bradfeld/ceos/ceos-quarterly

ceos-quarterly

Facilitate the EOS Quarterly Conversation — the formal quarterly check-in between each manager and their direct reports — or the 5-5-5, a lightweight 15-minute version. The full conversation follows a 5-point agenda (30-60 min). The 5-5-5 uses three time-boxed sections (15 min). Both are two-way conversations about alignment, role satisfaction, and obstacles — not performance reviews.

Not for: Quarterly planning sessions (use ceos-quarterly-planning), people evaluations (use ceos-people), or annual planning (use ceos-annual). Quarterly Conversations are 1-on-1 check-ins, not team-wide planning sessions.

When to Use

• "Run quarterly conversation for [person]" or "quarterly check-in with [name]"
• "5-5-5 with [person]" or "quick quarterly check-in with [name]"
• "Quick conversation with [person]" or "quick check-in"
• "Schedule quarterly conversations" or "who needs a quarterly conversation?"
• "Review quarterly conversations" or "show conversation history for [person]"
• "Quarterly one-on-one" or "manager check-in"
• Any discussion about formal quarterly conversations or quick 5-5-5 check-ins between managers and direct reports

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

Conversation File Format

Each conversation is a markdown file at data/conversations/YYYY-QN/firstname-lastname.md with YAML frontmatter:

person: "Brad Feld"
manager: "Daniel"
quarter: "2026-Q1"
date: "2026-03-15"
core_values_rating: 5       # count of + ratings out of total Core Values
gwc_status: pass             # pass | fail | evaluating
rocks_completion_rate: 80    # percentage (0-100) or null if no Rocks

File naming: firstname-lastname.md — lowercase, hyphenated. Matches the naming convention from ceos-people.

Quick Conversation File Format

Quick 5-5-5 check-ins use a separate file at data/conversations/YYYY-QN/firstname-lastname-quick.md with YAML frontmatter:

type: quick
person: "Brad Feld"
manager: "Daniel"
quarter: "2026-Q1"
date: "2026-02-14"
core_values_rating: null
gwc_status: null
rocks_completion_rate: null

File naming: firstname-lastname-quick.md — the -quick suffix prevents collisions with full conversation files. The type: quick frontmatter field distinguishes format.

Scoring fields: Always null for quick conversations. The 5-5-5 is informal — no formal ratings, pass/fail, or completion percentages.

Backward compatibility: Files without a type field are treated as full (the original format).

The 5-5-5 Format

The EOS 5-5-5 is a 15-minute check-in with three equal time-boxed sections:

Key difference from full conversation: The 5-5-5 is structured around who speaks, not topic sections. The employee gets uninterrupted time first, then the manager, then they collaborate.

Quarter Format

Quarters follow YYYY-QN format: 2026-Q1, 2026-Q2, 2026-Q3, 2026-Q4.

To determine the current quarter from today's date:

• Jan-Mar = Q1, Apr-Jun = Q2, Jul-Sep = Q3, Oct-Dec = Q4

The 5-Point Agenda

Key EOS Principles

• Every direct report gets one conversation per quarter. This is not optional — it's part of the system.
• Two-way conversation. The direct report should talk as much as the manager. It's a dialogue, not a lecture.
• Reference, don't re-evaluate. Core Values and GWC reference the People Analyzer results — this isn't a fresh evaluation. Rock completion is discussed, not re-scored.
• Document everything. The conversation is recorded and kept for future reference. Git history is the audit trail.

Process

Mode: Facilitate

Use when conducting a quarterly conversation with a specific person.

Step 1: Setup

1. Identify the person and manager. Ask for the person's name if not provided. Ask who is conducting the conversation (the manager).

1. Determine the quarter. Default to the current quarter. If near a quarter boundary, ask: "This conversation is for which quarter?"

1. Check for existing conversation. Look for data/conversations/YYYY-QN/firstname-lastname.md.

• Exists: Ask: "A conversation already exists for [person] in [quarter]. Open it to review, or start a new one?"
• New: Continue with Step 2.

1. Gather context. Read these files (silently — don't dump raw data to the user):

• data/vision.md — extract Core Values list
• data/accountability.md — find the person's seat(s) and their manager
• data/rocks/QUARTER/ — find Rocks owned by this person
• data/people/firstname-lastname.md — load People Analyzer evaluation if it exists

1. Create the quarter directory if it doesn't exist: data/conversations/YYYY-QN/

Display a brief preparation summary:

Quarterly Conversation — [Person Name]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
Manager: [Manager Name]
Quarter: YYYY-QN
Seat: [From accountability.md]
Core Values: [List from vision.md]
Rocks this quarter: [Count] ([List titles])
People Analyzer: [Status from people/ file, or "No evaluation on file"]
 
Let's walk through the 5-point agenda.

Step 2: Section 1 — Core Values Alignment

Read Core Values from data/vision.md. Display them and ask the manager to discuss how the person is living each one.

If a People Analyzer evaluation exists (data/people/firstname-lastname.md), show the most recent ratings as a reference point:

People Analyzer reference (last evaluated: 2026-01-15):
  Integrity: +
  Innovation: +/-
  Transparency: +

For each Core Value, prompt: "How is [person] living [Core Value]? Rate: +, +/-, or -"

Record ratings in the conversation file. Calculate core_values_rating as the count of + ratings.

Important: This is a reference discussion, not a re-evaluation. If the ratings differ significantly from the People Analyzer, note it: "These ratings differ from the People Analyzer. Would you like to update the People Analyzer after this conversation?"

Step 3: Section 2 — GWC

Read the person's seat from data/accountability.md. For each seat they hold, ask:

1. Get it? "Does [person] truly understand the [seat] role?" (yes/no + notes)
2. Want it? "Does [person] genuinely want to do [seat] work?" (yes/no + notes)
3. Capacity? "Does [person] have the capacity to excel at [seat]?" (yes/no + notes)

Display the result:

GWC — [Person] as [Seat]:
  Get it:     ✓ Yes
  Want it:    ✓ Yes
  Capacity:   ✓ Yes
 
  Right seat? Yes

Set gwc_status:

• All three yes = pass
• Any no = fail
• Not yet discussed = evaluating

If GWC differs from the People Analyzer, note it for follow-up.

Step 4: Section 3 — Rocks Review

Read all Rocks from data/rocks/QUARTER/ where owner matches the person.

If no Rocks found: Display "No Rocks assigned this quarter." Set rocks_completion_rate: null.

If Rocks exist, display:

Rocks — [Person], [Quarter]:
  Launch Beta Program: complete ✓
  Partner Outreach: on_track (2/3 milestones done)
  Redesign Onboarding: dropped ✗

Prompt: "How do you feel about your Rock performance this quarter? Any context on the results?"

Calculate rocks_completion_rate: (complete / total) * 100, rounded to nearest integer. Include only complete and dropped statuses in the calculation — ignore on_track and off_track (those are mid-quarter Rocks still in progress).

Important: Don't re-score Rocks here. Use the status from the Rock files. If the quarter hasn't ended yet and Rocks are still on_track/off_track, note: "Rocks are still in progress — final scoring happens at quarter end with ceos-rocks."

Step 5: Section 4 — Role Expectations

Prompt the manager and direct report to discuss:

1. Clarity: "Are the roles and responsibilities for the [seat] clearly defined?"
2. Delivery: "Is [person] meeting those expectations?"
3. Gaps: "Are there areas where expectations aren't being met — on either side?"

Record responses. This section is qualitative — no scoring.

Step 6: Section 5 — Feedback Both Ways

This is the most important section. Both sides share openly.

Manager → Direct Report:

• "What's working well about [person]'s performance?"
• "What needs improvement?"

Direct Report → Manager:

• "What's working well about your relationship with your manager?"
• "What do you need from your manager that you're not getting?"

Record both sides. Emphasize that this is a dialogue.

Step 7: Action Items

Ask: "What action items come out of this conversation?"

Record 1-3 specific, actionable items with owners.

Step 8: Save the Conversation

1. Show the complete conversation file before writing.
2. Ask: "Save this quarterly conversation?"
3. Write to data/conversations/YYYY-QN/firstname-lastname.md.
4. Update frontmatter: core_values_rating, gwc_status, rocks_completion_rate, date.
5. Remind: "Run git commit to save the conversation."

If the People Analyzer ratings differed, offer: "Would you like to update the People Analyzer for [person]? This would update data/people/firstname-lastname.md."

Mode: Quick

Use for a 5-5-5 quick check-in — a lightweight 15-minute conversation between a manager and a direct report. Triggered by phrases like "5-5-5 with [person]", "quick quarterly check-in", or "quick conversation with [person]".

Step 1: Setup

1. Identify the person. If not specified, ask: "Who is the 5-5-5 with?"
2. Determine the quarter. Default to the current quarter.
3. Check for existing quick file. Look for data/conversations/YYYY-QN/firstname-lastname-quick.md.

• If exists: Warn: "A 5-5-5 already exists for [person] this quarter. Overwrite, or open the existing one?"

1. Gather context (read these files, continue if any are missing):

• data/vision.md — Core Values list
• data/accountability.md — Person's seat and reporting structure
• data/rocks/YYYY-QN/ — Person's Rocks for the quarter
• data/people/firstname-lastname.md — Latest People Analyzer evaluation (if exists)

1. Display prep summary: