[Guest post] Further thoughts on a good question

By Street Wisdom

Inspired by Street Wisdom participant Nicole Kagan’s question, regular Street Wisdom Walkshop host Nicky Torode wrote this blog to offer some further thoughts on this question of What makes a good question?


A prudent question is one half of wisdom.

– Francis Bacon

At Street Wisdom, naturally, we couldn’t agree more with Francis there.

In our Walkshops – or wandershops as I call them – participants quest the streets, seeking, smelling, sensing and listening for answers to their top-of-mind question.

So, a good quest needs a good question, right? True.

But what makes a good question is the question!

Here are a few categories to ponder as you start to tune into your question.


Open without theme questions

Use What or How to get the juices flowing:

What is the next best step?

What am I waiting for?

What has the time come for me to invite into my life?


Open with theme questions

What’s the next step in my career?

What volunteering opportunities do I want to explore?

I’m at a crossroads in my love life. Show me some options for which way to go.


What if questions

This unlocks our thinking, takes us into the wonderous fields of infinite possibility.

What if I say yes?

What if I say no?

What if there is a half way?


Incisive questions

This kind of question has bounce!

We leapfrog over doubts, fears, objections and assumptions to ask thought-provoking questions to think afresh:

If you knew you had a choice, what….

If you could find time, what… 

A similar springboard question, this time from what is already known:

Knowing your values, what feels possible right now?


Hypothetical questions

On a Street Wisdom walkshop we invite you to ask a stranger your question to get a fresh perspective, for their first take on your topic. It’s insightful precisely because they don’t know you and don’t need the backstory.

But it’s easier said than done, surely? Well, here are some tips.

Ask perhaps, a friendly-faced barista? An eager-eyed florist outside the station?

I once asked a quiet barista, serving flat whites, minding his own. Turns out, he was a philosophy graduate. Now, the question is: did I come away with answers or more questions?

A hypothetical question like this can work well:

What would you consider if you were moving town?       

What would you do if you had a job you loved but hated the boss? 

Now, the stranger-turned-confidante might ask you about moving from where to where or what job do you do BUT it is just their top notes that’ll be helpful! It’s not an exchange.


Instructional/dialogue questions

It’s also worth pondering about the language and the focus.

We are in dialogue with the street so let’s talk to them directly, like our very own personal Yoda:

Streets, what’s …..

Give me…

Show me….

Tell me…..


Invitational questions

Or, a more invitational tone, perhaps?

Words like might, may, could invite our explorer’s mind to the streets, rather than us efforting to find the definitive answer.

What might the answer be?

Feel the air flow in, the freeness?


All the feels questions

I was once asked on a Walkshop whether the question had to be about positive topics only. No, it can be the thing that’s troubling you, which can include perhaps negative emotions that you’re experiencing like stress or worry.

Example of a difficult theme for a question, taken from the Street Wisdom website:

Show me some fresh ways of dealing with the grief I’m experiencing…

My word of caution is to be mindful you’re in a public space, so check if it feels like the right place and time for this topic.

You don’t have to share your question with the group but I find it’s always inspiring to hear others and can help participants savour them and land on their own question.

After the quest, it’s heartening to see surprised faces and smiles when wanderers return and share answers, or whispers of answers, they’ve gathered from the streets.


Coming up with questions can be addictive, wouldn’t you say?


We love a good question so share if you will, a question you took for a walk!

If you haven’t yet been to a Street Wisdom Walkshop, the only question to ask now is…


What are you waiting for?  



Inspired? Fancy some more Street Wisdom? Join a Walkshop near you, or head out for your own wander right now with our Tune Ups. Buy a copy of founder David Pearl’s book Wanderful, all profits go back into Street Wisdom to help keep it free. Share your insights and follow us @StreetWisdom_

Thanks to rawpixel for this wanderful photo!