Ceos Assistance

ceos-assistance

Manage the daily operational delegation workflow between a leader and their assistant using "The Stack" — a batch delegation queue. This skill implements the 5 disciplines of The Assistance Track: batching, The Stack, the daily meeting, the assistant's judgment, and a weekly review. It complements ceos-delegate, which handles strategic delegation (what SHOULD be delegated), by managing operational delegation (HOW items are delegated day-to-day).

Not for: Strategic delegation decisions (use ceos-delegate), task tracking without a leader-assistant relationship (use ceos-todos), or meeting facilitation (use ceos-l10). The Assistance Track is specifically about the daily delegation workflow between a leader and their dedicated assistant.

When to Use

• "Add to the stack" or "stack this for my assistant"
• "Run the daily meeting" or "daily standup with my assistant"
• "Review the stack" or "what's on the stack?"
• "Weekly assistance review" or "how's delegation going this week?"
• "Show stuck items" or "what's been on the stack too long?"
• "Hand off [item] to [assistant]" or "mark [item] as done"
• Any discussion about daily delegation queues, assistant standups, or The Assistance Track

Context

Finding the CEOS Repository

Search upward from the current directory for the .ceos marker file. This file marks the root of the CEOS repository.

If .ceos is not found, stop and tell the user: "Not in a CEOS repository. Clone your CEOS repo and run setup.sh first."

Sync before use: Once you find the CEOS root, run git -C <ceos_root> pull --ff-only --quiet 2>/dev/null to get the latest data from teammates. If it fails (conflict or offline), continue silently with local data.

Key Files

Stack Item Format

Each stack item is a markdown file at data/assistance/stack/stack-NNN-slug.md with YAML frontmatter:

id: "stack-001"
title: "Schedule board meeting"
from: "Brad Feld"
to: "Sarah Chen"
urgency: this_week        # today | this_week | whenever
status: pending           # pending | handed_off | done
created: "2026-02-16"
handed_off: null           # Date when handed to assistant
completed: null            # Date when marked done

File naming: stack-NNN-slug.md — zero-padded numeric ID, title slugified.

Daily Meeting Log Format

Each daily meeting is a markdown file at data/assistance/daily/YYYY-MM-DD.md with YAML frontmatter:

date: "2026-02-16"
leader: "Brad Feld"
assistant: "Sarah Chen"
items_reviewed: 5
items_handed_off: 3
items_completed: 1
duration_minutes: 15

Urgency Values

Status Values

The 5 Disciplines

The Assistance Track is built on 5 disciplines that make delegation work:

1. Batching — Don't interrupt your assistant throughout the day. Collect items on The Stack.
2. The Stack — A single queue of everything you need to delegate. Items wait here until the daily meeting.
3. The Daily Meeting — A structured 5-15 minute standup to review The Stack, hand off items, and check on progress.
4. The Assistant's Judgment — Once handed off, trust the assistant to handle it. Don't micromanage.
5. The Weekly Review — A weekly check on stuck items, completion rates, and delegation health.

Leader-Assistant Relationship

The leader-assistant relationship is derived from data/accountability.md. Look for reporting relationships where one person's seat includes assistant-type responsibilities (Executive Assistant, Office Manager, etc.).

If no clear assistant relationship is found in the accountability chart, ask the user: "Who is your assistant? (I couldn't find a clear assistant relationship in the accountability chart.)"

Process

Mode: Stack

Use when adding new items to The Stack. This is the primary way a leader batches delegation throughout the day.

Step 1: Identify the Relationship

Determine the leader and assistant. If only one leader-assistant pair exists in data/accountability.md, use it automatically. If multiple exist or none is clear, ask the user.

Check for existing stack items to determine the next ID:

1. Scan data/assistance/stack/ for all stack-NNN-*.md files
2. Also check data/assistance/daily/ meeting logs for any referenced IDs
3. Find the highest numeric ID
4. Increment by 1

Step 2: Capture the Item

Ask for the item details:

1. Title: Short description of the task ("Schedule board meeting", "Order new monitors")
2. Urgency: today, this_week, or whenever
3. Details: Any additional context or instructions (optional)

For quick stacking, accept a one-liner: "Stack: Schedule board meeting - this_week" and parse it.

Step 3: Create the Stack Item

Create a new file from templates/assistance-stack.md:

• Generate the next sequential ID (stack-NNN)
• Slugify the title for the filename
• Fill in the frontmatter fields
• Add any details to the body

Show the file before writing. Ask: "Add this to the stack?"

Step 4: Confirm

After writing, display a brief confirmation:

Added to stack: stack-003 "Schedule board meeting" (this_week)
Stack total: 5 pending items

Mode: Daily

Use when running the structured daily standup between a leader and their assistant. This is the 5-15 minute meeting where The Stack is reviewed and items are handed off.

Step 1: Load the Stack

Read all files from data/assistance/stack/ via Glob("data/assistance/stack/stack-*.md"). Parse YAML frontmatter.

If no items exist: "The stack is empty. Nothing to review today. Add items with Stack mode throughout the day."

Separate items by status:

• Pending — needs to be discussed and handed off
• Handed off — check on progress
• Today urgency — highlight these first regardless of status

Step 2: Display the Agenda

Daily Standup — [Date]
━━━━━━━━━━━━━━━━━━━━━
Leader: [Name]  |  Assistant: [Name]

🔴 TODAY (needs attention now):
  stack-005: "Call insurance broker" (pending)
  stack-003: "Send revised proposal" (handed_off — 2 days ago)

📋 PENDING (hand off today):
  stack-007: "Order office supplies" (this_week)
  stack-008: "Research conference venues" (whenever)

🔄 IN PROGRESS (check status):
  stack-001: "Schedule board meeting" (handed_off — 1 day ago)
  stack-004: "Book travel for March" (handed_off — 3 days ago)

Step 3: Walk Through Each Item

For each item in the agenda, ask the leader:

For pending items:

• "Hand off to [assistant]?" → Update status to handed_off, set handed_off date
• "Defer?" → Keep as pending, optionally update urgency
• "Cancel?" → Remove from stack (delete file)

For handed-off items:

• "Done?" → Update status to done, set completed date
• "Still in progress?" → No change, note in meeting log
• "Stuck?" → Note the blocker, optionally escalate urgency

For today-urgency items:

• Highlight with extra emphasis. These should be resolved or actively worked on by end of day.

Step 4: Capture New Items

After reviewing existing items: "Any new items to add to the stack?"

If yes, follow Stack mode Steps 2-3 for each new item.

Step 5: Save the Meeting Log

Create a daily meeting log from templates/assistance-daily.md:

• File: data/assistance/daily/YYYY-MM-DD.md
• Fill in frontmatter: date, leader, assistant, counts
• Populate the Stack Review table with decisions from Step 3
• Populate the New Items table from Step 4
• Record any action items discussed

Show the complete meeting log before writing. Ask: "Save this daily meeting log?"

Step 6: Update Stack Items

After the meeting log is saved, update all stack item files based on the decisions:

• Set handed_off date on newly handed-off items
• Set completed date and status on done items
• Update urgency if changed
• Delete cancelled items

Display a brief summary:

Daily standup complete:
  Handed off: 2 items
  Completed: 1 item
  Still pending: 3 items
  New items added: 1
  Duration: ~10 minutes

Mode: Review

Use when running the weekly review of The Assistance Track. This checks delegation health, identifies stuck items, and surfaces patterns.

Step 1: Load All Data

Read all stack items from data/assistance/stack/ and all daily meeting logs from data/assistance/daily/. Parse YAML frontmatter for both.

If no data exists: "No Assistance Track data found. Start by adding items with Stack mode and running Daily meetings."

Step 2: Stack Health Summary

Assistance Track — Weekly Review
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Stack Status:
  Pending: 4 items
  Handed off: 3 items
  Completed this week: 5 items
  Total active: 7 items

Urgency breakdown:
  Today: 1 item ⚠️
  This week: 3 items
  Whenever: 3 items

Step 3: Flag Stuck Items

Items that have been on the stack for more than 3 days without progress are flagged:

⚠️ Stuck Items (3+ days without progress):
  stack-004: "Book travel for March" — handed_off 5 days ago
    → Consider: Follow up with [assistant], escalate urgency, or reassign
  stack-006: "Update CRM contacts" — pending 4 days ago
    → Consider: Has this been discussed in a daily meeting?

For each stuck item, offer options:

• Escalate urgency (e.g., whenever → this_week)
• Add a note about the blocker
• Reassign to someone else
• Close as no longer needed

Step 4: Meeting Cadence Check

Review daily meeting logs for the past week:

Daily Meeting Cadence:
  Meetings this week: 4 / 5 expected
  Missing: Wednesday (2026-02-12)
  Avg items per meeting: 3.5
  Avg duration: 12 minutes

If fewer than 3 meetings in a week: "⚠️ Only [N] daily meetings this week. The daily standup is the core discipline — consistency matters more than perfection."

Step 5: Delegation Trends

If enough data exists (2+ weeks of daily meetings):

Delegation Trends (last 2 weeks):
  Items added: 12
  Items completed: 8
  Completion rate: 67%
  Avg time to completion: 2.3 days
  Most common urgency: this_week (58%)

Step 6: Cross-Reference with Delegate and Elevate

Optionally read data/delegate/ to check if any Quadrant 3 or 4 tasks from the D&E audit are showing up as stuck stack items. This connects strategic delegation decisions to daily execution:

"Note: stack-004 'Book travel for March' relates to the Q3 task 'Travel logistics' from [person]'s D&E audit. Consider permanent delegation of this category."

Step 7: Suggest Actions

Based on the review, suggest 1-3 specific actions:

Suggested Actions:
  1. Follow up on 2 stuck items (stack-004, stack-006)
  2. Schedule the missed Wednesday daily meeting
  3. Consider delegating 'travel logistics' permanently (shows up repeatedly)

Would you like to take action on any of these?

Output Format

Stack: Brief confirmation with item ID, title, urgency, and current stack count.

Daily: Structured agenda sorted by urgency (today first), followed by pending, then in-progress. Interactive walkthrough with decisions recorded. Summary showing handoffs, completions, and new items.

Review: Dashboard-style summary with stack health, stuck items, meeting cadence, and delegation trends. Actionable suggestions based on patterns. Complete data shown before any file modifications.

Guardrails

• Always show the complete file before writing. Never create or modify a stack item or meeting log without showing the content and getting approval.
• Don't auto-invoke other skills. When review results suggest creating To-Dos or running D&E, mention the option but let the user decide. Say "Would you like to create a To-Do for this?" rather than doing it automatically.
• Sensitive data warning. On first use in a session, remind the user: "Assistance Track data includes delegation details and daily meeting notes. This repo should be private."
• Respect the batch discipline. Don't encourage adding items AND immediately handing them off. The point of The Stack is to batch — items should generally wait for the next daily meeting to be handed off. Exception: today urgency items may warrant immediate handoff.
• Don't micromanage the assistant. Once an item is handed_off, trust the assistant. The Review mode flags stuck items, but the daily meeting is for status checks, not detailed oversight.
• One leader-assistant pair per session. If the organization has multiple leaders with assistants, each session should focus on one relationship. Ask which pair at the start if ambiguous.
• Stack IDs are permanent. Once a stack-NNN ID is assigned, it's never reused, even if the item is completed or deleted. This ensures meeting logs always reference valid IDs.

Integration Notes

Accountability Chart (ceos-accountability)

• Direction: Read
• What data: data/accountability.md — seat names, owners, reporting relationships
• Purpose: Identifies the leader-assistant relationship. The assistant is typically the person in a seat with assistant-type responsibilities (Executive Assistant, Office Manager) who reports to the leader. If the accountability chart doesn't define this clearly, the user specifies the relationship.

Delegate and Elevate (ceos-delegate)

• Direction: Read
• What data: data/delegate/firstname-lastname.md — quadrant assignments, delegation progress
• Purpose: Review mode cross-references stuck stack items with Q3/Q4 tasks from D&E audits. Recurring stack items in the same category may indicate a task that should be permanently delegated rather than repeatedly stacked. This connects strategic delegation decisions to daily operational execution.

To-Dos (ceos-todos)

• Direction: Related
• What data: data/todos/ — actions from the daily meeting can be promoted to tracked To-Dos via ceos-todos
• Purpose: Some items from the daily standup may need formal tracking with due dates and completion rates beyond the stack's simpler lifecycle. Currently stored as action items in the meeting log.

Write Principle

Only ceos-assistance writes to data/assistance/. Other skills may reference assistance data for delegation context, but do not modify stack items or daily meeting logs.