On how to have deep conversations – not just exchange pleasantries.

---

Put yourself in a moment where you were not fine. Maybe you were terrible, and maybe you were too good to be true. And you said, “I’m fine. Thank you.” Put yourself back in that moment when you lied. Why did you do it? Whose feelings were you trying to save? Write what you wish you would have said, and imagine where that honest conversation could have led you.

“How are you?” is a question we ask without intention and answer with white lies even when we are at a friend’s funeral.

When a terrible car accident instantly killed my friend, the wave of grief that settled over me was like a cloud threatening to steal every last ounce of oxygen from my lungs. When I watched the men from the funeral home wrap up my friend’s body and take it away, I doubled over in pain. The pressure of the physical pain went from my chest to my back and up my neck. I crumbled on the dusty floor feeling like something was crawling under my skin.

I took an 81-milligram aspirin and faced that awful day – her funeral.  

Friends and family members did not help. They asked empty questions. I nodded my head and lied, “I’m fine.” to their “How are you?”

I’m at my friend’s funeral and they ask me if I am fine.

We need to ask better questions if we’re looking for honest answers. I say this not just because I’m grieving a dear friend’s sudden loss, but because of the pandemic’s hellish nightmare, all of us are going through right now.

Perhaps the most important thing is to ask genuine questions that invite genuine answers. One of the kindest gestures we can extend to others in a global pandemic is to make sure that they don’t have to pretend they’re fine.

It’s time to drop the “How are you?” question altogether and ask something else, something that doesn’t send the respondent off to plumb the depths of how they are doing in the middle of a global pandemic only to resurface with “oh, pretty good.”

---

Rarely do people reveal much with “How are you?”

When you ask your friend, colleague, or a family member, “how are you?” at the beginning of a call or chat, they’ll default to some version of “fine.” The question is generic. It forces someone to lie straight to your face and say they’re fine. It doesn’t show your interest in someone’s answer.

You usually get a short, surface-level response.

That’s even true now when many things are definitely not “fine.” Rarely does the recipient reveal much, if anything, about how they’re actually doing – even if we sincerely want to know the answer.

Making people feel you care about them is almost impossible when the question you ask implies a common answer.

“How are you?” is not an honest inquiry.

I’m tired of the usual, compulsory breezy, “I’m good! You?”

When we keep asking the same question, we lose out on a chance for deeper connections with loved ones. We’re tricked into believing we know how they’re feeling or what they’re thinking when we haven’t even scratched the surface.

Since the pandemic hit, terror is a state most of share.

None of us are okay.

Everyone is doing badly. People are sick and dying in alarming numbers all around us. Maybe you’re lucky enough not to be sick or dying.

But everyone we know is in danger. COVID-19 has made us vulnerable – whether we are the sick, careers for the sick, or those who might become sick. It made us vulnerable in emotional ways too, whether through loneliness or lack of time and space alone, stagnation or rumination, avoidance or confrontation.

Our experiences differ in both specifics and intensity. But ever since the pandemic hit, we cannot take a single step forward without a black hole marching right alongside our footsteps. At any moment, this terrifying hole can open up beneath us and we will fall right through. If we’re lucky enough to escape this terror, we’re terrified someone we love has fallen right through.

Because of this terror, most of us feel stranded, abandoned, and alone.

Do you know what makes someone feel less alone?

Deepening your connections with others.

You can make someone feel warm and safe. Deep conversations can help us create more caring relationships. It can help us feel connected with others.

Asking more honest questions can help spark those compassionate conversations. Better questions lead to better answers. And better, deeper, more caring relationships.

Before my friend’s death, no matter who asked, I’d probably have said “fine,” and then kept walking down the hall even if my world was fully falling apart on the inside. But now, I never want to ask someone I care about, “How are you?”

What if we practice to say anything but fine? If I ask you how you are, or how your day was, you can say anything but fine. This means we’re more emotionally honest with one another.

What if we can send a message that we’re looking to have deeper conversations – not just exchange pleasantries? What if we ask a different, better, and honest question?

---

The next time you call or chat with a friend or a family member, try one of these better questions that go deeper than “How are you?”

These questions stretch beyond friends and family. They can also help remote work teams stay strong and connected, preventing physical distancing from introducing emotional rifts that complicate collaboration.

Here we go:

1. How are you today?

Often someone you care about feels comfort when they’re asked about their feelings on a specific day. Instead of the generic, “How are you?” my mom often asks me, “How are you today?” Adding that one word makes a difference.

This question is an inquiry into what is true for someone at this moment, in the past few hours, and can feel more approachable.

It’s intimate.

It shows you care.

2. How are you feeling?

These days, I sink into sadness too deep for words. I may appear fine one minute. And may lose it in another hour. The people who’re helping me grieve my friend are those who ask how I’m feeling. Feelings are fierce and wild. They don’t take well to anyone who attempts to domesticate them. They are impetuous. Their sole job is to make themselves heard.

When someone asks a question that opens the door for us to talk about our feelings, it’s a gift.

Instead of asking “How are you?” take things further. Ask how someone is feeling. It shows that you understand feelings are more complex than just being ’fine.’ It shows you want to know how someone feels emotionally and mentally.

3. I was thinking about you.

This one is not a question.

But it’s a million times better than asking, “How are you?” Sometimes it has been so long that it’s hard to remember anything specific about someone. In those instances, go with, “I was thinking about you.”

There’s something fantastic in knowing that someone was thinking about us.

4. How are you taking care of yourself these days?

When a friend asked if I was taking care of myself, I found it to be the sweetest way to check-in. Keeping things open-ended versus just asking a yes-or-no “are you taking care of yourself” will give you more of a roadmap for how to follow up their answer.

5. Want to do a FaceTime coffee later?

Offering a hug or a handshake is no longer a polite way to greet someone. So how can we check in on each other in a more meaningful way?

You can ask your friend or colleague for a FaceTime coffee.

The goal of identifying other ways to say how are you is to replicate the feel of hanging out in person and genuinely connecting. You can ask this question to make sure active one-on-one time to see how someone is doing, authentically.

6. How are you holding up?

We can’t tell a white lie with this question. Because the question acknowledges that things are hell right now.

7. How can I help?

Maybe your friend or colleague needs a sympathetic ear. When you ask, “How are you?” they cannot tell you what they need from you.

You can fix that.

Ask if there’s anything you can do to help.

---

Takeaway:

We can ask better questions. We can dive into some unchartered emotional territory. We can ask others out of genuine curiosity versus obligation. And then we can ask follow-up questions that show we’ve been listening.

So which of the above better questions will you ask others?

---