3 Mistakes to Avoid When Having Difficult Conversations

Handling difficult conversations is an inevitable part of leadership, but how we approach them can make all the difference in fostering trust, psychological safety, and engagement within teams. Conflict, missteps, and misunderstandings are guaranteed when individuals and teams are navigating a workplace where even now organizations are fine-tuning back-in-the-office and work-from-home policies post-pandemic. Being able to adapt to evolving customer needs, competitive pressures, automation, and unexpected challenges requires an ability to have the tough conversation without torching the relationships with the people who you need onboard to get the job done.

A 2023 Gallup survey of workers revealed that “only 21% of employees strongly agree that they trust the leadership of their organization,” which is down from 23% in 2019. That number increases to 95% when leaders demonstrate a “Trifecta of Leadership” which include the ability to lead and support change; communicate clearly; and inspire confidence in the future. Inspiring greater trust starts one conversation, even with one person, at a time.

To help level up your ability to have difficult conversations and build trust while doing so, here are three mistakes leaders you’ll want to avoid.

Mistake 1: Focusing on Why instead of What

Asking “why” questions can often lead to defensiveness and conflict escalation. When we focus on “why,” we tend to jump to conclusions based on our own opinions, biases, and past experiences. In “How to Be a Better Leader Amid Volatility, Uncertainty, Complexity, and Ambiguity”, authors Fletcher, Gaines & Loney explain that “When we ask why, the brain seeks answers in existing rules and prior judgments, which dismiss or explain away the new and unexpected.” (HBR.org, September 2023). That’s not exactly going to support a mindset of innovation or mental flexibility that is needed to create solutions to new problems old playbooks can’t solve.

Instead, shift the focus to “what” happened. By asking “what” questions, we can objectively examine the facts of the situation, identify the root causes of the conflict, and strategize on how to move forward constructively. This approach encourages a more collaborative and solution-oriented dialogue.

Mistake 2: Listening to Affirm Your View

Effective communication involves not just speaking, but also active listening. When you listen with the sole intent of affirming your own viewpoint, you erode trust and hinder collaboration. I remind my clients of the work of quality process expert W. Edward Deming who found that “85% of reasons for failure are deficiencies in the systems and process, rather than the employee. The role of management is to change the process rather than badgering individuals to do better.”

Instead, approach difficult conversations with curiosity and an open mind. Actively try to understand the perspective of the other person, empathize with their feelings, and acknowledge their concerns. This empathetic listening fosters a sense of psychological safety and promotes constructive dialogue, ultimately strengthening relationships within the team. Amplify your listening through asking open-ended questions.

Mistake 3: Not Addressing in the Moment

Procrastinating or avoiding difficult conversations only exacerbates the issue. Conflict left unaddressed can fester and escalate over time, leading to increased tension and decreased productivity. It’s crucial to address difficult matters directly and promptly.

Initiate the conversation at the earliest opportunity, but it needs to be done in a respectful and considerate manner. Agree on a mutually convenient time to discuss the issue, set clear intentions for the conversation, and share your goal of understanding the situation clearly so you can learn what needs to be addressed differently moving forward. This proactive approach not only resolves conflicts efficiently but also prevents similar issues from arising in the future, fostering stronger relationships and a healthier work environment.

Having strong relationships where people feel respected, heard and trusted is something that takes time and consistency to build. They can also be broken in an reactive moment that creates harm and never be fully restored. Avoiding these common mistakes will help you adopt a proactive, empathetic approach to difficult conversations, so you can cultivate a culture of trust, collaboration, and mutual respect. Remember, effective communication is the cornerstone of successful leadership, and mastering the art of handling difficult conversations is a skill that can drive organizational growth and success.

If you’d like support with leadership within your organization or team, let’s connect to explore whether the Adaptive Advantage (™) program or Level Up Leadership executive coaching program can help!