6 Common Mistakes Leaders Make During Difficult Conversations


6 Common mistakes leaders make during difficult conversations and what they should do instead

As a leader, engaging in difficult conversations is an inevitable part of your role. These conversations, whether they involve addressing performance issues, resolving conflicts, or discussing sensitive topics, can be challenging and uncomfortable. 

However, handling them effectively is crucial for maintaining a healthy and productive work environment. 

In this guide, we'll explore six common mistakes leaders make during difficult conversations and provide actionable advice on what to do instead.

Mistake #1. Avoiding the conversation altogether

Mistake: One of the biggest mistakes leaders make is hoping that the issue will resolve itself or waiting too long to address it. This approach rarely works and often allows the problem to escalate. 

Imagine you have an employee who consistently misses deadlines and submits work with numerous errors. If you avoid addressing this issue, the employee may believe their performance is acceptable, and the quality of their work will likely continue to decline. 

Or, when conflicts arise between team members, avoiding the conversation can allow tensions to escalate.

Instead: It's essential to act quickly. Part of this involves recognising signs that something needs addressing. For example, if you notice that an employee who is usually punctual starts arriving late to work consistently, recognize this as a sign that something may be amiss.

Or, if you need to address a performance issue with an employee, gather specific examples of their work that illustrate the problem. Schedule the meeting within the next few days, rather than waiting for weeks to have a "perfect" case built up.


  • Schedule a meeting with the individual as soon as you notice the issue.
  • Prepare for the conversation by gathering facts and examples.

Mistake #2. Being too indirect or dancing around the issue

Mistake: Using generalizations or avoiding directly addressing the problem can lead to confusion and misunderstandings. Vague feedback leaves the individual unsure of what needs to be improved.

Instead: Be specific, provide concrete examples, and clearly state the issue at hand. Apply the Radical Candor model, which emphasizes the importance of direct feedback while also showing personal care.

Direct feedback is specific, clear, and addresses the issue at hand without sugarcoating or beating around the bush. For example, instead of saying, "Your presentation could use some improvement," direct feedback would sound like, "Your presentation lacked clear objectives and had several grammatical errors." 

On the other hand, indirect feedback is vague, nonspecific, and often leaves the recipient confused about what needs to be improved, such as "your presentation wasn't quite what I was hoping for." 

But it's also crucial to combine directness with personal care, demonstrating that you have the individual's best interests in mind. Personal care involves showing genuine concern for the person, their well-being, and their growth. It's about delivering feedback in a way that shows you value them as a person and believe in their ability to improve. For example, in the above example you could say, "I know you're capable of delivering high-quality work, and I want to support you in reaching your full potential.”

Tips and examples:

  • Avoid using vague phrases like "You need to do better" or "Your work needs improvement." Instead, provide clear and actionable feedback.
  • Use specific examples to illustrate the problem, such as, "I noticed that the last three reports contained several errors, including X, Y, and Z"  
  • Show personal care by acknowledging the individual's strengths and contributions, while still addressing the issue directly: "I know you're capable of producing high-quality work, so let's discuss how we can ensure accuracy moving forward."

Mistake #3. Focusing on the person rather than the behavior

Mistake: Attacking an individual's character or making the conversation personal creates defensiveness and damages relationships. It shifts the focus away from the issue at hand and onto the individual.

Instead: Focus on the specific behavior or issue that needs to be addressed. Separate the person from the problem and address the actions or behaviors that need to change.

This means recognizing that an individual's actions or behaviors do not define their entire identity or worth. It involves acknowledging that everyone makes mistakes or has areas for improvement while still valuing them as a person and a team member.

Addressing specific behaviors requires careful observation. It means paying attention to patterns and gathering concrete examples to illustrate the issue, rather than relying on vague impressions or assumptions.

Tips and examples:

  • Use "I" statements to express your concerns, such as, "I've noticed that you've been arriving 15-20 minutes late to work several times this week."
  • Avoid using "you" statements that can feel accusatory, like "You're always late."
  • Keep the conversation focused on the specific behavior and its impact on the team or work environment.
  • Work together to identify the root cause of the behavior and find solutions.

Mistake #4. Not aligning on the common facts first

Mistake: Diving straight into disagreements or conflicting viewpoints can lead to unproductive arguments. It's easy to get sidetracked by differing opinions and lose sight of the overall goal.

Instead: Start by identifying and acknowledging areas of agreement or shared goals. Find common ground and use it as a foundation for the conversation.

Before the conversation, take time to consider the overarching goals that both you and the other person share. These might include a desire for a successful project outcome, a commitment to the company's values, or a mutual interest in maintaining a positive team dynamic. Recognizing these shared objectives helps you approach the conversation as a collaborative effort rather than an adversarial one.

Or, you can acknowledge common concerns Often, difficult conversations arise because both parties have valid concerns or challenges. 

As the conversation progresses, use the areas of agreement as a foundation for problem-solving and finding mutually beneficial solutions. By continuously referring back to your shared goals and concerns, you maintain a focus on collaboration. For example, you might say something like "since we agree that improving team communication is a priority, let's brainstorm some strategies we can implement to ensure this…” 

Tips and examples:

  • Begin the conversation by stating the facts that both parties can agree on, such as, "We both want what's best for the team and the company."
  • Review any relevant data, timelines, or deliverables that have been previously agreed upon.
  • Acknowledge the areas where you agree before addressing the disagreements.
  • Use phrases like, "I think we can both agree that..." or "Let's start by reviewing what we know for sure."

Mistake #5. Not listening or having a genuine desire to understand the other side

Mistake: Dominating the conversation is a sure way to shut down communication and erode trust. It sends the message that their viewpoint isn't valued – and you miss an important chance to understand what is truly at the root of the behaviour at issue.

Instead: Show genuine empathy by inviting and acknowledging the other person's feelings and viewpoints, even if you disagree.

The key is to separate empathy from agreement. Showing genuine empathy does not require you to agree with the other person's viewpoint. In fact, it's possible to empathize with someone's experience while still holding a different opinion or perspective. The key is to separate your understanding of their feelings from your evaluation of their thoughts or actions. An example would be, "I understand that you feel the project timeline is unrealistic given the current constraints. While I don't entirely agree with that assessment, I do recognize that you're feeling stressed and concerned about meeting the deadlines."

Tips and examples:

  • Give the other person your full attention and avoid interrupting.
  • Ask open-ended questions to gain a deeper understanding of their perspective, such as, "Can you tell me more about your concerns?"
  • Paraphrase what you've heard to ensure you've understood correctly, like, "So, what I'm hearing is that you feel overwhelmed with the current workload. Is that right?"
  • Validate their feelings with statements like, "I understand this is a challenging situation for you."

Mistake #6. Not focusing on a solution or plan of action

Mistake: Ending the conversation without a clear resolution or next steps leaves both parties feeling unsatisfied and can lead to recurring issues. It's not enough to simply discuss the problem; you must work together to find a solution.

Instead: Collaborate on finding a solution and agree on a plan of action with specific goals and follow-up. 

Here, it is ideal to involve the other person in the problem-solving process. This requires encouraging them to share their ideas, perspectives, and suggestions for improvement. This requires a willingness to let go of control and embrace a more facilitative leadership style – but the benefit is that you create a sense of ownership and empower the individual to take responsibility for the solution.

Tips and examples:

  • Ask the other person for their ideas on resolving the issue, such as, "What do you think we can do to address this problem?"
  • Brainstorm potential solutions together and evaluate their feasibility, and agree on a specific plan of action with clear responsibilities and timelines.
  • Set a date for a follow-up meeting to review progress and make adjustments as needed.
  • End the conversation with a summary of the agreed-upon actions and express your confidence in their ability to implement the changes.

Remember, the goal is not to "win" the conversation but to foster understanding, maintain strong relationships, and find mutually beneficial solutions. With practice and a commitment to continuous improvement, you'll become a master of navigating challenging conversations in the workplace.

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