roadmap-update

SKILL.md

Roadmap Update

If you see unfamiliar placeholders or need to check which tools are connected, see CONNECTORS.md.

Update, create, or reprioritize a product roadmap.

Usage

/roadmap-update $ARGUMENTS

Workflow

1. Understand Current State
If ~~project tracker is connected:

Pull current roadmap items with their statuses, assignees, and dates

Identify items that are overdue, at risk, or recently completed

Surface any items without clear owners or dates

If no project management tool is connected:

Ask the user to describe their current roadmap or paste/upload it

Accept any format: list, table, spreadsheet, screenshot, or prose description

2. Determine the Operation

Ask what the user wants to do:

Add item: New feature, initiative, or work item to the roadmap

Gather: name, description, priority, estimated effort, target timeframe, owner, dependencies

Suggest where it fits based on current priorities and capacity

Update status: Change status of existing items

Options: not started, in progress, at risk, blocked, completed, cut

For "at risk" or "blocked": ask for the blocker and mitigation plan

Reprioritize: Change the order or priority of items

Ask what changed (new information, strategy shift, resource change, customer feedback)

Apply a prioritization framework if helpful — see Prioritization Frameworks below for RICE, MoSCoW, ICE, and value-vs-effort

Show before/after comparison

Move timeline: Shift dates for items

Ask why (scope change, dependency slip, resource constraint)

Identify downstream impacts on dependent items

Flag items that move past hard deadlines

Create new roadmap: Build a roadmap from scratch

Ask about timeframe (quarter, half, year)

Ask about format preference (Now/Next/Later, quarterly columns, OKR-aligned) — see Roadmap Frameworks below

Gather the list of initiatives to include

3. Generate Roadmap Summary

Produce a roadmap view with:

Status Overview

Quick summary: X items in progress, Y completed this period, Z at risk.

Roadmap Items

For each item, show:

Name and one-line description

Status indicator (on track / at risk / blocked / completed / not started)

Target timeframe or date

Owner

Key dependencies

Group items by:

Timeframe (Now / Next / Later) or quarter, depending on format

Or by theme/goal if the user prefers

Risks and Dependencies

Items that are blocked or at risk, with details

Cross-team dependencies and their status

Items approaching hard deadlines

Changes This Update

If this is an update to an existing roadmap, summarize what changed:

Items added, removed, or reprioritized

Timeline shifts

Status changes

4. Follow Up

After generating the roadmap:

Offer to format for a specific audience (executive summary, engineering detail, customer-facing)

Offer to draft communication about roadmap changes

If project management tool is connected, offer to update ticket statuses

Roadmap Frameworks

Now / Next / Later

The simplest and often most effective roadmap format:

Now (current sprint/month): Committed work. High confidence in scope and timeline. These are the things the team is actively building.

Next (next 1-3 months): Planned work. Good confidence in what, less confidence in exactly when. Scoped and prioritized but not yet started.

Later (3-6+ months): Directional. These are strategic bets and opportunities we intend to pursue, but scope and timing are flexible.

When to use: Most teams, most of the time. Especially good for communicating externally or to leadership because it avoids false precision on dates.

Quarterly Themes

Organize the roadmap around 2-3 themes per quarter:

Each theme represents a strategic area of investment (e.g., "Enterprise readiness", "Activation improvements", "Platform extensibility")

Under each theme, list the specific initiatives planned

Themes should map to company or team OKRs

This format makes it easy to explain WHY you are building what you are building

When to use: When you need to show strategic alignment. Good for planning meetings and executive communication.

OKR-Aligned Roadmap

Map roadmap items directly to Objectives and Key Results:

Start with the team's OKRs for the period

Under each Key Result, list the initiatives that will move that metric

Include the expected impact of each initiative on the Key Result

This creates clear accountability between what you build and what you measure

When to use: Organizations that run on OKRs. Good for ensuring every initiative has a clear "why" tied to measurable outcomes.

Timeline / Gantt View

Calendar-based view with items on a timeline:

Shows start dates, end dates, and durations

Visualizes parallelism and sequencing

Good for identifying resource conflicts

Shows dependencies between items

When to use: Execution planning with engineering. Identifying scheduling conflicts. NOT good for communicating externally (creates false precision expectations).

Prioritization Frameworks

RICE Score

Score each initiative on four dimensions, then calculate RICE = (Reach x Impact x Confidence) / Effort

Reach: How many users/customers will this affect in a given time period? Use concrete numbers (e.g., "500 users per quarter").

Impact: How much will this move the needle for each person reached? Score on a scale: 3 = massive, 2 = high, 1 = medium, 0.5 = low, 0.25 = minimal.

Confidence: How confident are we in the reach and impact estimates? 100% = high confidence (backed by data), 80% = medium (some evidence), 50% = low (gut feel).

Effort: How many person-months of work? Include engineering, design, and any other functions.

When to use: When you need a quantitative, defensible prioritization. Good for comparing a large backlog of initiatives. Less good for strategic bets where impact is hard to estimate.

MoSCoW

Categorize items into Must have, Should have, Could have, Won't have:

Must have: The roadmap is a failure without these. Non-negotiable commitments.

Should have: Important and expected, but delivery is viable without them.

Could have: Desirable but clearly lower priority. Include only if capacity allows.

Won't have: Explicitly out of scope for this period. Important to list for clarity.

When to use: Scoping a release or quarter. Negotiating with stakeholders about what fits. Good for forcing prioritization conversations.

ICE Score

Simpler than RICE. Score each item 1-10 on three dimensions:

Impact: How much will this move the target metric?

Confidence: How confident are we in the impact estimate?

Ease: How easy is this to implement? (Inverse of effort — higher = easier)

ICE Score = Impact x Confidence x Ease

When to use: Quick prioritization of a feature backlog. Good for early-stage products or when you do not have enough data for RICE.

Value vs Effort Matrix

Plot initiatives on a 2x2 matrix:

High value, Low effort (Quick wins): Do these first.

High value, High effort (Big bets): Plan these carefully. Worth the investment but need proper scoping.

Low value, Low effort (Fill-ins): Do these when you have spare capacity.

Low value, High effort (Money pits): Do not do these. Remove from the backlog.

When to use: Visual prioritization in team planning sessions. Good for building shared understanding of tradeoffs.

Dependency Mapping

Identifying Dependencies

Look for dependencies across these categories:

Technical dependencies: Feature B requires infrastructure work from Feature A

Team dependencies: Feature requires work from another team (design, platform, data)

External dependencies: Waiting on a vendor, partner, or third-party integration

Knowledge dependencies: Need research or investigation results before starting

Sequential dependencies: Must ship Feature A before starting Feature B (shared code, user flow)

Managing Dependencies

List all dependencies explicitly in the roadmap

Assign an owner to each dependency (who is responsible for resolving it)

Set a "need by" date: when does the depending item need this resolved

Build buffer around dependencies — they are the highest-risk items on any roadmap

Flag dependencies that cross team boundaries early — these require coordination

Have a contingency plan: what do you do if the dependency slips?

Reducing Dependencies

Can you build a simpler version that avoids the dependency?

Can you parallelize by using an interface contract or mock?

Can you sequence differently to move the dependency earlier?

Can you absorb the work into your team to remove the cross-team coordination?

Capacity Planning

Estimating Capacity

Start with the number of engineers and the time period

Subtract known overhead: meetings, on-call rotations, interviews, holidays, PTO

A common rule of thumb: engineers spend 60-70% of time on planned feature work

Factor in team ramp time for new members

Allocating Capacity

A healthy allocation for most product teams:

70% planned features: Roadmap items that advance strategic goals

20% technical health: Tech debt, reliability, performance, developer experience

10% unplanned: Buffer for urgent issues, quick wins, and requests from other teams

Adjust ratios based on team context:

New product: more feature work, less tech debt

Mature product: more tech debt and reliability investment

Post-incident: more reliability, less features

Rapid growth: more scalability and performance

Capacity vs Ambition

If roadmap commitments exceed capacity, something must give

Do not solve capacity problems by pretending people can do more — solve by cutting scope

When adding to the roadmap, always ask: "What comes off?"

Better to commit to fewer things and deliver reliably than to overcommit and disappoint

Communicating Roadmap Changes

When the Roadmap Changes

Common triggers for roadmap changes:

New strategic priority from leadership

Customer feedback or research that changes priorities

Technical discovery that changes estimates

Dependency slip from another team

Resource change (team grows or shrinks, key person leaves)

Competitive move that requires response

How to Communicate Changes

Acknowledge the change: Be direct about what is changing and why

Explain the reason: What new information drove this decision?

Show the tradeoff: What was deprioritized to make room? Or what is slipping?

Show the new plan: Updated roadmap with the changes reflected

Acknowledge impact: Who is affected and how? Stakeholders who were expecting deprioritized items need to hear it directly.

Avoiding Roadmap Whiplash

Do not change the roadmap for every piece of new information. Have a threshold for change.

Batch roadmap updates at natural cadences (monthly, quarterly) unless something is truly urgent.

Distinguish between "roadmap change" (strategic reprioritization) and "scope adjustment" (normal execution refinement).

Track how often the roadmap changes. Frequent changes may signal unclear strategy, not good responsiveness.

Output Format

Use a clear, scannable format. Tables work well for roadmap items. Use text status labels: Done, On Track, At Risk, Blocked, Not Started.

Tips

A roadmap is a communication tool, not a project plan. Keep it at the right altitude — themes and outcomes, not tasks.

When reprioritizing, always ask what changed. Priority shifts should be driven by new information, not whim.

Flag capacity issues early. If the roadmap has more work than the team can handle, say so.

Dependencies are the biggest risk to roadmaps. Surface them explicitly.

If the user asks to add something, always ask what comes off or moves. Roadmaps are zero-sum against capacity.