7 Founders Share Their Worst Boss Horror Stories, and What They Learned From the Lunatics These entrepreneurs lived through bad boss nightmares, but they got the upper hand in the end.
By Frances Dodds Edited by Mark Klekas
Horrible bosses come in all kinds of unpleasant flavors: delusional, avoidant, narcissistic, rageaholic, bullying, undermining, insecure, micromanaging. The list goes on. Like a bag of Bertie Bott's Every Flavor Beans — yes, that's a Harry Potter reference — bosses come in nasty flavors you never even imagined until you find yourself chewing over something they said or did, and wondering, what is this awfulness?
But the one silver lining to having a bad boss is that it invariably makes you a better one. In fact, having a horrible boss is often the single biggest impetus for wanting to become your own boss. That's certainly true for the entrepreneurs who shared their terrible boss stories with us. Once they employed other people, they were acutely aware of how they did not want to treat them. So whether you're looking for commiseration, or to learn about a flavor of mismanagement you've never had the misfortune of experiencing, or you're the rare lucky devil who never had a bad boss, there's plenty to learn from other people's tribulations. So here's a sampling of horrible boss flavors for you to enjoy this spooky season.
1. The Angry Undermining Boss
"She was a narcissistic rageaholic who would yell and throw things at people."
"Without a doubt, the worst boss I ever had was a narcissistic rageaholic who would yell and throw things at people. This was a small company with only a dozen employees, so pretty much everyone experienced her wrath at some point.
She was also a complete control freak. She received copies of every email for the company, regardless of the intended recipient. Then she would answer those emails without copying the employee. This undermined our efforts to build client relationships or negotiate deals, because we didn't know what the owner had said in other emails.
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When she refused to promote me to the director role for our department, that was the final insult. The owner said I was far too valuable in my existing role, and then hired an unqualified director and required me to train her. I started sprucing up my resume the next day.
This experience taught me that if you aren't training your employees to move up, they will move out. And while everyone gets upset at some point, it is never okay to take it out on your staff. Abuse and bullying is no way to run a business. Clear communication is key, especially with outward-facing communications to clients. The company must present a consistent and unified face, meaning no secret emails or hidden deals."
— Donna Shannon is CEO of Personal Touch Career Services
2. The Freeloader Bully Boss
"He asked me to pick up a Rolex for him… and never paid me back."
"My worst boss would abuse his position of power to get free stuff. I remember once I was going on vacation in another country, and he asked me to pick up a Rolex for him. I happily agreed, but I had no idea how much trouble it would be. I had to pay an outstanding balance of $1200 on the watch that he hadn't paid, and on top of that, I had to pay customs in the local country when I was on my way out. I informed my boss about all of this and told him he could wire me the money or pass it to me when I see him. To this day, he's never paid me back, so I decided to keep the watch.
I was not the only one subjected to his antics. My coworkers and I would go out to lunch, and our boss would often ask us to pick him up a coffee, or lunch — and then never pay us back. He used people to get things for free, even if it was a bottle of water.
Now, as a business owner, I strive to understand my employee's needs and wants, and realize they have families to support, financially and emotionally. I also learned that toxic traits bring out the worst in people, and that leads to high turnover in the workplace. Management and leadership come from the top down. All it takes is one bad apple to ruin the bunch."
—Sam Carter is the founder of Challenge Coins 4
3. The Boss Who Calls You In On Christmas Eve
"'The work never sleeps,' was a pet phrase of his."
"Certainly, my most awful boss was one I had in my early years of practice. I was employed at a law firm where the boss had zero consideration for work-life balance. He expected his employees to be on call 24/7, with scant regard for personal commitments. 'The work never sleeps,' was a pet phrase of his. One particularly harrowing memory is when he called for a conference on Christmas Eve. He didn't seem to understand that people had families and other commitments, and that holidays should be respected.
This disregard for my personal time inspired in me an obsession for work-life balance when I started my own law firm. Now, I strive to respect my employee's work-life balance. We avoid scheduling meetings outside of office hours and on holidays. We believe everyone's time is valuable — both within and outside the office. I learned from experience that employees with a healthier work-life balance tend to be more productive and happier in their jobs. And of course, I admit, there's a bit of self-interest involved because really, who wants to work on Christmas Eve? Certainly not a certain lawyer who loves his eggnog and Christmas carols!"
— Min HwanAhn is a founding partner of immigration law firm Ahn & Sinowitz
4. The Avoidant, Blindsiding Boss
"She'd leave my messages on read for days — and I sat in a cubicle right next to her."
"I started my company nearly eight years ago after quitting my one and only job, and my boss was the primary reason I quit. She was terrible in a few ways. From the second I started at the company, there was zero training, but then I was berated if I interpreted something wrong or proceeded based on my own learning.
My boss was also introverted, and seemed to avoid me at all costs. She'd leave my messages on read for days — and I sat in a cubicle right next to her. When I'd pop my head over and ask, she'd just say, 'I'll get back to you later.' Then I'd be blindsided with criticism when we had a quarterly discussion.
Eventually, I gave up. She never got to know me, and I think it humanizes someone when you get to know a little bit more about them. You understand how they work, what helps them thrive, and how you can work with them to improve. The stress from this job was having negative effects on my health across the board, and I actually developed dyshidrotic eczema on my hands. The day after it popped up, I quit.
All of this directly affected what my company does now, and how I run it. One of my biggest takeaways was the importance of processes that allow you to seamlessly onboard new team members, so my company helps establish and implement content operations frameworks for companies scaling their content strategy. As a primarily remote company, I encourage phone calls, Zoom calls, or in-person meetings to easily get to the root of an issue — at least for the urgent things. And finally, I try to make my rounds across the globe to meet up with remote employees and contractors so that we know each other on more than just a robotic work level."
— Owen Cook is the founder and CEO of BlockChain SEO.
5. The "I Know Best" Boss
"He reminded me that the only reason I was in this job was that he was too busy to attend to these decisions himself."
"I worked as a software developer for years, and was hired by a consulting firm in Chicago to work on a time tracking tool they were developing for AmeriGas. The product was interesting, and I had a very fruitful interview process, so I was excited to start. But at the end of my first week I was called in for my first coaching session by the managing partner.
During this session, I spent 45 minutes listening to a critique of every decision I'd made in my first five days, and how my boss would have done it differently. He reminded me that the only reason I was in this job was that he was too busy to attend to these decisions himself, and instructed me to stop before I made any decision, and ask myself if that's something he would do. When I protested that I had only known him for a week, he told me I should have done my research. That job was hell. I only lasted 8 months, and ended up with two different managerial coaching sessions with VPs per week in the last couple months.
It made me approach my own management in a radically different way. I spent the next decade learning to build autonomous teams that I could set on a problem and watch them solve from a distance. I wouldn't interfere unless my guidance was sought, and I ended up with better results because of it. To this day, in my own company, I sign on different creators and don't dictate how they craft their show. I ask them what they feel they need to be successful, add in anything that I've learned from experience they might need from experience, and then set them loose to craft the best thing they can."
— Joshua Burgess is the founder of podcast production company Gas Station Drugs
6. The Stubbornly Delusional Boss
"He told our team that there was no such thing as an unclosable sale."
"The worst boss I ever had told our team that there was no such thing as an unclosable sale. When an agent failed to make a sale, it was because they lacked something. This caused an unhealthy amount of stress for me and the other agents, because we blamed ourselves for every person that did not buy a policy. Over time I learned that sales is a numbers game, and every 'no' from a prospect gets an agent closer to a 'yes.' I now realize this is a universal truth in sales, but my boss simply denied it, which is very odd.
This experience taught me that instead of making blanket statements, listening to an agent's actual calls is important. I learned to be transparent with agents on the numbers game aspect of sales, and by instilling this balanced mindset into my agents, they understand when it's appropriate to direct a healthy amount of criticism at themselves, versus an overwhelming amount of blame and stress that will ultimately make them worse at their job."
— Tim Connon is the founder of ParamountQuote Insurance Advisors
7. The Green Boss Who Hadn't Earned It
"She told me that a role I had 12 years into my career was my first job."
"My worst boss was in the startup world. She was inexperienced, and got her position as CMO through friendship, not merit. Once, while in a team meeting, she sneered when I inquired if the flagship conference of the brand should be trademarked. Mere months later, a competitor took the name and built a competing — arguably better — product, so now when you Google the flagship conference, you get the competitor instead. (It's called Coalesce; try it.)
Fast forward to when I was literally at my uncle's funeral, and she sent me a Slack message to let me know that my role on the leadership team was being consolidated under a new hire. I had been up for the position they were hiring for, and the reason she gave me for not promoting me was that I had not created a campaign she asked me to. In fact, the campaign I single-handedly created yielded 27% of the goal we needed to accomplish.
I'm 47, and active ageism runs rampant at the company, including with that boss, who told me that a role I had 12 years into my career was my first job. Apparently, she never read my resume
or peeped my LinkedIn. When I revealed this to her, she was shocked.
I suppose what goes around comes around, because investors ultimately required the company to demote her, and hire someone more experienced, so she resigned. I won't lie; I take satisfaction in having a bit of vindication. I now work with startups, small and medium businesses and Fortune 500s, so I'll take that any day over golden handcuffs."
— Heather Wilson, founder of The Brand Strategy Tank
