Mastering the Toughest Conversations: Management Lessons from Mahesh Guruswamy

“You’re Fired!”

Two words that are never easy to speak and are even harder to hear.

Dismissing employees is complicated — legally, emotionally, and professionally.

Mastering the art of letting employees go isn’t taught in business school, and too many managers fumble the process.

Mahesh Guruswamy, chief technology officer at Kickstarter, has spent much of his career delivering tough news — not just to employees but also to customers, investors, and even higher-ups. Now, he’s sharing his hard-earned wisdom in a new book — How to Deliver Bad News and Get Away With It: A Manager Guide.

Whether you’re a seasoned executive or a first-time manager, Mahesh's insights will arm you with tools to handle difficult conversations while building trust, retaining talent, and, yes — keeping your sanity intact.

Monday Morning Radio is hosted by the father-son duo of Dean and Maxwell Rotbart.

Photo: Mahesh Guruswami, How to Deliver Bad News and Get Away With It
Posted: February 17, 2025
Monday Morning Run Time: 52:16
Episode: 13.36

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