How can leaders navigate the messy middle of management, especially when it comes to delivering difficult news without damaging relationships or morale? In this episode, Kevin talks with Mahesh Guruswamy about the real-world challenges leaders face when communicating unwelcome information, from missed deadlines to ethical violations. Mahesh shares a thoughtful approach to raising the temperature of conversations gradually and when situations call for urgent, high-stakes responses. They also discuss the difference between technical and adaptive feedback, the importance of intentional communication, and the human side of letting team members go.

Listen For

00:00 Introduction 02:02 Meet Mahesh Guruswamy 06:03 The Messy Middle of Leadership 06:24 When Should Leaders Deliver Bad News 07:17 Listening to Your Intuition as a Leader 08:06 Raising the Temperature Slowly 10:24 When to Start at a Higher Temperature 12:04 When Urgency or Ethics Demand Immediate Action 13:04 Communicating the Stakes with Your Team 13:46 Writing as a Tool for Delivering Difficult News 14:51 Lessons from Amazon on Written Communication 16:06 Documenting Over Slide Decks for Clarity 17:17 Reviewing Recordings to Improve Communication 18:45 The Power of Leadership Language 21:11 Balancing Policy and Humanity in Difficult Conversations 22:09 Helping Team Members Find Better Fit Elsewhere 22:58 Avoiding Emotional Delivery of Feedback 23:59 Two Types of Feedback Technical and Adaptive 25:42 Giving Feedback to Your Boss 26:56 Should You Be a Manager Key Questions to Ask 28:28 Can You Succeed Without External Validation 28:55 Giving Credit to the Team Not Yourself 30:31 Mahesh’s Personal Interests 32:51 Final Thoughts and Call to Action

Mahesh's Story: Mahesh Guruswamy is the author of How to Deliver Bad News and Get Away with It: A Manager's Guide. He is a seasoned product development executive who has been in the software development space for over twenty years and has managed teams of varying sizes for over a decade. He is currently the chief product and technology officer at Kickstarter. Before that, he ran product development teams at Mosaic, Kajabi, and Smartsheet. Mahesh caught the writing bug from his favorite author, Stephen King. He started out writing short stories and eventually discovered that long-form writing was a great medium to share information with product development teams. Mahesh is passionate about mentoring others, especially folks who are interested in becoming a people manager and newer managers who are just getting going.

This Episode is brought to you by...

Flexible Leadership is every leader’s guide to greater success in a world of increasing complexity and chaos.

Book Recommendations

How to Deliver Bad News and Get Away With It: A Manager’s Guide by Mahesh Guruswamy
Leadership on the Line: Staying Alive through the Dangers of Leading by Ronald A. Heifetz and Marty Linsky
Never Flinch by Stephen King

Like this?

Join Our Community

If you want to view our live podcast episodes, hear about new releases, or chat with others who enjoy this podcast join one of our communities below.

Join the Facebook Group Join the LinkedIn Group

Leave a Review

If you liked this conversation, we’d be thrilled if you’d let others know by leaving a review on Apple Podcasts. Here’s a quick guide for posting a review. Review on Apple: https://remarkablepodcast.com/itunes

Podcast Better! Sign up with Libsyn and get up to 2 months free! Use promo code: RLP