Roadmap Planner

Roadmap Update

Update, create, or reprioritize a product roadmap.

Usage

/roadmap-update $ARGUMENTS

Workflow

1. Understand Current State

If the user can share project tracker data (paste or upload):

• 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

1. Acknowledge the change: Be direct about what is changing and why
2. Explain the reason: What new information drove this decision?
3. Show the tradeoff: What was deprioritized to make room? Or what is slipping?
4. Show the new plan: Updated roadmap with the changes reflected
5. 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.