personal-chief-of-staff

Conducts daily, weekly, and quarterly personal reviews across email, calendar, tasks, and Obsidian sources.

6|Updated Jul 10, 2026
One-click install
npx skills add https://github.com/jrgilbertson/the-rookery --skill personal-chief-of-staff-jrgilbertson
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: personal-chief-of-staff
Source: https://github.com/jrgilbertson/the-rookery/tree/main/skills/personal-chief-of-staff
Command: npx skills add https://github.com/jrgilbertson/the-rookery --skill personal-chief-of-staff-jrgilbertson

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes scripts (resource) and references (resource) and assets (resource) components.

What problem does it solve? Keeping a consistent personal review practice requires pulling evidence from scattered sources like email, calendars, task lists, journals, and CRM notes, then deciding what deserves attention. This Skill runs structured wind-down, weekly, and quarterly reviews that gather that evidence, propose corrections, and apply only the changes you explicitly approve. ## Core Features & Use Cases - Three review modes: Run an end-of-day Wind-down journal, a Weekly review with next-week planning, or a Quarterly strategy review, each with its own evidence retrieval and synthesis workflow. - Approval-gated actions: Every proposed change to tasks, calendar, notes, or CRM records is presented as an independently numbered action that you approve, edit, defer, or skip before any write occurs. - Private source bindings: A user-global JSON map (managed by a validated Python helper script) designates which accounts, vaults, and systems own each role, keeping personal and work identities distinct. - Use Case: At the end of your day, ask for a wind-down review. The Skill reads your calendar, tasks, and journal, drafts a daily journal entry, flags overdue tasks with proposed resolutions, and applies only the changes you approve. ## Quick Start Ask the assistant to run my daily wind-down review using my configured sources and propose any corrections for my approval.

Frequently Asked Questions about personal-chief-of-staff

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I run a daily review or wind-down journal with an AI assistant?▼

Request a wind-down review and the Skill retrieves evidence from your configured calendar, tasks, and journal sources, then drafts a daily journal and proposes corrections. Each proposed change is a numbered action you approve, edit, defer, or skip before anything is written.

How does the weekly review mode plan the next week?▼

The Weekly mode reconstructs the past week from journals, calendars, and task sources, runs an administrative sweep for overdue and at-risk tasks, then collaborates with you on next-week commitments. It checks calendar and capacity evidence before proposing any new deadline.

What sources and accounts does this review workflow support?▼

It reads email, personal and work calendars, canonical Obsidian notes, task and issue trackers, repositories, analytics, health data, and optional X read-only evidence through a CRM companion. You designate each source's owner in a private bindings map at ~/.config/the-rookery/personal-chief-of-staff/sources.json.

Does the Skill change my tasks or notes without asking?▼

No. Every write requires your exact approval of a displayed proposal showing the acting identity, target, and complete content. Approved actions are revalidated immediately before writing and read back afterward, with outcomes classified as applied, failed, indeterminate, or manual.

What are the system requirements for running this Skill?▼

It requires Python 3.8 or later on a POSIX system and access to your chosen authoritative sources. Obsidian-based workflows additionally require a running Obsidian app with its CLI, and all vault operations go through that CLI with explicit vault targeting.

When should I not use the chief-of-staff review Skill?▼

Do not use it for morning briefings, start-of-day planning, or same-day triage. Isolated task creation, issue writing, email processing, calendar editing, health analysis, meeting preparation, and project planning belong to the narrower workflows that own those operations.