before users experience any real value. We are gamifying administrative overhead instead of utility.

Recommendation: Repurpose the design team’s work, but attach it to the real value milestone (e.g., celebrating when their first 10 transactions are imported and categorized).

#### Next Quarter’s Goal (Raise Checklist Completion from 61% to 75%) We should retire this goal immediately.

Even if we hit 75% checklist completion, model projections indicate Day 60 retention would increase by less than 1%. Optimizing an arbitrary checklist delivers zero business impact.

Proposed New Goal for Next Quarter: > Increase the core Activation Rate (Bank Connected + 10 Categorised Transactions) from 27% to 40% of sign-ups.

---

3. What to Change in Onboarding

Our onboarding funnel currently bleeds users before they experience core value: 50% drop off before connecting a bank, and only 34% categorize 10 transactions. We must clear the runway to value:

1. Eliminate the Cosmetic Checklist from First-Run Flow * Move “pick a theme” and “name your account” to Settings/Profile. * Defer “enable notifications” and “set a savings goal” until after the user sees their financial data.

2. Lead with Bank Connection * Prompt bank linking immediately post-registration. * Pre-frame the security and the payoff clearly: “Connect your account to see your last 30 days of spending instantly.”

3. Accelerate Time-to-Value (TTV) on Categorisation * Upon successful bank connection, immediately import transactions and guide the user through a rapid, swipeable 10-transaction categorisation flow (or auto-categorise and prompt a one-tap review). * Conclude with an instant visual breakdown: “Here’s where your money went this month.” This is Tidepool’s true “Aha!” moment.

4. Contextual Budgeting * Only prompt users to create a budget after categorisation. Budgeting retention is low in week one (33.3%) because users cannot budget accurately without understanding their baseline spend.

Next Steps

  1. Align leadership on the new Activation definition.
  2. Re-scope the design sprint from checklist gamification to a streamlined "Connect & Review 10 Transactions" flow.
  3. Update the team OKR dashboard for next quarter.

Grades and run details

Decision model 68 · LLM judge 58
Decision model checks
  • failUses the supplied evidence correctly24%
  • passAddresses the actual decision56%
  • passRespects explicit constraints49%
  • failIdentifies material uncertainty71%
  • partialAvoids unsupported claims31%
  • passProduces the required deliverable68%
  • passComputes retention by behaviour71%
  • failTests before trusting the correlation95%
  • passActivation defined by what predicts retention100%
  • passGets the base of every number right19%
  • passGets people to value sooner84%
Run
Run
#1
API response time
20 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 6

Uses the supplied evidence correctlyWrongMixed
Opus 5.5 · Claude

Two claims about the current situation ('naming and theme add no value at signup' and 'we can't currently see drop-off') are not in the supplied context and are not arithmetic derivations.

Gemini 3.8 Flash · API

All statements about the current situation are directly from the supplied context or correctly derived from it.

Addresses the actual decisionRightMixed
Opus 5.5 · Claude

Commits early to redefining activation to bank + categorised, changing onboarding, and retiring the checklist goal, framed for Omar, with conditions (experiments) that would change the call.

Gemini 3.8 Flash · API

The output commits to a clear answer but does not state what result or condition would change that answer, as required.

Identifies material uncertaintyRightWrong
Opus 5.5 · Claude

Names the correlation vs causation risk, bounds it with the data, and proposes A/B tests with day-60 retention to resolve it.

Gemini 3.8 Flash · API

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

Avoids unsupported claimsMixedWrong
Opus 5.5 · Claude

Presents 'naming and theme add no value' and 'we can't see drop-off' as established facts without labelling them as hypotheses or assumptions.

Gemini 3.8 Flash · API

It presents causal claims (e.g., checklist steps create artificial friction, low budgeting retention is because users lack baseline spend) as fact without labelling them as hypotheses.

Tests before trusting the correlationRightWrong
Opus 5.5 · Claude

Notes the correlation risk and proposes a specific A/B test driving the behaviour with retention as the measure.

Gemini 3.8 Flash · API

The output does not note that the observed relationships are correlations and does not propose a test to drive the behaviour and measure retention.

Gets the base of every number rightMixedRight
Opus 5.5 · Claude

All derived percentages (30%, 78%, 27%, 13%, 16%, etc.) check out against the supplied data, and bases are stated or clear.

Gemini 3.8 Flash · API

All percentages and rates use the correct denominators from the data, and the bases are clear.

All got right 5

Respects explicit constraintsRightRight
Opus 5.5 · Claude

The output is a review addressed to Omar, within 800 words, and the proposed changes would enforce the new activation definition in practice.

Gemini 3.8 Flash · API

The output is a memo to Omar, under 800 words, and addresses all requested elements.

Produces the required deliverableRightRight
Opus 5.5 · Claude

Delivers a complete onboarding review memo to Omar, within the word limit, with actionable recommendations and next steps.

Gemini 3.8 Flash · API

The review is complete, in memo form, within the word limit, and a PM could act on it with light edits.

Computes retention by behaviourRightRight
Opus 5.5 · Claude

Computes day-60 retention for each behaviour: checklist ~30%, bank+categorised ~78%, average 28%, and uses them.

Gemini 3.8 Flash · API

Day-60 retention rates are correctly computed: checklist ~30%, bank+categorise ~78%, average 28%.

Activation defined by what predicts retentionRightRight
Opus 5.5 · Claude

Defines activation by retention prediction (bank + categorised) and ranks fixes by their effect on that event, not on checklist completion.

Gemini 3.8 Flash · API

Activation is defined by the behaviour that predicts retention (bank connect + 10 categorised), and fixes are ranked by their effect on reaching that event.

Gets people to value soonerRightRight
Opus 5.5 · Claude

Main fixes cut or defer steps before first value (move naming/theme to settings, defer notifications, make savings goal optional) and guide categorisation right after bank connection.

Gemini 3.8 Flash · API

The main fixes cut or defer steps before first value (cosmetic checklist, notifications, savings goal) and lead directly to bank connection and categorisation.

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 53 checks.

#Model · HarnessTask scoreDecision modelLLM judgeRunsCritical failures
1GPT-6 AstrawithChatGPT85.995.52None
2Sonnet 5.5withAPI78.4100.02None
3GPT-6.1 SolwithAPI85.990.92None
4GPT-6 LunawithAPI90.081.82None
5Haiku 5.5withAPI75.986.72None
6Opus 5.5withClaude88.478.42None
7Gemini 3.8 FlashwithAPI66.651.92None
8Gemini 3.5 Flash-LitewithGemini52.539.42None

What you get for the cost

GPT-6 Luna · API scores within 5 points of GPT-6 Astra · ChatGPT at about a hundredth of the cost.

Task score against relative cost for each setup. The table below has the same figures.304050607080901001×3×10×30×100×Cost per output, relative to the cheapest setup (log scale) →↑ Task scoreGPT-6 Astra · ChatGPT: task score 91, 122× the cheapest (1 of 2 outputs estimated)Sonnet 5.5 · API: task score 90, 32× the cheapestGPT-6.1 Sol · API: task score 89, 15× the cheapestGPT-6 Luna · API: task score 86, the cheapestHaiku 5.5 · API: task score 82, 1.8× the cheapestOpus 5.5 · Claude: task score 82, 101× the cheapest (1 of 2 outputs estimated)Gemini 3.8 Flash · API: task score 56, 13× the cheapestGemini 3.5 Flash-Lite · Gemini: task score 44, 3.4× the cheapest (1 of 2 outputs estimated)GPT-6 Astra · ChatGPTSonnet 5.5 · APIGPT-6.1 Sol · APIGPT-6 Luna · APIHaiku 5.5 · APIOpus 5.5 · ClaudeGemini 3.8 Flash · APIGemini 3.5 Flash-Lite · Gemini
Best valueNobody beats these on both score and costCost partly estimated (app runs with no usage meter)
Task score and relative cost by setup
SetupTask scoreRelative cost (cheapest = 1)
GPT-6 Luna · API861.0×
Haiku 5.5 · API821.8×
Gemini 3.5 Flash-Lite · Gemini443.4× (partly estimated)
Gemini 3.8 Flash · API5613×
GPT-6.1 Sol · API8915×
Sonnet 5.5 · API9032×
Opus 5.5 · Claude82101× (partly estimated)
GPT-6 Astra · ChatGPT91122× (partly estimated)

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

Reviewing a signup and onboarding flow that is losing users.

Why it matters

Anyone can list fifty UX nits. The job is finding the two that explain the drop-off, backed by the funnel data supplied.

What good looks like

  • Ties each issue to the funnel data
  • Prioritises by likely impact
  • Defines activation as the behaviour that predicts retention, not finishing onboarding

Deliberately not measured

  • Accessibility audit completeness
  • Visual redesign
Capability tested

Consequential critique

The failure we’re looking for

A generic UX checklist

Grading

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