Pocket Sized Pep Talks

How To Deliver Bad News And Get Away With It

Episode Summary

No one signs up for leadership because they love hard conversations. But avoiding them? That’s where trust, momentum, and team culture start to erode. Product development executive and author Mahesh Guruswamy sits down with Rob to explore how the toughest talks, when handled with clarity and care, can actually strengthen relationships. Drawing from years of experience in high-stakes environments, Mahesh shares how to approach difficult feedback without flinching, and without losing your team in the process.

Episode Notes

In this Pocket Sized Pep Talks, you'll learn:

• Why avoiding discomfort does more damage than the truth ever could.
• How to deliver tough messages with empathy, not ego.
• The mindset shift that turns hard talks into moments of leadership.
• The particular moment or conversation that inspired Mahesh to write this book.
• The title is bold — How to Deliver Bad News and Get Away with It. Mahesh explains why “getting away with it” was part of this title and content.
• Delivering bad news is part of a manager’s job, not a failure. Mahesh discusses how leaders shift their mindset to see these moments as opportunities rather than setbacks.
• How detecting early warning signs before bad news becomes unavoidable is critical, and what some of those warning signs would be.
• If you left with just one thing, what one idea to walk away with and implement would be.
• The impact Stephen King’s storytelling had on Manesh's writing style.

To learn more about this guest:

GUEST EMAIL mahesh.gkumar@gmail.com

GUEST WEBSITE: maheshguruswamy.com

SOCIAL MEDIA: 

https://www.linkedin.com/in/maheshguruswamy/

https://x.com/mahesh_gkumar

https://maheshguruswamy.substack.com/