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.

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 the roadmap-management skill for RICE, MoSCoW, ICE, and value-vs-effort frameworks
• 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)
• 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

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.