Empathy is essential
in your leadership toolkit
[I]t might be helpful to think of empathy as sympathy’s street-smart,
cooler cousin. She’s been through stuff, so to speak, and she knows things.
By Meg McKeen, CIC
Earlier this spring, my partner and I were out for a lovely walk in the woods of Western North Carolina. As we rounded a turn, there appeared a pile of you-know-what left behind by a dog ahead of us on the trail.
Unfortunately for the woman a few steps ahead of us, we noticed it just after she stepped right in it. So gross.
As we walked on, the woman had already begun the awkward, mostly ineffective, scrape-and-swipe motion that one often does when there’s something we’d rather not have on the bottom of our shoe. And I mouthed “I’m so sorry” as we passed.
As we continued down the trail, my partner, very aware of my people-pleasing, perfectionist tendencies, asked, with curiosity but not judgment, why I’d apologized to her for something I didn’t do.
“Oh, it wasn’t because I did it, but because I’ve been there before, too, and it’s the worst. It’s like a sign of solidarity or support,” I explained to him.
Even the smallest expression of empathy connects us in our humanity, and these expressions range from what went down in the woods that day to the ways we support others following profound loss. But for many leaders today, expressing empathy doesn’t come easily and is a missed opportunity in creating lasting connections with those around us.
I’m sorry for your loss
Our culture defines for us many events for which we might express sympathy: heavy experiences like the loss of a job, of a loved one, or of meaningful property in the case of a natural disaster, or the ending of a marriage or a business endeavor.
But empathy is not sympathy. And it might be helpful to think of empathy as sympathy’s street-smart, cooler cousin. She’s been through stuff, so to speak, and she knows things.
Our own lived experience almost automatically allows us a deeper and more personal knowing of another’s experience of loss, and that shared understanding allows us to relate to one another in even more impactful ways. But unless or until you’ve experienced a loss or ending, it might feel inauthentic or even impossible to express pure empathy.
Practice makes progress
Perhaps you’ve never lost a job or a loved one or been divorced. It’s your ability to reframe another’s experience through your own lens that ultimately allows you to offer empathy to others, but it may just require a deeper pondering of your own adjacent experiences for you to do so.
Though you may never have lost a job, can you think of a time in your life when your finances were unstable? Or a feeling of shame or fear in sharing a life change with your friends or family? If you’re content in your marriage today, can you remember a time in the past that you’ve had your own heart broken? And all that it entailed to separate and begin again?
Does this practice feel awkward? If your answer is yes, then you’re doing it right! Remember that leaning into empathy isn’t something you learn to do by reading a book or in a self-paced module or lecture—or even by reading this column. We will learn best by doing.
Empathy is weak
For some of us, expressing empathy requires us to access language that others (and even our own selves) might think appears as weakness. During times of loss, you may hear others express their fears, doubts, sadness, sense of being overwhelmed—and a host of other emotions. And these “feeling words,” as I affectionately refer to them, haven’t always been welcomed at work.
Let’s be honest: To hear them from someone deep in their pain or loss, particularly when you are in a position of leadership, can feel like the opening of a door you’d just rather not. What’s more, while the powerful phrase “I’ve been where you are” is the purest expression of empathy, it also reveals your own vulnerability if you’re brave enough to say it.
It’s logical, then, that we’d view empathy as something better left outside of work and better left to others.
Empathy is strong
Even the smallest expression of empathy has the power to connect us in times of grief or struggle, and doing so could be worth the risk if you take it.
Having experienced great loss herself and now working with others as they navigate their own journeys through grief, Jody Lavoie, founder and CEO of Widows in the Workplace and The Grief Company, shares, “Widows share a bond that no one would ever choose, but once you’ve walked through that fire, you recognize it in others. Empathy is immediate, support instinctive. We don’t have to explain; we just know. And in that knowing, there’s comfort, strength, and a reminder that we’re not alone.”
It might feel easier to skip over this part of our human experience—the part where you sit in the messiness of it all. But how much more deeply would our bonds be if we showed up for one another in moments like this?
But I’m not feeling particularly empathetic
Listen, I know that many of us working in the insurance industry are carrying the emotional loads of others these days. Most of us, including me, fit squarely into the definition of “helping professionals.” So, the idea that we’d go out of our way to show empathy when our proverbial plates are already full might seem impossible. Or just not worth it.

But what if we instead stayed open to the most basic moments to learn and check in with our own empathy capacity? Coming up for me as I consider this: Have you ever navigated a Trader Joe’s parking lot? Pure chaos, and no shortage of opportunities to relate to others over stolen parking spots or impatient fellow shoppers.
Or elevators—the closing doors, the mad dash in from the elements, and the awkward shuffle as you settle in for the ride—are all moments we’ve collectively been through, and can relate to, as well.
What if we slow down? Your energy is as important as your words when you’re expressing empathy. Can you take a few deep breaths and center yourself, sitting with another person in their struggle, and just listen? Can you be brave enough to be silent instead of filling the space between you with words you know aren’t needed?
Sometimes it’s simply the act of pausing to sit with another in their moment of struggle that creates the most lasting impact.
One last thing
Neurotypical and neurodivergent individuals express and experience empathy differently; it’s important we remember this as we consider others’ willingness and ability to add empathy to their own leadership toolkit.
The author
Once told “you’re someone I’d like to receive bad news from,” Meg McKeen, CIC, founded Adjunct Advisors LLC in 2018 with the simple belief that we can and must do more to support the individuals who choose a career in the insurance industry. Now in her 25th year, Meg’s experience working in underwriting, leadership, and sales within the industry informs her work as a consultant today, in which Meg now holds space, at the crossroads of personal and professional development, for insurance professionals as they navigate their shifting relationship with work and this current hard market. Meg’s work includes private and small group coaching, workshop facilitation, industry event speaking and planning engagements, and the podcast she hosts, Bound & Determinedsm. Learn more at www.adjunctadvisors.com.