roadmap-update

What this skill does

# Roadmap Update

> If you see unfamiliar placeholders or need to check which tools are connected, see [CONNECTORS.md](../../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