Lessons from Horrible Bosses

Early Work Ethic and Eye-Opening Lessons

Hard work was something both of my parents modeled from my earliest memories. My dad had one firm rule: No driver’s license unless you can pay for your own insurance. So, we worked.

By the age of 15, I was babysitting. At 16, babysitting was my daily part-time job. In college, I volunteered at a local non-profit. They would eventually ask me to work in the office part time, but it paid more than my babysitting gig! I picked pumpkins on a farm one fall. I made cookies and sold them by the dozen. I was always working. 

It didn’t take long to realize two things:

1. Every boss is not a leader.

2. Every leader has a communication and correction style—some better than others.

Three Bosses Who Taught Me Everything (By Doing It Wrong)

Let’s start with “Gwen.”

She led with a casual, almost relaxed energy. She was highly knowledgeable, but didn’t need to be the smartest person in the room. She was kind, taking the time to explain things even if they were elementary to her, she was always patient. Gwen was what my kids might call “chill.”

But chill has a downside.

She lacked boundaries, often blurring the lines between her personal and professional life. Her meetings felt scattered. Things got messy. Gwen’s lack of structure limited her capacity to grow or lead others effectively.

Then there was “Karen.”

Karen ruled the office with her mood. She stayed behind her desk, aloof and detached. We all knew if she was in a bad mood, the whole team felt it. On the “good days” we were cheerful and light. But on bad days? Silent. Intimidated. Tense.

Communication among team members dropped to whispers and text messages. No one challenged her, even when things were off-track. She led with fear and it worked, if the goal was compliance. But creativity, growth, and healthy culture? That all stayed locked away.

And then there was “Sam.”

Sam was kind. He meant well. But after our first one-on-one, I could tell he didn’t like his job. I’d ask questions, and he’d say, “Great question, I’ll find out.” But he never followed up. Conversations were surface-level. He didn’t engage unless someone initiated.

Sam wasn’t a bad person, but he was in the wrong seat.

What I Learned from Gwen, Karen, and Sam

• From Gwen, I learned that knowledge is only powerful when paired with structure.
  Her lack of boundaries and systems led to missed opportunities, for herself, her team, and her family.

• From Karen, I learned that leading with fear silences creativity.
  Her team had ideas. They had solutions. But her presence was too intimidating to invite honesty. I now believe: You can tell what kind of leader someone is by watching their direct reports. Are they stressed? Do they speak up? Do they shut down when the leader walks in?

• From Sam, I learned that when a leader loses their drive, it’s not a secret.
  Even if they show up every day. Even if they’re nice. A disengaged leader quietly drains energy from a team. Passion and purpose can’t be faked for long.

It All Starts with One Small Slip

The patterns I saw in these leaders didn’t happen overnight. Maybe one day they were too tired to follow up. Maybe they felt under-appreciated, so they pulled back.Then it happened again.
And again. Until that slip became a habit. And the habit became the new standard.

Reflection Challenge

Think back on your own work history:

• What did you learn from your worst boss?

• What did your best leader do that made a difference?

• How has your leadership been shaped by them?

• Is there anything in your current leadership style that’s slipping into unhealthy patterns?

Take 10 minutes today. Journal it. Pray over it. Bring it to God.

Because the kind of leader you’re becoming tomorrow, starts with the decisions you’re making today.