The Art of Difficult Conversations

This Deliberate Leaders podcast episode, hosted by Allison Dunn, centers around the crucial leadership skill of mastering difficult conversations. The episode begins by highlighting the common tendency for leaders to avoid these challenging discussions, such as addressing performance issues or team conflicts, and emphasizes that avoidance only exacerbates these problems. Dunn shares a personal anecdote about a client who delayed addressing an underperforming team member, resulting in a damaged relationship and frustration for both parties, illustrating the point that a leader's willingness to have difficult conversations significantly impacts whether problems become disasters or opportunities for growth. The core of the episode introduces a four-part framework for navigating difficult conversations: Prepare, Connect, Navigate, and Close. •  Prepare: This initial stage involves thoughtful preparation before the conversation. Leaders are encouraged to define their desired outcome, identify supporting facts, anticipate the other person's reaction, and choose an appropriate time and place. Dunn recommends writing down key points to maintain focus, while stressing that this is for clarity, not scripting. •  Connect: The opening of the conversation is critical for establishing psychological safety. Leaders should begin by expressing genuine appreciation and stating their positive intention to find a way forward that addresses the challenge and supports the other person's success. This helps build a foundation of respect. •  Navigate: This is presented as the stage where conversations most often succeed or fail. The episode emphasizes using "I" statements to present one's perspective without being accusatory, and provides an example: "I noticed the project deadline was missed" instead of "You missed the deadline". Crucially, leaders are advised to pause, genuinely listen by asking open-ended questions like, "I'd like to understand your perspective," and to use the powerful phrase, "Tell me more about that," to uncover important information. The primary goal during navigation is mutual understanding and finding a path forward together, not "winning". •  Close: The final part of the framework focuses on summarizing what was heard, confirming any agreements or next steps, and expressing confidence in future progress. An example provided is: "So we've agreed that you'll provide weekly updates, and I'll check in more frequently. I'm confident we can make this work together". This ensures shared understanding and reinforces the relationship. To help listeners apply these concepts, Dunn issues a "Conversation Audit" challenge. This involves taking 15 minutes to identify postponed conversations, noting the reasons for avoidance (fear, uncertainty, concern), selecting one conversation, scheduling it within a week, and applying the four-part framework. Listeners are then encouraged to reflect on the experience—what went well, what could be improved, and how the outcome compared to expectations—and even to email the host with their experiences. The episode concludes by reinforcing that how leaders handle difficult conversations significantly shapes their leadership reputation, especially more so than easier interactions. It highlights that teams observe how leaders navigate challenges and take cues from their approach. Mastering these conversations is presented not as eliminating discomfort, but as moving through it towards better understanding, stronger relationships, and improved outcomes. Listeners are encouraged to subscribe to the podcast and leave reviews to help others discover the content. The final message reminds listeners that the conversations they are avoiding are often the key to their next level of leadership. About the Host: Allison Dunn •  Host of the Deliberate Leaders Podcast •  Business Coach •  Founder of Deliberate Directions Connect: •  Website: Deliberate Directions •  Podcast: Deliberate Leaders Podcast Reminder: Subscribe and leave a review to support the podcast!