The Art of Asking Better Questions
Issue #46 - with curiosity consultant (and Quester!) Hannah Singleman
THE QUEST DIGEST by Creative Quests is a treasure chest of ideas & stories exploring what it means to live an illuminating, creative life. Written by Sam Furness and delivered when inspiration and creativity strike. Subscribe to receive each issue or send to a friend in need of a creative boost.
Dear Questers,
Sam here 👋 Excited to bring you a different kind of Quest Digest this week… our first in a new monthly series of guest edited newsletters. There are SO MANY brilliant people in this Quester community - it’s high time you started learning more about them. Please let us know if you like it in the comments!
Before you read more about Hannah Singleman (OG Quester and curiosity consultant) I wanted to let you know that we have a special virtual event coming up,
A preview of what’s to come in our new Quest Club programme… coming very soon.
If curiosity, questions and creative rabbit holes are your thing… join us!
The Art of Asking Better Questions with Hannah Singleman
🗓️ Tuesday 9th July
⏰ 5-6pm / 12-1pm EST
❤️ Free virtual session
Hannah Singleman is a curiosity consultant and researcher living in NYC and has been a Quester since January 2021.
She’s Head of Creative Questions at Now What, global insight, strategy, and design consultancy, where she designs curiosity curricula and facilitates skill-building workshops for clients including LEGO, PepsiCo, and Heineken. She loves walking around the city, checking out live music, and hanging with her rescue cat, Bachi.
SF: ‘Curiosity Consultant’ and ‘Head of Creative Questions’ is right up there with world’s best job titles… what does a day of work look like for you?
HS: It’s a split between research and consulting.
On the research side, it’s a lot of interviewing people in different professions about the role curiosity and questions play in their work and life. At Now What, we’re researchers at heart but what can we learn when we look outside of our swim lanes and into the worlds of other curious minds? Everyone from a Nobel Peace Prize winning activist to a historian of happiness and a parenthood clarity mentor.
My team and I created a Curiosity Styles Assessment based on our research. We all move through curiosity a bit differently – where we’re most comfortable and confident varies. Embracing a diversity of curiosity styles is where the magic happens.
On the consulting side, I’m lucky to get to spend time working with organizations to help them be more curious and ask better questions. I was at LEGO last summer running an offsite all about different curiosity styles for team cohesion and I’m currently partnering with Pepsi on becoming a more human-centric organization.
SF : You recently spoke about your work at SXSW! How was that experience?
HS : One of the best parts of my job! Nothing like a room full of 1000 people just as curious about curiosity as you are. We broke down our Four Curiosity Styles and featured case studies from some of our absolute favorite interviews to help people make curiosity contagious.
SF: It’s a very strange time in the world at the moment, especially when it comes to how we learn and discover new information. People are rightfully concerned when it comes to AI and the Algorithm overlords. I wondered what role you think human curiosity plays in all this?
HS: It’s something we think and talk a lot about at work. I always come back to the need for us all to get truly curious about and really spend time with the question around what kind of world it is that we want to create and live in.
We interviewed an amazing sci fi writer, Matthew Medney, who shared one of his favorite questions: "What's the world I want to live in tomorrow?" His advice was to ask that as a meditation every day. And then act on it.
I think pairing our natural curiosities with contemplation and action will become increasingly important.
SF: You also co-host the brilliant podcast ‘One Better Question’ about the go to questions of some of the worlds most curious people. What are some of the favourite questions you’ve heard?
HS: It’s hard to pick just one! But I think a lot about a question from our interview with Reverend Karen Hutt (Episode 3)...she’s an end-of-life chaplain who’s spent a lot of time with folks in hospitals, hospice, and even death row. She shared how she never walks into a patient’s room and asks, “How are you?” but instead asks questions like “What kind of day are you having today? What’s on your heart today?”
Another one is from Abigail Posner, a cultural anthropologist at Google (Episode 5) – ”What makes you weird?” That’s always a fun one to ask if people are willing to go there with you. You learn a lot!
SF: Now I’m curious… what is your go to Better Question?
HS: What can you joyfully give your energy to? (Inspired by a Human Design reading I got a couple years ago…a little woo woo but worth checking out!!)
SF: You’re hosting our first ever Quester Exchange session in the Quest Club on 9th July on ‘The Art of Asking Better Questions’ - can you tell us a little of what to expect?
HS: Woohoo! Questions are the language of curiosity and questioning is a skill that can be taught and practiced. The session will be equal parts introspective and interactive and we’ll get curious about our curiosity styles and learn some better questions that we can be asking in work and in life. It’ll be like a tasting menu of the best bits of the podcast and SXSW!
SF: You’ve done pretty much all 12 Quests we’ve run so far… what’s been your favourite theme to explore?
HS: Now this is impossible to pick just one! So I’ll pick three faves. In no particular order:
Poetry: The first Quest and will always hold a special place in my heart. I now carry poetry with me as a way of noticing and being and moving through life.
Collage: This Quest literally changed the way I see the world. I was just in Lake Como on vaca and took this picture of the layers of water and mountains and how it looked like a collage.
Light: When you had us pick a North Star word, Sam, I was drawn to “awe”, which led me to take a glassblowing class in Gowanus. I freakin’ love the Quest nudge to get out of your comfort zone and rock with whatever may come your way. And I made this bowl!!
SF: What role does Questing play in your life?
HS: There’s more room to learn and grow and make and play and dance when you move out of your comfort zone(s). All it takes is a few steps and Questing is the best way I’ve found to start. Forever grateful to Creative Quests for making it easy and fun to just follow your creative instincts and do the damn thing.
SF: We can’t have this chat without mentioning ‘PASTAROTICA’. It’s one of the greatest personal projects to come out of Creative Quests… could you tell us more about it and what inspired you?
HS: Haha! I remember we were in our first ‘throw paint at the wall’ session (where we all brain dump our associations when we think about the theme which was, in this case, Collage).
Half the things people were saying were about collage as something childish, like an arts & crafts project you’d do in kindergarten, and the other half was all about collage as this tool for provocation and subversion. I got to thinking about what would happen if you mashed these two opposing themes together and had this image flash in my head of macaroni art but on burlesque photos. I laughed out loud and thanks to the Questing spirit of following your creative instincts and doing the damn thing (plus Questers being some of the most supportive, fun-loving, game-for-anything people I’ve ever met) Pastarotica was born.
A round up of curious finds from Hannah’s Quester world.
Five things related to curiosity:
💭 This ~3 minute Curiosity Styles Assessment I created with my team at work to help identify your dominant curiosity style. Are you a Rebel, Tinkerer, Inner Child, or Voyager?
🎧 Some of my favorite podcasts for inspiration: ReThinking, Radiolab, and We Can Do Hard Things
❓ The 7 questions that changed Sahil Bloom’s life
🧠 A great read (or listen – I did the audiobook!) on the importance of psychological safety and belonging as underpinnings of organizational curiosity
📙 And this book by one of the many brilliant thinkers we've interviewed, Mónica Guzmán, as a toolkit for using your curiosity even when it's hard
Five Questy things:
🦁 The Walton Ford exhibit at the Morgan Library & Museum (one of my fave museums in the city). He paints these amazing watercolors based on insane stories throughout history about wild animals interacting with human kind. My favorite was this one, inspired by true events in 1913 Leipzig when a cage of lions from a circus caravan was hit by a trolley and 8 lions escaped and were wandering the city streets.
🖍️ Crayola’s campaign reuniting adults with their childhood art…I recently stumbled into their ‘Stay Creative’ gallery in Chelsea and it was beautifully Questy
💺 Anything Armchair Expert, including the recent episode with Amy Poehler which was equal parts vulnerable and hilarious
🤸🏼♀️ Recently became acquainted with fascia flossing, which is now my new favorite way to get some movement in in the mornings
👀 And in the spirit of the Poetry quest, my favorite poem from one of my favorite poets. I love how it’s not what you expect – from the form (as an email chain) to all the beautiful stuff that unfolds after starting with dog poop. I love how it poses a question: What is grass to someone who is always looking up?
Finally…
HUGE thank you to Hannah for this amazing dive into her curious world.
💛💛💛 You can connect with Hannah here.
If you want to dive deeper into asking better questions - join us on 9th July.
I love hearing from readers in the comments, and always value feedback. Did you enjoy this new feature? If so - let us know!
If you enjoy I’d love it if you shared it with a friend or two; you can send them here to sign up.
Big love,
Sam x
Quest Guide / Founder
@saaamfurness
THE QUEST DIGEST by Creative Quests is a treasure chest of ideas & stories exploring what it means to live an illuminating, creative life. Delivered when inspiration and creativity strike. Subscribe to receive each issue or send to a friend in need of a creative boost.
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Love this special! I took the test and discovered that I have the voyager curiosity type.