20 questions to ask instead of “How

are you doing right now?”

When we keep asking the same question, or no questions at all, we lose out on a chance
for deeper connections with our conversation partners, who also happen to be the people
we care most about. We are tricked into believing we know how they’re feeling or what
they’re thinking, when we haven’t even scratched the surface.

Even in the best of times (read: when we’re not in the middle of a global pandemic)
“How are you doing?” is more likely to be a conversation stopper than a conversation
starter, the journalist and author Warren Berger argues in The Book of Beautiful
Questions. As Berger notes, “A rote question often evokes a rote answer followed by an
echo of the original rote question (“How are you?” “Fine. How are you?”)”

In this challenging moment, let’s move beyond “how are you doing?” and get more
serious about the questions we’re asking our colleagues, friends, and family. It’s not just
a matter of enlivening phone, text and Zoom chats (after all, there are all kinds of
filters for that). It’s a matter of keeping our relationships strong and solvent during what
may be a long stretch of healthy spacing ahead of us. Fundamentally, learning how to
ask questions of ourselves and of the ones who we love can help us to embrace, rather
than avoid, the uncertainty that envelopes our lives. To paraphrase the poet Rainer
Maria Rilke, we are all now living our questions—dozens of them, everyday—whether
we like it or not.

The research on the power of questions to strengthen our relationship with others—and
ourselves—is clear. They are interpersonal relationship magnets, compelling us to
reveal personal information that builds mutual trust. They can make us more likable,
seem more competent, and even increase our ability to empathize.

And crucially, the relationship-deepening benefits of questions stretch beyond friends

and family. They also can help newly remote work teams stay strong and cohesive,
preventing physical distancing from introducing emotional rifts that complicate
collaboration.

Below are a selection of questions, from those that invite levity to others that prompt
more serious reflection, that you can ask your conversation partners to get beyond “how
are you doing?” and perhaps into some uncharted emotional territory. Of course, being a
great question-asker isn’t just about posing a single, powerful question. It’s
about listening deeply before and after you ask. It’s about asking out of genuine
curiosity versus obligation, and posing follow-up questions that show you’ve been
listening. It is both a mindset and a skillset.
Eleven questions for making a true connection or maintaining
team cohesion
Here are some sample questions for getting beyond “How are you?”

1. How are you taking care of yourself today?

2. What part of your shelter-in-place residence have you come to appreciate the
most?

3. What surprising thing have you been stocking up on (that isn’t toilet paper)?

4. What’s a story – from a book, a movie, an article, a conversation – that you’ve

been gripped by recently? Why did it capture you?

5. What habit have you started, or broken, during the quarantine?

6. Which specific place in your neighborhood are you most looking forward to
visiting once this is all over?

7. What’s the easiest part about the quarantine?

8. What are some things you have realized that you don’t really need?

9. What’s something you own that feels useful?

10. What is your Covid-19 nickname/alter-ego?

11. What problem—either yours, or something more global —do you wish you
could solve?

Nine questions for taking things a step further

These are questions to consider if you’re interested in deepening connections in your
1:1 meetings or virtual coffees, or with people outside of your work life:

1. What’s something that you miss that surprises you? What’s something that you
don’t miss that surprises you?

2. Which member of your family/ friend group have you been thinking about the
most during this time? Why?

3. What’s the most generous act you’ve seen recently?

4. What’s the last thing you experienced that made you laugh, or cry?
 5. What times of the day or the week are hardest?

6. What’s giving you hope right now?

7. What’s the best thing that happened to you today?

8. How do you want this experience to change you? How do you think it will?

9. What do you hope we all learn or take away from this experience?

If you use these questions, I’d like to know: What conversations did it spark? Reach me
on Twitter at @elizabethw723 or email me at eweingarten@ideas42.org, and let me
know what other questions have you found inspiring.

Elizabeth Weingarten