Questioning
What question are you not asking that would change everything?
The quality of your questions determines the quality of your life. Good questions find the gap. Great questions make you see what was always there.
| Weak Question | Strong Question |
|---|---|
| "Why isn't this working?" | "What would have to be true for this to work?" |
| "Who's to blame?" | "What system allowed this?" |
| "Is this good?" | "Good for whom? Compared to what?" |
| "What should I do?" | "What am I optimising for?" |
Question Types
Different situations need different questions:
| Type | Purpose | Example |
|---|---|---|
| Open | Expand thinking | "What do you think about...?" |
| Closed | Confirm or narrow | "Did you test this?" |
| Diagnostic | Identify the problem | "Where does it break?" |
| Upstream | Find root causes | "What caused the thing that caused this?" |
| Clarifying | Remove ambiguity | "What do you mean by...?" |
| Challenging | Test assumptions | "What's the strongest case against?" |
| Generative | Create options | "What would make this remarkable?" |
Default to open. Use closed only when you need a specific answer.
The Socratic Sequence
A structured path from confusion to clarity:
1. Define → "What exactly do we mean by X?"
↓
2. Probe → "What evidence supports that?"
↓
3. Challenge → "What if the opposite were true?"
↓
4. Synthesize → "So what we're really saying is..."
Each step opens a door. Rushing to step 4 means walking through the wrong one.
Question Traps
| Trap | What It Looks Like | The Fix |
|---|---|---|
| Leading | "Don't you think we should...?" | Remove the embedded answer |
| Loaded | "Why did you fail to deliver?" | Separate the claim from the question |
| False choice | "Should we do A or B?" | Add "or something else entirely?" |
| Validation | "This is good, right?" | Ask someone who'll tell you no |
| Rhetorical | "Who would disagree with that?" | Only ask if you genuinely want the answer |
Diagnostic Questions
Every domain has questions that unlock it:
| Domain | The Unlocking Question |
|---|---|
| Product | What job is the customer hiring this for? |
| Strategy | What are we saying no to? |
| Culture | What behaviour gets rewarded that we say we don't want? |
| Sales | What's the hidden objection they won't say aloud? |
| Self | What would I do if I weren't afraid? |
Practice Protocol
- Pause before answering — Ask a question instead. Count to three.
- "What else?" — First answers are rarely complete. Always ask.
- Question your questions — Are you seeking truth or validation?
- Sit in not-knowing — Discomfort is where learning lives.
- Record your best questions — Build a library. Patterns emerge.
The Shadow
Interrogation. Questions as weapons. Never committing because there's always another question. Asking without listening to the answer.
By Archetype
| Archetype | Question Style |
|---|---|
| Coach | Questions to unlock others — "What do you really want?" |
| Philosopher | Questions to find truth — "What's the first principle here?" |
| Realist | Questions to ground — "Where's the evidence?" |
Context
- Questions — The #10 playmaker
- Listening — Hear the answer fully before asking the next
- Critical Thinking — Questioning applied to claims
- Decisions — Where questions produce clarity