How to Reengage or Help People Move On

Mita recommends asking what would make employees happy at work, coaching conversations, and humane exits when roles no longer fit.

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What makes a boss “bad”—and why do so many talented people end up working for them? Author and marketing executive Mita Malick joins Chris Do to share the stories behind her new book, The Devil Emails at Midnight, including how childhood bullying shaped her empathy and her mission to create healthier workplaces.

Together, they break down 13 toxic boss archetypes, the hidden triggers that turn well-meaning leaders into bad ones, and how creatives can spot red flags before it’s too late. Whether you’re navigating a tough client, rebuilding a team, or learning how not to repeat the mistakes of past managers, this episode gives you practical tools and a fresh perspective on what better leadership really looks like.

Timestamps:

(00:00) – Intro

(01:30) – Culture starts at home

(03:25) – Driveway hate graffiti story

(06:10) – Principal’s office, suspension fallout

(09:33) – Book genesis: bad bosses

(11:44) – The midnight-email manager problem

(12:20) – Micromanagers, disengaged leadership explained

(14:50) – Who this book helps

(15:43) – Medusa: public team humiliation

(20:17) – Toxic environments feel like “home”

(24:50) – Friend’s mirror moment at work