Managers, founders & PMs · The AI Search / RAG Engineer

Chat With Your Docs

Everyone wants an AI that answers from their own documents — few teams can tell you whether it’s finding the right ones. When to trust it, what it costs, and who to hire.

Ch 1
Why the "Chat With Your Docs" Demo Lies
Nothing sells a project like watching an AI answer a hard question from your own handbook. Nothing predicts a failed launch like trusting that demo.…
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Ch 2
What a Healthy RAG Setup Looks Like
You don't need to build the pipeline — but you should recognize a working one. It has a shape, and a team that can't draw it for you probably can't…
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Ch 3
The Corpus Is the Asset
Teams obsess over which model to use. The thing that actually decides whether your assistant tells the truth is the pile of documents you point it…
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Ch 4
Retrieval Without the Math
You'll hear your team say "recall@5" and "MRR." You don't need the formulas — you need to know what question each one answers, so you can tell a…
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Ch 5
Why Your Bot Makes Things Up
"It hallucinated" is the complaint you'll hear most. Half the time the fix isn't the model at all — it's whether you told the system to answer only…
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Ch 6
Search That Actually Finds It
There are two ways to search your documents, they fail on different questions, and the teams that get RAG right usually use both. You don't need the…
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Ch 7
Measuring Whether It's Any Good
A single quality number is comforting and often a lie. The teams you can trust don't report one number — they report it broken down by the segments…
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Ch 8
When the Documents Change
Your corpus isn't a snapshot; it's a living thing that gets edited, added to, and deleted from every day. A RAG system that was accurate at launch…
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Ch 9
What It Costs — and How Not to Overpay
RAG can be remarkably cheap or shockingly expensive for the same feature, and the difference is an architecture choice your team makes early. You…
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Ch 10
Security & Privacy: The Worst Case
A RAG system is a machine that surfaces text from your documents on demand. That's the whole value — and, handled carelessly, the whole risk. The…
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Ch 11
Building a RAG Culture
The teams that ship trustworthy AI over documents don't have a secret model. They have habits — a few rituals that make quality visible and keep it…
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Ch 12
Build vs. Buy & Who to Hire
You can buy a "chat with your docs" product off the shelf or build one on your own stack, and both are right for different companies. The mistake is…
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Appendix
Hiring a RAG / AI Search Engineer
Five questions to ask candidates, what a strong versus weak answer sounds like, and a one-page scorecard. You don't need to build the system…
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Chat With Your Docs · AI Engineer Dojo · Other editions

Chat With Your Docs

Your test report card

Launching soon

Why the "Chat With Your Docs" Demo Lies

What a Healthy RAG Setup Looks Like

The Corpus Is the Asset

Retrieval Without the Math

Why Your Bot Makes Things Up

Search That Actually Finds It

Measuring Whether It's Any Good

When the Documents Change

What It Costs — and How Not to Overpay

Security & Privacy: The Worst Case

Building a RAG Culture

Build vs. Buy & Who to Hire

Hiring a RAG / AI Search Engineer