bradfeld/ceos/ceos-delegate

ceos-delegate

Categorize a leader's tasks and responsibilities into the Delegate and Elevate 4-quadrant matrix based on enjoyment and competency. Identify what to keep, what to delegate, and create action plans for handing off work that doesn't belong in the leader's "Love It / Great At It" quadrant.

Not for: People evaluation (use ceos-people), organizational structure (use ceos-accountability), or performance conversations (use ceos-quarterly). Delegate and Elevate is a leadership development tool — it helps leaders focus on their highest and best use, not assess fit or performance.

When to Use

• "Run delegate and elevate for [person]" or "delegation audit"
• "What should I be delegating?" or "am I doing the right work?"
• "Review delegation progress" or "how's [person]'s delegation going?"
• "Create a delegation plan" or "help me hand off these tasks"
• "What's in my bottom quadrants?" or "show my D&E results"
• "Time for a delegation audit" or "let's do delegate and elevate"
• Any discussion about task delegation, leadership focus, or highest-and-best-use

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

Delegate File Format

Each person has a markdown file at data/delegate/firstname-lastname.md with YAML frontmatter:

person: "Brad Feld"
seat: "Visionary"
date: "2026-02-15"
status: active            # active | reviewed | stale
quadrant_counts:
  love_great: 5           # Love It / Great At It — keep
  like_good: 3            # Like It / Good At It — delegate when possible
  not_like_good: 4        # Don't Like It / Good At It — delegate soon
  not_like_not_good: 2    # Don't Like It / Not Good At It — delegate immediately
delegation_progress:
  delegated: 3            # Tasks successfully delegated
  total: 6                # Total tasks in bottom two quadrants
  percent: 50
last_reviewed: "2026-02-15"

File naming: firstname-lastname.md — lowercase, hyphenated. Person-centric (survives role changes).

The Four Quadrants

The goal is to spend 80%+ of time in Quadrant 1. Tasks in Quadrants 3 and 4 drain energy and often become bottlenecks because the leader delays or underperforms them.

Status Values

Process

Mode: Audit

Use when running a Delegate and Elevate audit for a specific person. This is typically done 1-2x per year per leadership team member.

Step 1: Identify the Person

Ask for the person's name. Check if data/delegate/firstname-lastname.md already exists.

• Exists: Read the file, show current quadrant distribution: "You have an existing audit from [date]. Re-audit (start fresh) or update (add/move tasks)?"
• New person: Will create from templates/delegate.md

Step 2: Pull Context from Accountability Chart

Read data/accountability.md to find the person's seat(s) and their 5 key responsibilities per seat.

• Has a seat: Display responsibilities as a starter list: "Based on the Accountability Chart, here are [person]'s seat responsibilities. We'll use these as a starting point — you can add, remove, or modify."
• Multiple seats: Display all seats grouped separately: "Seat 1: [name] — [5 roles]. Seat 2: [name] — [5 roles]."
• No seat found: Warn: "[Person] has no seat defined in the Accountability Chart. List their tasks/responsibilities manually."

Optionally check data/people/firstname-lastname.md for additional context (GWC assessment, current status). Don't display unless relevant — this is about tasks, not performance.

Step 3: List All Tasks and Responsibilities

Walk the user through building a complete task list. Start with the seat responsibilities from Step 2, then expand:

"Beyond seat responsibilities, what else does [person] spend time on? Think about:

• Recurring meetings they run or attend
• Administrative tasks (email, reports, approvals)
• Projects they're leading or contributing to
• Tasks they've inherited or picked up informally
• Things 'only they can do' (real or perceived)"

Collect tasks as a numbered list. Aim for 10-20 tasks total. If the user lists fewer than 8, prompt: "Leaders typically have 12-20 distinct responsibilities. Are there tasks you're forgetting?"

Step 4: Categorize Each Task

For each task, ask two questions:

1. Enjoyment: "Do you love doing this, like it, or not like it?"
2. Competency: "Are you great at this, good at it, or not good at it?"

Map the answers to quadrants:

Batch processing: For efficiency, present 3-5 tasks at a time rather than one by one. Display a table and let the user categorize in batches.

Step 5: Display Quadrant Distribution

After all tasks are categorized, show the summary:

Delegate and Elevate — [Person Name]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 
Quadrant Distribution:
 
| Quadrant | Count | % | Action |
|----------|-------|---|--------|
| Love It / Great At It | 5 | 36% | Keep |
| Like It / Good At It | 3 | 21% | Delegate when possible |
| Don't Like It / Good At It | 4 | 29% | Delegate soon |
| Don't Like It / Not Good At It | 2 | 14% | Delegate immediately |
 
Total tasks: 14
Quadrant 1 focus: 36% — Target: 80%+
Tasks to delegate: 6 (43% of total)

Step 6: Identify Delegation Priorities

Highlight the bottom two quadrants with urgency:

🔴 Delegate Immediately (Q4):
  1. [Task] — Not good at it, doesn't enjoy it. Bottleneck risk.
  2. [Task] — Energy drain and quality risk.
 
🟡 Delegate Soon (Q3):
  1. [Task] — Competent but draining. Find someone who loves it.
  2. [Task] — Good at it but resents it. Delegate before burnout.
  3. [Task] — High skill, low passion. Perfect for a rising team member.
  4. [Task] — Taking time from Q1 work.

Step 7: Save the File

Show the complete file before writing. Ask: "Save this Delegate and Elevate audit?"

Write to data/delegate/firstname-lastname.md using the template. Update:

• YAML frontmatter: quadrant counts, delegation progress (total = Q3 + Q4 count, delegated = 0)
• Markdown body: populate all four quadrant tables with tasks
• Audit History: add dated entry

Mode: Review

Use when reviewing Delegate and Elevate results across the team or for a specific person.

Step 1: Read All Delegate Files

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

If no files exist: "No Delegate and Elevate audits found. Run an Audit for your first team member."

Step 2: Display Summary Table

Delegate and Elevate — Team Overview
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 
| Name | Seat | Last Audit | Q1 | Q2 | Q3 | Q4 | Delegation % | Flag |
|------|------|------------|----|----|----|----|-------------|------|
| Brad Feld | Visionary | 2026-02-15 | 5 | 3 | 4 | 2 | 50% | |
| Sarah Chen | Integrator | 2026-01-10 | 8 | 2 | 1 | 0 | 100% | |
| Mike Torres | VP Sales | 2025-09-15 | 3 | 4 | 5 | 3 | 25% | 📅 Stale |
 
Team averages:
  Q1 focus: 53% — Target: 80%+
  Delegation completion: 58%

Step 3: Track Delegation Progress

For each person, parse their delegate file for "Delegated?" column values:

• Count tasks in Q3 and Q4 that are marked as delegated
• Calculate delegation progress percentage
• Compare to last review if multiple audit history entries exist

Delegation Progress — [Person Name]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 
  Delegated: 3 / 6 tasks (50%)
  ████████████░░░░░░░░░░░░ 50%
 
  Completed delegations:
  ✓ [Task A] → [Person X] — Done
  ✓ [Task B] → [Person Y] — Done
  ✓ [Task C] → [Person Z] — Done
 
  Remaining:
  ○ [Task D] — No owner assigned yet
  ○ [Task E] — Training in progress
  ○ [Task F] — Not started

Step 4: Flag Stale Audits

Check last_reviewed date for each person. If > 120 days ago:

"📅 [Person]'s audit is [N] days old. Consider re-running before the next Quarterly Planning session."

Step 5: Quadrant Trends

If a person has multiple audit history entries (from re-audits), show the trend:

Quadrant Trend — [Person Name]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 
| Date | Q1 | Q2 | Q3 | Q4 | Q1 % |
|------|----|----|----|----|------|
| 2025-08-15 | 3 | 4 | 5 | 3 | 20% |
| 2026-02-15 | 5 | 3 | 4 | 2 | 36% |
 
Direction: Improving (+16% Q1 focus)

Step 6: Drill Down

Ask: "Want to view details for a specific person, or run a new Audit?"

Mode: Plan

Use when creating a concrete delegation plan for tasks in the bottom two quadrants.

Step 1: Select Person and Load Audit

Ask for the person's name. Read data/delegate/firstname-lastname.md.

If no audit exists: "No audit found for [person]. Run an Audit first to identify tasks for delegation."

Step 2: Review Delegation Candidates

Display tasks from Quadrants 3 and 4 that haven't been delegated yet:

Tasks Ready for Delegation — [Person Name]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 
🔴 Delegate Immediately (Q4):
  1. [Task A] — Not good at it, doesn't enjoy it
 
🟡 Delegate Soon (Q3):
  2. [Task B] — Good at it but draining
  3. [Task C] — Competent but would rather not
 
Which tasks would you like to create delegation plans for? (all / select by number)

Step 3: Collect Delegation Details

For each selected task, ask:

1. Who to delegate to? — Check Accountability Chart for candidates in related seats. Suggest if possible: "Based on the org chart, [Person X] in [Seat Y] might be a fit. Or name someone else."
2. Training needed? — "Does the delegate need training? If yes, what specifically?"
3. Timeline: — "When should this delegation be complete? (e.g., 2 weeks, end of quarter)"

Step 4: Create Action Plan

Build the delegation plan in the delegate file:

Delegation Plan
━━━━━━━━━━━━━━