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The Art of Crucial Conversations



“A team that can’t communicate about its most pressing issues isn’t really a team at all. It’s just a group of people who can’t work with each other effectively when it counts.” – Craig Weber


Most leaders dread the moment when a serious conversation with a department, team, or employee becomes necessary. Unfortunately, issues such as failing to meet company standards, past-due projects, or poor workplace behavior must be addressed.


How do you resolve these issues? How do you ensure the conversation doesn’t cause more conflict? How do you keep everyone accountable and productive without coming across as “the bad guy?” In this article, we answer these questions and share the secret to having conversations with positive outcomes.


It Starts With Leaders

The ability to facilitate meaningful and productive conversations about serious or emotionally charged topics is an important leadership skill.


Without the proper preparation and mindset, leaders risk offending others and prolonging the very issue they’re seeking to resolve. A disorganized process could even be costing the company money! A VitalSmarts study discovered that every conversation failure cost companies an average of $7,500 over seven work days.


According to research, 70% of employees avoid difficult work conversations. However, a vital component of psychological safety in the workplace is addressing sensitive topics with compassion, patience, and courage. This skill is known as conversational capacity.


Utilizing Conversational Capacity

So what’s the right way to approach important discussions? The following process can help you hold insightful conversations with an individual or group while encouraging teamwork and progress.


1. Prepare. Preparation is imperative for crucial discussions, especially if the topic is sensitive. If a problem needs to be addressed, make sure you understand what the problem is and can convey it clearly. Do research and avoid bias. Come up with ideas and ways to discuss the subject, and think about what you want to achieve by having the conversation.


We created the following chart using insight from leadership development architect Susan Scott. This can help you take steps to get ready for a productive conversation:



2. Initiate. After preparing, initiate the discussion. Reach out to the employee or department in a friendly, professional manner. Set up a time and place to talk without distractions.


Bring up the subject calmly. Remind yourself this is about finding solutions together. This Forbes article shares more ways to initiate a crucial conversation.


3. Actively listen. Pay attention to what others say. Find out how employees feel by analyzing their words and body language. Making an effort to understand their point of view builds trust and supports a successful resolution.


Keep the group conversing in what Craig Weber, founder of The Weber Consulting Group, calls “the sweet spot.” This is an environment where courage, candor, humility, and curiosity are present equally.


“In the sweet spot, we have the ability to raise our hands and speak up, and the ability to listen and learn from others, even in circumstances that don’t make it easy,” Weber explains. For leaders, this means providing a setting where the discussion is purpose-focused, people feel safe, and sharing and learning are valued.


4. Look out for triggers. Everyone has emotional triggers that could cause them to react defensively, get angry, withdraw, or demonstrate other emotional responses. If you sense this reaction happening during the conversation, stay calm. Keep your tone neutral and offer reassurance. Sometimes, light humor diffuses the tension.


Also, recognize your own triggers. You don’t want to impair your understanding of the situation and your decisions. According to The National MCH Workforce Development Center, some common triggers people experience in the workplace include:


  • Personal issues

  • One’s status or expertise

  • The seriousness of the issue

  • Others’ behaviors

  • Culture

  • Perceived risks

  • Fatigue

  • Stress


5. Work together. After everyone has the opportunity to give their opinion on the issue, come up with an action plan together. Incorporate the agreed-upon solutions and accountability structure and ensure everyone understands their role.


The Benefits of This Approach

Growing conversational capacity across your organization can lead to many positive changes. Here are some of the key benefits:


Inspires true teamwork. Conversational capacity makes it possible for people to work together productively, even under pressure.


Improves personal and collective performance. Successful conversations lead to solid action plans and accountability across the team. Also, respectful dialogue builds trust and a willingness to improve.


Increases reporting and problem resolution. Employees who don’t fear unfair blame or retribution for mistakes are willing to come forward when a problem occurs. Quicker reporting combined with the increased ability to create solutions means resources like time, money, and talent aren’t wasted.

Establishes psychological safety. Work becomes psychologically safer when sensitive or serious subjects can be discussed without emotional backlash. Learn more about psychological safety and its workplace benefits in our previous article.


Developing Conversational Skills

Conversational capacity is a skill, not an inherent trait. Leaders and employees alike stand to benefit from learning and practicing conversational capacity.


To start, you must build self-awareness. When you experience an emotional reaction to someone’s words or actions, pause and ask yourself why. Is your reaction because of the current dialogue, or is it because of something else? When you recognize the root cause of your reaction, you can control your response in a more effective way. This makes it easier to remain professional, curious, and candid during discussions.


The next step is to adjust your mindset. Accept that you’re not always going to feel comfortable or be right. Place the goal of learning above needing to be correct.


Finally, develop specific behaviors to help you converse in the sweet spot under pressure. You can do this in multiple ways such as…

  • Roleplaying common situations.

  • Learning how to state your thoughts clearly and succinctly.

  • Asking questions that encourage others to share their opinions and thoughts, even if they are different from yours.


You can reference this model while practicing:



When companies master the art of crucial conversations, leaders and employees can experience the results of true teamwork.



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