janellecipriano Roadmap Planning
Translate strategy into a sequenced, outcome-oriented roadmap that communicates what, why, and roughly when — without overpromising dates.
When to use
- Planning a quarter/half/year, or refreshing an existing roadmap.
- Prioritizing and sequencing a backlog of initiatives against goals.
Inputs to gather
- The objectives/strategy the roadmap serves (link to OKRs if they exist — see
okr-tracking). - Candidate initiatives/themes and any known sizing, dependencies, or hard dates.
- The audience and horizon (internal team vs. external; quarterly vs. now/next/later).
Process
- Anchor each initiative to an objective and a target outcome — drop work that maps to nothing.
- Choose a format: Now / Next / Later (theme-based, low date commitment) or timeline/quarterly (when dates matter).
- For each item: state the outcome/problem, rough size (T-shirt or weeks), confidence (H/M/L), and dependencies.
- Prioritize with a clear lens (impact vs. effort, RICE, or value vs. risk) and make the rationale visible.
- Sequence respecting dependencies and capacity (sanity-check against
capacity-planning). - Note assumptions and what would change the plan. Distinguish committed vs. exploratory.
Output format
Default to a Now/Next/Later table unless dates are required:
## Now (this quarter)
| Initiative | Objective | Outcome | Size | Confidence | Dependencies |
## Next
...
## Later
...
Close with prioritization rationale and key assumptions/risks. Avoid precise dates for low-confidence items — use ranges or horizons.