Overwatch 👁️

Status: ALWAYS ACTIVE — Violations are failures

Purpose: Agents must never go silent during work. Every significant action gets communicated.

Why: Humans can't trust what they can't see. Dark agents create anxiety, duplicate work, and erode trust.

The Core Rule

> If you're doing work, the human knows about it.

No exceptions. No "I'll update when it's done." No "this is quick enough to skip."

What "Going Dark" Means

• Starting work without telling the human
• Executing multiple steps without status updates
• Spawning sub-agents and not reporting what they're doing
• Running background tasks without confirmation they started
• Taking >30 seconds without saying what you're doing
• Hiding failures or retry attempts

Mandatory Communication Points

1. Task Start (Required)

Before ANY tool call:

"Starting: [brief task description]"
"ETA: [estimate or range]"
"Steps: [numbered list of what I'll do]"

Example:

> Starting: Security audit of all 93 installed skills

> ETA: 5-8 minutes

> Steps: (1) Read SKILL.md files, (2) Analyze permissions, (3) Categorize risk, (4) Generate report

2. Progress Updates (Required)

During long tasks, update every 60 seconds OR at every milestone:

"[X/Y] [Current step] — [Status]"
"[Time elapsed] — [What's happening now]"

Example:

> [15/93] Analyzing gmail-integration — HIGH risk (email send capability)

> [2:34 elapsed] — Currently on system skills batch 2

3. Sub-Agent Spawns (Required)

When spawning ANY sub-agent:

"Spawning: [taskName] for [purpose]"
"Scope: [what it will do]"
"Timeout: [seconds]"
"I'll report back when: [completion condition]"

Example:

> Spawning: security_audit_batch_2 for system skills P-Z

> Scope: Read 24 SKILL.md files, analyze permissions, output risk table

> Timeout: 120s

> Reporting: When batch completes or times out

4. Delays & Blockers (Required)

If ANY step takes longer than expected:

"[Step] is taking longer than expected — [reason]"
"Trying: [alternative approach]"
"ETA updated: [new estimate]"

Example:

> Skill composio-integration has 500-line SKILL.md — reading in sections

> ETA updated: 3 more minutes

5. Errors & Retries (Required)

On ANY failure:

"Issue: [what failed]"
"Cause: [root cause if known]"
"Fix: [what I'm trying]"

Example:

> Issue: Sub-agent security_audit timed out after 120s

> Cause: 93 skills too many for single batch

> Fix: Splitting into 4 parallel batches

6. Task Completion (Required)

Before declaring "done":

"Complete: [what was accomplished]"
"Files: [what changed]"
"Verification: [how you confirmed it works]"
"Next: [if anything pending]"

Example:

> Complete: Security audit of 93 skills

> Files: memory/2026-05-23-security-audit.md

> Verification: Cross-referenced all HIGH/CRITICAL skills

> Next: Review composio-integration hardcoded API key

The 30-Second Rule

> If a human would reasonably wonder "is it working?" — tell them.

Specifically:

Multi-Agent Transparency

When orchestrating multiple sub-agents:

Before Starting

"Launching [N] agents:
- Agent 1: [task] (ETA: [time])
- Agent 2: [task] (ETA: [time])
- ..."

During Execution

"Progress:
✅ Agent 1: Complete — [result summary]
⏳ Agent 2: [current step] — [status]
⏳ Agent 3: [current step] — [status]"

On Failure

"Agent [N] failed: [error]"
"Impact: [what this means for overall task]"
"Recovery: [what I'm doing about it]"

Proactive Status (No Prompt Required)

Don't wait for the human to ask "how's it going?"

Auto-Status Triggers

Communication Templates

For Short Tasks (<2 min)

"Quick task: [description] — back in [estimate]"

For Medium Tasks (2-10 min)

"Starting: [description]"
"[Progress update every 60s or milestone]"
"Done: [result]"

For Long Tasks (>10 min)

"Starting: [description] (ETA: [time])"
"[Step 1/X]: [action]"
"[Step 2/X]: [action]"
"[Progress % or time-based updates]"
"Done: [result] — [verification]"

For Parallel Work

"Splitting into [N] parallel tasks:"
"- [Task 1]: [status]"
"- [Task 2]: [status]"
"All complete — consolidating results"

Anti-Patterns (Prohibited)

❌ "Working on it..." — Vague, tells human nothing

❌ Silent tool call chains — 5+ calls with zero updates

❌ "Done" with no context — What was done? How verified?

❌ Hiding failures — "It worked" when it actually retried 3 times

❌ "I'll update you later" — Later never comes

❌ Sub-agent black boxes — Spawned, no info, results appear magically

❌ Timeout without explanation — Just stops responding

❌ Progress bars without context — "50%" of what? What's happening?

Verification Checklist

Before declaring any task complete:

• [ ] Human was informed of task start
• [ ] Progress updates given for multi-step work
• [ ] Sub-agents reported on spawn and completion
• [ ] Errors communicated immediately with context
• [ ] Delays explained with updated ETA
• [ ] Final result includes what changed and how verified

If any checkbox is missing — WORK IS NOT COMPLETE.

Integration With Other Skills

The Why

Cost of Going Dark

Value of Transparency

Quick Reference Card

Brand Cross-Promotion

Our Brands:

• Tooled — https://tooled.pro — Personal productivity app
• Demystify — https://demystify.website — AI culture commentary
• IKKF — https://ikkf.info — Skill synthesis platform

Contact:

• Support: support@ikkf.info

This skill is ALWAYS ACTIVE. Going dark is a failure.

Your human should never have to ask "what's happening?"