Shows
Modern CTOHow to Deliver Bad News and Get Away with It with Mahesh Guruswamy, CPTO at KickstarterToday, we're talking to Mahesh Guruswamy, CPTO at Kickstarter. We discuss how to effectively deliver bad news in corporate settings, why CTOs can no longer be the "nice guy" in today's business environment, and how AI tools are reshaping both personal and professional life.
All of this right here, right now, on the Modern CTO Podcast!
To learn more about Mahesh and pick up a copy of the bo
2025-08-2148 min
The Remarkable Leadership PodcastHow to Deliver Bad News – and Get Away With it! with Mahesh Guruswamy 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...
2025-08-2033 min
The 30 Minute Hour™#391-- How To Deliver Bad News And get Away With ItMahesh Guruswamy 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 technology officer at Kickstarter. Before that, he was an executive running product development teams at Mosaic, Kajabi, and Smartsheet.Listen NOW as Mahesh reveals principles from his book, "How to Deliver Bad News and Get Away With It".
2025-07-1050 min
School for Startups RadioJune 11, 2025 – Disruptors Dr. Imamu Tomlinson and Kickstarter CPTO Mahesh GuruswamyDr. Imamu Tomlinson -CEO of Vituity and Author of Less Than One Percent: How Disruptors Defy the Odds
As an award winning CEO of a multi-billion dollar healthcare company, Dr. Imamu Tomlinson MD, MBA knows all about what it takes to succeed against all odds. With his unique narrative and analytic bent, he highlights how often times we misjudge the qualities necessary to succeed. Tomlinson’s passion is to inspire others to exceed their own expectations. Dr. Tomlinson is CEO of Vituity, a physician-owned and led multispecialty healthcare partnership. Vituity has a network of 6,000 clinicians who provide care...
2025-06-1153 min
LaunchPod | Product Management PodcastKickstarter's Comeback | Mahesh Guruswamy, CPTO (Kickstarter)Today, we’re talking with Mahesh Guruswamy, CPTO at Kickstarter.
In this episode, we discuss:
How daily reflection on hard moments helped him grow as a leader—and led to his widely praised book How to Deliver Bad News and Get Away with It.
How Kickstarter went from “printing money” and experiencing “insane” PMF to plateauing - and how they created urgency and competition to quickly turn it around
The actual process Kickstarter used to activate its creator and backer communities to shape a better UX, build real loyalty, and re-ignite growth
Links
LinkedIn: ht...
2025-06-1035 min
IT Horror StoriesPoint of No RollbackWhen a huge cloud platform migration stalls out mid-flight with no hope of changing course, panic lunges to take the wheel. In this episode, Mahesh Guruswamy, CPTO at Kickstarter and author of How to Deliver Bad News and Get Away with It, recounts the night he took down production and had no other choice but to push through. Tune in for the blow-by-blow — from anxiously watching the clock as queries time-out to the tightrope walk of breaking bad news without breaking trust. You'll leave with the brutally simple playbook Mahesh now swears by to make sure your next migration do...
2025-06-1034 min
The Proteus Leader Show#102 How to Deliver Bad News WellErika talks with Kickstarter CTO Mahesh Guruswamy about his new book "How to Deliver Bad News and Get Away with It," discussing what may be the hardest task for any leader: sharing tough news in a way that works.For more Proteus, subscribe to our newsletter.Follow us on YouTube.
2025-05-1912 min
Speak Up: Develop Your Executive Presence & Leadership Communication Style404: How To Instantly Build Trust With Senior Executives AND Avoid Being Laid OffIn today’s episode you’ll discover how to have tough conversations successfully at work AND be the one who DOES NOT get laid off.If you're a leader or aspiring executive, delivering bad news is part of the job — but most people aren’t trained to do it well. Whether you're an introvert, a people-pleaser, or just afraid of rocking the boat, learning how to communicate hard truths without hurting your credibility is crucial for career growth and company success.To chat with Laura to see if her Executive Presence Mastery System is right for you...
2025-05-0724 min
How I Got HerePart 2 — Mahesh Guruswamy — CTO of Kickstarter on How to Tell Your Boss You'll Miss the DeadlineIf you missed part 1 of my conversation with Mahesh Guruswamy, Chief Technology Officer at Kickstarter and author of How to Deliver Bad News and Get Away With It, you can watch it here: In this part, we get more into the tactics on how to give bad news:* What most people get wrong when delivering bad news* The core framework of delivering bad news* How to handle underperforming employees* What to do when you miss a deadline * How to do a performance improvement plan* As...
2025-04-2343 min
Enterprise Podcast Network – EPNRed Flags at Work: Recognizing Problems and Delivering the Bad News Mahesh Guruswamy, a seasoned product development executive who has been in the software development space for over twenty years and has managed teams of varying … Read more The post Red Flags at Work: Recognizing Problems and Delivering the Bad News appeared first on Top Entrepreneurs Podcast | Enterprise Podcast Network.
2025-04-2216 min
Sales POP! Podcasts: Insights from Top Experts in Sales, Marketing, Leadership & More.Tough Talks Made Easy with Mahesh GuruswamyIn this episode, Mahesh Guruswamy, CTO at Kickstarter, shares smart ways to deliver bad news at work. With over 20 years in tech, Mahesh knows how to talk about hard things in a kind and clear way. He says don’t wait—speak up early, but do it with care. Whether it’s with your team, your boss, or a client, honesty and empathy matter. Want to learn how to give feedback without fear? Mahesh explains how to do it right—and still keep strong relationships. 💡 Key Tip: Be kind, be clear, and don’t delay the hard talk
2025-04-1721 min
How I Got HereMahesh Guruswamy — CTO of Kickstarter Shares How to Deliver Bad News and Get Away With It (Part 1)I interviewed Mahesh Guruswamy, Chief Technology Officer at Kickstarter and author of How to Deliver Bad News and Get Away With It.Mahesh always saw himself as an average kid growing up in Chennai—and assumed he’d stay that way. Today, he’s an executive at a major U.S. tech company, and I was curious how he changed his trajectory.We talk about his journey as an immigrant, dealing with racism, being broke, working night shifts at McDonald’s, and how he ultimately climbed the ranks in tech.We also dive into rea...
2025-04-1659 min
Out of the Comfort ZoneHow to Deliver Bad News with Mahesh GuruswamySend us a textAs a manager, you have to deliver bad news – probably more of it than you would like to deliver. If you like making people happy, delivering bad news is probably even more difficult. So how can you say no, deliver negative feedback, go back on a promise or any other difficult news and survive, whether you are talking to senior leaders, your manager, your team or your customers? Listen in for tips.⬇️ Connect with me!► LinkedIn: https://www.linkedin.com/in/wanda-wallace-publicspeaker-author-podcasthost/► Instagram: https://www.instagram.com/wandatwallace/► Main YouTube...
2025-03-2642 min
The Insight Interviews - Powered by Rewire256 Mahesh Guruswamy - If You Want a Slice, You Gotta Roll The DiceMahesh Guruswamy is a seasoned product development executive with over twenty years of experience in software development and more than a decade of managing teams of varying sizes. He is currently the Chief Technology Officer at Kickstarter and previously led product development teams at Mosaic, Kajabi, and Smartsheet. Inspired by his favorite author, Stephen King, Mahesh began his writing journey with short stories before discovering long-form writing as a powerful way to share insights with product development teams. His essays over the years culminated in his book How to Deliver Bad News and Get Away With It. Passionate about...
2025-03-1439 min
Living The Red LifeKickstarter’s Former Tech Chief on Hiring, Scaling & Startup FailsSUMMARYMahesh Guruswamy, a seasoned tech leader and author, joins the podcast to share invaluable insights on entrepreneurship, business strategy, and hiring for success. With a background in major tech companies like Amazon, Mahesh has a unique perspective on what it takes to scale a business, the common pitfalls entrepreneurs face, and how to build a winning team.Throughout the episode, Mahesh dives deep into the importance of market research, why competitor analysis is crucial, and why being first to market isn't always the best move. He also shares hard-earned lessons from his own entrepreneurial...
2025-03-0326 min
Get Down To Business with Scott "Shalom" KleinPodcast of “Get Down To Business” – 3/02/2025 - Mahesh Guruswamy, Anjali Sharma and Jimi GibsonJoin Scott "Shalom" Klein on his weekly radio show, Get Down To Business with guests:Mahesh GuruswamyAnjali SharmaJimi Gibson
2025-03-0140 min
Monday Morning Radio“You’re Fired:” Delivering Bad News with Clarity, Empathy, and Integrity“You’re Fired!” Two words that are never easy to speak and are even harder to hear. Dismissing employees is complicated — legally, emotionally, and professionally. Mastering the art of letting employees go isn’t taught in business school, and too many managers fumble the process. Mahesh Guruswamy, chief technology officer at Kickstarter, has spent much of his career delivering tough news — not just to employees but also to customers, investors, and even higher-ups. Now, he’s sharing his hard-earned wisdom in a new book — How to Deliver Bad News and Get Away With It: A...
2025-02-1752 min
Badass Direct Sales MasteryMahesh Guruswamy: How To Deliver Bad News (And Get Away With It!)About Mahesh Guruswamy:Mahesh Guruswamy 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 technology officer at Kickstarter. Before that, he was an executive running 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. The essays he...
2025-02-0334 min
The Power of ConnectionsMahesh Guruswamy: Leading with Empathy and Intentional ConnectionsIn this episode, Rich and Mahesh Guruswamy discuss:How his wife’s advice became a pivotal moment in his career at AmazonLessons learned from building and rebuilding relationships in new environmentsThe importance of empathy, apologies, and honest conversations in leadershipThe power of small gestures, like waving to neighbors or checking in with old friendsCreating value in relationships, both personal and professionalKey Takeaways:Simple actions, like waving to your neighbors or having a quick conversation, can profoundly impact how connected you feel to your community. These gestures contribute to your sense of happiness and belonging.Apologizing is...
2025-01-2030 min
UnleashedMahesh Guruswamy: Transforming Leadership, Crowdfunding, and Guided ChaosMahesh Guruswamy is a tech industry powerhouse and current CTO of Kickstarter, with over two decades of experience turning bold ideas into reality. Known for his no-nonsense leadership style and knack for mentoring rising managers, Mahesh doesn’t shy away from tackling the tough stuff—his book, “How to Deliver Bad News and Get Away with It”, says it all. When he’s not shaking up the tech world, he’s running Orange County trails or exploring the eerie depths of cosmic horror fiction.In this episode, Wendi and Mahesh discuss:How crowdfunding platforms li...
2025-01-0750 min
Light Bulb Moments: It's All About The EnergyMahesh Guruswamy: Selling Your Vision To People Who CareMahesh Guruswamy 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 technology officer at Kickstarter. Before that, he was an executive running 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. The essays he wrote over the last few years culminated...
2024-12-2554 min
The Nice Guys on BusinessMahesh Guruswamy: A Manager’s Guide To Delivering Bad NewsMahesh Guruswamy is a seasoned product development executive and a published author 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 technology officer at Kickstarter. Before that, he was an executive running product development teams at Mosaic, Kajabi, and Smartsheet. Mahesh is passionate about mentoring others, especially folks who are interested in becoming a people manager and newer managers who are just getting going. Mahesh resides in Orange County with his wife, Krishma, and son, V...
2024-12-2325 min
IT Visionaries‘Monetize Your Knowledge’ with Mahesh Guruswamy, CTO, KajabiStarting a new creative endeavor can often seem like a major gamble, but what if there existed a tool that helped creators minimize their entrepreneurial risk? Mahesh Guruswamy is the CTO of Kajabi, a multifaceted online business platform designed to help entrepreneurs, experts and influencers succeed. Tune in to learn the approach to innovation at the company, and how Mahesh and his engineering team have effectively scaled the platform during a time of major growth.Tune in to learn:About Kajabi and what makes it special (02:30)Kajabi’s various product domains (08:20)The Kajabi playbook of scale, sp...
2022-11-0844 min
Building With People For People: The Unfiltered Build PodcastEp. 04: Mindful Management with Mahesh Guruswamy - Chief Operator of the Rube Goldberg MachineAre you trying to decide if software engineering is the right path for you? Are you currently an engineering manager and want tips on how you can grow and foster a better team? Join me as I speak with Chief Operator of the Rube Goldberg machine (CTO of Kajabi), Mahesh Guruswamy, as he guides us through how he measures success in his role as CTO, his 6 tenants of conflict resolution, ways to build a learning culture, how to know if engineering management is right for you, and much more.
Mahesh has been in tech for over two...
2022-02-2255 min