The Devil Emails at Midnight: What Good Leaders Can Learn From Bad Bosses

During the course of my career, I have worked for several bad bosses.

In my latest 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 survived and endured.

And here’s the silver lining that comes from working for several bad bosses: you can learn what not to do as a leader.

Here are three lessons on how not to be a bad boss.

1. Stop Normalizing Emailing at Midnight

I was so excited to meet my new boss. Apparently, the feeling wasn’t mutual.

This was my former boss, who I nicknamed the Devil. She was the boss who never had any time for me during the day, but did have time to consistently send me emails between 10:00 PM and 2:00 AM.

Years later, the question I continue to ponder is, Why didn’t she have time for me?

One of the biggest complaints we hear when it comes to relationships is “You never have time for me.” As a leader, if you can’t make time for your teams during the day to coach them, you have to ask yourself, Why are you leading in the first place?

I challenge everyone to treat calendars like decluttering a wardrobe: focus on high-value meetings, remove meetings that are no longer needed, and delegate meetings to others.

Find time to connect with your teams during the day. Let’s stop normalizing emailing at midnight.

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.

The foundation of good leadership is taking care of yourself by getting enough sleeping, eating well, and exercising so that you can be in service to others and fend off bad boss behaviors.

2. Silence Can Fuel Bullies

My full name is Madhumita Mallick. For most of my life, my name has evoked a swirl of emotions for me, including anxiety and joy.

I started just going by “Mita” and stopped bothering trying to teach people how to say my full name. When I graduated from business school and rejoined corporate America, I attempted to reclaim it.

My former boss, who I nicknamed the Sheriff, was popular and a bully. When it came to my name, the Sheriff decided to completely rename me because he didn’t want to learn how to pronounce it.

He called me “Mohammad” because he could and wanted to.

I’m embarrassed to admit that for many weeks, I responded to a name that was not my own. Years later, I still wonder why no one around us ever said anything.

Microaggressions like the one I experienced repeatedly can become a manifestation of bullying. They deplete our energy and make us question our contributions.

Our collective silence can fuel those bullies. The burden shouldn’t be placed on the target to speak out and stop this behavior. If you see someone being targeted in the workplace, intervene.

3. Find the Courage to Help People Move On

My former boss, the Napper, literally slept on the job. He dozed off in meetings—large or small.

The Napper came and went as he pleased, gossiped loudly, and enlisted others to talk about how much it sucked to work here. He even started interviewing for jobs in the cubicle next to mine, for all to hear.

Years later, I still wonder why my former boss was allowed to repeatedly nap and be disengaged at work without any consequences. Disengagement can spread. It can become contagious, erode trust on the team, and negatively affect productivity.

More of us need to intervene when we witness disengagement.

Start by becoming a mirror. Take your team member to lunch or coffee. Remind them of their behavior. Focus on the facts and not your feelings.

Next, allow space for the individual to reveal what’s going on. You may or may not agree with what is shared, and you don’t have to respond to everything. You can ask open-ended follow-up questions or simply thank them for sharing, letting them know that you’re processing the information and will get back to them.

Finally, ask them what must change. As leaders, we must have the courage to stop this downward spiral and help people move on to what they’re meant to do next.

Remember

Bad bosses aren’t born. Bad bosses are made.

Let’s be on a mission to help each other spot these bad boss behaviors— and show up to do better and be better in our workplaces.

*Mita Mallick is a Wall Street Journal and USA Today bestselling author and her new book, The Devil Emails at Midnight: How Good Leaders Can Learn From Bad Bosses, was published by Wiley on September 30, 2025.

Mallick is a highly sought-after speaker who has advised Fortune 500 companies and start-ups alike. She is a LinkedIn Top Voice and was named on the Thinkers 50 Radar List.

She’s a contributor to Harvard Business Review, Fast Company, Adweek, and Entrepreneur. Mallick has been featured in The New York Times, The Wall Street Journal, The Washington Post, Time Magazine, Forbes, Axios, Essence, Cosmopolitan Magazine and Business Insider.

She holds a B.A. from Barnard College, Columbia University, and an M.B.A. from Duke University’s Fuqua School of Business.