/shepherding-an-initiative

name: shepherding-an-initiative
description: Five-phase umbrella playbook for an initiative shepherd. Dispatches to phase-deep skills (Research, PoC, Scoping, Implementation) at the right moment.
when_to_use: Use when an approved ARCH idea enters the Software Initiative Funnel, or when choosing which phase deep-dive applies. Triggers — "ARCH-X just got approved", "I'm assigned shepherd", "what phase am I in". Not for pre-funnel championing (use `championing-a-strategy-idea`).
allowed-tools: Skill, mcp__plugin_bitwarden-atlassian-tools_bitwarden-atlassian__get_issue, mcp__plugin_bitwarden-atlassian-tools_bitwarden-atlassian__get_issue_comments, mcp__plugin_bitwarden-atlassian-tools_bitwarden-atlassian__get_issue_remote_links, mcp__plugin_bitwarden-atlassian-tools_bitwarden-atlassian__search_issues, mcp__plugin_bitwarden-atlassian-tools_bitwarden-atlassian__get_confluence_page, mcp__plugin_bitwarden-atlassian-tools_bitwarden-atlassian__get_confluence_page_comments, mcp__plugin_bitwarden-atlassian-tools_bitwarden-atlassian__search_confluence, mcp__plugin_bitwarden-atlassian-tools_bitwarden-atlassian__search_confluence_cql

End-to-end umbrella playbook for an initiative shepherd, covering all five phases of the [Software Initiative Funnel](https://bitwarden.atlassian.net/wiki/spaces/EN/pages/584515614): Identification → Research → Proof of Concept → Scoping & Commitment → Implementation. Maps each phase's effort, deliverables, and decision gate; holds the line on what the shepherd produces vs. what gets handed to teams. Fetch the canonical funnel page via `get_confluence_page` when entry/exit criteria or full template detail is needed.

The Rule of Ownership (Hold Throughout)

**You own the initiative. Each receiving team owns how it executes its part.**

Every phase has a single sentence to remember: when you start writing the team's stories, the team won't own the work. When you stop coordinating across teams, the initiative drifts. Both failures are yours to prevent.

For the agent-neutral, team-side view of the same boundary (the version tech leads read), invoke `Skill(navigating-the-initiative-funnel)` in `bitwarden-delivery-tools`. Reading both perspectives keeps you honest about where the line actually sits.

Time and Effort Expectations

The funnel page sets these benchmarks. They're not aspirational — they're the basis for capacity planning when leadership asks "what does it cost to shepherd this?"

| Phase | Duration | Shepherd Effort | Decision Maker | | ------------------------ | ---------- | ----------------- | ------------------------------------- | | 1 — Identification | ~1 week | 4–8 hours | Holistic engineering leadership | | 2 — Research | 3–5 weeks | 40–80 hours | Eng leadership + Architecture Council | | 3 — Proof of Concept | 2–4 weeks | 40–80 hours | Eng leadership + Architecture Council | | 4 — Scoping & Commitment | 2–4 weeks | 30–50 hours | Engineering leadership (Director+) | | 5 — Implementation | 2–6 months | 10–20 hours/month | Teams execute; shepherd coordinates |

Total: 150–300 hours of shepherd time over 4–9 months for a medium initiative — roughly 5–10% of one person's time with higher concentration in Research and PoC.

Phase-by-Phase: What the Shepherd Does

Phase 1 — Identification

**Purpose:** Capture enough context for meaningful evaluation without premature commitment of resources.

**You produce:**

• A BW Initiative issue under the Bitwarden Company (BW) project. Type: Initiative. Assignee: you (the proposed shepherd). Reporter: whoever surfaced the problem. Priority: a placeholder ("TBD - Awaiting Research" or Medium).
• A description distilled from the upstream ARCH idea (if one exists) into an executive-readable summary — not a copy of the full TSI template. Pattern, link inventory, and field-by-field guidance live in [Idea-Based Initiatives](https://bitwarden.atlassian.net/wiki/spaces/EN/pages/2785181779).
• A **work item link** from the ARCH idea (in Jira Product Discovery) to the BW initiative. This is the foundational traceability link — every idea-based initiative must have one.
• Initial "Relates to" links: prior attempts, adjacent SRE/BRE/TSD/PM tickets, anything the ARCH idea's own research surfaced.
• An ARCH idea status update to "1️⃣ Identification" in JPD.

**Decision gate:** Holistic engineering leadership decides Proceed / Hold / Decline.

**What you do NOT do:** Pre-scope the solution. Research hasn't happened yet. Resist the urge to come in with an answer.

Phase 2 — Research

**Purpose:** Deeply understand the problem space and explore potential solutions before committing to direction.

**You produce:**

• 3–5 stakeholder interviews (the affected teams' tech leads are likely subjects).
• A current-state analysis surveying existing implementations across the codebase — inconsistencies, workarounds, technical debt — with impact quantified where possible.
• 2–4 documented solution approaches with explicit trade-offs.
• An **Architectural Assessment** in Confluence under the EN-space assessments folder, refined through stakeholder review.
• Optional preview at Architecture Council for major initiatives.
• ARCH idea status updated to "2️⃣ Research".

**Decision gate:** Engineering leadership with Architecture Council input. Proceed to PoC / Continue Research / Hold / Decline.

**Deep skill:** `Skill(running-an-architectural-assessment)` for stakeholder interview structure, current-state analysis, options generation, and the Architectural Assessment template.

Phase 3 — Proof of Concept

**Purpose:** Validate the recommended solution works in practice within Bitwarden's codebase before committing to full implementation. Reduce risk through hands-on experimentation.

**You produce:**

• A PoC area chosen in coordination with the owning team's tech lead — representative but contained (~1–5 fil