Why is it so difficult for human beings to speak with candor about challenging issues? In our daily interactions, we often find ourselves navigating a complex web of emotions, social norms and personal fears, making it incredibly challenging to express ourselves openly, especially when addressing difficult issues and topics. Understanding these barriers is crucial in fostering more genuine and transparent communication, paving the way for deeper connections and more effective problem-solving.

So, what are the underlying issues associated with having courageous conversations, and what approaches should be considered by anyone who needs to engage in difficult dialogue in an increasingly divisive and complex corporate world?

Why We Avoid Courageous Conversations

Avoiding difficult conversations is often motivated by various elements of fear. Many people have a fear of conflict, which can prompt the avoidance of difficult conversations. All of us have experienced emotionally charged discussions at one time or another, leading us to choose to sidestep or ignore any difficult conversation that might result in strong emotional reactions.

We also often fear rejection. As humans, we are hardwired for social belonging and sensitive to any cues that might indicate we are no longer welcome in a group. If rocking the boat means that you get labeled “the difficult one,” we will likely choose not to engage in difficult conversations — especially if it means social rejection will follow.

Finally, fear of jeopardizing a relationship can prevent necessary conversations from taking place. Some people avoid challenging conversations with the justification that it’s better to maintain the status quo. If we raise an issue, it may damage the relationship and create awkward, ongoing tension.

Unfortunately, each of these fears ignores the reality that when known issues are not addressed, there’s already a growing crack in the foundation of the relationship.

Predictable Behaviors in Courageous Conversations

When engaging in conversations where elements of fear or risk are present, people frequently engage in two typical behavior patterns: winning and minimizing.

Winning

Winning is defined as any attempt to dominate, overpower or control the conversation by making sure you end up being “right.” It may present as pushing your agenda at the expense of the other person’s or as interrupting, intimidating, shutting down discussion or simply taking up more than your fair share of the talk time. This may feel like a victory in the moment (it’s called “winning,” after all). However, the impact is that it ultimately creates more harm than good. In other words, you may have won the battle but failed to recognize that war was never the goal.

Minimizing

Minimizing is downplaying your own perspective to avoid conflict or discomfort. It can look like speaking softly, apologizing unnecessarily, holding back concerns or agreeing too quickly at the cost of your own views. This often leads to feeling unheard or undervalued.

In a courageous conversation, minimizing prioritizes short-term comfort over long-term trust and growth. Avoiding discomfort by being overly cautious or failing to address significant issues may bring temporary relief, but it also prevents necessary progress. Over time, this too damages relationships, as others may feel they can’t trust you to engage in honest, meaningful dialogue.

Finding the Balance

Both behavior patterns cater to your own comfort at the expense of addressing an issue appropriately. To be effective with courageous conversations, you need to get comfortable with being uncomfortable.

The Business Case for Courageous Conversations

In July 2024, cybersecurity firm CrowdStrike pushed an untested software update, which crashed millions of Windows systems worldwide. This cataclysmic outage, with its sweeping “blue screen of death,” cost Fortune 500 businesses $5.4 billion. The airline industry was hit especially hard by this crash. With systems down for days, it absolutely paralyzed global travel.

For travelers at that time, a routine flight home became a multi-day ordeal as airlines were unable to provide timely information to passengers, increasing the frustration levels of customers and airline workers alike. Rental cars and hotels became scarce, making it even more challenging for customers who were stuck navigating the situation.

One potential source of this disaster stemmed from conversations that were avoided at various levels: engineers who didn’t voice testing concerns, executives who sidestepped deployment-risk discussions and team members who dismissed concerns about unproven processes and artificial intelligence (AI) designed to catch flaws in their system updates.

This incident powerfully demonstrates how avoiding difficult conversations can turn routine problems into significant failures with far-reaching consequences.

Reasons Why This is Relevant

The need for leaders, teams and employees at all levels to increase their communication effectiveness is certainly on the rise. Demand for improved performance and effective leadership — along with accelerating change in the workplace — requires that we must recalibrate communication practices and shorten the timeline for engaging in various types of dialogue.

The increasingly divisive nature of our society is showing up more in the workplace, and ignoring the divide is no longer an option. To be on the cutting edge, we must have open and honest conversations more frequently. When our competition’s team members can be candid with each other about what’s not working, they’re gaining an advantage. We simply can’t afford to waste time.

Fostering the Conditions for Courageous Conversations

Courageous Conversations are unlikely to spring up spontaneously; the need for them is more likely to grow over time. Therefore, creating the conditions to stay out of winning or minimizing behaviors and finding balance in dialogue requires psychological safety.

Dr. Amy Edmondson defines psychological safety as a shared belief among team members that the group is safe for interpersonal risk-taking, meaning individuals feel they can bring up ideas, questions, concerns or mistakes without fear of negative consequences. Dr. Edmondson’s research has found that when organizations engage in courageous conversations, it improves information and knowledge sharing and other performance metrics.

Fostering the Conditions for Courageous Conversations

Courageous Conversations are unlikely to spring up spontaneously; the need for them is more likely to grow over time. Therefore, creating the conditions to stay out of winning or minimizing behaviors and finding balance in dialogue requires psychological safety.

Dr. Amy Edmondson defines psychological safety as a shared belief among team members that the group is safe for interpersonal risk-taking, meaning individuals feel they can bring up ideas, questions, concerns or mistakes without fear of negative consequences. Dr. Edmondson’s research has found that when organizations engage in courageous conversations, it improves information and knowledge sharing and other performance metrics.

The Courageous Conversations Framework

The framework below is based on decades of real-world experience working with leaders and individual contributors across the globe and informed by the principles of action science pioneered by leading researchers. This approach provides a practical guide to navigating difficult conversations.

Preparation

In the most effective courageous conversations, preparation begins well before either person starts to speak. Begin by elevating your self-awareness and paying attention to your own raw emotions about the situation. Ask yourself what the other person is experiencing and take a moment to imagine yourself in the other person’s situation. This is not about making assumptions that you later project, it’s about expanding your empathy and being open to possibilities from another perspective.

State Your Intention

Share the intent of the conversation by clarifying desired outcomes. What do you hope will be different because of this conversation? Is that a realistic expectation? Many people find it helpful to craft a written statement of intent. This does not need to be formal; a simple sticky note or a sentence in your notes app will get the job done. The goal is to challenge yourself to be honest about your true intentions and prepare to keep the conversation focused. Use language that is neutral, non-blaming, clear and kind. Focus on specific observations of behavior or instances and stay away from generalized attacks on a person’s character.

Listen

Remember that you are not delivering a speech. This is a two-way dialogue. Assume positive intent from the other person’s behaviors and words. Ask open-ended questions that expand the dialogue and stay curious from a place of non-judgement. Throughout the conversation, listen to your words. Are you minimizing? Are you attempting to win? Watch your tone and your body language, and if you get off track, pause and redirect back to your intention for the conversation.

Reflect Together

The most effective courageous conversations anticipate the follow-up before the conversation closes. Before you part ways, review and reflect on what has been discussed, explored and discovered. Confirm understanding and create shared meaning around what’s been discussed. Most difficult discussions don’t begin and end with a one-time conversation. To accomplish your goals, expect that you may need to engage in a series of conversations.

Set Agreements

Clarify what action steps need to be taken or what processes need to be different in the future. What needs to be done to demonstrate a commitment to action? Both parties should summarize what they are going to do because of the conversation, and by when.

Conclusion

While assuaging our discomfort by avoiding challenging conversations may momentarily feel more pleasant, there is a potential explosion brewing. Complex issues do not have simple solutions. They require greater transparency, honest feedback and a willingness to unlock a diversity of perspectives.

By embracing and committing to more frequent and effective courageous conversations, organizations will bridge divides, enhance communication, create stronger cultures of accountability, reduce miscommunication and prevent conflict escalation — all of which ultimately leads to stronger relationships and better outcomes.