roadmap-planning

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Create outcome-based roadmaps using Now/Next/Later instead of Gantt charts. Use when asked to create a roadmap, plan quarterly, organize milestones, or figure out what to build over the next few months. Anti-date, anti-feature-list, pro-outcome.

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Sourceassimovt/productskills

Added on2026-02-21

NPX Install

npx skill4agent add assimovt/productskills roadmap-planning

SKILL.md Content

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Build roadmaps organized by outcomes, not feature lists. A roadmap answers "what problems are we solving and in what order?" — not "what features will we ship and when?" Dates on a roadmap beyond 6 weeks are fiction. Treat them that way.

Now / Next / Later

Three time horizons, decreasing in certainty:

Now (Committed — this cycle)

Currently in progress or about to start
Fully shaped: problem defined, solution scoped, appetite set
Team assigned, expected to ship this cycle
1-3 items maximum

Next (Shaped — next 1-2 cycles)

Problem validated, solution partially shaped
Not yet assigned to a team
May change based on what we learn from "Now" items
3-5 items maximum

Later (Raw — ideas worth exploring)

Problems we believe are real but haven't validated
No solution shaped yet
Will be promoted to "Next" when evidence supports it, or killed
No limit, but prune quarterly

Roadmap Items Are Outcomes, Not Features

Each roadmap item is framed as a problem to solve or an outcome to achieve:

Bad (feature-list roadmap):

Build team collaboration features
Add CSV export
Redesign settings page

Good (outcome-based roadmap):

Reduce time-to-first-value for team signups from 15 min to under 5 min
Enable users to get their data out without contacting support
Reduce settings-related support tickets by 50%

The solution emerges during shaping, not during roadmap planning.

Shape Up Cycle Planning

For teams using Shape Up cycles:

Betting table: Leadership reviews shaped pitches and bets on what to build next cycle. Not everything gets picked.
Cool-down: 1-2 weeks between cycles for bug fixes, exploration, and shaping future work.
No carry-over: Work that doesn't ship in a cycle is not automatically carried over. It must be re-pitched.

Presenting the Roadmap

Keep it to one page or one screen. If your roadmap needs scrolling, it's too detailed.

Format as a simple table:

Horizon	Outcome	Evidence	Status
Now	Reduce onboarding drop-off to under 30%	5 interviews, 60% current drop-off	In progress, week 2/3
Next	Enable self-serve data export	12 support tickets/month	Shaped, needs team
Later	Multi-workspace support	3 enterprise prospects requested	Unvalidated

Guidelines

CRITICAL: NEVER put dates on roadmap items beyond 6 weeks. You don't know and pretending you do erodes trust.
NEVER build a feature-list roadmap. Organize by outcomes and problems.
ALWAYS limit "Now" to 1-3 items. If you're working on 8 things, you're finishing none of them.
NEVER let "Later" items skip to "Now" without shaping and evidence.
ALWAYS prune "Later" quarterly. Kill items that haven't gained evidence in 3 months.
ALWAYS review and update the roadmap at the start of every cycle, not just quarterly.
NEVER present a roadmap without evidence for each item. A roadmap without evidence is a wish list.

Built on Shape Up (Basecamp) cycle planning and the Now/Next/Later framework. Skills from productskills.