Product
Your roadmap document and your tracker disagree
A weekly diff between what the roadmap claims and what the tracker actually says.
What the worker does
Roadmap planning with an AI worker means a weekly reconciliation rather than a quarterly rewrite. The worker reads every initiative in the roadmap workstream, compares tracker state to the dates written in the roadmap document, and posts a comment listing what moved, by how long, and which initiatives now have no owner. The product manager decides what to cut, resequence or tell the board.
- Runs
- Weekly
- Connections
- Linear, Notion, Slack
- Output
- A drift comment
Roadmaps do not go wrong all at once
They go wrong two days at a time. An initiative slips a sprint and nobody updates the document, because updating the document is a twenty-minute job with no deadline attached. Three of those in a quarter and the roadmap you present is a work of fiction that everyone in the room politely agrees with.
The information needed to fix this already exists. It is in the tracker, it is accurate, and reconciling it against the document is pure comparison work.
How to brief a roadmap worker
Five minutes of setup, then it runs without being asked.
- 1
Point it at the roadmap document
Name the document in the worker's SKILL.md: where it lives, what each column means, and which field holds the committed date. If the roadmap lives in Polaris Docs it is versioned, so every weekly state is recoverable.
- 2
Define what counts as drift
Two weeks of slip may be noise for a six-month initiative and a crisis for a two-week one. Write your threshold down rather than leaving the worker to guess at it.
- 3
Give it Linear and Notion
Linear for issue and project state, Notion if the roadmap document lives there. Both are one click from the connections catalog and are authorised once for the whole organisation.
- 4
Set the acceptance criteria
A useful set: every initiative in the document accounted for, every date discrepancy stated with both dates, every unowned initiative listed separately. The worker ticks these as it goes.
- 5
Read it before planning
Schedule the task for Monday morning so the delivery comment is waiting before your planning meeting rather than being written during it.
What the delivery comment contains
One table, three lists, no narrative.
| Section | What it holds | Why it is separate |
|---|---|---|
| Moved dates | Initiative, document date, tracker date, days of slip | This is the part you take to the board |
| Unowned | Initiatives with no assignee in the tracker | Usually the result of someone changing teams |
| Not in the tracker | Roadmap items with no matching issues at all | Often the ones that were never actually started |
| Not in the roadmap | Active projects the document does not mention | Scope that arrived without a decision |
What changes after a month of this
Slips get discussed while they are small
A two-day slip surfaced on Monday is a scheduling note. The same slip found in week nine is a missed commitment.
Ownership gaps stop hiding
Initiatives lose their owner quietly when people change teams. A weekly list of unowned work makes that a five-second fix.
The document becomes worth reading
A roadmap that is reconciled weekly is one people check before asking. One that is rewritten quarterly is one people ignore.
Questions people ask
+What if our roadmap is a spreadsheet rather than a document?
Put it in Google Drive and give the worker the Google Drive connection. The brief is the same: name where the committed date lives and what each column means. The connection catalog covers Google Drive, Notion and Linear, which between them hold most roadmaps.
+Can the worker update the tracker to match the roadmap?
That would be backwards. The tracker holds what is true and the document holds what was promised, so the reconciliation runs in one direction and the fix is a human decision about the promise. The worker delivers the comparison, not a correction.
+How much does a weekly roadmap check cost?
Hours are estimated from observable effort and billed at about $2 per human-hour delivered, with a five-minute floor per session. A reconciliation over a few dozen initiatives is a short session, and every line of the estimate is visible on the worker's work log.
+Does this work if half the roadmap lives in someone's head?
Partly, and the report will say so. Initiatives with no matching tracker issues appear in their own list, which is usually the fastest way to discover which commitments were never actually started.
Related
Product management with an AI worker on the roster
Five jobs a product team can hand to an AI teammate, and the ones it should never hand over.
Sixty requests, and no idea how many people asked
Clustered requests with a real count of who asked, so the argument is about value rather than recall.
The two hours before planning that nobody schedules
Carry-over, gaps and blockers assembled the day before, so the meeting is about commitment.
Connect Linear to Polaris
A Linear API key carries one person's visibility, so the account you make it on decides what every worker can see.
Connect Notion to Polaris
Notion decides what Polaris can see, page by page, because an internal integration only reaches what you explicitly share with it.
Hire an AI project coordinator
The unglamorous half of running projects, done every week without anyone having to be the person who nags.
Workstream
A strand of work that keeps going, rather than a project that ends.