Every leader eventually discovers a universal truth: employees always have something going on beneath the surface—personally, professionally, or emotionally. The leaders who recognize and navigate these challenges with leadership empathy build stronger teams, trust, and performance. Here’s a powerful example.
I recently overheard a conversation between two managers. One was clearly frustrated with an employee on his team.
“I just don’t understand Randy,” he said flatly. “He’s a good guy. But with him? It’s always something.”
I didn’t know the managers, and I didn’t know Randy (not his real name). But the frustrated manager wasn’t wrong. There is always something happening in people’s lives. And recognizing that fact helps intentional leaders respond with steadiness and understanding when employee issues inevitably surface.
Below are four leadership realizations that make responding to employee challenges at work easier—and far more effective.
Realization #1: Every Employee Is Managing Something—Always
Everyone wrestles with issues sooner or later—whether they’re personal or professional, temporary or long-lasting, predictable or completely unexpected.
These challenges take many forms:
- financial pressures
- health issues or injuries
- relational strain
- workplace conflicts
- major life transitions
- unexpected responsibilities or crises
Regardless of shape or size, challenges can’t be ignored. People carry them into conversations, decisions, and interactions.
Look around your workplace, neighborhood, or even your dinner table. Every person you see has something on their mind.
Empathic leaders assume there’s more going on beneath the surface—and lead accordingly.
Realization #2: People Manage Their Challenges Differently
Some individuals talk openly about what they’re facing. They process externally and invite others into the conversation.
Others do the opposite. They keep their difficulties private, working through them quietly and independently.
Neither approach is “right” or “wrong.” But recognizing these differences matters. Extroverted processors may need space to share. Private individuals may need room to think before discussing anything.
This means leaders must:
- avoid assuming they know how someone will communicate
- respect personal boundaries
- show genuine interest without pushing too hard
- offer support even when details are limited
When someone doesn’t open up immediately, it doesn’t mean they don’t want help. It often means they’re still processing what the problem really is.
A gentle, non-intrusive offer of support opens the door. And once that door is cracked, trust can grow.
Realization #3: Some Challenges Run Deep and Require Sensitivity
There is no faster way for a leader to lose credibility than by minimizing someone’s struggle.
Statements like:
- “That’s not a big deal.”
- “You’ll be fine.”
- “Just don’t worry about it.”
may be intended to calm… but they often come across as dismissive.
For the person wrestling with the issue, it is a big deal. And when leaders downplay it, employees often feel:
- hurt
- misunderstood
- emotionally dismissed
- less willing to trust or share in the future
Before people can work through a problem rationally, the emotions surrounding it must be acknowledged. Empathy doesn’t mean leaders must solve everything—it means they take someone’s experience seriously.
Instead of minimizing, leaders can say:
“You seem unsettled by something. If you’d like to talk through it, I’m here.”
The employee may not open up right away. They may share only a little—or nothing at all.
But your offer plants a seed. It conveys care, not pressure. And that matters.
Realization #4: Some Challenges Don’t Go Away Quickly
Every leader has wished they could snap their fingers and make their employees’ problems disappear. If only.
Some challenges have long shelf lives and can significantly affect employee well-being and engagement.
- chronic illnesses
- prolonged financial strain
- major life responsibilities
- declining confidence
- difficult relationships
- unhealthy habits
- job-related stressors
These issues don’t resolve overnight, and leaders must be prepared to support people through extended seasons of difficulty.
To help employees make sense of what they’re facing, it can be useful to remember that challenges generally fall into three categories:
- Challenges with identifiable causes
- When the source is clear, solutions are often easier to find.
- Challenges that are temporary and seasonal
- They require patience and reassurance that things will improve with time.
- Challenges that may not go away anytime soon
- These call for acceptance, resilience, and steady support.
Understanding which category someone’s challenge falls into can help leaders respond more wisely and compassionately.
FAQs: Questions to boost Leadership empathy & supportive conversations
Leaders often struggle with what to say when an employee seems overwhelmed or withdrawn.
The following questions help open a caring, non-intrusive dialogue:
- What’s weighing on you today that I might be able to help with?
- Is there anything affecting your work or stress level that you’d like to talk through?
- Would it help to think through options together?
- What feels most challenging right now?
- What support would be most helpful to you in this moment?
These questions build connection and trust—without forcing anyone to disclose more than they’re comfortable sharing.
A Timeless CALL for Leadership EMPATHY
As you walk with people through short-term issues and long-term challenges, it helps to remember the wisdom in Reinhold Niebuhr’s “Serenity Prayer”:
God, grant us the serenity to accept the things we cannot change,
the courage to change the things we can,
and the wisdom to know the difference.
— Reinhold Niebuhr
Leaders don’t have the luxury of eliminating the “somethings” their people face—but they do have the opportunity to respond with empathy, curiosity, and steadiness. When we acknowledge that every employee carries unseen struggles, we lead with clarity and compassion that builds loyalty and trust.
What “something” might someone on your team be carrying today—and how can you show up for them?
