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Translate strategy and OKRs into a sequenced product roadmap. Use when you need to communicate what's next, why, and in what order.
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| name | roadmap-planning |
| description | Translate strategy and OKRs into a sequenced product roadmap. Use when you need to communicate what's next, why, and in what order. |
Turn your strategy, OKRs, and backlog into a roadmap that stakeholders can understand and the team can execute against — in 2-4 hours instead of a multi-week planning offsite. Claude handles the synthesis and formatting. You handle the sequencing judgment and stakeholder reality.
| Step | Time | Claude Does | You Do |
|---|---|---|---|
| Gather inputs | 30 min | Structure OKRs, backlog, and constraints into a planning view | Provide context on dependencies and political realities |
| Sequence work | 45 min | Propose sequencing based on dependencies, risk, and value | Apply judgment on what ships when and why |
| Format the roadmap | 30 min | Generate roadmap views for different audiences | Validate accuracy and add narrative context |
| Stress-test | 30 min | Flag capacity conflicts, dependency risks, and coverage gaps | Confirm with engineering leads and stakeholders |
A roadmap is only as good as its inputs. Start by bringing together everything that informs sequencing.
Help me build a roadmap for [time horizon: quarter / half / year].
Inputs:
- OKRs / goals: [paste or summarize your objectives and key results]
- Current backlog: [top initiatives, epics, or themes with rough sizing]
- Commitments: [anything already promised — customer commitments, partner deadlines, compliance dates]
- Team capacity: [number of teams/squads, any planned absences or ramp-ups]
- Dependencies: [cross-team dependencies, platform work, external integrations]
- Carry-over: [unfinished work from last cycle that still matters]
Structure this into a planning view:
- Group initiatives by which OKR/goal they serve
- Flag initiatives with no clear goal alignment
- Identify dependencies between initiatives
- Note rough sizing (S/M/L or sprint count) for each
This is the judgment-heavy step. AI proposes; you decide.
Propose a sequencing for this roadmap:
Sequencing criteria (in priority order):
1. Dependencies: what must ship before something else can start?
2. Commitments: what has a hard external deadline?
3. Value: what moves the highest-priority OKR the most?
4. Risk: what has the most uncertainty and should start earlier?
5. Quick wins: what can ship fast and build momentum?
For each time bucket [month / sprint / now-next-later]:
- What ships in this period
- Why it's sequenced here (which criteria drove the decision)
- What's at risk if it slips
- Dependencies on other teams or initiatives
Flag:
- Capacity conflicts (more work than team can absorb)
- Sequencing trade-offs (two things that should go first — which one wins?)
- Items that don't fit (lower priority, should be cut or deferred)
Different audiences need different views of the same plan.
Generate three roadmap views from the sequenced plan:
1. Now / Next / Later view (for the team):
- Now: actively in progress or starting this sprint
- Next: planned for the next 1-2 cycles
- Later: on the radar but not yet committed
For each item: name, goal it serves, owner, rough timeline
2. Timeline view (for leadership):
- Monthly or quarterly columns
- Initiatives mapped to time periods
- Key milestones and decision points marked
- Dependencies shown as connections
Include: what we're betting on and what we're explicitly NOT doing
3. Theme-based view (for stakeholders and customers):
- Grouped by strategic theme or user outcome
- No internal implementation details
- Focused on "what changes for you and when"
- Appropriate level of commitment language (exploring / planned / committed)
Review this roadmap for:
Capacity:
- Does the work fit the team's capacity in each period?
- Are there periods that are overloaded?
- Is there buffer for unplanned work (bugs, incidents, support)?
Dependencies:
- Are any items sequenced before their dependencies are resolved?
- Are we depending on other teams? Have they committed?
- What happens to downstream work if an upstream item slips?
Coverage:
- Does every OKR have at least one initiative mapped to it?
- Are any OKRs under-invested (one small initiative for a stretch goal)?
- Are we spreading too thin across too many goals?
Reality check:
- What are we NOT doing? Is the team clear on what's been cut?
- Where are we most likely to be wrong about estimates?
- What's our contingency if the top-priority item takes 2x longer?