How To Ask Beautiful Questions — A Guide

8 July 2022 | BY ANDJELKA JANKOVIC | Life

I was having lunch with my friend Ande a while ago, and the first thing she asked me when she sat down was: “What is a revelation you have had lately?”

Okay WOW, I was blown away. I had not been asked such an imaginative question in a while.

Around this time, my life had become a quest for the most beautiful question in the world.

It is now a day-to-day practice and discipline of mine to ask more thoughtful, provoking and invitational questions.

This all started with a poet asking me the most beautiful questions I’d ever heard, and me realising that I had missed many opportunities to do so myself.

A beautiful question always enlarges the context in which you’re living – deepening the horizon – and taking you out of yourself and into yourself at the same time. One of David Whyte’s personal definitions is:

A beautiful question shapes your identity as much by asking it, as by having it answered. It deepens your sense of yourself.

In this search, everything I know about asking better questions can be distilled into this:

Ask beautiful questions, get beautiful answers.

It is as simple and terrifying as that. And also quite hard.

How you ask a question is important.

If you’re going to ask a beautiful question, be prepared to actually listen to the answer. The job is only half done otherwise.

Sometimes the best question to ask is listening.

In Maps to Ecstasy, Gabrielle Roth writes:

In many shamanic societies, if you came to a shaman or medicine person complaining of being disheartened, dispirited, or depressed, they would ask one of four questions:

When did you stop dancing?
When did you stop singing?
When did you stop being enchanted by stories?
When did you stop finding comfort in the sweet territory of silence?

Where we have stopped dancing, singing, being enchanted by stories, or finding comfort in silence is where we have experienced the loss of soul, Roth says.

These are examples of beautiful questions. Ones that lead us to more real, honest, and refreshing conversations.

There’s a brilliant video by Alan Watts where he asks: What would you like to do if money were no object? How would you really enjoy spending your life? Alan Watts tells you to do that and forget the money. Anything you can be interested in will find others.

A beautiful question can completely reshape your life.

There is something so satisfying about a really good question like this. It awakens you, shaking off the sleepiness and inviting you to reveal something new.

A friend once asked me casually in a cafe: What would it take to be yourself?

I am always interested in the shape of your solitude: Can you be alone and do you like the company you keep?

And perhaps there are some questions that will always be unanswered like: What happens if I eat too many pappadums?

A real question is beautiful and a beautiful question is real.

We’re all just waiting to be asked.

Being engrossed in this pursuit of beautiful questions has led me to uncharted territory where I am map-making as I go along. Let me give you an example.

I was having lunch with my beloved mama on Mother’s Day last year and she asked me when I was going to give her grandkids. This is the most asked question in my family (after, where is the salt?) and a bit of a trigger for me. I have told them many times that yes, I wish to have children when I meet the person I want to have children with. My mum explicitly knows this, and yet – I was being asked the same annoying question again as if I could be spontaneously pregnant (like when she bought me a cute wooden tea set for, as I pointed out, the children that I do not yet have). Normally I would blow up, but this time I took a looooong breath and I said instead: ‘Mum, if you ask a beautiful question you will get a beautiful answer.’

We were silent for about thirty seconds. I resolved to not speak until my mum did. Then she asked: ‘What kind of joy do you want to bring into your life?’ Now THAT is a beautiful question and finally, we could have a real conversation.

It is true: joy is coming.

A beautiful question like this leads to a better foundation for understanding.

A real conversation is noticeably different to the humdrum of other ones. It will bring you to a new frontier of understanding yourself, and others as well.

As David Whyte writes:

There is no self that will survive a real conversation. There’s no self that will survive a real meeting with something other than itself… And after a while you realise you don’t want to actually keep that old static identity. You want to move the pivot of your presence from this thing you think is you, into this meeting with the future, with the people you serve, with your family, with your loved ones. It’s in this self-forgetfulness where you meet something other than yourself that all kinds of astonishing things happen.

Glorious as usual, David.

A beautiful question is going to leave you hungry for more.

An average question tends to get an average response.

As David Whyte writes in his 10 Questions That Have No Right To Go Away: ‘A real conversation always contains an invitation. You are inviting another person to reveal herself or himself to you, to tell you who they are or what they want. To do this requires vulnerability. Now we tend to think that vulnerability is associated with weakness, but there’s a kind of robust vulnerability that can create a certain form of strength and presence too.’

So, why is it difficult to ask a beautiful question?

I’ve been sitting with this very question for many months now, and have failed multiple times in the attempt (although they make great examples of what not to say).

I have noticed we often don’t have time or space in a conversation to pause, and really be present with what question wants to be asked.

When I overhear myself asking the same boring thing to a friend mid-sentence; I try to stop and recalibrate. Often I even say out loud, ‘Wait, let me ask a more beautiful question’ and then I try to.

As I’m learning, you have to practice the ability to ask beautiful questions on a daily basis. To know how to ask such a question, this is where the real power is. And it is so delicious when it happens!

Another step forward towards beautiful questions is practising silence in a conversation. Just a little bit of clear air-time for the other person to be able to actually digest the question and answer it back. Also speaking openly about yourself first always encourages intimacy and safety in sharing.

A huge part of being in a beautiful conversation (that is a real one, where both of you stand to actually be changed) is giving up the strategic part of yourself that always wants to say the right thing. We’re all conditioned to be socially pleasing and nice and acceptable. But under the surface is always a more imaginative or brave or real question that could disturb that constructed veneer; so we don’t go there.

We also must practice having a beautiful mind.

David Whyte says that the cultivation of a ‘beautiful mind’ (a term he inherited from his close friend, Irish poet and philosopher John O’Donohue) is noticing what is not being said. This quote is from my most listened to podcast episode ever:

When is the last time that you had a great conversation, a conversation which wasn’t just two intersecting monologues, which is what passes for conversation a lot in this culture. But when had you last a great conversation, in which you overheard yourself saying things that you never knew you knew, that you heard yourself receiving from somebody words that absolutely found places within you that you’d thought you had lost, and a sense of an event of a conversation that brought the two of you onto a different plane, and then, fourthly, a conversation that continued to sing in your mind for weeks afterwards? And I’ve had some of them recently, and it’s just absolutely amazing. They’re like, as we would say at home, they’re food and drink for the soul. – John O’Donohue

If you’re feeling overwhelmed with this skill that feels so elemental to being a human and yet no one taught you how to do it – join the club.

I didn’t know where to start. So I started small, gloriously small. I have been testing what kind of questions open people up, enhance conversations and which ones make people shut down.

Five powerful ways I have found to start having beautiful conversations right now is by asking:

• What is it like to…?
  Asking someone to talk through their life experience of something.
• Tell me about…?
  Asking someone to reveal more about something they are passionate about, an expert on, or getting started in.
• What about you?
  A beautiful invitation to turn a question around. This one always surprises me with how nice it is to be asked a question back.
• What do you mean by that?
  A gentle way to get more information on something that confounds you, sounds concerning or doesn’t make sense.
• Is it possible…? or Have you considered…?
  To get more clarification before you make your mind up.
  

I have also discovered that most people can’t handle a big question (I’m currently reading a book trying to answer how we came to talk and it’s dense). It can clog up a conversation. I’ve been experimenting with asking smaller, perceptive questions – especially to understand how willing someone is to go there, that is risk being vulnerable and have a real conversation.

Here is a guide to asking more beautiful questions:

1. A beautiful question is your question. If you’re absolutely fresh to the idea of a beautiful question, start with noticing what is not being said or acknowledged in your own life. Ask: What question has no right to go away in my life right now? Journal it, walk it out, or bring it up with a friend. This question is a frontier. As David Whyte says, each epoch of our life has a beautiful question attached to it. Asking yourself a new kind of question is a doorway to a richer inner you that is then capable of asking it to others.

Your life is a question in which no one else is being asked. – David Whyte

2. Stop the current conversation. To have a deeper conversation, we must stop the one that we are having right now. By definition, “the courageous conversation is the conversation you are not having right now and the one you don’t want to have,” David said in a talk at Kripalu. Stopping can look like this: silence, attuning to the other person, and presence. Also, a little dose of courage goes a long way. Putting a pause on the surface-level chatter for a moment can be useful to reroute the conversation, and then a more nourishing and life-giving exchange can happen.

The first invitation is just to stop entirely the conversation that you’ve been having until now and meet what is arriving without naming or planning. Just to hear and feel the annunciation of a new energy, a new life. – David Whyte

3. Refuse to narrow the conversation. To ask a beautiful question can take a few times. This is a key I have found. It is a friendship with the unknown. You might be feeling anxious or like you’re afloat. Honesty is the best principle here, like saying to a friend: “I feel a little anxious about bringing this up, but I’d like to ask…” instead of diverting to mindless talk while your heart is beating with the question it really wants to ask. As David Whyte says, the language of intimacy and vulnerability is the only way to make a real invitation. To feel all the belonging you want in the world. Every real conversation begins in this shyness.

Read and admire, but then go back to first principles and ask the question yourself, in your own way. Dare to disagree. – David Whyte

4. Speak from a deeper interior. A lot of us don’t speak from our larger identity in the day-to-day. Fair enough, we’ve got a lot of things going on. So to invite in a beautiful conversation – from this place of your higher self or soul – we have to go to this place of origin within us that is capable of asking a courageous question. Your surface mind and everyday personality will tell you not to go there (possibly screaming and releasing fire rockets for your ego’s safety!), but your larger identity will be excited and a little thrilled that you’re allowing that part of you to speak. This is from where you can begin to ask beautiful questions.

Soul as the faculty of intimate belonging inside every human being. The soul as a presence that is always inside you and smothered by to-do lists and burdens and responsibilities. – David Whyte

5. Consider the conversation that is not happening. We often have the same repetitive conversation patterns with friends and family, I know I do with my father. It is what keeps us connected in a familiar and comfortable way. However, there is another side to explore. David Whyte calls it ‘the other side of the question we have refused to ask.’ Read that twice (It’s so good, I know). Consider as David says: “What is the conversation I’m refusing to have? Almost always, by definition, this is the conversation we need to follow.” If you feel like running away in terror, I don’t blame you. But the unasked questions we carry within are often the things we long most to know, and when asked with intention and vulnerability, they can set us free.

What would it be like to allow a revelation or even just the beginning of an answer to come back from staying in the gravity field or the energy of the question we ‘refuse’ to ask? This question is always felt to begin with, more like a physical ache, than a verbalised inquisition. – David Whyte

6. You don’t have to know the answer right away. The ‘other side of the question you refused to ask’ might take a week to know. A month or years even. That person might never reply to your own beautiful question or have the words to speak about it back. They may sleep on it forever. But you asked, and that matters for something. The ability to self-reflect and sit with a question that does not have an answer right now is starting a real conversation with yourself too.

Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer. – Rainer Maria Rilke

My life motto is literally to ‘live the questions’. Thank you Rilke.

7. A good sense of humour about yourself is necessary. The universe has a wicked sense of humour and is having a grand old time making us realise we control very little. I love how David Whyte often says, ‘life will out humour you’. And I often remind myself and say to my friends of his words: ‘Everyone is doing their best and it’s often never very good.’ We are the only language-centric species and yet animals seem to have it all figured out (observe your cat sleeping in the sun or dogs fetching a ball at the beach, they know what’s up!) So you’ve got to laugh about it – the awkwardness and sheer panic and humanness of it all.

The courageous part of you that is willing to take more losses, immediate ones, because it knows there’s no true path forward without having your heart broken. And the only choice you have is to take the path that you care about so you don’t have your heart broken over things you actually don’t care about. – David Whyte

8. Sometimes your life depends on a question being addressed; not necessarily solved. Speaking a beautiful question out loud is the courageous part. The answer is important but not integral to the practice. Speak questions into your life so they don’t die with you. Address the questions that you can live your life into. Create horizons beyond yourself that beckon you closer to a place of wholeness. You may not get a complete answer or a profound revelation by asking a beautiful question, but that’s not a reason to not try to. You might get even more.

Go to a deep part of the psyche that has hardly spoken yet. A more mature part of you than the one that walks around with you all day. To articulate from this unknown place and start to build a vocabulary and a new language. – David Whyte

9. Make a beautiful invitation. Ultimately, a conversation that enlarges your life starts with someone making a real invitation to the other – for a beautiful interaction to happen. David proposed this in a talk and I think about it often: Is it the question or the beautiful mind of the person asking the question? Now you can ponder it too.

A condition of complete simplicity (Costing not less than everything). – T.S Eliot

10. Sometimes no question is needed. Occasionally I fail at my own apprenticeship to beautiful questions. I was chatting to a new friend about hormones and contraception, and she mentioned she recently had a miscarriage. I automatically asked: “Was that really hard for you?” And she said: “Well it wasn’t easy for me”. Of course, I thought, how could I be so daft. What I should have said was, “I’m deeply sorry for your loss, that must have been really hard for you.” FULL STOP. This is not a time for words. Or when someone has died, you should not ask (like I stupidly did when I didn’t know what to say) – “Were you close with your grandfather?”, and they replied: Yes. Duh Andjelka, I thought. A more beautiful question would have been, “Would you like to share a favourite memory of your grandfather?” And be more than okay if the answer is silence. When no question is needed, you will know. Resist the urge to fill the space.

I had a beehive here inside my heart. And the golden bees were making white combs and sweet honey from my old failures. – Antonio Machado

The thing is we all want to ask beautiful questions and be asked them.

We do.

We all want to feel that moment of connection with someone, to express our inner lives and ancient longings. To share the absurdities of being human and the honesty that comes with it.

There are questions that light us up, make us feel seen, and laugh our heads off.

You just have to ask it.

How do you feel right now, today? Please trace each nuance of your feelings to its origins, be they mundane or complex, current or ancestral; there is no wrong or boring answer. – Miranda July to Michaela Coel

Someone is going to be very grateful that you did. And we’re all better for it.

If you’re in the groove and want to try it out, think of a beautiful question you want to know the answer to.

I recently read from Esther Perel that she prompted her friend, “The last time I felt free… what is it for you?”

“When I went diving in the Red Sea,” he said.

“What makes that a feeling of freedom for you?” she asked.

“I feel playful, unrestrained, unbounded. I feel at one with the underworld of the sea.”

Now that is a beautiful question, one we can all learn from. Ask it of yourself now.

The answer is never the answer. What’s really interesting is the mystery. If you seek the mystery instead of the answer, you’ll always be seeking. I’ve never seen anyone really find the answer — they think they have, so they stop thinking. But the job is to seek mystery, evoke mystery, plant a garden in which strange plants grow and mysteries bloom. The need for mystery is greater than the need for an answer. – Ken Kesey

As Ra Uru said of Projectors (my energy type!) in Human Design, we are here to ask questions and ‘there is nothing more profound than a question’.

My favourite ones are Frequently Unasked Questions (FUQs).

To ask a beautiful question, and another and then another – that is a life’s work.

I’m certainly going to keep messing up, and I am going to keep trying to get there.

I don’t care what your favourite colour is.

Tell me what song you played on repeat during a time you thought your whole fucking world was ending. – cwpoet 

I don’t know if I’ll find the most beautiful question in the world.

But I might without noticing – as Rilke said…

Live into the answers now.

When was the last time you overheard yourself saying things that you never knew you knew?

I love night conversations best. Bonds somehow grow deeper in the dark, our stories climbing to the surface to be seen. These are some of the times that live on longest in our minds – conversations by candle or moonlight with our sleep deprived eyes. When I speak on the heart, I’m talking about your creative self, your internal self, your intuition, and your source of power. ― Victoria Erickson