I can’t believe I’m saying this, but Thursday will mark the 24th anniversary of the day my cousin Matt was murdered.
Yes, murdered. There’s no softer way to put it.
Matt was one of the victims who died in the Twin Towers on September 11, 2011.
He worked there. He was 26 years old. Full of life. A good man. So much fun. And in an instant, he was gone.
There’s no playbook for what to do when something that tragic befalls a family.
But in many ways, I’ve found that how others respond to that tragedy can be even more revealing.
Because for most people, the overwhelming feeling is helplessness. That aching desire to do something—to say the right thing, offer comfort, ease the pain, make the future more imaginable. But the words rarely come.
And if they do, they often feel futile at best, and clumsy at worst.
As a leadership communication coach, I’ve seen time and again how hard it is for even the most seasoned executives to know what to say when someone is grieving. Whether it’s a death in the family, a serious illness, or another kind of personal crisis, the struggle is real:
How do you support someone going through something so personal—especially in a professional setting?
Common Responses to Grief and Crisis in the Workplace
In moments of loss or trauma, most people fall into one of three patterns:
- The Talkers.
These are the people who try to empathize, lighten the mood, or simply fill the silence. They lean on words because words are their go-to tools. - The Doers.
They cook. They clean. They run errands, take over tasks, cover meetings, watch the kids. They express love through action. - The Avoiders.
These folks may feel they have nothing helpful to offer, are afraid of saying the wrong thing, and may figure if the other person would feel better if everything else felt “normal” or are just uncomfortable in emotionally intense situations—so they say nothing and figure if the person in pain reaches out then they’ll help.
Each approach comes from a place of care. But in the fragile and distorted lens of grief, anything can be misinterpreted.
Why Grief Communication Challenges Even the Best Leaders
In executive coaching conversations, this is one of the most fundamentally human challenges I hear.
Leaders can manage a public crisis like a pro. Market crash? There’s a playbook. Cyberattack? They’ve rehearsed that drill.
But when someone on their team experiences a personal tragedy—the death of a parent, a child, a beloved pet, a miscarriage, a diagnosis, a divorce—many otherwise confident executives freeze like deer in headlights.
Why?
Because this kind of leadership requires a different skill set:
- Tact
- Empathy
- Diplomacy
- Emotional intelligence
- Timing
- Framing
- Delivery
- And, critically, doing it all within professionally appropriate boundaries
Sometimes, it is complicated. But just as often, we overcomplicate what’s actually quite simple.
I've coached many leaders who admit these are the most emotionally difficult situations they’ve ever had to navigate—because the risk of saying the wrong thing feels paralyzing. And avoidance feels safer.
But silence doesn’t build trust. It builds distance. And it rarely goes unnoticed.
If you want your team to trust you, to follow you, to believe in you—it starts here.
Because people willingly follow the leader they believe genuinely cares.
Not the one who always appears polished or perfect.
If you’re a leader who consistently agonizes (or fumbles) over what to say when a team member is grieving or otherwise struggling—or you want to develop stronger emotional intelligence and communication skills you can count on during moments that matter—this is where executive coaching can make all the difference.
What to Say When Someone Is Grieving or Struggling
One of the most meaningful things you can say in these moments is a humble, transparent disclaimer like:
“I know there's nothing I can say to make things better. I feel helpless, and every word that comes to mind sounds stupid. I'm probably going to say or do the wrong thing—so if I do, please forgive me. Just know that my heart wants to say and do whatever you need. So if there's anything I can do—now or at any point in the future—just say the word.”
That kind of vulnerability—acknowledging your own lack of skill and imperfection—can actually dissolve the discomfort. It makes space for real connection and shows your heart is in the right place.
Additionally, when people are in the depths of grief, they often can’t identify what they need, much less articulate it. So offering some “multiple choice” options can go a long way:
- “Want me to cover your client calls this week?”
- “Would you like help picking up the kids?”
- “Can I drop off dinner tomorrow night?”
- “Want company, or do you need space?”
- “Need a bear hug?”
- “Or would you rather I just check in again next week?”
They may say no to all of it—and that’s okay. You’ve still shown up with intention and care.
“I See You. I Hear You. What You Say Matters.”
Oprah Winfrey once said:
“I’ve talked to nearly 30,000 people on this show, and all 30,000 had one thing in common: they wanted validation. They wanted to be seen. They wanted to be heard. And they wanted to know that what they said mattered.”
That’s it. That’s the whole formula.
Especially in times of pain and vulnerability—whether it’s grief, illness, burnout, heartbreak, or personal loss—what people want most is to know:
- I see you.
- I hear you.
- You matter.
And as Maya Angelou so beautifully reminded us:
“People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”
So if you're not sure what to say, let that be your guiding principle. Make them feel seen. Make them feel remembered.
The Text That Costs Nothing and Means Everything
For Matt’s family—his parents (my aunt and uncle) and his sister—what has mattered most over the years isn’t grand gestures or deep conversations.
It’s simply knowing that people still remember him.
Every year, on September 11th (and on his birthday in January), I send them a short text along the lines of:
“Thinking of Matt and you today. Missing him and love you all.”
That’s it.
No expectations. No reply needed.
But I know it’s enough, and it matters. Because a few years ago, my aunt lamented that so few people even acknowledged the date anymore.
“I guess the world has just moved on,” she said.
The simple fact is that I can’t bring him back, and she’s not asking me to. But I can make sure she knows he’s not forgotten.
That’s what matters to her, and I can totally do that.
It’s not about being stuck in the past.
It’s not about fixing anything. It’s about witnessing.
What to Say When You Don’t Know What to Say
So if someone you care about—personally or professionally—is hurting, and you don’t know what to do, try this:
“I just want you to know that if there’s anything I can do to support you, you know where to find me. Just say the word.”
Sometimes, once is enough. Other times, you repeat it every day, week, or year.
It shows you are present.
Because when words fail, presence speaks volumes.
