How to Ask Good Questions

Small talk can be painful. Toronto poet Lee Suksi wanted to ask questions that would spark real connections. Here's what they learned.

Text—Lee Suksi
Illustration—Gabrielle Deronde


This summer I felt alienated, so I experimented. Every morning, I’d ask three questions to my followers on Instagram. I tried to ask questions that I myself had trouble answering.

“Are you more often: Bored?/Overwhelmed?”
“Is it easy to make other people happy: Yes?/No?”
“Is it easier for you to: Apologize?/Forgive?” 

I adapted the practice from the writer and teacher Leah Sophia Dworkin, who encourages her students to be attentive to the questions they ask in their writing — especially the ones they’ve never asked before.

“Play with asking different kinds of questions,” she offers. “Play with asking questions from a different part of the self.”

When I started my experiment, I’d been watching Dworkin bring her expansiveness to polling people on Instagram in the temporary Stories feed, many times daily. Her writing had long inspired me with its unexpected turns, its visions of swimming through cities and facial wounds that drip honey.

“Ponds?/Rivers?” her almost-hourly polls asked me. “Live with your lover?/See them a few times a year?” “Make something great?/Make something famous?” Tiny stories unfolded with each answer.

“I’d make guesses in the morning as to where the majority would fall, and I loved it every time I was right and loved it even more every time I was wrong,” Dworkin told me.


Pleasant surprises

When I launched my experiment, a few hundred people habitually responded to my polls: a scattershot sample of everyone I’ve ever met, from close friends and exes to former co-workers and distant acquaintances. Like Dworkin, I was delighted by the often unexpected and contradictory results. Exactly half clicked yes on “It’s easy to make myself happy.” The other half clicked yes on “It’s easy to make others happy.”

After so much time spent in pandemic isolation out of concern for the health of close ones, some degree of wonder returned to me as the responses came in.

Polling my networks helped me realize how many assumptions I’d been making about the wider world without context, and how those assumptions sometimes calcified into bitterness.


The pandemic unsettled me badly. Leaving and returning to the city, suffering minor griefs and losses, and witnessing so much political despair, all while removed from a sense of community — these experiences took their toll on my social faith. All my answers were coming from the deliberately crafted thoughts of authors and journalists and the echo chambers of those closest to me.

But the playfully polarized format of the questions was eye-opening. Someone I had perceived as arrogant would repeatedly acknowledge their self-doubt or compassion. Someone I had perceived as an adventurous loner would click yes on paired domesticity and write to me about their yearning.

What started as a silly daily rite — the crowdsourcing of angst — started to feel optimistic. A mutual trust between mostly-strangers was at work.


Five questions to answer boldly

1. Are you better at working or relaxing?

2. Are you more sensitive to news or fiction?

3. Given the choice, would you live alone or with others?

4. Which is more important to you when you dance, connecting with others or expressing yourself?

5. Which comes more naturally to you, gratitude or generosity?

The courage of not knowing

The most optimistic line of questioning I know of is the protocol on anonymous crisis lines, those rare free mental health resources, where I answered phones for many years.

Volunteers with very brief training ask a series of questions that can be uncannily effective at taking the pressure off urgent despair. They start from the vague and general — “What’s going on right now? What are you feeling?” — and move into greater precision around sources of pain or sources of safety or comfort as needed.

To tell you the truth, I’ve occasionally been on the other end of these lines, and I know from both directions how reassuring a curious, empathetic stranger can be when the world feels especially untrustworthy.

My friend Dillon Katrycz also volunteered with a crisis prevention line and is now qualifying to be a psychotherapist. A deeply patient person whose voice has the cadence of a public radio classical music host, he felt like an ideal person to help me understand the mysterious power of the Instagram questions

What, for instance, is the difference between the questions we ask ourselves in private and the ones we ask of other people?


“Sometimes the questions we ask ourselves can feel unspeakable,” Katrycz told me. When we pose those questions to someone else, we make ourselves vulnerable. This vulnerability has the power to expand our sense of what is possible in relationships. A poor answer may confirm our worst fears about ourselves.

This risk becomes more manageable when we keep ourselves open, as a crisis volunteer does, to ambiguity and difference. On Instagram, the stakes are low, so it’s easy to enjoy the thrill of taking a strong position and potentially disagreeing with your friends. In everyday life, people may avoid the crisis of disagreement by not asking the questions they’d like to.

“Certainty,” says Katrycz, “is security.”

That may be, but the deeper our relationships, the more we may feel threatened by confusion and doubt.

“Sometimes people think they need to have a conclusive and stable answer to a question,” my friend said.

“It is often the case that ‘I don’t know’ is the most honest and meaningful answer to a question and the most conducive to exploration and discovery.”

Five questions that allow uncertainty

1. Do you often forgo transparency for kindness?

2. What’s the scariest question you could ask your partner or friends?

3. Do you have a secret you will never tell?

4. What do you love most about yourself that’s hard to share with others?

5. What’s the easiest thing that someone could do that would help you the most?

The space of reception

Making space for doubt is a skill that can be learned and refined. During the lockdown days of the pandemic, Katrycz and I, among other friends, bonded across long distances over the astonishing Showtime show Couples Therapy, now in production of its fourth season.

On the show, real-life psychoanalyst Dr. Orna Guralnik offers her measured intensity to couples in crisis in a facsimile of her comfortable New York office. The couples, tempted by free, world-class counselling, agree to be filmed, but seem markedly unguarded behind one-way glass.

Couples Therapy is a subversion of shows like Love Is Blind or Dr. Phil, in that the couples, offered space and patience, often provide more uplifting drama through slow coming to terms with one another than through mutually assured destruction.

I got in touch with Dr. Guralnik, whose capacity for close attention was palpable even over the phone. Over a tenuous connection, I could hear her listening almost louder than her speaking. I asked whether there were questions she thought every couple should ask one another. She didn’t name one in particular, but instead offered a few principles to follow.

“When you ask the question, be sure that you want to know something that you don’t know already,” Dr. Guralnik told me. A good question opens space for the unexpected.


For Guralnik, perhaps the most important part of asking questions is what comes next. “There’s a really big difference between expressing oneself . . . and listening,” she advised. “If you’re asking a question, then move into listening mode and actually listen.”

It startled me to hear her describe listening as a precise movement. I tend to see communication as a frenzied dance floor, but Guralnik was suggesting something more definitive: a clear crossing of the threshold into the space of reception.

Beyond small talk

In the show, Guralnik often helps ranting couples make the movement into listening by stopping them in their tracks to ask one or the other what they are feeling in that moment. The effect of this simple question is always powerful. I wondered, how might that work outside the therapeutic context?

“I think a lot of the time when people say, ‘How are you doing?’ or ‘How are you feeling?’ they don’t mean it,” she told me, underscoring the grief around small talk. “But a real question, like, ‘I really want to know how you’re feeling,’ can immediately deepen the situation. It can bring you a lot closer to the heart of the matter.”


But this type of penetrating question shouldn’t be used indiscriminately, Guralnik warned me. Asking questions is profoundly intimate, and we have to be ready to receive what comes.

Questions lead us into the unknown — as frightening and joyful a place as the wilderness at night. Part of asking good questions is also accepting that you may not get an answer.

In the Instagram polls I adapted from Leah Sophia Dworkin, “I don’t know” was not an option, and many answers were delightful revelations. We may long for this certainty, but in life, Dillon Katrycz emphasized that those we ask answers of must be afforded more grace.

Learning to listen precisely is an invitation to make our worlds much larger. Receiving an unexpected answer will perhaps help us know and deepen the questions we ask.

Five questions to go deeper

1. What are you feeling right now?

2. What time of day do you listen best?

3. Whom do you most want answers from?

4. How do you react when you don’t get an answer?

5. Who makes you feel most heard?

Lee Suksi’s first book, The Nerves, is available from Metatron Press. It won a Lambda Literary Award. See an archive of their questions on their Instagram. A book of their drawings, Acting on You, is forthcoming with fine. press. They live in Toronto.

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