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.

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.

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:

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.

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.

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.

What Changed When I Started Talking

The shift happened when I started speaking publicly about my mother’s death. 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.

Practical Lessons for Leaders Carrying Grief

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.

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.

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.

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.

About Khary Penebaker

Khary Penebaker is a Regional General Manager at Great Day Improvements, overseeing operations across Chicago, Madison, Milwaukee, and Minneapolis. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership experience in construction, operations, and civic engagement.

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