In this episode of Expert Insight Interview, host John Golden talks with Mahesh Guruswamy. Mahesh is the Chief Technology Officer at Kickstarter. He’s also the author of How to Deliver Bad News and Get Away with It. With 20+ years in tech and leadership, Mahesh knows how to handle hard talks at work.
Why It’s Hard to Share Bad News
John and Mahesh talk about how people today often avoid giving bad news. Mahesh shares a personal story. Early in his career, he didn’t tell a team member what needed to change. That person was shocked later. It was a hard lesson. Since then, Mahesh has learned to be kind—but honest.
Tip: Waiting too long to give feedback can hurt the other person more.
Why Mahesh Wrote His Book
Mahesh wrote his book to help others give hard news the right way. He says it’s better to be clear and kind than to wait. When you’re honest, people have time to grow, improve, or plan.
Expert Tip: Feedback helps people do better—even when it’s tough to hear.
Tips for Talking About Tough Stuff
1. Speak Early
Don’t wait. Talk about issues when they happen.
2. Be Clear and Kind
Say what needs to be said, but show care.
3. Know Your Boss
If you have to share bad news with your manager, learn what matters to them first. Start with small talks before the big ones.
4. Show Empathy
Try to understand how the other person feels. Use kind words like, “I know this is hard.”
5. Be Honest with Clients
If a project goes wrong, tell the client the truth. Bring a plan to fix it. If needed, offer something extra to make it right.
6. Own Your Mistakes
If you break a promise, be open about it. People respect honesty.
7. Choose the Right Setting
Talk face-to-face when you can. If not, use video. Mahesh says a walk-and-talk can also help people feel more relaxed.
Avoid This: Don’t hide the bad news between two good things. It confuses people.
Final Thoughts
Mahesh says that being kind, clear, and honest builds trust. Hard talks will always happen at work. But if you handle them the right way, you help people grow.
John thanks Mahesh for sharing his experience and recommends his book to anyone who wants to get better at giving feedback.
Want to get better at tough talks?
Check out Mahesh’s book and learn how to lead with empathy and strength.
Our Host
John is the Amazon bestselling author of Winning the Battle for Sales: Lessons on Closing Every Deal from the World’s Greatest Military Victories and Social Upheaval: How to Win at Social Selling. A globally acknowledged Sales & Marketing thought leader, speaker, and strategist, he has conducted over 1500 video interviews of thought leaders for Sales POP! online sales magazine & YouTube Channel and for audio podcast channels where Sales POP! is rated in the top 2% of most popular shows out of 3,320,580 podcasts globally, ranked by Listen Score. He is CSMO at Pipeliner CRM. In his spare time, John is an avid Martial Artist.
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