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Difficult Conversations at Work: Guidance, Tips and Best Practices

difficult conversations at work

You’ve probably seen the recent headlines about how Vishal Garg, CEO of Better.com, sparked outrage when he laid off 900 employees over a Zoom call. This story became an example of how not to have difficult conversations at work. This circumstance, framed within the grander series of events that sent shockwaves through American workplaces over the last year, clearly illustrates the need for leaders to be intentional about how they navigate difficult conversations.

Here is the #229 episode of the Strategy Skills Podcast. For this episode, we interviewed Michael Reddington, an expert forensic interviewer about the common mistakes leaders make when approaching these discussions and best practices on how to handle them better.

Common mistakes leaders make when dealing with difficult workplace conversations: 

  • Scheduling/conducting difficult conversations in a way that is convenient for them, regardless of how it impacts their audience.
  • Focusing on “getting a conversation over with”, as opposed to opportunities to create value and/or minimize exposure. Time is the enemy of empathy.
  • Seeking rational solutions to emotional issues.

Best practices for handling these issues in the future: 

  • Schedule/build your conversations around what your audiences need to experience to achieve the preferred outcome.
  • Value quality over time and embrace a strategic approach over a tactical approach. Focus on the solution, not the problem.
  • Increase your situational awareness and consider the long-term ramifications of decisions; select the best alternative for achieving long-term goals, not relieving short-term stress.

About our guest, Michael Reddington:

President of InQuasive, Inc., and author The Disciplined Listening Method:  How a Certified Forensic Interviewer Unlocks Hidden Value in Every Conversation.

Michael Reddington, CFI is a certified forensic interviewer and president of InQuasive, Inc., which  integrates key components of effective non-confrontational interview techniques with current business research for executives. In his new book, The Disciplined Listening Method:  How a Certified Forensic Interviewer Unlocks Hidden Value in Every Conversation (Per Capita Publishing, March 2021), Reddington draws on his background in forensics and his understanding of human behavior through interrogation to teach readers how to improve their listening, communication and relationship-building skills—and how to use truth to their advantage.

Reddington developed his innovative Disciplined Listening Method by combining the persuasive, perceptive methods of certified forensic interviewers with current research, theories and expectations from the business world. His new book reveals the shortcomings of traditional listening techniques, illustrates the need for a more strategic approach and outlines the seven core behaviors of disciplined listening. The Disciplined Listening Method also describes the seven phases of potentially contentious conversations so leaders can truly understand what their audience experiences during important interactions.

Reddington founded InQuasive, Inc. to help leaders and their teams reduce missed opportunities and increase commitments to action by activating the truth in all of their business interactions. InQuasive, Inc. integrates current business communication research and best practices with non-confrontational interview and interrogation techniques to provide customized training and advisory services in the areas of sales, negotiations, leadership communication, conflict resolution, customer service, candidate interviewing and public speaking.

Reddington leads programs on the application of strategic, ethical, persuasion techniques in the areas of leadership communication, sales, negotiation, conflict resolution, customer service, candidate interviews and family conversations. He has led more than one thousand five hundred programs and educated over 15 thousand participants from companies, government agencies and executive groups around the world.

Additionally, Reddington has spoken about the international applications of the Disciplined Listening Method at Kellogg School at Northwestern, and he was given the Outstanding Contribution Award from  the U.S. Department of Homeland Security. He has also been cited as an expert resource in Fast Company, Training Industry, CEO World, and The $100 MBA Show.

Reddington received his bachelor’s degree in business administration and management from Southern New Hampshire University, as well as additional education on negotiation and leadership from Harvard University. He currently lives in Waxhaw, N.C. For more information, please visit inquasive.com.

This episode is available on iTunesYouTube, and StrategyTraining.com.

The Strategy Skills Podcast is the channel where strategy partners and the world’s top thinkers teach you the tools and techniques to solve mankind’s greatest problems. Every week, we release powerful episodes where we discuss concepts to help listeners advance their strategy, operations, implementation, and communication skills, enhance their critical thinking ability and build their executive presence.

If you genuinely find our podcasts helpful, we would greatly appreciate you supporting us with a review for our Apps (Apple or Android) and iTunes channels.

About Kris Safarova (FIRMSconsulting’s CEO and co-host of the Strategy Skills podcast):

Kris Safarova is a USA Today, Wall Street Journal and Amazon bestselling author who has published 20+ books on business strategy, leadership and problem solving. She is the CEO of FIRMSconsulting.com and StrategyTraining.com, the latter which is the largest business strategy video training platform in the world. Two of her podcasts, Strategy Skills and Case Interviews & Management Consulting, are often ranked in the Top-10 for careers in many countries.

She holds a Diploma in Music, a B.Comm, cum laude, and a MBA with distinction and on the deans list, the latter from Ivey Business School in Canada. She worked as a management consultant and corporate finance director, where she managed a >USD$1 billion portfolio. Kris was a master classical concert pianist and official music representative of the Russian Federation, who toured Europe. Kris has studied voice for decades, most recently under Roger Love, the world’s top voice coach, to become a reputed and certified executive presence and speaking coach, helping clients manage all aspects of communication including handling difficult conversations at work. Kris Safarova is a professional with a decades-long track record of rapid promotions in the corporate world and building successful businesses.

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