skinnyandbald/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

| File | Purpose | |------|---------| | data/delegate/ | Delegate and Elevate audit files (one per person) | | templates/delegate.md | Template for new delegation audits | | data/accountability.md | Source of seat responsibilities (read-only — use ceos-accountability to modify) | | data/people/ | People Analyzer evaluations (read-only — reference for context) |

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

| Quadrant | Enjoyment | Competency | Action | Priority | |----------|-----------|------------|--------|----------| | Love It / Great At It | High | High | Keep | — | | Like It / Good At It | Medium | High | Delegate when possible | Low | | Don't Like It / Good At It | Low | High | Delegate soon | Medium | | Don't Like It / Not Good At It | Low | Low | Delegate immediately | High |

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

| Status | Meaning | When | |--------|---------|------| | active | Current audit, delegation in progress | After initial audit or re-audit | | reviewed | Audit reviewed, delegation actions updated | After a Review or Plan session | | stale | Audit is > 120 days old | Flagged automatically by Review mode |

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:

| Enjoyment | Competency | Quadrant | |-----------|------------|----------| | Love it | Great at it | Q1: Love It / Great At It | | Like it | Good at it | Q2: Like It / Good At It | | Love it | Good at it | Q2: Like It / Good At It | | Like it | Great at it | Q1: Love It / Great At It | | Don't like it | Good/Great at it | Q3: Don't Like It / Good At It | | Don't like it | Not good at it | Q4: Don't Like It / Not Good At It |

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
━━━━━━━━━━━━━━

| Task | Delegate To | Training Needed | Timeline | Status |
|------|-------------|----------------|----------|--------|
| [Task A] | Sarah Chen | Yes — shadow for 1 week | 2026-03-01 | Not started |
| [Task B] | Mike Torres | No — already has skills | 2026-02-28 | Not started |
| [Task C] | New hire (VP Ops) | Yes — full onboarding | 2026-Q2 | Blocked (hiring) |

Step 5: Note To-Do Integration

Display: "Delegation actions saved to the delegate file. Once the ceos-todos skill is available, these can be promoted to tracked To-Dos with owners and due dates."

Step 6: Save Updated File

Show the complete updated file before writing. Ask: "Save this delegation plan?"

Update:

• YAML frontmatter: delegation_progress.total = count of Q3+Q4 tasks, last_reviewed = today
• Markdown body: populate delegation plan table
• Audit History: add dated entry for plan creation

Output Format

Audit: Quadrant distribution table with counts and percentages. Delegation priority flags (Q4 = immediate, Q3 = soon). Complete file shown before save.

Review: Summary table with all team members, quadrant counts, delegation progress %, and stale flags. Quadrant trends if multiple audits exist. Progress bars for delegation completion.

Plan: Delegation candidate list from Q3/Q4. Action plan table with delegate, training, timeline, and status. Complete file shown before save.

Guardrails

• Always show the complete file before writing. Never modify a delegate file without showing the change and getting approval.
• One quadrant per task. Each task can only be in one quadrant. If a user tries to add the same task to multiple quadrants, ask them to choose.
• Don't force delegation. Some Q3 tasks may need to stay temporarily (no one else can do them yet). Flag them but don't pressure.
• Seat responsibilities are starter prompts, not requirements. The Accountability Chart provides a starting list, but tasks can come from anywhere — meetings, informal responsibilities, inherited work.
• Don't confuse with People Analyzer. Delegate and Elevate is about tasks and leadership focus, not about whether a person is a fit. If the user seems to be evaluating a person's performance, suggest ceos-people instead.
• Sensitive data warning. On first use in a session, remind the user: "Delegate and Elevate audits contain information about leadership capacity and task ownership. This repo should be private."
• Don't auto-invoke other skills. When delegation results suggest creating To-Dos or IDS issues, mention the option but let the user decide. Say "Would you like to create a To-Do for this?" rather than doing it automatically.
• Respect the quarterly cadence. Suggest running D&E before Quarterly Planning sessions. Flag audits > 120 days old. But don't nag — once per session is enough.

Integration Notes

Accountability Chart (ceos-accountability)

• Direction: Read
• What data: data/accountability.md — seat names, owners, and 5 key responsibilities per seat
• Purpose: Provides the starter list of tasks/responsibilities during Audit mode. The seat responsibilities give structure to what might otherwise be a blank-page exercise.

People Analyzer (ceos-people)

• Direction: Read
• What data: data/people/firstname-lastname.md — GWC assessment, current status
• Purpose: Optional context during Audit. If a person is wrong_seat, their D&E audit might reveal why — they may be great at tasks outside their current seat. If below_bar, D&E can help identify whether it's a skill gap (Q4 tasks) or an energy gap (Q3 tasks).

To-Dos (ceos-todos)

• Direction: Related (future integration)
• What data: Will write to data/todos/ once CEO-14 is implemented
• Purpose: Delegation actions from Plan mode could become tracked To-Dos with owners and due dates. Currently stored as markdown checklists in the delegate file.

Quarterly Planning (ceos-quarterly-planning)

• Direction: Related
• What data: No direct data access
• Purpose: Delegate and Elevate is ideally run before or during Quarterly Planning sessions. Delegation decisions often surface during quarterly reviews when leaders assess their capacity for new Rocks.

Annual Planning (ceos-annual)

• Direction: Related
• What data: No direct data access
• Purpose: Annual planning often triggers a fresh D&E audit as leaders reassess their focus for the coming year.

Write Principle

Only ceos-delegate writes to data/delegate/. Other skills may reference delegation audits for leadership development context, but do not modify them.