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avelikiyavelikiy/great_cto/skills/outcome-roadmap/SKILL.md

outcome-roadmap

Skill112 starsChanged 2 months agoMITView on GitHub

Transform an output-focused roadmap (feature list) into an outcome-focused one. Rewrites initiatives as outcome statements reflecting user and business impact. Use when a roadmap lists features instead of results, when making a roadmap more strategic, or when communicating what success looks like vs what will be built.

8 other projects use a version of this, 7 of them edited.

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  • miovragSkill

    strategy-red-team

    Red-team a PRD, roadmap, or strategy by attacking its load-bearing assumptions before reality does. Steelmans then attacks each claim, ranks failure modes by impact × likelihood × cheapness-to-test, and returns the cheapest test and kill criteria for each. Use when stress-testing a plan, pressure-testing a strategy, challenging assumptions, or preparing a doc for executive review.

    Also in 4 projects that use this

The file

We split this skill into the rules it gives an agent

7 rules. 0 are common, 7 are distinctive, and 0 are very specific to this project.

  • 0

    Common

    Most of the 8 edited versions we read keep these.

  • 7

    Distinctive

    This author's own choices. Worth a look.

  • 0

    Very specific

    Tied to their project's names, files or tools. Probably skip.

  • Common
  • Distinctive
  • Very specific
  1. Distinctive:

    If the user provides a roadmap file, read it.

    line 52
  2. Distinctive:

    Rewrite: Use the formula above. Include a metric if possible.

    line 66
  3. Distinctive:

    If the roadmap has 5+ items, group related outcomes into themes:

    line 76
  4. Distinctive:

    Every outcome has a measurable component (%, number, ratio, frequency)

    line 106
  5. Distinctive:

    When the pm agent receives a feature list without a PRD:

    line 127
  6. Distinctive:

    Check if the list looks like outputs (feature names) or outcomes (result statements)

    line 128
  7. Distinctive:

    If outputs → apply this skill to transform before decomposing into tasks

    line 129

“Common” is measured: kept by at least 6 in 10 of the 8 edited versions of this file we could read. “Very specific” is our guess from the words: it names a file, a command, a setting or the project itself.

Keep what fits and drop the rest. Your version, ready for your agents.
Files
SKILL.md

Outcome Roadmap — from features to results

Converts a feature-focused roadmap into an outcome-focused one.

Core principle: Teams build features, but customers and businesses care about outcomes. An outcome roadmap communicates WHAT CHANGES, not what gets built.


The transformation formula

For every initiative on the roadmap, apply:

Enable [customer segment] to [desired customer outcome] so that [business impact]

Examples:

Output (old)Outcome (new)
Q2: Build advanced search filtersQ2: Enable customers to find products 50% faster through intuitive discovery
Q2: AI recommendationsQ2: Increase average order value 20% through personalised recommendations
Q3: Dashboard redesignQ3: Help operators monitor all systems with 80% less time spent on dashboards
Q3: SSO integrationQ3: Remove auth friction for enterprise admins so we can close 3+ enterprise deals
Q4: Mobile appQ4: Enable users to complete core workflows on mobile so 7-day retention increases from 20% to 35%

How to apply

Step 1 — Read the existing roadmap

If the user provides a roadmap file, read it. If they describe it verbally, extract the initiative list.

For each initiative, ask internally:

  • What feature / project is planned?
  • Why are we building it? What changes for customers or the business?
  • What metric will improve, and by how much?
  • Is there a better, different way to achieve the same outcome?

Step 2 — Rewrite each initiative as an outcome

For each item in the roadmap:

  1. Identify the output: What feature or project is planned?
  2. Uncover the outcome: Why are we building it? Keep asking "So what?" until you reach real customer or business value.
  3. Rewrite: Use the formula above. Include a metric if possible.

"So what?" chain example:

  • "We're adding search filters" → So what?
  • "Users can narrow results" → So what?
  • "Users find what they're looking for faster" → So what?
  • "Users convert at higher rates because they find products before abandoning" ✅ That's the outcome.

Step 3 — Group by strategic theme (optional)

If the roadmap has 5+ items, group related outcomes into themes:

  • Retention (outcomes that reduce churn)
  • Acquisition (outcomes that improve conversion)
  • Monetisation (outcomes that increase revenue per user)
  • Ops efficiency (outcomes that reduce internal cost/time)

Step 4 — Output format

## Outcome Roadmap — <Product> <Quarter/Year>

### Strategic context
<1–2 sentences on what the team is optimising for this period>

### Q<N> Outcomes

| Initiative | Outcome Statement | Primary Metric | Target |
|------------|------------------|----------------|--------|
| <original feature name> | Enable [segment] to [outcome] so that [business impact] | <metric> | <target> |

### What we're NOT doing this quarter (and why)
- <deprioritised initiative>: <reason — not enough signal / too early / wrong priority>

### Key assumptions
- <assumption this roadmap depends on — if it's wrong, the outcomes change>

Step 5 — Validate

Before presenting, check:

  • Every outcome has a measurable component (%, number, ratio, frequency)
  • "So what?" has been applied to every item — no pure feature descriptions remain
  • At least one "Not doing" item is stated — otherwise scope is unbounded
  • Outcomes align with stated OKRs or strategic goals in PROJECT.md

Anti-patterns

❌ "We will build X" — that's an output, not an outcome.

❌ "Improve UX" — unmeasurable. Rewrite as: "Reduce time to complete checkout from 4min to 90sec".

❌ Outcome without a metric — if you can't measure it, you can't know if you achieved it.

❌ Outcomes that require building a specific solution — "Enable users to access features via mobile app" locks the solution. Better: "Enable users to complete core workflows on any device".


Integration with pm agent

When the pm agent receives a feature list without a PRD:

  1. Check if the list looks like outputs (feature names) or outcomes (result statements)
  2. If outputs → apply this skill to transform before decomposing into tasks
  3. Pass the outcome statements into the PLAN doc as the "Why" for each task group

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