An Ode to Great Questions

part science, mostly art, all surrender

The Webs We Weave is a free weekly-ish newsletter on being in flux, staying connected to ourselves and our creativity, and feeling more connected in the world.

In the past month I’ve written about poetry as a vehicle for feeling our feelings, lessons from last year’s Word of the Year, and assembling my notebook stack for 2024. I love hearing which pieces resonate with you, so I can create more of them! 💛

Thank you for being here.

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Photo via Jacob Mishler on Unsplash

We sat facing each other in thick stillness.

It never occurred to me that we might not spend New Year's Eve together but there we were at an impasse, each realizing the other was uncharacteristically unwilling to yield: my husband, his heart set on going to a party where all his college friends would be; and me, who refused to be talked out of a quiet evening in, after somewhat begrudgingly giving the ‘party’ thing a try last year (and who quietly felt like maybe it was his turn to make the concession this year.)¹

We rooted around in the tense quiet for hidden passageways, some elusive third option that would somehow give us both what we wanted. At one point he said, "I just don't want this to be a unilateral decision."

I stiffened. The engine of my mind revved, kicking up all kinds of uncharitable interpretations of that sentence and indignant retorts. Miraculously, I said none of them out loud. Instead some wiser part of me took over and intervened, asking with stunning neutrality:

"Ok, what does the alternative of a 'unilateral decision' look like to you?"

Within seconds, my jaw unclenched. The skin between by eyebrows laid down its arms and I sat there in feather-light relief—stunned by how wrong I’d been in my assumptions, and grateful for the alchemical power of a humble, expansive question.

When I enrolled in coach training in the fall of 2020, I had high hopes that such an official, fancy program would load me up with secrets and tools that would demystify the art of great coaching, and turn it into a replicable science. I couldn't wait to feel forever inoculated against that panicky on-the-spot feeling of, "oh god, what the hell do I say to be helpful here?"

While I absolutely did come out the other side of my training with armfuls of tools that have helped me facilitate really impactful coaching sessions, a stunning percentage of those nine intensive months were spent learning and mastering one specific skill:

how to ask really good questions.

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The power of a good question is something I witnessed and experienced constantly when I was working with coaching clients, but it's also one of those things I can't un-see in my everyday life.

I think about it all the time: in my closest relationships, during work meetings, on long-distance phone catch-ups, when I'm making small talk with strangers at events. In an instant, the right question has the power to jolt a dying conversation back to life, to cloak another person in the warmth of feeling understood, to reveal constellations of possibility where there was once only inky night.

What makes a great question?

There are the practical, sciency criteria, of course.

Open-ended questions over closed-ended ones (most of the time).
Concise, focused questions over rambly, intricate ones.
Ideally relevant to the conversation at hand, and asked in good faith.

But at least in my experience, the rest is art: guided by instinct, and in the best cases, an unfurling follows.

Like art, what makes a great question is highly subjective. Having said that, I've found a few common threads that powerful, evocative questions all seem to share: tough to quantify but unmistakable when you bump into them.

Great questions have a physicality.

I know I'm on the receiving end of a great question when it knocks me back in my seat a little, widens my eyes, like I subliminally feel some need to make physical space to take in the expansiveness of it. Anytime the first words to tumble out of my mouth are, "wow, good question...", even if it's just to buy myself a little time to digest it, it's a sign they've hit on something.

Great questions defy ego.

Anyone who's ever found themselves in a debate-style argument knows exactly what it feels like when a question has an agenda: to lead you down a particular path and into a trap. These types of questions might succeed in winning the argument, but at the cost of trust and intimacy.

In my experience, the most powerful questions are less interested in victory than they are in discovery and connection. They're insatiably curious and unattached, asked in good faith without agenda or assumptions. Questions that doesn't presume to already know, but delight in finding out tend to be the best ones.

Great questions have teeth.

For a while, I thought asking good questions meant staying waaaay zoomed out, hovering so far above judgment or binary thinking that everything just stayed benignly amorphous and fuzzy. But I've found great questions are often the ones that puncture. They have an edge, a point of view that comes from being highly attuned—finding a tiny soft spot worth sinking its teeth into, turning pinholes into portals.

Around the holidays last year, Jenny Rosenstrach of

Dinner: A Love Story

shared a brilliant tip from a reader named Tracy for more meaningful gift giving.

Instead of asking her adult children to hand over lists of things they wanted, Tracy sent them each a questionnaire with questions about their lives:

"It resulted in the coolest responses and really helped me come up with good gifts and ideas for how to make the holidays more meaningful. For instance, in one response, my youngest son mentioned he wanted a yule log class we had taken during Covid Christmas to be a yearly tradition. Another son noted that after recent a move to a new town, he still didn't really know what the best local restaurants were. So I researched restaurants for him and gave him a collection of gift cards to new restaurants and coffee shops."

An approach like this is profound in how it manages to get at the question underneath the question.

When we give gifts and ask for wishlists, most of us are really wanting to understand, how can I both show you how much I care AND give you something that brings you actual joy, function, relief? The novelty and specificity of her questions elicited more interesting and meaty responses from them that opened up whole new pathways of gift-giving possibilities.

It begs the question: why let "what do you want?" and "what's on your list?" lead us down the same stale gravel roads—when we could lace up our sneakers, seek out the hidden trail between the trees and watch new terrain open up before our eyes:

What do you long for on a winter day? How do you most want to feel, and what helps you feel that way? What do you gravitate toward when no one is around? What are you craving? What do you long for?

One of the highest compliments I think I've ever received was when a coaching client emailed me at the end of our six months to say, "my experience with you is that you are an expert at drawing out our inner truths."

And yet, to be honest, I think this sentiment is less about me and more about the power and the novelty of being asked neutral, expansive questions. In coaching, it's REALLY important to stay present and responsive, unattached to any one outcome. To ask questions without assumption, to release any agendas and preconceived judgments, and to simply be a trusted guide holding a flashlight: here's what I see, here's what I hear, where will it lead us next?

The humble not-knowing is part of the thrill—it's what leaves the door open to new terrain, to unexpected specificity, to revelations and truth unmarred by assumption. It's true in a coaching context, and it sure as hell was true on New Year's Eve.

Where else in my life can I tame my ego and embrace my not-knowing?

Where might we experience more ease and delight by surrendering to our not knowing—then grabbing a flashlight and chasing the humble thrill of finding out?

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🎧 Revisiting

Old episodes of the Maintenance Phase podcast (ahem, while I wait impatiently for new episodes...) And speaking of my undying love for this show—if you didn’t catch it, Aubrey’s guest appearance on We Can Do Hard Things was *chef’s kiss.* Highly, highly recommend. ⬇️

🥰 Relishing

Reading! After a months-long (ahem… years-long?) book-reading rut, I’m finally back in a rhythm of reading before bed and loving it. I just finished devouring

Nic Antoinette

’s new adventure memoir What We Owe to Ourselves and just last night I started Jennette McCurdy’s I’m Glad My Mom Died.

Also in the queue: Know My Name, Somebody’s Daughter, and We Are the Luckiest. What other memoirs by women, trans, or nonbinary folks should be on my list? Share your favorites in the comments!

✨ Weekly Dose of Internet Delight

(Talking Heads for me. Name your band!)

Until next time,
Michelle

1. This story was shared with my husband’s consent. :)