Leadership & Loss
On Leadership, Grief & Perseverance
I recently lost someone very close to me and it got me thinking about how leaders deal with personal loss.
Do you keep quiet or do you talk about it?
Do you let work distract you from it or do you give in to your grief/pain?
Do you take a break or just keep soldiering on?
One thing I realized is that loss is always around us. Its always happening. In fact, it’s been happening since we were kids.
I remember how heartbroken I was when we moved in sixth grade and, overnight, I lost all of my friends. Or how sad I felt after breaking up with Maria Gonzales. Or standing at the foot of my grandfather’s grave, tears streaming down my face, realizing he was truly gone — and that our last visit with him had, without us knowing it, been the last time I would ever see his sweet, toothless smile.
Life is crammed full of loss. Packed to the brim with it, really — for everyone. And yet, learning how to deal with loss is not something most of us are particularly good at. We spend years mastering careers, responsibilities, routines, and practical skills, but grief? I don’t think most of us are very “good” at managing it.
Sometimes I wonder whether psychologists handle grief better than the rest of us. After all, they spend their lives studying the mind, understanding emotion, and helping others navigate pain. You would think that expertise might offer some kind of advantage when loss comes knocking at their own door.
But my hunch is….I don’t think they are any different.
Knowledge may help explain grief, but explanation and immunity from it are not the same thing. In the end, loss is one of those things that no amount of expertise fully exempts us from.
The Professional Impact of Loss
As I’ve gotten older, and as more people around me have begun facing the reality of loved ones getting ill, aging, and the final stretch of life, I’ve started to observe what loss actually does to people professionally.
People who were once vibrant, relentless executors, or charismatic visionaries begin to change. Sometimes subtly. Sometimes profoundly. They may not even realize it themselves. But inch by inch, as the personal losses accumulate, something shifts.
They don’t shine quite as brightly. Their edge softens. The wins don’t come as easily or at the same level they once did.
Perhaps this is simply part of being human. Loss is woven into life, after all. No one escapes it. And if that’s true, then maybe periods of diminished performance are not an anomaly but a natural consequence of carrying grief, stress, caregiving, fear, or change.
Maybe we all move through seasons where loss weighs heavier than love, growth, momentum, or possibility — until, slowly, those forces begin to return and rebalance us again.
Lessons from a Quiet Man
I grew up with a very strong father. But he was also not the most emotive.
He had experienced an extraordinary amount of loss himself. At a young age he lost his mother, his older brother, another older brother, and his little brother.
I remember standing beside him at a family funeral when I was a boy. Like many children, I wanted one last hug. One last moment with the person we had lost.
But my father stopped me.
“You shouldn’t do that,” he said. “It’s just an empty shell now.”
As a child, that was painful.
My father did not talk about grief. He did not sit with it, analyze it, or linger on it. He was always looking forward. Always moving ahead.
I’m not exactly like my father but I definitely took a bit of the “only look ahead” approach from him.
Breaking the Pattern
With this recent experience of loss, I wanted to try responding differently.
My normal instinct — and the norm for many executives — is silence. Keep personal pain tucked away somewhere out of sight.
But this time I chose to share a little of what was happening with colleagues including CEOs, CFOs, CTOs, engineering friends and more.
Part of the reason was something a mentor once did for me. A highly accomplished leader, someone very high up in an organization, shared a deeply painful personal tragedy with me. I remember being struck by it. Not just by the loss itself, but by the fact that he was willing to let people see that part of his humanity.
It changed something in how I thought about leadership. I remember feeling: if someone at his level can speak openly about a difficult life event, maybe I can too.
The reaction I received from talking about it was incredible.
I expected a few kind words. What I got instead was an outpouring of humanity.
People didn’t just offer support. They shared their own stories of grief. The loss of a mother. A father. A sister. Stories of illness, tragedy, caregiving, heartbreak, and somehow, perseverance. So many examples of people carrying enormous pain while continuing to move forward.
One story, in particular, stuck out.
Someone I had worked closely with years ago told me that one of his parents had died during a period when we were working together intensely. I knew exactly the timeframe he was talking about.
And I had no idea.
He had never mentioned it. Never hinted at it. He just kept showing up, doing excellent work, staying diligent, carrying the load.
I couldn’t believe it.
My first reaction was admiration but also sadness.
I wished he had told me. I wished I could have been there for him.
And it made me wonder how many people around us are quietly carrying profound loss while we discuss roadmaps, deadlines, meetings, and deliverables — never realizing the weight they are holding beneath the surface.
Engineers & The Instinct to Persevere
I’ve spent a lifetime in technology, and one thing I’ve learned over the years — reinforced even more recently after opening up a bit myself — is that many engineers keep things bottled up.
Maybe it’s because a lot of us are introverts. Maybe it’s because we’ve spent years feeling unheard, misunderstood, or operating behind the scenes. Engineers are not usually the loudest people in the room.
But I think a big part of it is something else: the instinct to soldier on.
Engineers tend to have what I call a *persevere mentality*. When something breaks, we fix it. When something isn’t working, we troubleshoot it. When the path forward is unclear, we grind through the ambiguity until we find an answer. That mindset is deeply baked into the culture and identity of engineering.
And I think many of us apply that same concept to our personal lives.
We compartmentalize. We absorb the hit. We keep moving. (Like my father? Funnily enough, he was an engineer too!)
The archetype of the quiet engineer — heads down in the back office, diligently solving difficult problems without complaint — runs deep in our profession.
The problem is that grief, loss, and human suffering inside of us does not behave like a technical problem.
A Better Approach for Leaders
I won’t advocate for being overly vulnerable as a leader. I think that can be dangerous, misplaced, or even undermining in certain situations.
But I will say this: sometimes sharing matters.
Not performative sharing.
I mean the quieter kind of honesty. The kind that simply acknowledges reality.
“I’m dealing with something difficult” or “Life is heavy at the moment.”
Small admissions like these can do something surprisingly powerful. They give others permission to be human too.
Because the truth is that many people around us are carrying far more than we realize. They are navigating illness, loss, fear, divorce, aging parents, struggling children, or private grief that never appears in the day-to-day.
And yet they keep showing up. They keep building, leading, solving, supporting, and persevering.
Perhaps leadership is not about pretending we are untouched by life. Perhaps it is about demonstrating that strength and humanity can coexist.
That we can continue moving forward without denying what we carry.
That we can make room for dignity, compassion, and the occasional honest sentence that reminds people they are not alone.
Life will keep delivering its mixture of love/growth and loss. None of us get exempted from that arrangement.
The best leaders may not be the ones who hide it perfectly.
They may be the ones who learn how to carry it openly enough to create a little more understanding for everyone else.