First Contact

First-Run Red Team

Use this skill to attack the first 5-15 minutes of the product experience.

A first-run red team is about finding where a new user:

• gets confused
• hesitates
• grants a permission without understanding it
• denies a permission and never recovers
• thinks the app is broken
• never reaches the promised “aha” moment

When to Use

Use this skill when reviewing:

• install flow
• onboarding
• permission requests
• setup checklists
• first successful action
• first failure recovery
• menu bar or background apps where state is easy to miss

Core Principle

The first-run experience fails when the product asks the user to do too much, trust too much, or infer too much before value is obvious.

Step 1: Map the first-run path

Build a minute-by-minute path from:

• discovery / install
• launch
• first window or menu
• setup tasks
• permission prompts
• first success moment
• first screenshot / first sync / first alert / first rename / first whatever the product does
• first failure state and recovery

If there are multiple likely paths, audit the default path first.

Step 2: Simulate multiple user mindsets

At minimum, simulate these personas:

• In a hurry — wants value in under 2 minutes
• Skeptical — suspicious of permissions, billing, AI, or privacy
• Normal but inattentive — will miss subtle text and icon changes
• Slightly unlucky — hits one bad edge case early

For each persona, walk the path step by step.

Step 3: Find first-run failure points

Look for:

• unexplained permissions
• unclear prerequisites
• too many decisions too early
• jargon, hidden defaults, or settings that matter more than they look
• moments where the app appears idle or dead
• weak proof that setup succeeded
• confusing recovery after a denial, skip, or transient failure
• ways an early failure poisons the user’s mental model permanently

Step 4: Score the friction

For each failure point, include:

• Moment
• What the user is trying to do
• What blocks or confuses them
• Likely user interpretation
• Abandonment risk — low/medium/high
• Recovery quality — good/weak/bad
• Fastest fix — product / copy / diagnostics / state visibility / defaults

Step 5: Present the walkthrough

Use this format:

# First-Run Red Team: [Product / Feature]

## Executive Read
- First-run step most likely to lose the user:
- Permission moment most likely to fail:
- Moment where the app most likely looks dead:
- Fastest improvement to lift activation:

## First-Run Timeline
1. [step]
2. [step]
3. [step]

## Failure Points

### 1. [Title]
**Moment:**
**User goal:**
**What goes wrong:**
**Likely interpretation:**
**Abandonment risk:**
**Recovery quality:**
**Fastest fix:**

## Persona Notes
### In a hurry
- ...
### Skeptical
- ...
### Normal but inattentive
- ...
### Slightly unlucky
- ...

## Activation Killers
- [issue]
- [issue]
- [issue]

## Highest-Leverage First-Run Fixes
1. [ ]
2. [ ]
3. [ ]

Success Criteria

The red team is complete when it identifies:

• where the user is most likely to bail
• where the app most likely looks broken or suspicious
• where a denied permission or skipped step becomes unrecoverable
• the smallest changes that would materially improve activation

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: carlkibler
• Source: carlkibler/agent-skills
• License: MIT

Install and usage instructions live in the source repository linked above.