Roadmap reconcile

Roadmap reconcile

Invocation: user only.

Every roadmap drifts. This skill measures the drift and makes it visible — what shipped, what slipped, what's in flight that's not on the roadmap, what's on the roadmap that nobody's working on.

Workflow

1. Load the canonical roadmap

From $ARGUMENTS:

• Default: current quarter's roadmap page in Notion
• Or a specific link / quarter / theme

If no roadmap exists or it hasn't been updated in >30 days, stop and tell the user: the roadmap isn't the source of truth, so reconciliation is meaningless. Suggest drafting a fresh one first.

2. Pull reality

In parallel:

• Shipped: Notion "shipped" page, #ship Slack, GitHub merged PRs this quarter tagged with roadmap items
• In flight: open Notion specs, active PRs, current-sprint items in whichever tool the team uses
• Queued: backlog items the team has committed to but hasn't started
• Decisions: recent decisions that added or removed items from the implicit roadmap

3. Classify

For every item on the roadmap, classify:

• ✅ Shipped — done, customer-visible
• 🏗 In flight — actively being worked, on track
• ⚠️ Slipping — in flight but past original target, or still not started with target passed
• ❓ Orphaned — on the roadmap, but nobody owns it, no recent activity, no blocker
• ❌ Quietly dropped — removed from active work, never formally cut

For every item not on the roadmap but visible in reality:

• 🆕 Undeclared — work being done that isn't on the roadmap (either should be added or should be stopped)

4. Diagnose

Classification produces a shape. Common shapes and what they mean:

• Lots of undeclared work → the team isn't updating the roadmap when priorities shift. Process problem.
• Lots of orphaned items → commitments were made without owners. Ownership problem.
• Lots of slipping items → either estimation is off or capacity is overbooked. Planning problem.
• Lots of quietly dropped items → decisions to cut happened informally, never recorded. Decision-log problem.

Name the shape in the report. Don't just list items.

5. Sequencing check

Look for sequencing issues:

• Blocked-but-nobody-knows — roadmap item depends on another item that's slipping or dropped
• Out-of-order — item B is in flight but was supposed to come after item A, and A hasn't started
• Wasted parallelism — two items touching the same code / team that could have been sequenced more efficiently

6. Output

# Roadmap reconciliation — <quarter>

**Source of truth:** <Notion roadmap link>
**Last roadmap update:** <date>

## TL;DR
<2-3 sentences. The overall shape. "7 shipped, 3 in flight on-track, 2 slipping, 1 orphaned, 2 undeclared." + what the shape means.>

## What shipped
- [x] <item> — shipped <date> — <link to shipped page>

## In flight — on track
- [ ] <item> — owner, target, status

## Slipping
- [ ] <item> — target was <date> — current reality <date / uncertain> — cause if known

## Orphaned (on roadmap, no ownership / activity)
- [ ] <item> — recommend: assign, re-scope, or formally drop

## Quietly dropped (not on roadmap anymore, never formally cut)
- <item> — recommend: capture the decision in `/role-ceo:decision-log` or drop from roadmap

## Undeclared work (in flight, not on roadmap)
- <item> — recommend: add to roadmap or stop the work

## Sequencing issues
- <issue> — what's happening — suggested fix

## Diagnostic
<Name the shape. Is this a planning problem, process problem, ownership problem, or decision-log problem?>

## Proposed actions
1. <specific next step, owner, date>
2. ...

7. Act (only on approval)

Show the report. Common edits:

• Reclassify an item (user knows a status that wasn't in the system)
• Adjust the diagnostic
• Trim or sharpen the proposed actions

On approval, the user picks what happens next:

• Update the Notion roadmap to match reality (which items to add, drop, reassign)
• Open /role-ceo:decision-log entries for quiet drops that should be formalized
• Schedule conversations with owners whose items are slipping
• Post a team summary to Slack (/team-core:draft-email flow for Slack)

Don't make any of these changes unilaterally. Roadmap edits are political artifacts.

Don't

• Don't reconcile monthly — quarterly is usually right. Weekly creates noise; annual creates catastrophic drift.
• Don't classify ambiguously. If you can't tell whether something is slipping or orphaned, ask the user rather than guessing.
• Don't recommend cutting items because the roadmap has too many. Recommend cutting because a specific item is misaligned, blocked, or no longer worth the cost. "Too many" is a symptom, not a reason.
• Don't auto-edit the roadmap. The roadmap is a public artifact; edits are decisions.