How to have interesting conversations using the process of creativity

Jane Harbison
6 min readMay 6, 2021

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Have you had your child ask you a question to something that is so mundane and everyday, that you should know the answer to, but you have no idea what it is?

Like this from my 4 year old son recently, when we were pulling out of the driveway.

“Mum why do you push the gear stick forward to reverse and pull it back to go forward?”

“That is a very good question Harry. I don’t really know.”

And on reflection it was something that I do everyday, but I don’t even question it. I just do it.

I teach creativity to tweens and teens and I think these questions from our young are fearless. There is no wrong or silly question. Just this beautiful curiosity applied to something that doesn’t seem logical.

Consequently we had a really interesting conversation. Which I looove!

Interesting conversations start with interesting questions

I find interesting conversations so rewarding so how can I have more of them?

I had this problem I wanted to solve and so began the process of creativity for me: Saturate, Percolate, Create, Celebrate, Rejuvenate.

Like all good creative processes they start with a problem and I had my problem that I needed to solve:

“How do you ask an interesting question?”

Stage 1 : Saturate

I started to Saturate my mind with new information

I like to use two or three new sources of information in this stage to add to what I already know.

I like to call the three sources the 3Ss — Search Engine, Someone Else, Self or Software. It lends itself to what we naturally do.

First stop — Google. I typed in “How to ask interesting questions + research”

I like to add the word ‘research’ to my search criteria because I like to have my much of my creativity founded in research. I just think it makes what I create a little more interesting. You can also add +forum (to understand what people are thinking/saying/feeling about a topic).

There is quite a bit of information on the internet on this topic.

Harvard Business Review has published a list of things that are contained in asking good questions. One I found particularly interesting is getting the sequence right. How sensitive the question is up front has an impact on how following questions are perceived, but it depends on which situation you are in. Read the situation the wrong way around — it could backfire.

Second stop — ask an expert. I reached out to Vanessa Van Edwards to see what her answer to this question would be. She spends her life working and understanding the nuances of people and has built a business around it called “The Science of People.” I didn’t know her but she very kindly replied with the following:

The only way to make a good question great is to try multiple variations of it with different people and which one sparks great answers. Try a new one every day and different versions of the same one until you consistently see people’s eyes light up and you have great conversation. That’s the only way I do it!”

Third stop — use a tool. This time I went in search of a piece of software that could help me with my problem, but sometimes I go in search of a new insight for Self. Something fun that helps me understand myself better so I am better able to resolve the problem (e.g. my character strengths or love languages). This software comes from Vanessa as well. It is an amazing app of conversation starters called ConversationHQ.

It contains over 200 really interesting questions to ask when networking, at work, at social occasions, with kids and teenagers. Questions that take you beyond the small talk.

Stage 2 — Percolate

Armed with these new pieces of information — I thought, ok who do I want to have some interesting conversations with?

Well anyone really.

What question would I ask someone that is interesting?

A question that that person will enjoy responding to. One that you have an opinion on that lets us get to know each other but also provides some value.

In addition, the question needs to fit in with my values. What I mean by this is, I am comfortable asking it. In turn they get to know me better because it is an authentic question from me.

Stage 3 — Create

I then ask it.

In person or online.

Austin Kleon wrote a book called “Show Your Work” about putting your creativity out their and letting others into your process.

The world needs our curiosity to solve problems so we keep evolving and growing.

Sometimes I ask questions on social media that no one responds to. Sometimes I get lots of responses.

Either scenario, I learn. I learn what is interesting to others and what is not. In saying that, it doesn’t stop being interesting to me. I of course could not know any of this, if I didn’t put it out there.

Stage 4 — Celebrate

I then celebrate — either way

If it failed — I celebrate trying

If it worked — I celebrate knowing you just a little bit more.

In knowing you I can then share stories or insights that might be useful or entertaining or maybe even both!

Stage 5 — Rejuvenate

And finally Rejuvenate.

I don’t ask questions everyday. I don’t have interesting conversations everywhere I go. Just like I don’t go live on social platforms or write an article here or design a new collection everyday.

It is too much — for you and for me. We need to take a break to sustain our creativity and we need to make a habit of that break. James Clear talks about ‘sticky habits’ meaning we need to attach a new habit to something we already do so we don’t forget to do it.

This is one habit that needs to stick and I always like to make sure I do it after celebrating no matter how insignificant it might seem. It could be as simple as not saying anything at all.

Creative process taught to girls 10–15 y/o through Dreaming Big for Little Girls

In summary

The purpose of this article was not to give you a list of interesting questions, it was to show you how using the creative process can help you come up with your own interesting questions.

Saturate — I always use 2–3 different sources in my saturate stage

Percolate — I use those sources, combined with my values and the purpose

Create — I give it a go. If I get crickets, I try to always have a story ready to share, just like the one I shared at the beginning of this article with my son. It can take you down interesting paths.

Celebrate — I celebrate and reflect on the wins and the fails

Rejuvenate — I take a break and I make sure I stick to this by setting goals and creating habits — taking a break becomes part of the plan.

One final thought

Asking interesting questions makes you memorable, because you made them feel valued. They may not remember your name but they will remember how you made them feel and that’s pretty special.

So I wonder what curious path you are going to take someone down in your next interesting conversation of your own making?

I still haven’t worked out why the gear stick goes forward to reverse and back to go forward.

A nice looking transcript and video from this can be accessed on my blog.

Have a nice day.

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Jane Harbison
Jane Harbison

Written by Jane Harbison

I write and think about the importance of creativity in education

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