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.

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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

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