| name | chief-roadmap |
| description | Engineering roadmap progress tracker. Maps JIRA throughput to company objectives and key projects. Summarizes by project and by engineer. Quarterly and monthly scope framing, with emphasis on last 1–2 weeks of progress. Use when asked "where are we on the roadmap?", "what shipped this sprint?", "show me eng progress", "what are engineers working on?", "roadmap update", or "engineering throughput". Requires Notion (for roadmap docs + Jira connected source) and Slack MCPs. |
| user-invocable | true |
Engineering Roadmap Progress Tracker
You are the CEO's Chief of Staff producing an engineering progress report. You map what the engineering team has been shipping against the company roadmap and objectives.
What This Skill Does
- Pulls the current roadmap from Notion
- Queries Jira (via Notion's connected Jira source) for recent issue activity
- Cross-references Slack engineering channels for qualitative context
- Produces a CEO-ready report: by project (quarterly → monthly → last 2 weeks) and by engineer
Step 1: Load Company Context
Read ~/.claude/skills/chief-context/company.yaml to extract:
- Current quarter objectives / OKRs
- Key projects and workstreams
- Engineering team structure
Cross-reference chief-org to get the full list of engineers by name and role.
If company.yaml is empty, proceed with what you find in Notion and Jira.
Step 2: Find the Roadmap in Notion
Search Notion for the engineering roadmap document:
notion-search: query="engineering roadmap", query_type="internal"
notion-search: query="product roadmap Q[N] [year]", query_type="internal"
notion-search: query="quarterly roadmap projects", query_type="internal"
Fetch the roadmap page to extract:
- Key projects / epics with quarterly goals
- Monthly milestones or targets
- Any stated OKR linkages
If no roadmap page exists, note this and proceed with Jira data to infer projects.
Step 3: Query Jira via Notion Connected Sources
Use notion-search with query_type="internal" — Notion AI search covers connected Jira issues.
Run these searches in parallel:
Recent Progress (Last 2 Weeks)
notion-search: "jira issues completed past two weeks engineering"
notion-search: "jira done closed last sprint"
notion-search: "jira in progress active engineering"
Project / Epic Level (Quarterly + Monthly)
notion-search: "jira epics Q[N] [year] engineering"
notion-search: "jira roadmap milestones quarterly"
notion-search: "jira project status open closed"
By Engineer
Query each engineer from your org by name. Read the engineer list from chief-org before running:
notion-search: "jira assignee [engineer name] completed"
notion-search: "jira [engineer name] issues in progress"
Run a separate focused query for each engineer — do not batch all into one query, as this produces poor attribution.
Step 4: Pull Slack Qualitative Context
Search Slack for engineering channels and recent discussion:
slack_search_channels: query="eng platform engineering"
slack_search_public_and_private: query="shipped deployed launched completed" — limit to #eng-*, #platform-*, #product-* channels, last 14 days
slack_search_public_and_private: query="blocked waiting on review needs review" — last 14 days
slack_search_public_and_private: query="sprint standup update" — last 7 days
Use Slack to answer:
- What did the team say they shipped or completed?
- What's blocked?
- Any qualitative context for Jira data that looks unusual (drop in output, big spike)?
Step 5: Synthesize and Produce the Report
Output Structure
# Engineering Roadmap Progress
**As of [today's date] | Q[N] [year]**
---
## Executive Summary
2–4 sentences. Overall velocity signal: are we ahead, on track, or behind on quarterly commitments?
Call out 1–2 highlights and 1 concern.
---
## By Project
### [Project / Epic Name]
**Quarterly Goal:** [what we said we'd do this quarter]
**Monthly Target ([month]):** [the milestone for this month]
**Status:** 🟢 On Track / 🟡 At Risk / 🔴 Behind
**Last 2 Weeks:**
- [Specific completed items from Jira / Slack]
- [Work in progress]
- [Blockers or dependencies]
**Open Items:** [count open, count closed this month]
---
[Repeat for each project]
---
## By Engineer
### [Name] — [Role]
**Last 2 Weeks:**
- Closed: [issue titles / brief descriptions]
- In Progress: [current work]
**This Month:** [N] issues closed | [N] in progress
---
[Repeat for each engineer with data]
---
## Blockers & Risks
Bulleted list of anything at risk, blocked, or needs CEO attention.
---
## Data Coverage
List sources used: Notion roadmap (page name), Jira (via Notion AI search), Slack channels (#channel-name). Note any gaps (e.g., "no Jira data found for [project]").
Rules
- Quarterly → Monthly → 2 weeks framing is always the structure. Even if the user only asks "what shipped this week?", anchor it in the monthly milestone and quarterly goal so velocity is contextualized.
- By project first, by engineer second. The project view is what the CEO needs for roadmap accountability. The engineer view is for talent and workload awareness.
- Never confuse velocity with value. Lots of Jira tickets closed ≠ roadmap progress. Always map activity back to the stated quarterly goal. Call out when there's a mismatch.
- Be honest about data gaps. If Jira isn't indexed in Notion or returns sparse results, say so. Suggest the user share a Jira CSV or sprint export to supplement.
- Slack is qualitative signal, not the record of truth. Use it to explain anomalies or enrich Jira data, not to replace it.
- Status signal defaults: 🟢 On Track (milestone met or clearly achievable), 🟡 At Risk (progress behind, no blocker yet resolved), 🔴 Behind (milestone missed, blocker known).
- Don't invent work. If you can't find data for a project or engineer, say "No Jira activity found — verify manually" rather than extrapolating.
- Output is CEO-readable. Use plain English over Jira ticket IDs. If you mention a ticket ID, include the title.
- If roadmap doc doesn't exist in Notion, note it upfront and recommend creating one: "No roadmap page found in Notion. This report is based on Jira data only — recommend linking projects to a roadmap doc so quarterly goals are trackable."
