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

1. Anchor each initiative to an objective and a target outcome — drop work that maps to nothing.
2. Choose a format: Now / Next / Later (theme-based, low date commitment) or timeline/quarterly (when dates matter).
3. For each item: state the outcome/problem, rough size (T-shirt or weeks), confidence (H/M/L), and dependencies.
4. Prioritize with a clear lens (impact vs. effort, RICE, or value vs. risk) and make the rationale visible.
5. Sequence respecting dependencies and capacity (sanity-check against capacity-planning).
6. 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.