Roadmap Update

What This Skill Does

This skill helps product managers and teams update, create, or reprioritize product roadmaps. It streamlines the process of managing product direction by gathering context, determining the necessary operation, and generating a roadmap summary. It is useful for anyone needing to adjust product plans based on new information or changing priorities.

When to Use

• Adding a new feature to the roadmap.
• Updating the status of existing roadmap items.
• Reprioritizing roadmap items based on new data.
• Moving timeline dates for roadmap items.
• Creating a new product roadmap from scratch.
• Responding to a strategy shift with roadmap changes.

Key Features

Connects to project trackers to pull current roadmap data. Supports adding, updating, reprioritizing, and moving items. Suggests item placement based on priorities and capacity. Identifies downstream impacts of timeline changes. Offers prioritization frameworks like RICE and MoSCoW. Generates a roadmap summary in various formats.

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 v