Breathing Space May 2025

by Dan Comer

Have That Difficult Conversation!

How many conversations have you rehearsed but never had? Difficult conversations feel like walking on a tightrope—a balancing act most people try to avoid. The cost of avoidance usually far exceeds the risk of addressing tensions or other difficult topics.

The good news? Difficult conversations, when managed well, create positive results. Research shows that 81 percent of people report better understanding, stronger relationships, and more effective solutions by going ahead and having the conversation.

Why We Avoid Difficult Conversations

Avoiding difficult conversations is more common—and costly—than we realize. What keeps us silent, even when the stakes are high? The answer lies in three interconnected factors: personal fears, team dynamics, and organizational culture.

Personal Factors: Self-Centered Narratives

  • We like to be liked. Let’s face it, nobody enjoys being the bad guy. Whether it’s in friendships or at work, we filter our thoughts, fearing that honesty might damage relationships.
  • We don’t want to hurt others. Kindness is core to who we are, or at least who we want to be. But our desire to protect others’ feelings often backfires. By withholding critical feedback, we end up causing more harm.
  • Empathy is harder than we think. Research shows that empathy demands significant mental and emotional labor—it’s a heavy lift. Understanding others (the key to difficult conversations) requires hard work that most aren’t willing to invest.

Team Factors: The Fear of Being Rejected

  • We need to belong. The fear of exclusion is ancient and primal, but it also runs deep in modern teams. Members choose silence or groupthink over risking their seats at the table.
  • We protect a sense of harmony. Many teams often preserve artificial harmony at the expense of progress. This illusion might feel comforting, but it hinders honest dialogue, which leads to growth.
  • We fear retaliation. Power dynamics in teams are real. The threat of professional fallout—being excluded from projects or sidelined for promotions—makes silence the safer option.

Organizational Factors: The Way We Avoid Things Here

  • Our culture is too nice. When organizations prioritize loyalty over candor, courageous conversations are avoided. Speaking up gets labeled as harsh or not being a team player.
  • Leaders model avoidance. Leaders set the tone for handling difficult conversations. When they dodge holding others accountable or making tough decisions, they normalize avoidance.
  • Without clear approaches or tools, employees develop their own ways of managing tensions. A lack of support and training leaves teams unprepared to handle conflict constructively.

The Cost of Avoidance

Avoided conversations very often compound into major problems. Teams often discover that early intervention could have prevented their biggest challenges.

But here’s the good news: Confronting issues often reveals they weren’t as daunting as imagined. The benefits—clarity, connection, and progress—consistently outweigh the risks.

While avoidance may feel like self-preservation, active participation is the real act of courage. The breakthrough your team needs awaits on the other side of the tightrope.

Transforming Avoidance into Courageous Action

Let’s explore three key areas to move from avoidance to action: Have the conversation, design the conversation, and address conversational debt.

Have the Conversation

  1. Don’t put it off
    • The perfect moment is now. Waiting for ideal conditions is the best excuse for procrastination. Commit to addressing issues as they arise. The longer you wait, the more the anxiety and stakes escalate.
    • Prepare for impact. Before starting a difficult conversation, ground yourself—what impact do you want to create? Consider potential reactions and prepare thoughtful responses. You don’t need to script the conversation, just have a clear approach and plan.
    • Model embracing discomfort. Having difficult conversations is not easy. You get better with practice, but the discomfort never really goes away. Share your own struggles with discomfort and model courage in action. For instance, “I know this is hard for everyone, but it’s necessary to discuss.”
  2. Be direct and constructive
    • Clarity is kindness. Stick to observable facts, not assumptions or judgments. State your intentions clearly and upfront. Explain why this conversation matters and what you want to achieve.
    • Keep it focused, not personal. Tackle one tension at a time rather than trying to solve everything at once. Replace vague concerns with specific observations.
    • Stay respectful. Direct doesn’t mean harsh. Use concrete examples to make your point. Example: “I noticed a pattern over the past two weeks where tasks are being delayed. How can we better ensure we are getting things done on time?”
  3. Use structured approaches
    • Metaphors lighten the toll. Ask, “What was the weather like for your work last week?” Similarly, invite your team to address the “stinky fish” (problems that are starting to smell bad) and solve them before they rot.
    • Address the root cause. Teams often get stuck discussing the wrong problem. By trying to fix the symptoms, they create more confusion. Take the time to drill down to core issues.
  4. Promote a blameless culture
    • Replace blame with curiosity. Shift the conversation from “Who’s at fault?” to “What can we learn?” and “How can we prevent similar incidents in the future?” This mindset encourages people to raise issues early and often.
    • Lead with empathy. Seek to understand others’ perspectives. Use phrases like “Help me understand __” or “What I hear you saying is __” This promotes understanding and also de-escalates emotions.
  5. Transform cultural norms
    • Create clear expectations. Establish guidelines for raising concerns: when and how to speak up, emphasizing that avoidance is more harmful than engagement. For example, one team I know implemented a 24-hour rule so that if someone on the team experiences interpersonal tension, they have 24 hours to address it with the individual.
    • Celebrate courage. Recognize those who initiate difficult conversations constructively. Share success stories in team meetings or newsletters. For example, celebrate the courageous conversation of the month, highlighting how speaking up benefits everyone.

As Brené Brown says, “Hard conversations are never easy—it’s a commitment and a practice to choose courage over comfort.”

Dan

Adapted from: Razzetti, G. (2025, Jan. 26). Why we avoid difficult conversations—and how to change that. Demystify Culture. https://think.fearlessculture.design/p/how-to-stop-avoiding-difficult-conversations