Mahesh Guruswamy: How To Deliver Bad News (And Get Away With It!)

By Jennie Bellinger | February 3, 2025 |

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 wrote over the last few years culminated in his first book “How to Deliver Bad News and Get Away With It” which is out now for purchase here: https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN

In this episode, Jennie Bellinger and Mahesh Guruswamy discuss:

  • Transparency in delivering bad news
  • Frameworks for delivering critical feedback
  • Importance of understanding recipient’s personality
  • Balance between business skills and people skills in leadership
  • Creating a common language and culture within teams

Key Takeaways:

  • Being upfront and keeping customers/employees informed goes a long way in managing expectations and maintaining trust, even in difficult situations. 
  • The approach to delivering critical feedback should be tailored to the specific context and recipient. 
  • When providing critical feedback to superiors, it’s important to be mentally prepared for potential backlash or even job loss, and Mahesh advises being ready to handle the worst-case scenario, as the benefits of having the difficult conversation often outweigh the risks.
  • Incorporating a more people-centric approach can lead to better long-term outcomes.
  • Establishing behavioral tenets or principles that guide team interactions can create a unifying framework for resolving conflicts and improving communication. 

“Companies don’t hire CEOs for their people skills. You look at the most successful leaders in the world, most successful like technology leaders or corporate leaders there, because they can make the impossible happen, right? They have extremely good business skills.” — Mahesh Guruswamy

Connect with Mahesh Guruswamy:  

Website: https://www.maheshguruswamy.com/

LinkedIn: https://www.linkedin.com/in/maheshguruswamy/

Book: https://www.amazon.com/How-Deliver-Bad-News-Away/dp/B0D7FHTTNN

Link to Gift from Mahesh Guruswamy:

Connect with Jennie:

Website: https://badassdirectsalesmastery.com/

Email:  jennie@badassdirectsalesmastery.com

Facebook personal page: https://facebook.com/jbellingerPL

Facebook podcast page: http://facebook.com/BadassDirectSalesMastery

Facebook group for Badass Crew: https://facebook.com/groups/BadassDirectSalesMoms

Instagram: https://instagram.com/BadassDirectSalesMastery

Personal Instagram: https://instagram.com/jenniebellinger

LinkedIn: https://linkedin.com/in/BadassDirectSalesMastery

The Badass Direct Sales Mastery Podcast is currently sponsored by the following:
Bella Grace Elixir: https://shopbellagrace.com/?ref=jenniebadassdirectsalesmastery

LeadBuddy Digital Marketing: Use code BDSM when checking out at https://leadbuddy.io/pro-monthly-9310?am_id=jennie582

Show Notes by Podcastologist: Hanz Jimuel Alvarez

Audio production by Turnkey Podcast Productions. You’re the expert. Your podcast will prove it.

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