Creating Team Training Materials from Documentation

New hire starts Monday.

You have:

• 47 Confluence pages
• 12 GitHub repos with scattered READMEs
• 3 Notion databases nobody maintains
• A Slack channel called #engineering-docs that's 90% unanswered questions

Zero time.

Good luck.

Table of Contents

• The Onboarding Documentation Nightmare
• Why Scattered Docs Fail New Hires
  • Context Switching Overload
  • No Reading Order
  • Can't Read Offline
  • No Annotation
• Building a Training PDF Stack
  • 1. Audit Your Existing Docs
  • 2. Consolidate by Topic
  • 3. Generate PDFs
  • 4. Package as Onboarding Kit
• The Framework: First Week to Ongoing
  • Day 1-2: Environment Setup
  • Day 3-5: Architecture Understanding
  • Week 2: Deep Dives
  • Week 3-4: External Knowledge
  • Ongoing: Reference Library
• Real Example: Onboarding a Fullstack Developer
• Making Docs Printable for Annotation
• Build Your Team's First Guide
  • Option 1: Dev Setup Guide
  • Option 2: Architecture Overview
  • Option 3: Your Most Complex System
• Start Today

The Onboarding Documentation Nightmare

Every engineering team has this problem:

Documentation exists. Technically.

It's just:

• Scattered across 5 different tools
• Outdated (last edited 2 years ago by someone who left)
• Incomplete (assumes you already know things)
• Unfindable (good luck searching across Confluence + Notion + GitHub)

New hire shows up. You point them at 20 links. They're overwhelmed by lunch.

By day 3, they're asking the same questions everyone else asks.

By week 2, they've developed the same workarounds everyone else has.

The docs didn't fail because they were bad. They failed because they were scattered.

Why Scattered Docs Fail New Hires

Context Switching Overload

New hire opens Confluence. Reads half a page. Link goes to GitHub. They read that. Link goes to Notion. Different login. Different interface.

They spend more time navigating than learning.

No Reading Order

Where do you start? What's important? What can you skip?

Scattered docs don't have chapters. They don't have sequence. They're a maze.

Can't Read Offline

"Take this home and review it before your first day."

Sends 20 links that require VPN access.

Cool. Very helpful.

No Annotation

New hires want to highlight. Take notes. Mark "come back to this."

You can't annotate a Confluence page. You can't highlight Notion.

Building a Training PDF Stack

Here's the fix:

Consolidate your scattered docs into structured PDFs.

One PDF for setup. One for architecture. One for workflows.

Readable in order. Annotatable. Offline-capable. Printable.

The process:

1. Audit Your Existing Docs

List everything a new hire needs to know:

• Local dev setup
• Architecture overview
• Deployment process
• Code conventions
• Key systems (auth, database, APIs)
• Team workflows (PR process, on-call)

2. Consolidate by Topic

Don't organize by tool. Organize by what they need to learn:

3. Generate PDFs

Use OfflineDocs to pull from multiple sources.

For internal docs, export to markdown first, then convert to PDF.

For external dependencies (frameworks you use), generate from the official docs.

4. Package as Onboarding Kit

New hire gets a folder:

• 01-dev-setup.pdf
• 02-architecture.pdf
• 03-our-apis.pdf
• 04-team-workflows.pdf
• 05-external-react-docs.pdf
• 06-external-postgres-guide.pdf

Read in order. Everything they need. One place.

The Framework: First Week to Ongoing

Day 1-2: Environment Setup

PDF: Dev Setup Guide

Contents:

• Machine setup (brew, node, docker)
• Repo cloning and structure
• Running locally
• Common gotchas

Goal: They can run the app locally.

Day 3-5: Architecture Understanding

PDF: Architecture Overview

Contents:

• System diagram
• Key services and their purpose
• Database schema overview
• How requests flow through the system

Goal: They understand what we built and why.

Week 2: Deep Dives

PDFs: Domain-Specific Guides

• Authentication system
• API documentation
• Payment flows
• Whatever's relevant to their role

Goal: They can work on real tickets.

Week 3-4: External Knowledge

PDFs: Framework/Tool Docs

Generate PDFs for key external dependencies:

• Your frontend framework (React, Vue)
• Your ORM (Prisma, Drizzle)
• Your infrastructure (Kubernetes, AWS)

Goal: They can reference standard docs offline.

Ongoing: Reference Library

Leave them with:

• All onboarding PDFs
• Key external docs
• Team conventions guide

They'll reference these for months.

Real Example: Onboarding a Fullstack Developer

Here's a real onboarding kit for a fullstack dev joining a React + Node.js team:

Total: ~230 pages of focused, organized documentation.

Compare that to: "Here's 47 Confluence links. Good luck."

Making Docs Printable for Annotation

Some people learn better on paper.

For onboarding, consider printing the setup and architecture guides. New hires can:

• Highlight important sections
• Write questions in margins
• Physically check off completed steps
• Keep it on their desk for reference

Cost of printing: ~$20

Value of a new hire who doesn't ask the same question five times: Priceless.

Learn more about the benefits of printed docs.

Build Your Team's First Guide

You don't need to fix everything today.

Start with the highest-friction onboarding doc:

Option 1: Dev Setup Guide

If new hires take days to get running locally, fix this first.

Consolidate your setup docs into one PDF. Test it with the next hire.

Option 2: Architecture Overview

If new hires are confused about "how things work," start here.

One PDF. System diagram. Key components. Request flow.

Option 3: Your Most Complex System

What do you explain over and over? Auth? Payments? Data pipeline?

Turn that tribal knowledge into a PDF.

Start Today

Your next new hire deserves better than "here's 47 links."

Pick one onboarding topic. Consolidate the scattered docs. Generate a PDF.

Test it with your team. Improve it. Add another.

Within a few months, you'll have an onboarding kit that actually works.

Build Your First Training Guide

Because "just ask Sarah" isn't scalable. Good documentation is.