The Boss Who Emails At Midnight And Other Leadership Nightmares That Drive Employees Away

“People don’t leave jobs. They leave bad bosses.”

There is truth to this unattributable quote. (I searched Google and ChatGPT, and neither could give me the definitive origin of this quote.) Validation comes from numerous articles and studies that claim a large percentage of employees quit their jobs because of bad managers.

A Harvard Business Review article, Quiet Quitting Is About Bad Bosses, Not Bad Employees by Jack Zenger and Joseph Folman, explains that employees don’t have to outright leave their jobs to “quietly quit,” or do only the bare minimum needed to keep their jobs. According to Gallup’s 2024 State of Global Workplace Report, only 23% of employees are engaged, 62% are “not engaged” and 15% are “actively disengaged.” And 70% of the variance in team engagement is due to the manager.

When you look at the best companies to buy from, you often find they are also listed on Glassdoor.com as the best companies to work for. That direct correlation isn’t a coincidence. In my customer service and customer experience (CX) work, I recognized decades ago that what’s happening on the inside of an organization is felt by customers on the outside. The employee experience is as important, if not more so, than the customer experience, and the boss can “make or break” that experience.

Meet Mita Mallick, who once had a boss who would only communicate with her via email between 10 p.m. and 2 a.m. That seemed to be the only time the boss was available. Trying to meet with her boss during normal business hours was an exercise in futility. The message was clear: “I don’t have time for you.” And as a junior employee, Mallick thought she had to respond in real time to keep her job.

That experience, along with others, is why Mallick, who is now an author and speaker on a mission to “fix what’s broken in the workplace,” wrote the book, The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses. This book shares the details of 13 bosses, herself included, who demonstrate what not to do.

I interviewed Mallick for an episode of Amazing Business Radio to learn about some of these bad bosses, in hopes that anyone who falls into that category of leadership might learn a lesson and make their employees’ experience better. Here are descriptions of just a few of the bad bosses Mallick talked about in our interview, along with some of my commentary:

The Boss Who Never Had Time for Employees—Except at Midnight

As mentioned, this is where the book begins, with a boss who didn’t respect employees’ time or explain that just because she worked at midnight, she didn’t expect her employees to do the same. A simple explanation that immediate responses to her late-night emails weren’t necessary would have been easy, but unfortunately for Mallick, that was not the case. Everything seemed urgent, and Mallick emphasized this by saying, “When we treat everything as urgent, nothing is urgent.”

The Lesson: Leadership means making time for your team. Respect employees’ time and boundaries.

The Boss Who Wouldn’t Call an Employee by Name

Mallick shared that a boss didn’t want to call her by her full first name, Madhumita. Because he struggled to pronounce her full name, he renamed her Mohammed. One day, she worked up the courage to say, “You can call me Mita,” but the insensitive boss smiled and said, “Oh, Mohammed is funny. Everyone loves it. Don’t be so sensitive!” No doubt an HR issue by today’s standards, this boss showed a lack of respect for a good employee.

The Lesson: Calling people by their correct names is a basic courtesy and sign of respect. But there’s more to this. It’s not just about a name. Recognizing something sensitive and/or important to an employee should be acknowledged and accepted. Teasing about it will, at a minimum, put distance between the boss and employee.

The Boss Who Was Filled with Toxic Positivity

An upbeat and energetic boss is great, but ignoring real problems and acting like everything is fine is known as toxic positivity. If the facts indicate that something isn’t possible, then pretending it is can set a team up for failure and disappointment. Cheerleading only helps so much. If the boss hypes everyone up to believe something impossible can be done, and then the team fails, it can be demoralizing to the team.

The Lesson: Leaders should inspire, but not at the cost of reality.

Final Words

The worst behaviors in any workplace become part of its culture if they are allowed to continue. Whether it’s disrespect, slacking off or bullying, what leaders let slide becomes the norm. Look at yourself in the mirror and ask, “Am I one of these people causing the problem?” Creating a positive environment means taking action when problems arise, not ignoring them. A healthy workplace looks out for everyone, not just the loudest or most powerful voices.

The Final Lesson: Culture is defined by what is tolerated and demonstrated by the boss.