Ask the Killer Question: Leading Opponents Into Their Own Trap
9 min read · Technique 9 of 12
Socrates never told anyone they were wrong. He asked questions. Simple, innocent-seeming questions that led his opponents step by step into contradictions they could not escape. Two thousand years later, skilled debaters still use the same technique. The killer question does not attack. It invites the opponent to defeat themselves.
Mehdi Hasan writes extensively about questioning techniques in "Win Every Argument." The best questions are not requests for information. They are traps. They appear neutral or even friendly, but the answer, any answer, exposes a weakness in the opponent's position.
The Question Arsenal
Mehdi Hasan identifies several types of devastating questions:
The Contradiction Question
Forces the opponent to choose between two positions they have taken. "You said X earlier. Now you're saying Y. Which is it?" There is no good answer.
Example: "You claim to support small businesses, but you voted for the tax increase that hurt them most. How do you reconcile that?"
The Yes-or-No Question
Demands a simple answer that damages the opponent either way. Both yes and no lead to uncomfortable territory.
Example: "Did you know about the risks before you approved it? Yes or no." (Yes means negligence. No means incompetence.)
The Hypothetical Question
Creates a scenario that exposes the logical conclusion of the opponent's position. "If that's true, then wouldn't it also mean that...?"
Example: "If privacy doesn't matter because you have nothing to hide, would you share your browser history with us right now?"
The Clarifying Question
Appears innocent but forces the opponent to elaborate on a weak point. "I want to make sure I understand. You're saying that... is that correct?"
Example: "Just so I'm clear: your position is that climate scientists worldwide are all part of a conspiracy. Is that what you're claiming?"
"A good question, asked in the right way, at the right moment, can be more devastating than any statement. It puts the burden of proof on your opponent and exposes their weaknesses."- Mehdi Hasan, "Win Every Argument"
The Strategic Advantage of Asking
Mehdi Hasan explains why questions are often more effective than statements:
Shifts the Burden
When you make a statement, you must defend it. When you ask a question, your opponent must defend their answer. You control the terrain.
Appears Reasonable
The audience sees you as curious and fair-minded, not aggressive. "I'm just asking questions" is a powerful position even when the questions are devastating.
Forces Specificity
Vague claims survive general attacks. Questions demand specific answers. "How exactly would that work?" exposes hand-waving.
Creates Self-Defeat
The best killer questions make opponents defeat themselves. They cannot blame you for their own answer. The trap is their own logic.
How DebateClub Trains the Socratic Method
Crafting killer questions under pressure is difficult. You need to listen carefully, identify the weak point, formulate the question, and deliver it naturally. DebateClub builds this skill through structured practice:
Killer Question Training Pipeline
┌──────────────────────────────────────┐
│ PREP: QUESTION BANK │
│ │
│ Your prep materials include │
│ pre-crafted killer questions: │
│ │
│ • Questions targeting likely │
│ opponent arguments │
│ │
│ • Yes/no traps for key claims │
│ │
│ • Hypotheticals that expose │
│ logical conclusions │
│ │
│ Each includes the setup: "Use when │
│ opponent claims X" │
└──────────────┬───────────────────────┘
│
▼
┌──────────────────────────────────────┐
│ DURING DEBATE │
│ │
│ Your AI opponent creates openings: │
│ │
│ • Makes claims with obvious holes │
│ that questions can expose │
│ │
│ • Takes contradictory positions │
│ you can trap with questions │
│ │
│ • Overreaches in ways that invite │
│ clarifying questions │
│ │
│ Quick Reference keeps your │
│ prepared questions accessible │
└──────────────┬───────────────────────┘
│
▼
┌──────────────────────────────────────┐
│ POST-DEBATE ANALYSIS │
│ │
│ Your coaching evaluates: │
│ │
│ • Did you use questions effectively │
│ to expose weak points? │
│ │
│ • Did you ask or just assert? │
│ │
│ • Were there opportunities for │
│ killer questions you missed? │
│ │
│ • Did you follow up on weak answers │
│ or let opponents off the hook? │
└──────────────────────────────────────┘The Art of the Follow-Up
A killer question is only as good as your follow-up. When opponents evade, you must press. Mehdi Hasan emphasizes persistence:
Follow-Up Techniques
Restate the question: "I notice you didn't answer my question. Let me ask it again..."
Name the dodge: "That's an interesting point about something else. But I asked about X. Can you address that specifically?"
Escalate gently: "I've asked three times now. Is there a reason you won't answer?"
Let silence work: After asking, wait. Do not fill the silence. The pressure to respond grows with each second.
The follow-up is where many debaters fail. They ask a great question, get a non-answer, and move on. The audience notices. The opponent escapes. Persistence is what makes the question land.
The Killer Question in Action
Here is how a well-crafted question sequence works:
"We can't afford to raise the minimum wage. It will hurt small businesses."
"At what dollar amount do you believe a full-time worker should be able to afford basic necessities?"
(Forces them to either name a number they must defend or refuse to answer, which looks evasive.)
"If businesses can only survive by paying workers less than a living wage, should taxpayers subsidize those businesses through food stamps and housing assistance for their employees?"
(Exposes the hidden subsidy in low wages. Either answer is uncomfortable.)
"You mentioned small businesses. Can you point to a single state that raised its minimum wage and saw widespread small business closures as a result?"
(Demands evidence they likely do not have. Exposes assertion without support.)
What Changes After Practice
After practicing the Socratic method across multiple debates, you will notice:
Faster Pattern Recognition
You start hearing weaknesses as opponents speak. Questions form in your mind before they finish their sentence.
Natural Delivery
Your questions stop sounding rehearsed. They flow from the conversation even when you prepared them in advance.
Persistence Instinct
You stop accepting non-answers. The follow-up becomes automatic, not awkward.
Control of Pace
Questions let you set the tempo. You decide what gets discussed and what gets exposed.
The Bottom Line
Socrates understood something profound: people resist being told they are wrong, but they cannot escape their own logic. A well-crafted question leads opponents into contradictions of their own making. They defeat themselves.
DebateClub trains this ancient skill for modern debates. Your prep includes pre-crafted killer questions. Your AI opponent creates openings for you to use them. Your analysis evaluates whether you asked effectively or let opponents escape.
Don't tell them they're wrong. Ask the question that makes them prove it themselves.
Ready to Master the Killer Question?
Get prepared questions for your next debate and practice leading opponents into their own contradictions.
Start Practicing