256 Mahesh Guruswamy - If You Want a Slice, You Gotta Roll The Dice

Mahesh 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 mentorship, Mahesh especially enjoys guiding aspiring people managers and those new to leadership roles.

In this episode, Jason and Mahesh discuss:

• Navigating difficult conversations as leaders through the book How to Deliver Bad News and Get Away With It
• Insights on business innovation, growth, and career risk-taking
• Importance of changing roles every two years for new challenges
• Strategies for delivering honest feedback with emotional intelligence
• Framing problems as collaborative puzzles for effective problem-solving

Key Takeaways: 

• Navigating difficult conversations requires a balance of emotional intelligence and long-term thinking, ensuring feedback is constructive rather than reactive. Leaders who approach tough discussions with empathy create environments where honesty leads to growth.
• A strategic approach to delivering feedback starts with open-ended questions and progressively increases in directness if issues persist, avoiding emotional language while presenting clear solutions.
• Career growth accelerates when individuals embrace calculated risks, change roles every two years for new challenges, and remain open to opportunities rather than instinctively rejecting them.
• Adaptability is essential in navigating career instability, as it demands identifying transferable skills, exploring entrepreneurship, and maintaining persistent networking to pivot effectively when needed.
• True fulfillment extends beyond financial success, emphasizing the importance of mentorship, altruism, and leaving a lasting positive impact on others as the ultimate measures of a meaningful life.

“I actually encourage people to take risks. The way I see it, life is short. If you have a goal in mind and are committed to achieving something, then take the risk. You have to roll the dice.”

 - Mahesh Guruswamy

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