Have you ever gotten yourself into a tight spot because you were asking too many questions? Or, just asking the wrong one question?

Welcome to the club.

I was got sucker punched by a drunk guy that I thought was my friend, because I asked if he was seriously that mad about someone else having wronged him.

What a guy.

Something that I’ve heard repeated from some of the smartest people I’ve had the privilege to listen to or read. Are often advocates for asking not more, but, better questions.

Why are you so upset at Steve for saying those things about you? Would have been better than getting between him and Steve and asking if he was really that pissed off at him.

For me, I come across a gem of a question and never do anything with it…except admire it.

I finally put a file together for better questions.

Here are a few that I’ve added:

• What do you want to stand for?
• What are y our principles and values?
• What is your single responsibility in oreder to reach your current target?

Some people call them notes. Some people call it a swipe file. I just called it a file.

I’m cataloging those questions that make me do a double take. They’re the questions that stand out to me.

I can’t tell you how many ties I’ve listened to Fim Ferriss’s podcast and heard a guest compliment him on the question he just asked…those are gold nuggets.

Will I be the next T-Ferriss? No, no I will not.

But I can learn from him. I can learn from him and any of the other podcaster, youtuber, authors, whoever I care to pay attention to.

Learning isn’t just consuming what they’ve created. You’ve got to pay close attention to what they’re saying and doing. And ask yourself why?

Why is Ryan Holiday such a prolific author? What type of questions does Tim use to really dig deep with his guest? How do those questions differ from first time guests to friends?

Truth be told, those aren’t great questions! They could use some work, some refining, and some practice.

At least I’m aware that I ask shallow and easy questions more often than not. But I know that I’m capable of getting deeper and learning more about them with my questions.

I think the biggest impediment to asking good questions is not being boring.

Not all informative questions are good, but all good questions are informative.

How can you ask better questions?

Here’s how:

1. Listen to what they’re telling you. You have to pay attention to what they’re saying in order for you to respond with a question based on their reality.
2. You have to practice going with the flow. Sometimes, these great questions are diminished by injecting them at points in a natural conversation where it just fucks up the flow of everything.
3. Borrow questions from the pro’s. There is no shame in asking someone a question you picked up elsewhere, and there is no shame asking multiple people the same question. You’ve got to experiment to see what’s going to work.
4. Be specific. Don’t be too broad in your questioning. The more specific and narrow you’re able to direct your question, the easier for your guest to answer.