Leading Through Loss

What to Say, What to Do, and How to Lead When Someone on Your Team is Grieving

Table of Contents

1. Leading Through Loss - Introduction

2. Why Grief at Work is Everyone’s Business

3. What Leaders Get Wrong About Grief (And What It Costs Them)

4. How to Build Safety, Connection and Trust in the Hardest Moments

5. When Presence Isn’t Enough Anymore

6. What About Everyone Else?

7. The Work Isn’t Over. It’s Just Becoming Yours.

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Grief doesn’t clock in and out. It doesn’t wait for your calendar to clear or your team to hit its targets. It enters the workplace the same way it enters our lives—uninvited, unwelcome, and often when we least expect it.

And when it does, most leaders don’t know what to do. Some freeze. Some fumble. Many go silent. Not because they don’t care, but because no one ever taught them how to lead through loss.

But it goes deeper than that. We don’t just struggle to lead people through grief—we struggle to understand it at all. Grief is rarely talked about in our culture. When it is, it’s often misunderstood. We treat it like a problem to solve or a private matter to be quietly managed. We confuse it with sadness. We assume it follows a clean timeline. We expect people to quickly get through it and return to normal.

But anyone who has lost someone or something important to them knows grief touches every part of life - body, mind, work, and relationships. And anyone who hasn’t experienced it yet, will. Likely sooner than they think.

If you lead people, you need to understand this part of the human experience. Not as a therapist. Not as a savior. But as a steady, emotionally intelligent leader who knows how to stay present when life gets hard.

Why This Matters to Me

I lost my wife, Cindy, to suicide on March 26, 2010. For five years, we fought for her mental health—through hospitals, treatment centers, moments of hope and heartbreak. Every person has a threshold for suffering. In the end, Cindy reached hers and chose to end her life.

At the time, I was a father to two very young girls. I didn’t have the time—or the understanding—for grief. I thought grief was something weak people indulged in while strong people got on with it. There were bills to pay. A new life to build. I told myself I’d “moved on” because I didn’t see any other choice. I drank away the pain I refused to admit I was in.

It took nearly five years and countless failed attempts to finally put down the bottle for good. And then, six months into sobriety, the emotions I’d buried started flooding in - anxiety, sadness, regret, and anger seemed to come out of nowhere. I thought I was losing my mind. Until my wife, Tanja, looked at me and said, “You’re grieving.” She was right. I had finally slowed down enough to start to feel what needed to be felt.

Almost thirteen years after Cindy died, I lost my daughter Chloe.

On February 1, 2023, she died in a horrific car accident. She was nineteen years old. She was driving drunk and high, trying to outrun the pain of losing her mom. There is no playbook for that kind of loss.

For two months, I could hardly function. I was wracked with mental anguish and a level of physical exhaustion I didn’t know was possible. Some days, a single task would leave me in bed for the rest of the day.

Thankfully, my business partners stepped in with compassion and strength. They picked up the load. One even led Chloe’s memorial service. They checked in. They listened to me as a rambled about my experience. They validated my emotions without trying to fix my problems or give me advice. And I will be forever grateful for that.

I’m writing this a little over two years since Chloe died. Grief remains an ever-present companion. The sharp edges have (mostly) softened, but the pain and emptiness are still there. Sudden, intense waves still hit me out of the blue. In fact, just last week, I canceled all my meetings for the day because I was overcome with it

And still—I continue to heal. To rebuild. To lead. To try, every day, to turn this experience into something that helps others.

That’s why I wrote this guide.

Because I’ve seen what happens when leaders get it wrong - when they avoid, overcompensate, or say the wrong thing with the best of intentions. And I’ve seen what happens when they get it right—when they show up with presence instead of perfection, empathy instead of avoidance, and courage instead of control.

What to Expect

This isn’t a collection of abstract ideas. It’s not a collection of platitudes or corporate sympathy templates. It’s a practical, real-world manual for leaders who want to do right by their people – while maintaining their standards, their team, and their humanity.

Because here’s the truth no one says out loud: Someone on your team is probably grieving right now. It might be from a loss that happened last week or one from years ago. And how you respond - how you speak, how you listen, how you show up - will shape whether they ever trust you again.

This isn’t about being soft or being taken advantage of. It’s about being steady. It’s about making it safe to be human - especially when things are as hard as they’ve ever been.

The tools in this guide will help you:

• Show up with confidence, even when you don’t have the perfect words

• Ask better questions that build trust instead of distance

• Validate emotions without crossing boundaries and while maintaining yours

• Hold space for grief without lowering the bar for performance

• Lead conversations that are both honest and compassionate

• Support your whole team without creating chaos or resentment

But more than that, these skills will reshape how you lead in every relationship that matters: with your partner. With your kids. With your team. With yourself.

Leading through grief isn’t a niche skill—it’s one of the most important leadership capabilities you can develop. Why? Because the same qualities that allow you to support someone in deep pain are the exact ones that fuel high-performing teams: emotional intelligence, trust-building, steady presence under pressure, and the courage to communicate clearly even when it’s hard.

If you can lead through grief, you can lead through anything.

You’re about to. So the next time someone on your team is grieving—and there will be a next time—you won’t avoid it. You won’t freeze.

You’ll lead.

And that’s what people will remember. Not how many targets your team hit. But who you were when it mattered most.

Let’s get started.

Here's How this Guide is Laid Out

1. Why Grief at Work Is Everyone’s Business

Grief isn’t a disruption—it’s already in the room. This section builds the business case for supporting grieving employees, grounded in research and real leadership impact.

2. What Leaders Get Wrong About Grief—And What It Costs Them

Most leaders respond to grief with silence, avoidance, or overcompensation. This chapter breaks down common missteps, why we fall into them, and what they unintentionally signal to the team.

3. What to Say and What to Ask

You don’t need perfect words, but you do need to speak. This section provides concrete phrases, questions, and follow-up practices that help leaders connect without overstepping.

4. How to Validate Emotions When Someone’s Grieving

Emotional validation is one of the most essential—and overlooked—relationship skills in leadership. Here, you’ll learn the LEAD model: a simple framework to help people feel seen, heard, and supported.

5. How to Have a Hard Conversation with Compassion

When someone’s performance or behavior is suffering, silence isn’t support. This section introduces the Experience Cube, a powerful tool for addressing difficult situations with clarity and care.

6. What About Everyone Else? Leading the Team When Someone Is Grieving

Grief doesn’t happen in isolation. Learn how to lead the broader team with intention, reinforce your values in action, and support culture without creating confusion or resentment.

7. The Work Isn’t Over. It’s Just Becoming Yours.

This final chapter challenges you to turn insight into action. You’ll leave with a clear call to lead not when it’s easy—but when it’s needed most.