When Caring Feels Scary- Empathy at Work in Practice
- Elios Collective Team
- Jan 10
- 5 min read
“He’s been wearing the same shirt for two weeks. I’m worried.”
I sat across from the earnest manager, who was clearly concerned about one of his team members. He hovered awkwardly in the doorway — neither fully in my office nor fully out — whispering intensely. His body was tense, shoulders tight, eyes darting, as though being seen near Human Resources might put him at risk.
I grabbed my purse and keys.
“Let’s grab a coffee so you can tell me the whole story.”
I don’t actually believe that managers today lack empathy, but I do believe that many are afraid.
Afraid of saying the wrong thing.
Afraid of crossing an invisible line.
Afraid of blurring “professional boundaries.”
Afraid of opening something they don’t know how to close.
With our coffees in hand, sitting side-by-side on a bench in the late fall Calgary sunshine, faces tilted upward to catch the last warmth of the season, the manager continued.
“He’s quieter than usual. Something is wrong. I asked him how he was doing, and he said he was fine — ‘All good,’ that’s what he said. But I can tell. Something isn’t right.”
He paused.
“Can you please talk to him?”
Think about that for a moment.
How did we get to a place where asking someone you spend a third of your waking hours with each week — for years — how they’re doing feels awkward or inappropriate?
One would think that checking in on another human being would be the bare minimum of decency. But it’s not the asking that trips people up. It’s everything wrapped around it.
How do I ask?
Where do I ask?
What if others overhear?
What about cultural differences? Hierarchy? Personal boundaries?
What if they actually tell me something real?
So instead of connection, we create distance. Instead of curiosity, we default to caution. Instead of care, we outsource concern.
We have built artificial divisions at work that keep us from engaging with one another at a human level — even when the concern is genuine.
And underneath it all sits fear.
We talk about fear all the time in workplaces, but usually in coded ways: risk, liability, optics, exposure. What we don’t talk about is how deeply fear shapes everyday behaviour.
Fear of doing the wrong thing.
Fear of being misunderstood.
Fear of being vulnerable.
Fear of being fired.
It might sound ironic coming from someone who has held senior roles — COO, Interim CEO — but I know that fear intimately.
I remember a day when my boss asked to see me privately. My first thought wasn’t curiosity or confidence. It was: I’m getting fired. There had been no incident. No warning signs. Financially, things were stable. I hadn’t dropped any balls that I knew of. And yet, that was where my mind went.
Why?
Because many of us carry a quiet, primal understanding that no matter how valued we are, no matter how competent or liked, we are still replaceable.
With my background in Human Resources, I know that not all terminations are about poor performance. I’ve led large-scale downsizing initiatives. I’ve been part of mergers and acquisitions. I’ve watched organizations exit entire lines of business because they were no longer viable. In those moments, good people lost their jobs — not because they weren’t talented, but because the roles no longer existed. And in many cases, if those decisions hadn’t been made, the organization itself wouldn’t have survived.
Intellectually, I understood all of this. But fear doesn’t live in the intellect. It lives in the body. So if I — someone who understood the system — could jump straight to that conclusion, how could I expect others not to?
Back on the bench, I asked
“Don’t you think asking HR — asking me — to speak to him will freak him out even more?”
The manager shifted uncomfortably.
“Well… I don’t want you to talk to him as HR. Can’t you just… you know… talk to him?”
I laughed — not because it was funny, but because I understood what he wasn’t saying.
HR has become a symbol of fear, even when the individuals working in it care deeply. As a function, it is often experienced as the velvet glove — warm in tone and relational in language — while enforcing employment systems that punish vulnerability and protect harmful norms.
What this moment made clear for me is that empathy at work doesn’t fail because people don’t care — it fails because we don’t know how to act without fear taking over. Empathy with action requires practice, not personality. In situations like this, that practice looks surprisingly simple:
First, naming concern without diagnosing it — noticing a change without attaching a story or a judgment.
Second, creating space for sharing without pressure — making it clear that someone can speak, but doesn’t have to.
And third, responding proportionately — resisting the urge to escalate every human moment into a formal process or a problem to be solved.
When care is practiced this way, conversations happen sooner, escalation slows down, and people stay engaged instead of pulling back or bracing for impact.
With this guidance in mind, the manager felt more confident having the conversation himself. He didn’t book an intervention or escalate the situation. Instead, in their next regular check-in — after the employee had shared his work updates — the manager practiced noticing.
“Thanks for the update,” he said. “Your work looks on track and as thorough as ever. I don’t have any concerns there. I have noticed, though, that you seem a bit more subdued lately, and I just wanted to check in to see how you’re doing. You don’t need to share anything you don’t want to — but if there’s something you need, or support we can offer, I want you to know I’m here.”
The result wasn’t a tearful overshare or a stoic rebuff, but a quiet acknowledgment of a recent breakup. It had led to a move into a new apartment, some late nights settling in, and a bit less sleep than usual as he adjusted.
The first time the manager checked in, the situation was still too new. Many managers would have stopped after that initial conversation. But sometimes care requires more than one moment. People don’t always know what they’re ready to share right away — especially when they’re still in the middle of it. Safety often builds through consistency, not a single question.
The manager was relieved. While breakups are hard, they are also part of life. And the employee’s willingness to share opened the door to ask the question that had been quietly lingering.
“Can I ask you about that shirt?” the manager said, smiling. “You’ve been wearing it a lot.”
The employee grinned and glanced down. “Yeah,” he said. “I love this shirt. I keep it on my chair! I sit right under that vent, and it’s the perfect weight — warm enough to keep the chill off my back without the bulk of a sweater.”
Join us live:
This is the kind of situation we’ll explore in January’s Integration Session — practicing empathy at work in moments where fear of getting it wrong often leads to silence, escalation, or avoidance. Together, we’ll work through how to respond with clarity and care, without letting fear dictate the outcome.
When Caring Feels Scary: Practical Empathy Skills for Managers, Leaders, and HR
Date: January 30, 2026
Time: 10:00 AM (GMT -07:00 MT (Edmonton))
Format: Live Online
Cost: Free
In this session, we’ll explore:
where the fear of “getting it wrong” actually comes from — individually and systemically
how to create space for employees to share without becoming a therapist or overstepping your role
how to respond with care and accountability without escalating unnecessarily
when and why it is appropriate to involve HR — including the policy, legal, and safety considerations, and how to do so transparently.
Practicing genuine care is less about fixing what’s wrong, and more about small, deliberate actions — noticing change, naming it clearly, and staying in the conversation instead of handing it off or backing away.
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