Techniques to Asking Useful Questions

Which leads to better communication? Hacking our listening or questioning skills? The latter.

Wait, what?

“Creativity is problem formulation.” Murray Gell-Mann.

Let’s think about it. Useful questions come from clear listening, empathy, the alchemy of analysing and intuiting, self control, patience, curiosity … Practice asking questions is a ultimate compound exercise. It trains a bunch of communication “muscle groups.” It is the “burpees” of communication workouts.

With that, I would like to share a tested practice to better questioning. I call it S.T.A.R.T. 

You can practice S.T.A.R.T. in any conversation you might have with your team, your boss, your kids, yourself, real and or imaginary. 

What is it?

S.T.A.R.T. = 

S= Shut up

T= Think

A= Ask


T= Talk

– You shut up and listen. 

– How can I keep my mouth shut longer? Think about what the other person is saying. 

– What should I be thinking about? Start with what questions to ask.

– Then ask the question.

– Repeat, meaning shut up and think of what questions to ask. 

– Ask another question.

– Good job, now you can talk.

Why this works?

First, it’s guaranteed to reduce your speaking time, which is foundational in improving you chances of becoming a better conversationalist. Some other hacks suggest you to “listen more” and “speak less.” That isn’t helpful because the approach is vague and the impact is inaccurate.

Second, S.T.A.R.T. is meant to be contrarian and obnoxious, so you won’t forget it. If S.T.A.R.T. does not work for you, instead of S= shut up, feel free to spice it up: Shut the XXXX up, shut that hole in your ….

Third, it is structured in a way that you can tweak it and make it work for you. Some people write it down on a stickie note. Some find emojis work better 🙊🤔🙋🏼‍♂️. Or, bring a pen and notebook with you, and draw this before every single conversation:

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Lastly, pay close attention to how you fumble and when you are successful, and review often. Some people learn faster when they conduct postmortem self-talks. Some find reflecting with another person revelatory. You should have a robust review mechanism. Experiment and discover what works best for you. 

Bottom Line:

Do the work. Practice this as often as you can. If you believe baking more muffins will make you a better muffin baker, then I shouldn’t need to convince you that asking more useful questions will make you a better useful question asking person.

What else do you need before we start? 🙊🤔🙋🏼‍♂️🔁🗣

Tell me how it goes after 5 days.