A Manager’s Guide on Mastering Tough Conversations – An Interview with Mahesh Guruswamy

Delivering bad news is one of the most challenging aspects of leadership, yet it is an unavoidable reality for managers across industries. Mahesh Guruswamy, a seasoned product development executive, tackles this often-dreaded task in his book, How to Deliver Bad News and Get Away with It: A Manager’s Guide. In a recent interview, Guruswamy shared his insights on navigating difficult conversations, building trust, and using storytelling techniques to improve communication.

Filling a Critical Gap in Management Resources

Guruswamy’s motivation for writing this book stemmed from both personal experience and a noticeable gap in management literature. “There isn’t a book dedicated to helping managers handle difficult workplace conversations,” he explained. “As a new manager, I struggled considerably with delivering unpleasant news. I’m a people pleaser by nature, so the idea of upsetting someone was daunting. But with guidance from mentors and extensive research, I developed a framework that made these conversations easier.” By sharing his learnings, he hopes to spare others from the challenges he once faced.

Lessons from the Toughest Conversations

One of the most difficult conversations Guruswamy had to navigate involved telling an employee that they were underperforming. Reflecting on the experience, he acknowledged his mistake of delaying the feedback and then delivering it too abruptly. “When giving performance-related feedback, you need to gradually increase the tone and intensity based on the employee’s response,” he advised. A sudden escalation can catch employees off guard, creating an emotionally charged situation and eroding trust. His takeaway? Address performance issues early and communicate expectations clearly to prevent unnecessary tension.

Humor vs. Professionalism: Striking the Right Tone

While Guruswamy uses humor in his book to make the subject more engaging, he warns against using humor when actually delivering bad news. “It’s best to maintain a neutral tone that conveys empathy and clarity,” he said. He emphasized three key principles for delivering bad news effectively:

1. Ensure the recipient understands and agrees with why they are receiving the news.
2. Show that you care about their well-being.
3. Provide a clear path forward with actionable next steps.

Advice for New Managers: Practice and Mentorship

For new managers struggling with difficult conversations, Guruswamy offers two essential pieces of advice:

1. Practice – The more you engage in these discussions, the better you’ll become. Reflection and refinement of your approach are key.
2. Find a mentor – Learning from someone who has been in your shoes can be invaluable. Guruswamy even invites readers to reach out to him for mentorship or connections to others who can help.

The Hardest Audience for Bad News: Customers

According to Guruswamy, customers are the toughest group to deliver bad news to. “Mishandle a customer situation, and they will not only leave but also influence others to do the same,” he warned. He cited Sonos’ botched app rollout as a cautionary tale, demonstrating how a poorly managed crisis led to lasting reputational damage.

Maintaining Trust and Credibility

Many managers fear that delivering bad news will harm their relationships with employees, stakeholders, or customers. However, Guruswamy argues that avoiding tough conversations does more damage in the long run. “Managers who fail to communicate difficult truths will eventually lose both their jobs and their team’s trust,” he said. Instead, he recommends delivering news with empathy and a focus on solutions to build lasting credibility.

Framing Bad News in the Tech Industry

In industries like tech, where product delays and unexpected challenges are common, how managers frame bad news can determine whether they maintain customer confidence. Guruswamy suggests two key strategies:

1. Take accountability – Avoid shifting blame; instead, assure customers that you are taking charge of the situation.
2. Outline a future plan – Provide a clear course of action to address the issue, and if necessary, offer compensation for disruptions.

Stephen King’s Influence on Management Communication

An unexpected source of inspiration for Guruswamy’s writing is Stephen King. “King is a master of storytelling, and I apply his techniques even in a business context,” he shared. He believes that difficult workplace situations can be framed like compelling narratives, complete with protagonists, conflicts, and resolutions. This approach makes his advice more engaging and relatable for readers.

The Role of Empathy in Leadership

Guruswamy firmly believes that empathy is the cornerstone of effective management. “Without empathy, you will fail as a manager,” he stated. Developing empathy, he suggests, doesn’t necessarily require formal training—simply caring for someone who depends on you, such as a pet or a child, can enhance your ability to understand and support others.

Embracing the Challenges of Leadership

Many promising leaders shy away from management roles due to the challenges of handling difficult conversations. Guruswamy hopes his book provides the tools and confidence they need to succeed. “Delivering bad news is part of the job, but it doesn’t have to be a nightmare,” he assured. By applying the right frameworks and fostering empathy, managers can turn difficult conversations into opportunities for growth and stronger relationships.

With How to Deliver Bad News and Get Away with It: A Manager’s Guide, Guruswamy offers a practical, engaging, and much-needed resource for leaders navigating the complexities of workplace communication.

Find How to Deliver Bad News and Get Away with It on Amazon Today.