The Forbidden Questions¶

Uncomfortable Reading

Why These Questions Are Forbidden¶

Some questions aren't asked because:

• They're career-limiting: Asking implies doubt, and doubt is weakness
• They're socially awkward: Everyone else seems to accept it, so who are you to ask?
• They challenge authority: The people in charge don't want them asked
• They expose uncomfortable truths: The answers might derail the project
• They're "not your lane": Someone else is supposed to worry about that
• They slow things down: We don't have time for philosophical questions

But these are precisely the questions that prevent disasters.

This document collects the questions that should be asked at every stage of an AI project—the ones that get suppressed, dismissed, or deferred until it's too late.

How to Use This Document¶

1. Before major decisions: Review relevant questions. Ask them, even if uncomfortable.
2. In meetings: When something feels off but you can't articulate why, find the question here.
3. For governance: Use as a checklist for what steering committees should be asking.
4. For onboarding: Give to new team members as permission to ask the hard questions.
5. For pre-mortems: Use to surface what's being avoided.

The Documents¶

The Meta-Questions¶

Before diving into specific questions, consider:

Why isn't anyone asking this?¶

When a question seems obviously important but no one is asking it, the silence itself is information. Ask yourself: - Is it forbidden by culture? - Is it forbidden by authority? - Is it forbidden by fear? - Is it forbidden by incentives?

Who benefits from this question not being asked?¶

Every avoided question protects someone or something: - A timeline - A budget - A reputation - A decision already made - A comfortable assumption

What would change if we knew the answer?¶

If the answer wouldn't change anything, maybe the question doesn't matter. But if the answer might change everything—why aren't we asking?

Permission Granted¶

You have permission to:

• Ask uncomfortable questions in meetings
• Request answers before proceeding
• Escalate when questions are dismissed
• Document that questions were asked (and what happened)
• Refuse to proceed without answers to critical questions
• Share this document with colleagues who need permission

The goal is not to stop projects. The goal is to ensure projects that proceed are ones that should proceed, designed by people who have asked the hard questions.

A Warning¶

Asking forbidden questions can be career-limiting. This is not theoretical—people have been marginalized, passed over, and pushed out for asking the wrong questions at the wrong time.

This doesn't mean you shouldn't ask. It means:

1. Pick your moments: Not every question needs to be asked in every forum
2. Document carefully: Keep records of what you asked and what response you got
3. Build allies: Find others who share your concerns before raising them publicly
4. Frame constructively: "I want to ensure we succeed, so I need to understand..." works better than "This is going to fail because..."
5. Protect yourself: Know your rights, know your exits, know your limits

The questions in this document are worth asking. But ask with awareness of the context you're in.

"The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function."

The test of a first-rate organization is the ability to hear uncomfortable questions and still retain the ability to function.

Most organizations fail this test.

Navigation¶

Start with before-you-start.md if you're early in a project.

Start with unspeakables.md if you're brave.

Start with about-power.md if you're cynical.

All paths lead to the same place: understanding.