Why Your Devs Hate Documentation (And What Smart Teams Are Doing Instead)

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A former colleague told me this week that their dev team is planning to hire a technical writer.

Because “devs don’t like writing documentation.”

Sounds logical, but the problem runs deeper.

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The Real Problem Isn’t Writing Docs. It’s the System.

Let me guess what your setup looks like:

• Some documentation is in Notion

• Some in Jira

• A few Google Docs floating around

• And the rest? It’s in Slack threads, tribal knowledge, or gone with the last dev who left.

So now your senior devs are constantly asked:

“Where’s the API for X?”
“Is this endpoint rate limited?”
“What’s the auth flow for the new version?”

It’s not that developers hate documentation.

They hate writing the same answers 20 times.

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Why Hiring a Technical Writer Might Backfire

Most teams think hiring a dedicated writer will clean things up. Here’s what usually happens instead:

1. They document the current mess

2. That doc is outdated within 2 weeks

3. Devs still get asked the same questions

You’ve just created a second layer of documentation hell.

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What Smart Teams Are Doing Instead

We helped a remote product team across Lagos, London, and NYC go from “Where’s the payment API?” to a Slack/Teams bot answering that in 30 seconds.

Here’s the transformation:

Phase 1: Systems Audit

• Scan all GitHub repos for undocumented APIs

• Categorize endpoints by usage (Auth, Payments, etc.)

• Interview tribal knowledge holders

Phase 2: AI-Powered Documentation

• Auto-generate API docs from code comments and structure

• Add smart search: “Show me all endpoints with rate limits”

• Create onboarding templates based on roles

Phase 3: Workflow Integration

• Integrated with Slack and internal dashboards

• Added auto-updating triggers when code changes

• Built role-specific onboarding flows

Results:

• New dev productivity: Day 2 instead of Week 6

• Internal support tickets: down 87%

• Docs update automatically, no “writer” needed

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The Principle: Automate Repetition, Not Just Documentation

If a process happens twice, it gets documented or automated.
— WeAreQuest Operating Principle #1

Stop hiring people to patch a broken process.
Start fixing the system so you don’t need the patch.

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Want To See How This Could Work For You?

If your dev team is still searching Slack for API URLs…

If your PM is becoming an accidental technical writer…

If onboarding takes weeks instead of days…

You don’t need a better Notion doc.
You need a system that eliminates the confusion.

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To Get Started

• Take our AI Readiness Assessment
  You’ll get:

  • A free audit

  • Automation opportunities

  • A system improvement roadmap

Then we can decide if a call makes sense.

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Want to See What a 30-Day AI Transformation Looks Like?

We don’t do vague calls or generic sales pitches.

Instead, we start with a quick diagnostic that uncovers:

• What’s broken in your current systems

• What can be automated right now

• How far you are from being AI-ready

Start with the 5-Minute AI Readiness Assessment
We’ll send back a free audit, and if it makes sense, we’ll book a call.
👉 Take the Assessment

Already filled it out?
👉 Book a 30-Minute Readiness Call

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Questions? Reach out anytime: ship@wearequest.co

🏴 Your success is our quest
⚡ Ship Different. Scale Different. Win Different.
Follow for more: LinkedIn | Twitter

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Written by Usman Alabura, Founder of WeAreQuest — helping lean teams accelerate with AI systems, not just tools.