Roadmap From Data

roadmap-from-data

Anchor: A roadmap is a prioritized view of what we want to learn. Data tells you what to learn first.

When to use

Use this skill when the user needs to convert signals from dashboards, usage logs, support tickets, or interviews into a sequenced set of product bets. Works for:

• A quarterly or semester planning cycle that is overloaded with feature requests.
• A new PM or team inheriting a backlog that lost its narrative.
• A pivot or repositioning that needs a clear sequence of bets.
• A portfolio-level view across multiple product areas.

Do not use when:

• The user is writing a PRD for an already-chosen feature. Use prd-authoring.
• The user is pitching a single feature for approval. Use feature-proposal.
• The user is scoping a client engagement with fixed deliverables. Use proposal-scoping.

Philosophy

A roadmap is not a forecast. Three handbook concepts apply directly. Output vs outcomes: the roadmap is a sequence of changes in user or business behavior, not a list of features. Product as a portfolio of bets: each line is a bet with a known size, placed deliberately among others. Roadmap as conversation, not contract: the roadmap's purpose is to help the team and the business agree on what to learn first, not to lock commitments against which the team will be measured in a quarter. A roadmap that cannot change when the data changes is theater.

Voice rules (apply to all outputs)

• No buzzwords: leverage, empower, synergy, resonate, tapestry, delve, elevate, captivate, explore, dynamic, testament.
• No em dashes.
• No filler openings.
• Decision-oriented over descriptive.
• High-context, no overexplaining.
• Standard sentence case for formal outputs.
• ES outputs match the register of the handbook: direct, self-aware, no reverence for process, comfortable naming failure.
• EN outputs use direct US business register. Do not soften bluntness into corporate-speak.
• Language switches based on audience, not author.

Bilingual handling

• ES. Rioplatense register. Vos over tú. Keep standard terms in English: bet, backlog, roadmap, MVP, feature flag, experiment, OKR, north star, cohort, retention, activation, churn, funnel, sprint, quarter.
• EN. Direct US business register. Avoid "strategic" and "transformative" as adjectives for bets.
• Metric names and flag names stay in the language of the data model.

Method

Step 1. Decide what you are prioritizing

Roadmaps go wrong when teams confuse what they are prioritizing. Pick one:

• Outcomes. Changes in user behavior or business metrics.
• Bets. Hypotheses to test, each with a potential outcome.
• Themes. Problem areas that contain multiple bets.
• Features. Concrete deliverables. Avoid this at the roadmap level; it collapses the conversation back into a backlog.

This skill defaults to bets. Themes become groupings. Outcomes become success measures on each bet. Features show up only inside individual bets, not in the roadmap row itself.

Step 2. Pull the data

Before any opinion, assemble the evidence. Three categories:

• Behavioral. Event data, funnels, cohorts, retention curves, session traces.
• Qualitative. Interview notes, support themes, sales objections, win-loss patterns.
• Business. Revenue by segment, margin, CAC, churn, expansion, pipeline.

For each data source, note:

• What it measures.
• Its freshness.
• Its known biases.
• Whether it is trusted by the team that will read the roadmap.

If a source is mistrusted, say so and include it anyway. Do not hide data the audience could pull themselves.

Step 3. Cluster signals into problem areas

Group the data into themes. A theme is a cluster of signals that point at a shared user problem or business constraint. Themes are coarse, not features.

For each theme:

• Name. Short, names the problem.
• Signals. Three to seven pieces of evidence that define it.
• Scale. How many users, how much revenue, how frequent.
• Current hypothesis. What the team believes is driving the signals.

A theme without signals is an opinion. Drop it.

Step 4. Convert themes to bets

A bet is a hypothesis that, if true, would move an outcome. For each theme, write one to three candidate bets.

Each bet has:

• Hypothesis. If we change X for user Y, metric Z would move by roughly W.
• Type. Discovery (learn something), product (ship something), operational (change how we work).
• Expected outcome. The metric and direction.
• Magnitude band. Rough impact size: small, medium, large.

Two bets on the same theme are candidates, not both commitments. Choose.

Step 5. Size each bet on three axes

Every bet gets three scores, ranked within the portfolio, not in absolute terms.

• Impact. If the bet pays off, how much it moves the outcome.
• Uncertainty. How confident the team is about the causal link. High uncertainty does not disqualify a bet; it changes the validation method.
• Cost. Effort to validate first, then effort to ship if it validates.

High impact, high uncertainty, low cost is the shape of the best bets. Move those to the top.

Step 6. Sequence the bets

Sequencing is not just prioritization. Consider:

• Dependency. Which bet unlocks which.
• Learning order. Which bet, if it fails, invalidates others.
• Calendar constraints. Quarterly, regulatory, seasonal, or commercial gates.
• Team shape. Which teams can run which bets concurrently.
• Risk distribution. Do not concentrate all high-uncertainty bets in one window.

The output of this step is a sequence per team, not a single list.

Step 7. Name kill criteria per bet

Every bet in the sequence carries a kill criterion. Without it, nothing ever leaves the roadmap.

• Signal. Behavioral, qualitative, or economic.
• Threshold. Concrete.
• Check point. When we look.

A roadmap where every bet survives every quarter is a roadmap that has stopped learning.

Step 8. Write the roadmap as a conversation

The delivered roadmap has three parts:

1. Theme-level narrative. Two to four paragraphs. What we believe about the product based on the data. Which themes matter most and why.
2. Sequence. Bets in order per team, per window, with confidence bands.
3. Cadence. How and when the roadmap is revised. Monthly, after every major experiment, or on explicit trigger.

Do not ship a roadmap as a Gantt chart. Gantt implies contract; this skill rejects the contract framing.

Step 9. Review cadence and change policy

• Cadence. When the roadmap is re-examined with fresh data.
• Trigger. Which signals, outside the cadence, would cause an early revision.
• Who decides. The one person who can change the sequence between cadences.
• How changes are communicated. Channel, audience, lead time.

Step 10. Stress-test before handoff

Read the roadmap as three adversarial readers:

• An engineer. Can they see which bets their team will run, and roughly when.
• A skeptic. Can they see why this sequence and not another.
• Finance. Can they see which bets depend on spend and which do not.

If any of the three cannot, fix it.

Templates

• templates/en/roadmap-brief.md: full roadmap brief with themes, sequence, and cadence.
• templates/en/bet-card.md: single bet card for use inside the brief or standalone.
• templates/es/roadmap-brief.md: brief completo de roadmap con temas, secuencia, y cadencia.
• templates/es/bet-card.md: tarjeta de una apuesta para usar dentro del brief o sola.

Related skills

• prd-authoring: move to it once a bet is chosen and the feature needs a spec.
• feature-proposal: use it when pitching a single bet for approval, not sequencing the portfolio.
• proposal-scoping: use it when the work is a client engagement with fixed deliverables.
• ticket-triage: use it to clear the backlog at the ticket level once the roadmap sets direction.

Anti-patterns

This skill must never produce:

• A roadmap that is a list of features with dates.
• A theme with no supporting signals.
• A bet with no hypothesis or expected outcome.
• A sequence that names no dependencies and no risk distribution.
• A roadmap without a review cadence.
• A roadmap where every bet is high-confidence low-cost. That is a backlog, not a roadmap.
• A roadmap framed as a commitment the team will be measured on as a deliverable schedule.
• A roadmap that treats customer asks as ranked bets without analysis.
• A roadmap that ships with no kill criteria on any bet.

Checklist before delivery

• The unit of prioritization is bets, themes, or outcomes, not features.
• Evidence for each theme is named and dated.
• Every bet has hypothesis, expected outcome, and magnitude band.
• Every bet has impact, uncertainty, and cost scored within the portfolio.
• Sequence considers dependency, learning order, calendar, team shape, risk.
• Every bet has a kill criterion.
• Roadmap reads as a narrative, not a schedule.
• Review cadence, trigger, and decision owner are named.
• No buzzwords from the voice rules appear.