The Devil Emails at Midnight
What Good Leaders Can Learn from Bad Bosses
A boss that throws shoes or takes naps in meetings may seem funny on the surface, but it’s no laughing matter.
Bad bosses can have more impact on people’s mental health than partners, parents, friends, or kids. Bad bosses can destroy cultures of inclusion and safety. They can cause real harm to people’s mental and physical health. They can get in the way of collaboration and work products, and they can cost organizations real money.
Bad bosses are not necessarily bad people.
- But are they ready to lead everyone on their teams through this BANI (brittle, anxious, nonlinear, and incomprehensible) world?
- Were they adequately trained when they got promoted from being high performing individual contributors?
- Can they manage in a way that creates inclusion for everyone in today’s diverse teams?
In my work with organizations, the answers to these questions is usually "no." Or at least "not yet."
There is some rampant bad bossing happening.
I recently had a fascinating conversation with bestselling author Mita Mallick whose new book The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses, addresses all of these topics. The book is not only insightful and practical, but it’s also a joy to read.
In our conversation, we talked about:
- Common ways that bad boss behavior happens and what the negative consequences of this can be.
- How fear-based leadership can produce short-term results and long-term destruction.
- The "toxic rock star" boss and why their performance numbers are a house of cards.
- What good leaders do differently when their workforce is scared and struggling.
- Why you should not ask "what should I do differently?" if you actually want honest feedback.
- And so much more.
This is the start of Season 2 of The Culture Advantage podcast! Audio version here and video version here. In addition to this episode with Mita, we’ve got more incredible guests lined up.
Because of some hosting nonsense, you will have to re-follow the podcast if you were following before. And if you left a review before, that got reset to zero too, so we’d be incredibly grateful if you could review again here.
What are some of your best “bad boss” stories?


