How Grief Changes the Way You Lead

Nobody teaches you how to grieve and lead at the same time. There’s no chapter in any MBA program about what to do when you’re running a team of 50 and you can barely get out of bed. No workshop on how to run a quarterly review when you’re processing a loss that rewrites your understanding of yourself.

I know because I’ve been there. My mother Joyce died by suicide when I was 20 months old. I didn’t talk about it for 36 years. During that time, I built companies, managed hundreds of employees, and showed up every day as a leader. But grief was there the entire time, shaping every decision I made without my conscious awareness.

This isn’t a motivational story about how adversity made me stronger. It’s an honest look at what grief does to your leadership when you don’t deal with it, and what changes when you finally do.

TL;DR: My mother died by suicide when I was 20 months old. I didn’t talk about it for 36 years. During that time I built companies, managed hundreds of employees, and made every leadership decision with unprocessed grief running in the background. This is what I learned when I finally dealt with it.

Grief in the workplace is more common than anyone admits

Most leaders treat grief like a personal problem that doesn’t belong at work. The research says otherwise. The Grief Recovery Institute estimates that grief-related productivity losses cost U.S. employers over $75 billion annually. A New York Life Foundation survey found that 57% of people have hidden their grief at work. One in four employees returns to work within three days of losing a close family member. Not because they’re ready. Because they feel they have no other option.

That was the world I grew up in, professionally speaking. Grief was something you handled privately. You showed up, you performed, you pushed through. I didn’t just adopt that framework. I perfected it. For 36 years, I ran companies, managed payrolls, hired and fired people, and won contracts, all while carrying a loss I had never once spoken about out loud.

The invisible weight

Grief doesn’t always look like sadness. Sometimes it looks like over-functioning. You become the person who never drops a ball, never misses a deadline, never shows weakness. That was me for three decades. I wasn’t processing my mother’s death. I was outrunning it. And from the outside, it looked like high performance.

The problem with grief-driven performance is that it’s brittle. You can sustain it for a long time, years, even decades. But it costs you the ability to connect authentically with the people you lead. You’re so busy proving you’re fine that you never let anyone see you as human. Your team follows a competent leader, but they never trust you completely because they sense the wall.

I ran Penebaker Enterprises from $1.5 million to $15 million. I helped grow Roofed Right America to $35 million with 180 employees. By every external measure, the leadership was working. But internally, I was operating on a set of rules that had nothing to do with business strategy and everything to do with survival. Don’t let people get too close. Don’t show vulnerability. Don’t stop moving, because if you stop, you might have to feel something.

How unprocessed grief shows up in leadership

After years of reflection and therapy, I can identify the specific ways my unprocessed grief shaped my leadership. I suspect other leaders carrying grief will recognize themselves in at least one of these patterns.

Conflict avoidance dressed as diplomacy. When you’ve experienced profound loss, you develop an almost pathological aversion to more loss. That includes losing relationships, losing approval, losing control. So you avoid hard conversations. You frame it as being diplomatic or strategic, but it’s really just fear of disruption. I spent years delaying difficult personnel decisions because the idea of someone leaving, even when they needed to leave, activated something deeper than a business concern.

Hyper-competence as a coping mechanism. If you’re the person who handles everything, nobody questions you. Nobody gets close enough to see what you’re carrying. I built my identity around being the person who could handle anything because handling things was the only strategy I knew. It worked, until it didn’t. When you’re the only one who can do everything, you become a single point of failure for the entire organization.

Difficulty with transitions. Every ending triggered the original ending. Letting go of a project, losing an employee, closing a chapter of the business. Each one activated a grief response I didn’t recognize because it was disguised as a business reaction. I would hold onto underperforming team members too long, or resist strategic pivots because the change itself felt threatening, not the business outcome.

Emotional distance as professionalism. There’s a difference between appropriate professional boundaries and an inability to connect. I confused the two for years. I could run a meeting, close a deal, and motivate a team, but I couldn’t have an honest conversation about how I was doing. I thought that was strength. It was actually the opposite.

Overreaction to perceived abandonment. When a key employee quit, my reaction was always outsized. Not angry, exactly, but deeply affected in a way that wasn’t proportional to the business impact. A resignation felt personal in a way it shouldn’t have. Once I understood where that reaction came from, I could separate the business reality from the emotional trigger.

The research on vulnerability and trust

Gallup’s 2025 State of the Global Workplace report found that 70% of employee engagement variance ties directly to the manager. Not compensation, not perks, not mission statements. The manager. And the single biggest driver of that engagement is whether employees feel their manager cares about them as people.

You can’t demonstrate authentic care while hiding behind a wall of competence. Amy Edmondson’s research at Harvard on psychological safety shows that teams perform better when leaders model vulnerability. Not weakness. Vulnerability. The willingness to say, “I don’t have all the answers” or “I’m working through something difficult.” Teams that see their leaders as human, not just capable, take more risks, communicate more openly, and solve problems faster.

I didn’t read these studies first and then decide to open up. I opened up and then found the research that explained why everything changed when I did.

What changed when I started talking

The shift happened when I started speaking publicly about my mother’s death. I wrote about it for TIME. I spoke about it at the DNC. I talked about it on CBS News. Not as a performance. Not as a motivational story with a neat resolution. Just the truth: this happened to me, here’s how it affected me, and here’s what I’m still learning from it.

The response was immediate and unexpected. Team members who had never opened up about their own struggles started sharing. Clients saw me differently, not as weaker, but as more trustworthy. My relationships deepened. And my leadership improved because I was no longer spending energy maintaining a facade.

There’s something specific I want to name here: speaking about grief publicly didn’t fix it. Grief isn’t something you fix. What it did was remove the secondary burden of secrecy. I was no longer managing a business and managing a secret at the same time. That freed up mental and emotional bandwidth I didn’t even know I was using.

The people I lead noticed. Not because I told them to look for it, but because authenticity is something people feel. When you stop performing and start being present, the energy in every room you walk into changes. I’ve written about this dynamic in more detail in what 36 years of silence taught me about vulnerability in leadership.

Grief and leadership identity

One thing nobody talks about: grief doesn’t just affect how you lead. It affects why you lead. For years, my drive to build companies and lead teams was partially fueled by a need to prove that the kid who lost his mother wasn’t damaged. That I was capable, strong, successful despite the loss. That’s a powerful engine, but it runs on the wrong fuel.

When I started processing the grief, my motivation shifted. I went from leading to prove something to leading because I genuinely cared about the people in front of me. The output looked similar on paper, revenue, growth, results, but the input was completely different. And sustainable in a way that grief-driven performance never was.

I see this pattern in other leaders, too. Many of the most driven people in business are running from something. That’s not inherently bad. But if you don’t eventually turn around and face it, the running becomes the only thing you know how to do. And when the business doesn’t need you to sprint anymore, when it needs you to be still and present and thoughtful, you won’t know how.

Practical lessons for leaders carrying grief

I’m not a therapist. I’m a business leader who spent decades getting this wrong before starting to get it right. Here’s what I’ve learned.

Get professional help. This isn’t optional. You wouldn’t try to fix a broken leg yourself. Don’t try to process grief alone, especially if you’re responsible for other people’s livelihoods and wellbeing. Find a therapist who understands the intersection of grief and professional performance. They exist. It took me too long to find one.

Separate the grief from the performance. You can be grieving and still be effective. But you can’t be grieving and pretending you’re not. The pretending is what damages your leadership. Your team can handle knowing you’re going through something difficult. What they can’t handle is sensing that something is off and having no context for it.

Give yourself permission to be inconsistent. Some days you’ll be sharp and present. Other days you won’t be. Both are okay. The worst thing you can do is demand consistent performance from yourself when you’re processing something that is fundamentally inconsistent. Resilience isn’t about being consistent. It’s about getting back up when you’re not.

Tell someone on your team. Not everyone. Not the whole story. But someone who can support you and help manage the workload when you’re having a hard day. Isolation makes grief worse and it makes leadership worse. I wasted years thinking silence was strength. It’s not. It’s just loneliness with a professional title.

Understand that grief changes over time. The grief I carry at 48 is different from the grief I carried at 25. It evolves. It gets triggered by different things. A song, a season, a milestone your loved one will never see. As a leader, you need to know that grief isn’t linear and it doesn’t have an expiration date. Plan for that.

Stop using busyness as a coping strategy. This is the hardest one. When you’re leading a team, there’s always something to do. The inbox is never empty. The meetings never stop. It’s easy to hide in the work and call it dedication. But if you’re honest with yourself, you know the difference between productive work and avoidance. I learned the difference too late. Don’t make that mistake.

The leader you become after

Grief does not make you a better leader. I want to be clear about that. Losing someone you love doesn’t unlock some hidden potential. What it can do, if you’re willing to do the work, is strip away the things that were never real to begin with. The performance, the posturing, the need to be perceived as having it all together.

What’s left is a leader who knows what actually matters. Not the quarterly numbers, though those matter. Not the next deal, though that matters too. What matters is that the people who show up for you every day know that you see them. That you’re not just managing their output. That you care about who they are when they walk through the door.

I spent 36 years building a version of leadership that looked impressive but felt hollow. The version I’m building now, the one shaped by honesty about what I’ve been through, is smaller, quieter, and infinitely more effective.

If you’re a leader carrying grief, you don’t have to tell the world. But you have to tell someone. And you have to stop pretending it isn’t there. Your team deserves a leader who is present, not one who is performing. And you deserve to lead from a place that doesn’t cost you everything.

Last updated: March 18, 2026