

How to Deliver Bad News and Get Away with It with Mahesh Guruswamy, CPTO at Kickstarter
Aug 21, 2025
Mahesh Guruswamy, CPTO at Kickstarter and author of 'How to Deliver Bad News and Get Away With It,' shares his expertise on conveying tough messages in the workplace. He emphasizes the importance of accountability for CTOs and explores the delicate art of delivering bad news effectively. The discussion also touches on the impact of AI on both personal and professional communication, and Guruswamy offers insights into navigating the complexities of leadership and the evolving work landscape for young professionals.
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Learning From A Decade Of Tough Talks
- Mahesh began writing notes after every difficult conversation for ten years to learn and improve.
- Those essays eventually became the book "How to Deliver Bad News and Get Away With It."
Be Direct And Empathetic
- When delivering bad news, state the reality plainly instead of spinning it into good news.
- Feel empathy; if you don't feel bad delivering it, you're likely doing it wrong.
Act Quickly On Tough Issues
- Act quickly when you sense a problem; don't sit on bad news or delay tough conversations.
- Speed reduces prolonged harm and preserves your sanity and the team's trust.