A good question can cut through bullshit. A great question can teach others. Your questions are a reflection of  your mind; the easiest way to improve your thinking is to ask better questions

To ask great questions is a skill that you can teach yourself. The first step in learning this is by noticing great questions and being more present during conversations. To dig into complex arguments you have to actually listen to others. Most people don’t actually listening when they’re talking to you. Their minds are filled with thoughts – what should I say next? will I embarrass myself? what’s for lunch? They are planning their next statement, thinking about how they can appear interesting. (Most people don’t realize that the key to being interesting is to be interested in someone else).  You can’t effectively question if you’re not truly hearing what is being said.

The ability to ask an honest question (to yourself as much as to others) will pay dividends over time. When was the last time you asked yourself “what do I suck at?” or “what am I slacking on?” or any other honest reflective questioning? These questions are uncomfortable. But answering these questions will help you think critically.

“Judge a man by his questions rather than by his answers.”—Voltaire

Frameworks for asking better questions

Socratic Approach

The framework that has withstood the longest stretch of time is the Socratic approach. The general structure of Socrates’ approach to teaching was:

  1. Getting students to clarify their thinking
  2. Challenging students about assumptions
  3. Evidence as a basis for argument
  4. Alternativeviewpoints and perspectives
  5. Implications and consequences
  6. Question the question

Socratic dialogue is grounded in consistent clarification of the argument. This forces a refinement of assumptions and thinking. It’s grounded in higher order thinking, each questions move the conversation deeper.

The final step in the dialogue is to question the questions and look at the progression of your thought. (pretty meta) How did you arrive at the conclusion? Is your logic sound? 

Socrates played devil’s advocate because he saw people were getting confused in their own minds. By digging deeper into their thought process he was able to force clarity. Not everyone looks favorably upon this progression of questioning. People might see it as a personal attack on their fundamental assumptions.

“A wise man can learn more from a foolish question than a fool can learn from a wise answer.”—Bruce Lee

Inductive vs Deductive

Aristotle built upon Socrates’ approach by developing his method of inductions vs. deductions. He thought the best questions were those that asked what something is for. During his time he spent a lot of time asking What is government for? What is art for? Today he might be asking What is the news for? What is pornography for? What are drugs for? 

He would either start with a general hypothesis and work towards specific instances (deductive) or begin with a specific example and reason specific rules (inductive).

In deductive questioning Aristotle would link premises with conclusions. He would begin an argument by defining the terms and logic used, and boiling down questions into a binary outcome. If all of the premises are true, the terms are clear, and the logic is sound, then the conclusion is true. For example, Aristotle might flow the following argument:

  1. All men will die.
  2. I am a man.
  3. I will die.

This is a high level simplification of a deductive proof. Deductive reasoning links premises with conclusions. If all premises are true, the terms are clear, and the rules of logic are followed, then the conclusion reached is necessarily true.

What’s it for?

Seth Godin posted a great blog  on the questions you should ask before shipping any new marketing materials. His questions are simple to ask, but difficult to answer. But if you want your project to have a shot at success, you should have most of these answered.

  • What’s it for?
  • Who is it for?
  • What does this remind you of?
  • What’s the call to action?
  • What is the urgency?

“Question everything. Learn something. Answer nothing. Euripides
The common question that gets asked in business is, ‘why?’ That’s a good question, but an equally valid question is, ‘why not?’”—Jeff Bezos

The Five Whys

Ask yourself why. Then question the answer. Do it again. And again. And again.

Why? Why? Why? Why? Why?

It may seem simple, but by digging systematically deeper you will be able to arrive at the root cause of the problem (and maybe even a solution). This approach to questioning was critical to helping Toyota create their Production System.

“The way that you become world-class is… by asking good questions.”—Tim Ferriss

After Action Review

After shipping a project into the world (be it a marketing campaign, blog post, etc.) it is important to probe into what happened and why. These questions are simple, but nebulous. These seven simple questions can facilitate a multi hour conversation among a team. They force you to get to the root cause of why things worked (or didn’t).

  • What was supposed to happen?
  • What actually happened?
  • Why was there a difference?
  • What worked?
  • What didn’t work?
  • Why?
  • What would you do differently next time?

Mattan Griffel of OneMonth.com published this helpful template to help you guide your AAR meetings.

A final tip for asking questions

Embrace the Silence

After asking a great question don’t be afraid to hold the pause. Feel the silence and wait it out.






Someone might fill that void with something worth hearing.



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