Best Boss Take 5 | Difficult Conversations

Navigating tough workplace discussions can feel like a tightrope walk. So, let’s shed some light on this topic and discuss practical advice designed to help you become the Best Boss. 

Here’s a breakdown of the key points to consider:

  • Recognize the Elephant in the Room: Before diving into tough discussions, identify and address the unspoken issues that might be lingering. This preemptive approach helps set the stage for a more effective conversation.
  • Monitor Escalating Behaviors: Be aware of your own behaviors and those around you that might exacerbate conflicts instead of resolving them. Using tools like the saboteur assessment at can provide insights into how you might inadvertently add to the conflict.
  • Choose Your Conflict Style Wisely: Familiarize yourself with the Thomas-Killmann Conflict Mode Model for conflict resolution. Whether you choose to compete, collaborate, compromise, accommodate, or avoid, each style has its time and place. Selecting the appropriate approach can significantly influence the outcome of your discussions.

Mastering the art of difficult conversations is crucial for any leader aiming to foster a healthy and productive workplace. By addressing the unspoken, monitoring harmful behaviors, and strategically choosing your conflict style, you’re better equipped to handle challenging interactions gracefully and effectively.

About Danny

With over 20 years experience in training and leadership development  — and holding an MBA and an MA in Organizational Development — Danny Ceballos has worked with organizations across the country to strengthen their effectiveness in leading and managing others through supervision+motivation best practices and strategies.