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Why it’s so hard to ask coworkers ‘how are you’—and how to move past that

Starting every correspondence with “I hope you’re well,” is the wrong approach. Assume no one is and use these strategies to connect.

Why it’s so hard to ask coworkers ‘how are you’—and how to move past that
[Source photo: Catherine Falls Commercial/Getty Images]

Do you ever feel like if you were to ask a coworker how they’re doing, you’d open a Pandora’s box that robs you of getting work done?

You’re not alone.

Since COVID-19, things beyond our control constantly get in the way of work. The pandemic itself pushed us out of our offices. That was followed by the presidential election, the war in Ukraine, the BLM movement, the stop-the-Asian-hate hashtag, the Supreme Court abortion ruling, and now the terrorist attacks in Israel.

If that wasn’t enough, we all deal with private and individual challenges that disrupt our work, like PMS or IBS (google it if you’re unfamiliar). We have parental leave, kids home sick from school, spotty WiFi from our remote locations, and, of course, an increasing sense of burnout.

Why does it feel so hard to work with other people? No one seems capable of working eight hours straight, five days a week anymore.

Why is that?


For the past decade, or at least since the early WeWork days, the “bring your whole self to work” movement has seen the most significant growth. Tech companies made it their number one goal and created workplace environments to allow employees to bring their full selves to work. Well, now it’s paying off—everybody is bringing their full self to work.

But surprise! Their full self is complicated, messy, and often sick. We all have things that are upsetting us, whether internally or externally. Women have periods every month, parents have kids, leaders are overworked, Gen Zers have mental health issues, and everybody else is just burned out, quiet quitting, or having to deal with families who live in war zones.

This is what Tyler Sellhorn framed as your “identity stack,” all the parts that make you you. And after the unspeakable terrorist attacks that touched families, elderly, and young people in Israel last weekend, I, a Future of Work leader at Density, had to face my own identity stack.

In a post I shared on LinkedIn shortly after the attacks in Israel, I said: “People know me as a thought leader. They know I am French, and they often call out my always-on positivity. But I never thought I had to share publicly about the most inherited part of my identity stack — that I am Jewish—because I didn’t think it mattered. But now it does.”

With the rise of remote work, it is getting harder for everyone to show up and focus on just work when facing struggles, pain, and atrocities at their doorstep. Employees’ emotions are spilling over “beyond the walls of their home,” and they’ve started using social networks and social platforms to share their frustration. But they’re not the only ones to suffer.

Leaders and employees read about their coworkers’ problems on social media and don’t know what to do about it.


As Peter Benei, the CEO of Leadership Anywhere, wrote, “The biggest shift in how we work is not about location. It’s about having more empathy toward each other.”

We all default to the same starting line in our work emails. “Hi . . . I hope you’re well.” But assuming that people are well is a problem these days. We should rather assume that everyone is not okay. How about starting all our emails with: “I know you’re not well given X, Y, or Z, but I’d love to work on this project with you today. Do you feel well enough to do that?”

It may be a longer line, but it is more inclusive, empathetic, and inviting and can bring better business outcomes. As evidenced in his book Speak-Up Culture, Stephen Shedletzky argues that by fostering a genuine sense of care, leaders set the stage for innovation, collaboration, and significant organizational development.

Since the October 7 attacks, people have flooded social platforms with screenshots of texts they received from friends, colleagues, or managers with words of kindness, care, and support regarding the current situation, encouraging more people to reach out. However, many people and leaders still feel awkward and shy to do so.

If you’re still struggling with asking colleagues if they’re okay (when you actually know they’re not), here are a few tried and true tips:

  1. The longer people’s pain and frustrations are ignored, the more they feel isolated and resentful. Start every conversation by first asking how they’re doing and be ready to get a real answer (that may make you feel uncomfortable).
  2. Be compassionate and use shoshin, a concept from Zen Buddhism, to approach things with a beginner’s mind. Invite them to express the pain they’re facing at the moment, keep an open mind and heart (despite your own beliefs or opinion), and only offer support if you actually can help.
  3. Only then (the order matters) can you leverage to your advantage the incredible power of humans to perform context switching and tap into our innate desire to work, be helpful, and contribute. Ask people permission to change matters after completing the first two steps above, and move the conversation towards the work to be done.

We no longer live in the 9-to-5 era. People want a greater integration of life and work. This means they also want more “real” relationships with their coworkers. If that’s the case, we must all unlearn the “proper” etiquette that used to prevail at work and build up our capacity to be brave and have courageous conversations.

Or do we?


A little while ago, a funny experiment at the University of Texas led to shocking news: ChatGPT could write a more compassionate letter to patients than doctors could. This anecdote was then confirmed on a larger scale by researchers who compared AI vs doctors’ answers to nearly 200 questions submitted by patients. Conclusions confirmed the same fact: “While less than 5% of doctor responses were judged to be ‘empathetic’ or ‘very empathetic,’ that figure shot up to 45% for answers provided by AI.”

Unbelievable, you say? Yes, because we view love, care, empathy, and sympathy as inherently human. But as Robert Pearl, author of Uncaring: How the Culture of Medicine Kills Doctors and Patients, explains, due to the harsh reality of the medical system today, on average, physicians spend only 17.5 minutes with each patient. Given the demand to move quickly, physicians interrupt patients after just 11 seconds to eliminate “wasted time.”

These rapid-fire exchanges can leave patients feeling uncared for. In fact, nearly three-quarters of patients surveyed reported having seen a doctor who failed to be compassionate.

Sadly, it doesn’t affect only doctors and patients. We’ve all been told that if we want to make it in the world and make it through a workday, we need to toughen up. And “after a decade of disuse, our softer skills atrophy,” writes Robert Pearl.

Should we have AI ask our colleagues how they’re doing because we humans are too triggered, awkward, or complicated to handle real emotions from other humans?

AI is this super intelligent being who never gets tired or hurt, who doesn’t have an opinion on any war or conflict in the world. It is a 24/7 available love machine that can send 1,000 compassionate letters.

Many believe that AI will kill us all. Actually, it’s proving that it will teach us how to be better humans.

Nellie Hayat is the workplace innovation lead at Density, the host of the Beyond Work webcast, and a leader of the future of work movement. 

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Nellie Hayat is the workplace innovation lead at Density, the host of the Beyond Work webcast, and a leader of the future of work movement. More

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