Four tips for asking better questions

An Executive of a large global company recently asked me a great (and super meta) question after recognising the value of coaching his team: how do I ask better questions?

Here’s a version of what I shared back:

Be curious

If you remember only one thing let it be this: always be curious (ABC). The best question to ask is the one based in a genuine curiosity of wanting to understand more. It’s like improvised comedy. We can wait to hear what has been shared and then respond to the part we’re most curious about.

Ask one at a time

Have you ever had the experience of listening to an interview and the interviewer asks multiple questions at once? They’ll say something like:

“So what are you excited about right now? What are you working on? What’s capturing your attention? Is there anything that comes to mind? Because I heard you’ve been doing some kayaking, is that true? I’ve been kayaking before, it’s quite challenging isn’t it? I would love it if you could share…”

What? Where does one even start?! Instead, take the opposite approach, ask one question at a time.

Avoid binary questions

Binary questions are those that can be answered with either ‘yes’ or ‘no’ and tend not to be conducive to uncovering possibility. Instead, ask open ended questions. So instead of: are you okay? Try: what’s on your mind? Instead of: Do you agree with this approach? Try: How would you solve this problem?

Don’t steal the revelation

When asking questions it is possible you’ll hear someone start to answer and try and guess where they are going. You will pre-empt their thought, revelation or aha moment. When this happens, be patient and remain silent (or throw in an “…and what else?” if you really can’t help yourself). Let them get there themselves. As the brilliant Paul Jun would say: don’t steal the revelation.

Why fear explains weird behaviour (like arguing about broccoli)

When trying to make sense of your own behaviour it can be helpful to ask the question “where’s the fear?”

It’s fear that makes us stay up till 11 pm reviewing notes ahead of a big presentation convincing ourselves “I need to practice so that I don’t make any mistakes”.

It’s fear that stops us from committing to a project or job because “what if the grass isn’t greener?”.

It’s fear that explains why you’re arguing with your partner about the size of broccoli florets or the kind of toothpaste you just purchased because you want to feel appreciated (I feel called out).

Fear explains procrastination, perfectionism, and feeling like an imposter.

Fear explains why some people give unsolicited feedback and why it can be so hard to ignore.

Fear is hard-wired into how we behave.

Knowing this, it’s worth cutting ourselves (and others) some slack, especially when it comes to the broccoli florets, which admittedly were far too big for human consumption.

Recent reads and listens – March edition

G’day, curious legend.

Somehow we’ve made our way to the end of March which means it’s time for me to send you a small collection of books and podcasts that might provoke some noodling for you over the next month.

If you ever find yourself wondering what it means to be a good human (but like, in a funny way):

How to Be Perfect by Michael Schur (creator of The Good Place and co-creator of Parks and Recreation) is a hilarious guide to moral philosophy sure to make you think.

If you’re stuck in a rut:

Awareness by Anthony De Mello might just make you question everything (in a good way).

If you’re curious or scared about what the future might hold:

Me too. You MUST listen to this interview with Jane McGonigal.

If you’ve ever found yourself thinking about regrets:

Don’t miss this interview with Brené Brown and Dan Pink.

In the meantime, keep being awesome.

Things that don’t scale

Three questions I’ve been pondering since revisiting this interview with Airbnb co-founder Brian Chesky.

What if the opposite to scaling a project is humanising a project?

What does an 8, 9, and 10-star experience look like when working with you?

Where might it pay to do things that don’t scale?

PS. If this feels like a noodle you want to stir around some more in that brilliant brain of yours, checkout this week’s episode of The Long and The Short Of It.

The real skills of leadership

In 2017 bestselling author and world-renowned speaker Seth Godin wrote this viral Medium article encouraging leaders to stop calling soft skills, soft.

Instead, he proposed, we call them what they are: the real skills of leadership and human connection.

Skills like curiosity, coaching, and creativity.

Skills like decision making, storytelling, and question-asking.

Skills like empathy, enrolment, and dancing with imposter syndrome and fear.

Skills that can’t be memorised or looked up online.

Skills that everyone has the ability to cultivate.

Skills that require deliberate and intentional practice.

Seth provided language for something I had felt for a long time having worked with thousands of leaders from hundreds of companies around the world.

That the framing and importance of ‘hard skills’ versus ‘soft skills’ is increasingly less relevant.

That what our rapidly shifting world calls for is not merely people who fit a technical job description.

That what the world calls for is people who choose to lead, no matter where they are in an organisation. People who choose to practice, model, and hone these real, human-centered skills.

These are the leaders, and organisations, who will create lasting, meaningful change.

The question is: will that be you?


This piece was a guest post for ICMI Speakers Bureau and was originally published here.

On dealing with critics

At some point in your journey, you will meet a critic. Someone who decides it’s their duty to attempt to knock you down (usually for reasons unknown to you and because of their own insecurities). It’s as certain as gravity.

When it happens, consider doing two things:

  1. Lookup your all time favourite book on Amazon, and read the 1-star reviews. The Harry Potter series, for example, has thousands of them despite being a #1 best seller. Thousands! Turns out you’re not alone.
  2. Remind yourself of what George Herbert once wrote:

“Living well is the best revenge.”

Recent reads and listens – February edition

G’day curious legend.

It’s the end of the month which means it’s time for me to send you a bespoke and made-to-measure collection of books and podcasts to provoke some noodling for you over the next month.

Let’s dive in:

If you’re telling yourself a story you need to be better at time management:

Four Thousand Weeks by Oliver Burkeman is sure to elbow you in the ribs.

If you’re looking for a novel that confronts our relationship with the environment:

Bewilderment by Richard Powers will make you pause and think.

If you’re interested in a no-bullshit take on philosophy and ethics:

Try this interview with Michael Schur.

If you’re a fanboy of Debbie Millman’s interview style (just like me):

Don’t miss this interview where she was the one being interviewed by Brené Brown.

In the meantime, keep being awesome.

Get better together

The best way to get better at a skill isn’t by memorising facts so that you can regurgitate them in a multiple-choice test taken in a sweaty exam hall in the middle of summer. If it were, you’d still remember how to do algebra and long division (shout out to the maths nerds who do still remember, you’re the exception to my rule).

No, the best way to learn is by practicing skills that interest you with other people doing the same. It’s to be in a space where you can ask questions and be curious. To give and receive feedback. To watch others and reflect on how you can learn from them.

Or, as my friend Jen said far more eloquently in this podcast: “get better by surrounding yourself with other people who are also getting better.” 

A lesson on writing

I was recently struck by this metaphorical punch in the gut from William Zinsser’s book On Writing Well:

The essence of writing is rewriting.”

The best writer in the world doesn’t sit down and create a finished, polished, publishable piece. They sit down, they write and they dance with the voice that tells them it’s terrible. Then they review. Then rewrite. Then dance with the voice some more. Then repeat this process. Over and over again until eventually, it molds itself into something worth sharing.

Day by day, word by word, iteration by iteration.

The lesson I take is that if you, like me, feel stuck every once in a while (ie every day) start by giving yourself something (anything) to react to.

Journal prompts worth trying

A random selection of tried and tested prompts for you to noodle on. See if you can fill a page based on one of the below:

  • Right now I’m feeling…
  • 10 awesome things that happened today are…
  • Where am I most often experiencing friction in my day?
  • What’s the hard part?
  • A successful day for me looks like…
  • Who am I becoming?
  • What would 80 year old me say to current day me?

Once you’ve picked one of these the process might look something like this:

Grab a new notepad out of the cupboard > spend 10min summoning up the courage to put ink onto the beautiful fresh pages > write the neatest first 3 lines you’ve ever written, as if you were back in grade 3 going for your pen license > swear under your breath as you realise you misspelled a word > in your frustration to scribble out said word spill coffee all over the fresh pages of your brand new notepad > swear under breath some more > revert back to your regular, barely legible writing technique on your now coffee-stained page.

The joys of introspection. Go go go.

Recent reads and listens – January edition

Well hey there legend 👋🏽.

Here’s your very own artisanally crafted and hand-picked collection of books and podcasts to provoke some noodling:

If you’re looking for a refreshingly honest take on the journey to being world-class:

Will by Will Smith has got you covered.

If you loved the Octopus Teacher documentary and are curious to learn more of the backstory (complete with incredible photos):

Underwater Wild by Craig Foster and Ross Frylinck

If you’re wondering what it sounds like to reinvent your life:

Try this interview with Rich Roll.

If you’re still chuckling at, or curious about, the story of me hitting my head from this previous post (🤦🏽‍♂️):

This interview on Tommy Jackett’s new podcast, Tomversations

That’s it for this month, friend. Keep being awesome and I’ll see you in your inbox next week.

PS. If you have a friend who you think would love to join you in reading these posts, consider forwarding it on with the subject line “New noods for you” (it’s been at least 3 months since I made that joke).