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 real-world scenarios from his book, including:
* How to talk to your boss when you’ve missed a deadline
* How to address poor performance with an employee
* How to tell a client their project is delayed
If you manage people, this one’s a must-watch.
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Topics We Discussed
* Growing up in Chennai and moving to the US
* Life in the US as an immigrant
* Feeling "average" growing up—and how that shifted
* Early career struggles and the decision to never go back
* Climbing the ladder: how he grew from engineer to executive
* What Mahesh did differently than his peers
* The role of risk-taking in his career journey
* The real meaning behind “get away with it”
* Influence of Stephen King on Mahesh’s writing style
* His writing routine, challenges, and how the book came together
* Advice for aspiring authors
* Traditional vs. hybrid vs. self-publishing—what he learned
* Common types of tough conversations leaders face
* What most people get wrong about delivering bad news
* The core framework Mahesh uses: empathy, kindness, ownership, and a path forward
* Why writing is more effective than talking (especially in leadership)
* What happens when you don’t handle tough conversations well
* Does giving tough feedback get easier over time?
* How to handle underperforming employees
* What to do when you miss a deadline (with team or customers)
* The importance of breaking big projects into smaller milestones
* Owning mistakes and rebuilding trust with stakeholders
* Navigating performance improvement plans with empathy
* The difference between empathy vs. sympathy, and staying objective during performance reviews
* How to stay technical while managing a team
* Dealing with brilliant individuals who lack soft skills
* Aligning incentives across teams, partners, and customers
* How Mahesh combines Product + Engineering leadership at Kickstarter
* His thoughts on "disagree and commit" and how to do it authentically
* Building teams with aligned behaviors and shared leadership tenets
* Keeping teams focused with simple, visible goals
* Why bottom-up planning works best—and when to override it
Insights from Mahesh
“Success isn’t about being born exceptional—it’s about showing up, doing the work, and saying yes when others hesitate.”— Mahesh Guruswamy
“Climbing the ladder is overrated. My career was a lattice—sometimes sideways, sometimes backwards—but always forward in learning.”— Mahesh Guruswamy
“You don’t grow by staying safe. Every bold move I made—quitting jobs, switching roles, taking risks on a visa—brought me closer to who I am today.”— Mahesh Guruswamy
“Delivering bad news isn’t about being harsh—it’s about being clear, kind, and honest. People remember how you made them feel, not just what you said.”— Mahesh Guruswamy
“The hardest conversations are where leadership really shows up. If you can’t deliver tough news with empathy, you’re not ready to lead.”— Mahesh Guruswamy
“I didn’t write a book to teach others. I wrote it to make sense of my own mistakes. Writing is just thinking clearly in public.”— Mahesh Guruswamy
“PowerPoint hides complexity. Writing forces clarity. If you can’t write it down clearly, you probably don’t understand it well enough.”— Mahesh Guruswamy
“As a leader, your job is to underwrite decisions—not micromanage them. Stay close enough to guide, but far enough to let people grow.”— Mahesh Guruswamy
“Empathy is not weakness. It’s the strength to hold someone accountable while still caring about what happens to them next.”— Mahesh Guruswamy
“Your team isn’t your family. You can’t fire your family. But you can build trust, set expectations, and lead with fairness.”— Mahesh Guruswamy
“Every customer wants to feel taken care of. Even when you mess up, ownership and transparency go a long way.”— Mahesh Guruswamy
“Kindness and clarity are not opposites. The best feedback I’ve given was also the hardest to say—but I said it with care.”— Mahesh Guruswamy
“When your career is over, no one will remember your title. They’ll remember how you made them feel—and how you helped them grow.”— Mahesh Guruswamy
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