The Entrepreneurs Weekly
No Result
View All Result
Saturday, November 29, 2025
  • Login
  • Home
  • BUSINESS
  • POLITICS
  • ENTREPRENEURSHIP
  • ENTERTAINMENT
Subscribe
The Entrepreneurs Weekly
  • Home
  • BUSINESS
  • POLITICS
  • ENTREPRENEURSHIP
  • ENTERTAINMENT
No Result
View All Result
The Entrepreneurs Weekly
No Result
View All Result
Home Business

My Terrible Bosses Taught Me 5 Unexpected Leadership Lessons

by Brand Post
November 24, 2025
in Business
0
My Terrible Bosses Taught Me 5 Unexpected Leadership Lessons
152
SHARES
1.9k
VIEWS
Share on FacebookShare on Twitter


Opinions expressed by Entrepreneur contributors are their own.

Key Takeaways

  • Enduring bad bosses is exhausting, but there are invaluable lessons to be learned from them, which can teach you what kind of leader you don’t want to be.
  • If your boss — or even you yourself — exhibits any of the following traits, there are ways to turn things around and become a better leader.

In my new book, The Devil Emails at Midnight: What Good Leaders Can Learn From Bad Bosses, I share hilarious and heartbreaking stories of bad bosses I have endured and survived. It’s easy to paint a bad boss as a Disney villain or Marvel character. It’s much harder to sit and reflect on what we have learned from these experiences. And how these bad bosses can actually make us better leaders.

As I practice gratitude this holiday season, I am reflecting on how I am grateful for those bad bosses. Here are five lessons my bad bosses taught me.

Related: The 6 Most Familiar ‘Bad Boss’ Types and What to Do About Them

1. Stop normalizing emailing at midnight

My former boss, who I nicknamed “The Devil,” was the boss who never had any time for me during the day. But did have time to consistently send me emails between 10 p.m. and 2 a.m. I started responding to her emails in the early morning hours.

Years later, the question I continue to ponder is, Why didn’t she have time for me? As a leader, if you can’t make time for your teams during the day to coach, guide and teach them, you have to ask yourself, Why are you leading in the first place?

And I’m not ashamed to say that on most evenings I’m asleep at midnight. It doesn’t mean there aren’t periods of my life when I’m working incredibly hard and constantly burning the midnight oil, but that isn’t sustainable. I have to be able to lead myself and my team through intense drive periods, and then take the time to rest and recover.

2. Let individuals do their jobs

“The Chopper” was my former boss who hovered like a helicopter, ready to dive into details that didn’t matter. He loved overcomplicating the simplest of tasks. He genuinely seemed to enjoy and mastered the art of micromanaging all of us. Doing all of our jobs seemed to bring him so much more joy than doing his own job.

If we hire individuals for their expertise and experience, please don’t do their jobs for them. Give them the space to work. Teach them new skills. Coach them through mistakes. Stop micromanaging on details that don’t matter. Focus on the output and be clear on expectations.

Related: This Is the No. 1 Mistake People Make as a Boss — But It’s Easy to Fix

3. Ruling with fear leads to burnout

No one in my life had ever screamed at me — not my parents, my brother, my husband or my friends — until I worked for “Medusa.” My former boss ruled with fear. She would scream, curse and aggressively point her fingers at people during meetings. I had never heard a boss drop so many F-bombs. She even hurled one of her Chanel shoes at my colleague, though thankfully it missed her head.

Ruling with fear can drive results in the short term. And showing up scared to work every day is exhausting. Fear kills communication, isolates team members, inhibits creativity and innovation and leads to burnout. Creating a culture where everyone is treated with respect shouldn’t be a luxury. We don’t want another free meditation app, an endless supply of fancy snacks, happy hours and definitely not another oversized hoodie. We want to be respected and valued.

4. If you love people, let them go

My former boss, nicknamed “Tony Soprano,” expected loyalty at all costs. Tony told me I was going to do a one-year assignment on his team and I’d be promoted at the end of that assignment. When the year mark was approaching, I started networking within the organization to figure out what I wanted to do next. When he found this out, he was livid. He told me the assignment would actually last two to four years because I had not even begun to make an impact in this role. He told me that he decides when I can leave.

Hoarding talent holds individuals back. Hoarding talent can also have a negative ripple effect on your organization. Help talent move on to what they are meant to do next for their growth and development. Also, help them move on to their next assignment to tackle the most important initiatives for the organization. If we love our team members, we let them go. If we don’t let them have ownership of their own careers, they will leave the organization and move on elsewhere.

Related: I’m the Former VP of HR at Microsoft. I’ve Witnessed Many Bad Managers in My Career — and They Almost All Had These 4 Traits.

5. Show up with more empathy

I’ve been a bad boss. And chances are, so have you. Over the years, I have gained more perspective and empathy for myself, other leaders and colleagues, because we all can have a bad boss phase. This doesn’t mean that we excuse bad boss behaviors; it means I try to understand why individuals may behave badly in the workplace.

Bad boss behavior can be triggered for three reasons. First, there’s stress in the marketplace impacting your business. Second, your own boss exhibits bad boss behaviors, and you absorb them. Third, you experience a personal earthquake, loss of a loved one, a breakup or divorce, or moving countries, all of which can trigger bad behaviors.

Finally, I remind myself that the foundation of good leadership is taking care of yourself. Step away from the keyboard. Get enough sleep, eat well and get your body moving. If we can’t take care of ourselves, it’s hard to then be in service to others at the kitchen table and at the conference room table. Fend off those bad boss behaviors. I’m grateful to those bad bosses who remind me every day how I can be a better leader.

Key Takeaways

  • Enduring bad bosses is exhausting, but there are invaluable lessons to be learned from them, which can teach you what kind of leader you don’t want to be.
  • If your boss — or even you yourself — exhibits any of the following traits, there are ways to turn things around and become a better leader.

In my new book, The Devil Emails at Midnight: What Good Leaders Can Learn From Bad Bosses, I share hilarious and heartbreaking stories of bad bosses I have endured and survived. It’s easy to paint a bad boss as a Disney villain or Marvel character. It’s much harder to sit and reflect on what we have learned from these experiences. And how these bad bosses can actually make us better leaders.

As I practice gratitude this holiday season, I am reflecting on how I am grateful for those bad bosses. Here are five lessons my bad bosses taught me.

The rest of this article is locked.

Join Entrepreneur+ today for access.



Source link

Tags: Bad BossesBossesBusiness Culturecompany cultureCultureLeadershipLessonsManagementTaughtTerribleThought LeadersToxic PeopleToxic WorkplaceUnexpected

Related Posts

The Secret to Making Your Customers Feel Truly Understood
Business

The Secret to Making Your Customers Feel Truly Understood

November 28, 2025
How to Successfully Scale and Manage a Global Remote Team
Business

How to Successfully Scale and Manage a Global Remote Team

November 28, 2025
Stop Pretending One Meeting a Year Will Fix Your Business
Business

Stop Pretending One Meeting a Year Will Fix Your Business

November 28, 2025
  • Trending
  • Comments
  • Latest
Meet Amir Kenzo: A Well Known Musical Artist From Iran.

Meet Amir Kenzo: A Well Known Musical Artist From Iran.

August 21, 2022
Behind the Glamour: Bella Davis Opens Up About Overcoming Adversity in Modeling

Behind the Glamour: Bella Davis Opens Up About Overcoming Adversity in Modeling

April 20, 2024
Dr. Donya Ball: Pioneering Leadership Solutions for Tomorrow’s Challenges

Dr. Donya Ball: Pioneering Leadership Solutions for Tomorrow’s Challenges

May 10, 2024
Nasiyr Bey’s Journey from Brooklyn to Charlotte: The Entrepreneurial Path to Owning a Successful Cigar Lounge

Nasiyr Bey’s Journey from Brooklyn to Charlotte: The Entrepreneurial Path to Owning a Successful Cigar Lounge

August 8, 2024
Augmented.City Startup Developers Appeal To US Politicians With An Open Letter

Augmented.City Startup Developers Appeal To US Politicians With An Open Letter

0
U.S. High Court Snubs Challenge To State And Local Tax Deduction Cap

U.S. High Court Snubs Challenge To State And Local Tax Deduction Cap

0
GOP Lawmaker Blames Biden For Russia-Ukraine War: Putin ‘Could never have Invaded’

GOP Lawmaker Blames Biden For Russia-Ukraine War: Putin ‘Could never have Invaded’

0
Brad Winget’s Tips and Tricks on Having a Career in Real Estate

Brad Winget’s Tips and Tricks on Having a Career in Real Estate

0
The Secret to Making Your Customers Feel Truly Understood

The Secret to Making Your Customers Feel Truly Understood

November 28, 2025
How to Successfully Scale and Manage a Global Remote Team

How to Successfully Scale and Manage a Global Remote Team

November 28, 2025
Stop Pretending One Meeting a Year Will Fix Your Business

Stop Pretending One Meeting a Year Will Fix Your Business

November 28, 2025
5 High-Growth Markets That Could Make You Rich in 2026

5 High-Growth Markets That Could Make You Rich in 2026

November 28, 2025

The EW prides itself on assembling a proficient and dedicated team comprising seasoned journalists and editors. This collective commitment drives us to provide our esteemed readership with nothing short of the most comprehensive, accurate, and captivating news coverage available.

Transcending the bounds of Chicago to encompass a broader scope, we ensure that our audience remains well-informed and engaged with the latest developments, both locally and beyond.

NEWS

  • Business
  • Politics
  • Entrepreneurship
  • Entertainment
Instagram Facebook

© 2024 Entrepreneurs Weekly.  All Rights Reserved.

  • About Us
  • Advertise
  • Contact Us
No Result
View All Result
  • ENTREPRENEURSHIP
  • ENTERTAINMENT
  • POLITICS
  • BUSINESS
  • CONTACT US
  • ADVERTISEMENT

Copyright © 2024 - The Entrepreneurs Weekly

Welcome Back!

Login to your account below

Forgotten Password?

Retrieve your password

Please enter your username or email address to reset your password.

Log In