How to Deliver Bad News – and Get Away With it! with Mahesh Guruswamy
The Remarkable Leadership Podcast
Release Date: 08/20/2025
Mastering the Art of Questions with Dave Reynolds
The Remarkable Leadership Podcast
What if mastering the art of asking questions could turn you into an unstoppable leader? In this episode, Kevin chats with Dave Reynolds about how powerful questions can unlock deeper thinking, foster ownership, and promote growth in individuals and organizations. Dave shares insights on building a coaching culture where curiosity sparks conversations in every direction—up, down, and across. He explains the science behind how our brains respond differently to questions compared to directives and offers strategies for shifting from transactional to transformational leadership. From mirroring...
info_outline
Does the Seasoning Make the Meal? - Thoughts from Kevin
The Remarkable Leadership Podcast
Does the seasoning make the meal? In this episode of Remarkable TV, Kevin Eikenberry takes us into the kitchen to explore how small changes can transform good into great — both in cooking and in leadership. Discover why one small, intentional improvement can have a big impact on your effectiveness as a leader. Just like seasoning, leadership skills don’t need to be added in overwhelming amounts — the right one, in the right dose, makes all the difference. Watch now to learn how you can sprinkle in the right skill to elevate your leadership. Want more growth opportunities? Join us at...
info_outline
The Power of Mattering with Zach Mercurio
The Remarkable Leadership Podcast
What happens when you realize you matter? In this episode, Kevin talks with Zach Mercurio about the often-overlooked human need to feel important and how leaders at all levels can foster this through everyday interactions. Zach explains how his early research with custodial staff showed that small, intentional moments—like being seen, acknowledged, and validated—are the building blocks of meaning at work. These "moments of mattering," he says, aren't about big gestures but about real human connection. Kevin and Zach also explore the link between mattering and trust, the challenge of...
info_outline
The Power of Conflict - Thoughts from Kevin
The Remarkable Leadership Podcast
Conflict is often seen as something to avoid—but what if it could actually fuel growth? In this episode, Kevin Eikenberry explores how leaders can reframe conflict as a source of creativity, perspective, and stronger communication. Discover how to: See conflict as a driver of creativity Use conflict to explore perspectives Clarify expectations and prevent future misunderstandings Lead your team toward constructive conflict rather than destructive tension 💡 Remarkable Reminder: What would change in your work and life if you looked for the power in conflict instead of fearing it?...
info_outline
Creating a Work Culture Everyone Wants with Jennifer Moss
The Remarkable Leadership Podcast
What does it mean to build a workplace culture that people want to join? In this episode, Kevin talks with Jennifer Moss about this important leadership question. They discuss the societal shift in how we view work, the psychological idea of mortality salience, and how these concepts are influencing employee expectations today. Jennifer also shares the basic elements of a strong work culture: inspiring hope, creating purpose, and fostering genuine community, whether your team works remotely, in a hybrid setting, or in-person. Additionally, Jennifer challenges the one-size-fits-all approach to...
info_outline
Why Buy-In is Just the Start - Thoughts from Kevin
The Remarkable Leadership Podcast
Getting buy-in sounds great—but it's not the end goal. It's just the beginning. In this episode, Kevin Eikenberry explains why buy-in alone isn’t enough to drive results and how leaders can bridge the gap between agreement and action. Discover the three leadership actions that move your team from “I’m in” to actual implementation. In this episode, you’ll learn: Why buy-in is a low bar What the real goal of leadership influence should be 3 specific steps leaders can take to drive action 🎯 Remarkable Reminder: “Gaining buy-in to a project or change is a good first step,...
info_outline
How to Deliver Bad News – and Get Away With it! with Mahesh Guruswamy
The Remarkable Leadership Podcast
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...
info_outline
Are You a Curious Expert? - Thoughts from Kevin
The Remarkable Leadership Podcast
Are you an expert who’s stopped being curious? In this episode of Remarkable TV, Kevin Eikenberry explores the idea of the curious expert—a rare but powerful combination of knowledge and curiosity. You’ll discover why expertise alone isn’t enough in today’s fast-changing world, and why curiosity is the key to staying relevant, adaptable, and effective as a leader. Kevin shares how to balance what you know with what you still need to learn, and how doing so can help you build trust, grow as a leader, and remain a lifelong learner. 🔑 What you’ll learn in this episode: Why...
info_outline
Maximizing Influence with Dave Durand
The Remarkable Leadership Podcast
Do you realize how much greatness lies within you? In this episode, Kevin talks with Dave Durand about the mindset and virtues necessary for leading others effectively and ethically in today’s complex world. Dave describes the concept of giants, those we lead who have incredible potential, and stresses that leading them involves creating an environment that promotes autonomy, impact, and growth. He shares his four core virtues: prudence, justice, fortitude, and temperance. He clarifies that these are not outdated ideals but timeless strengths that help leaders make better decisions, act...
info_outline
Putting on Your Learning Glasses - Thoughts from Kevin
The Remarkable Leadership Podcast
Are you wearing your learning glasses? 🕶 In this episode of Remarkable TV, Kevin Eikenberry shares how changing your perspective can turn everyday moments—whether frustrating or joyful—into powerful learning opportunities. From handling setbacks to pursuing goals, coaching others, and even enjoying a good book or movie, Kevin explains practical ways to keep your "learning glasses" on and see the world differently. 📌 You’ll discover: What “learning glasses” are and why they matter When to put them on (hint: almost anytime!) How to practice this mindset in just 15...
info_outlineHow 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.