For Better Conversations, Ask Shorter Questions

A post-it pad with short questions like 'Why not?' and 'How so?' next to a larger post-it with a long and rambling question written on it?

Which one makes you think too hard?

A long query exposes your worries and cuts off possibilities

If you want to stop getting in your own way, you need to start asking shorter questions.

Too often we try to guide things, direct the answers, and control the situation. We over-explain in our questions and sometimes even pack an array of possible responses in them, too!

I hear it in podcasts all the time, but also in everyday conversations.

The most engaging, free-flowing, and balanced interactions often include short, open-ended questions, such as:

  • Why is that?

  • Meaning what?

  • How so?

  • And if?

You too?

If you’re feeling a bit exposed by this, don’t worry, I’m calling myself out as well. It’s a life-long struggle and I’m still working on it every day.

Lately, I’ve been catching myself in the middle of a long query spin-out. I’m still working on stopping.

Regardless, when the long-winded inquisition happens, I spot something else, too.

Where’s that from?

What I notice is that when I’m lobbing an unweildy question at someone, it’s usually coming from a place where I’m worried about their response.

What’s that about?

The long, specific question is a preventative measure to control the response or frame the narrative. There may be good reasons for this. It may be unnecessary.

So then I ask myself, “Why is that?”

In three words, this follow-up question digs deep into intentions and values. It seeks to understand my desire to direct things. It targets the insecurity or perhaps unmet need.

That’s a good thing.

Because with the answer comes awareness, which is the start of letting go of old ways that no longer serve us.

And the point?

Long questions with limited options built in can lead us into a constrained way of thinking. This can close off possibilities, unnecessarily steer the conversation, and curtail creativity.

Shorter questions widen the enquiry.

Try this in your next conversation, writing prompt, or other question-asking opportunity.

What do you notice?


A version of this article was first published at Medium on Sep 27, 2023.

Kim Witten, PhD

Kim is a Transformational Coach, Business Consultant and Experience Designer who helps people make better sense of what they do. Gain clarity and actionable insights to help you achieve your goals and make a huge impact in all areas of your life and work.

https://witten.kim
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