# Onboarding — Marketing Skill for AI Agents

User onboarding works when you get someone to their "aha moment" — the action that most correlates with retention — as fast as possible, then build a habit around it. Start by defining that activation event (create first project, install tracking and see a report, complete first transaction), remove every step between signup and value, and give each session one clear goal instead of a feature tour. Use a 3-7 item onboarding checklist ordered by value with the quickest win first, treat empty states as guided first actions rather than dead ends, and coordinate trigger-based emails to pull people back. Then measure activation rate, time-to-activation, and Day 1/7/30 retention, and fix the biggest funnel drop-off first.

> Maintained by Corey Haines · v2.0.0 · Updated 2026-05-13

Install: `npx skills add coreyhaines31/marketingskills`
Source: https://github.com/coreyhaines31/marketingskills/tree/main/skills/onboarding

## When to use it

- "onboarding flow,"
- "activation rate,"
- "user activation,"
- "first-run experience,"
- "empty states,"
- "onboarding checklist,"
- "aha moment,"
- "new user experience,"

## What's inside

**The playbook covers:** Initial Assessment, Core Principles, Defining Activation, Onboarding Flow Design, Multi-Channel Onboarding, Handling Stalled Users, Measurement, Output Format, Common Patterns by Product Type, Experiment Ideas, Task-Specific Questions

### Reference library

- [Onboarding Experiment Ideas](https://github.com/coreyhaines31/marketingskills/blob/main/skills/onboarding/references/experiments.md) — Comprehensive list of A/B tests and experiments for user onboarding and activation.

## Example

**Prompt:** Help me optimize our onboarding flow. We have a project management tool and only 30% of trial users create their first project within the first week. We need to get them to value faster.

**Onboarding checklist (design collaboration tool)**

Get set up — 5 quick steps
▓▓▓░░ 40% complete

[✓] Upload your first design  (30 sec — quickest win)
[✓] Add a project name
[ ] Invite a teammate
[ ] Leave a comment on a design
[ ] Share a review link

Ordered by increasing commitment. Dismissable anytime.
Confetti + "You're all set!" on completion.

## FAQ

### What is a user's "aha moment" and how do I find it?

It's the action that correlates most strongly with long-term retention — the point where a user "gets it." Find it by comparing what retained users do that churned users don't, and looking for the earliest signal of future engagement. Examples: a project tool's aha is creating a first project and adding a teammate; an analytics tool's is installing tracking and seeing a first report.

### How many steps should an onboarding checklist have?

Three to seven items — enough to guide, not so many they overwhelm. Order them by value with the quickest win first to build momentum, show a progress bar or completion percentage, celebrate completion, and always include a dismiss option so users aren't trapped.

### Users sign up but never come back — what do I do?

Treat it as a stalled-user problem, not a signup problem. Audit the first session for friction or missing value, then add multi-channel recovery: trigger-based emails (welcome, then incomplete-onboarding nudges at 24h and 72h), in-app "pick up where you left off" prompts, and personal outreach for high-value accounts. Fix the biggest first-run drop-off before adding new features.

## Related skills

- **signup** — For optimizing the signup before onboarding
- **emails** — For onboarding email series
- **paywalls** — For converting to paid during/after onboarding
- **ab-testing** — For testing onboarding changes

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Canonical: https://marketing-skills.com/skills/onboarding