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Difficult Conversations with Great Results

    Who enjoys having those challenging employee conversations? You know, the ones where you need to address performance issues, behaviors, or sensitive matters like body odor or inappropriate dress. These discussions often linger on the to-do list, as we secretly hope that the problem will magically resolve itself without our intervention. Unfortunately, there’s no company genie to grant such wishes. But here’s the good news: once you confront these issues head-on, you’ll feel a tremendous sense of relief. Better yet, it’s entirely possible to handle difficult conversations with respect and make a lasting impact.

    Sharing My Own Experience

    I can definitely relate to mishandling difficult conversations in the past. I’ve had people become angry, shed tears, storm out of my office, slam the door, or simply stare at me blankly without uttering a word. However, I’ve also had some truly positive experiences where individuals appreciated our discussion, thanked me, and moved forward. 

    Understanding the Importance of Difficult Conversations

    During my career, I was fortunate to receive professional coaching, which proved to be a humbling and enlightening experience. Allow me to share a lesson that has stuck with me ever since.

    I was observed by my coach while I engaged in a conversation with one of my employees. We discussed why she had repeatedly failed to meet her commitments. She presented a few excuses, and I let her off the hook. My coach observed that this wasn’t the first time I had done so. I admitted my oversight and offered a few excuses of my own. That’s when my coach asked a profound question: “So, you let her off the hook again? How does that help your employee move forward?”

    This question struck a chord with me, and it resonated every time I avoided a tough conversation. As a leader, my goal was to help individuals grow and reach their full potential. By evading difficult discussions, I hindered their success by failing to communicate how their actions were negatively impacting themselves and their team.

    The Value of Difficult Conversations

    While tough conversations may be challenging, they often present the best coaching opportunities. Even if an employee doesn’t respond positively to your coaching, you have given them a chance to progress. On the other hand, choosing to avoid difficult conversations sends a message that their current actions are acceptable. By tolerating the behavior, you essentially endorse it.

    Now that we understand the importance of difficult conversations and the impact they can have, let’s explore some practical tips and strategies to navigate these discussions effectively. By following these guidelines, you can ensure your conversations are productive, respectful, and lead to positive outcomes for both you and your employees.

    Tips for Navigating Difficult Conversations

    Before you tackle any difficult conversation make sure to put on a pair of clear lenses so that you address the facts, removing any assumptions, judgments and emotion.

    Think Before You Act

    When we leave things unresolved for too long, it’s inevitable that something will eventually trigger a quick reaction. For instance, imagine you’ve been tolerating an employee’s sloppy job filing for a while, and then one day you find something misfiled and lose your temper. Reacting while angry rarely leads to productive conversations. Difficult conversations should generally be free from excessive emotions, except when empathy is necessary.

    Clarify Your Purpose

    Before diving into a difficult conversation, ask yourself what you hope to achieve through this conversation. Are you seeking a behavior change, addressing a performance issue, or resolving a conflict? Having a clear objective in mind will guide your approach and keep the conversation focused.

    Plan Your Talking Points

    Gather relevant facts and details before having the conversation so that you have an understanding of the situation, including any specific incidents, observations, or feedback received. Use the information to plan out your talking points in advance. Jot down the key messages you want to convey and the specific behaviors or situations you need to address.

    Focus on Behavior and Impact

    Avoid making the discussion personal. Instead, direct your attention towards the specific behavior or requirement that needs addressing to ensure that the conversation remains focused on the issue and not on the individual’s character. Additionally, highlight the impact of the behavior or requirement in question. Explain how it affects the team, the organization, or even the individual themselves. By emphasizing the consequences and outcomes, you provide context to help the person understand the importance of the conversation and the need for change.


    Original: I need to talk to you about that strong perfume you always wear. You are making people sick. Don’t you know this is a scent-free office?

    Improved: I’ve noticed that you are wearing something scented. We have a scent-free office to provide a comfortable environment for all our employees. Here is where you can find the policy on our website.

    The improved example avoids attacking the person and conveys the behavior (wearing a scent), specifies the requirement (scent-free environment), and highlights the impact (comfortable environment) without directly targeting the individual.

    Anticipate Reactions

    Consider how the other person might react during the conversation. Put yourself in their shoes and think about their potential concerns, emotions, or points of view. While it is not possible to anticipate every scenario, nor do you want to spend time stressing over every imaginable outcome, this can help you mentally prepare for different scenarios and approach the discussion with empathy and understanding.

    Prioritize Privacy and Patience

    Publicly shaming employees is never the right approach. Always ensure that tough conversations take place in a private setting. Dedicate sufficient time for discussion, and make sure to silence your phone and notifications to give the employee your undivided attention. Practice active listening by being fully present in the conversation, maintaining eye contact, and giving the other person your undivided attention. Avoid interrupting and genuinely try to understand their perspective. Reflect on what they say and ask clarifying questions to ensure you grasp their viewpoint accurately.

    Manage Your Emotions

    Difficult conversations can sometimes stir up emotions for both parties involved. Recognize and manage your own emotions before the conversation to ensure you remain calm and composed. Take a few deep breaths, remind yourself of your purpose, and focus on maintaining a respectful tone. Remember, your goal is to create a safe and constructive space for open dialogue.

    Rip Off the Band Aide

    Once you’ve taken a brief amount of time, (not two weeks), to think it through and plan your approach, don’t delay any further. Avoiding the conversation only worsens the situation. Remember, your employees notice when issues go unaddressed, and it reflects on your credibility as a manager. Instead of procrastinating, bravely rip off the band-aid. The discomfort will be short-lived, and the anticipation is often worse than the actual conversation itself.

    Express Genuine Intent

    Make sure the employee understands that your intention is to genuinely assist them. The purpose of the conversation is for them to understand your expectations, recognize the impact, and be clear on what needs to change. Your goal is to help them adjust behavior positively and to reach their full potential by having this conversation.


    Let the employee talk! Allow them a few minutes to digest what you’ve said, and resist the urge to fill the silence. Remember the acronym WAIT – Why am I Talking? Employees need an opportunity to provide input; otherwise, it is difficult to reach agreement and move forward. It’s alright if they become angry or upset. Listen to their perspective and engage in a conversation because it’s better than having them walk away silently without understanding how they feel.

    Check for Understanding and Action

    Avoid rushing to conclude the conversation as quickly as possible. It’s tempting when you detect a little nod to take it for agreement, breathe a sigh of relief, and show the employee the door.  Don’t pat yourself on the back yet. Are you confident the employee fully understood and agreed to change or modify a behavior? 

    While having a constructive discussion and an engaged and responsive employee is ideal, it’s not always the case. Sometimes, you will need to probe further and check for clarity.  Instead of using condescending language like “Understood?” or “Is that clear?”, use open-ended questions based on the person and the nature of the discussion:

    Document your Discussion

    Always jot down the key points of your conversation. Seriously, take notes! Not only does it help you remember what was said, but it also lets you keep track of any commitments made and follow-ups needed. 

    You can use these notes for multiple purposes. First, to review and assess how effective your talk was and spot areas for improvement. Second, to document any promises made by the employee and schedule those necessary follow-ups. If you ever find yourself in need of another chat down the road, you’ll have your trusty notes to refer back to.

    Follow-Up and Support

    After a difficult conversation, it’s essential to provide follow-up and support to ensure the conversation’s impact extends beyond the immediate discussion. Here are some steps you can take to offer ongoing assistance and maintain a supportive environment:

    a) Offer Resources: Depending on the nature of the conversation, provide resources that can help the individual improve or address the issue at hand. This may include training materials, reference documents, or links to relevant articles or online resources. Sharing these resources demonstrates your commitment to their growth and gives them the tools they need to make positive changes.

    b) Schedule Check-Ins: Schedule follow-up meetings or check-ins to assess progress and provide further guidance. These follow-up sessions allow you to monitor their development, answer any questions that may arise, and offer support or adjustments as necessary. Regular check-ins show that you genuinely care about their progress and provide an opportunity to address any ongoing concerns.

    c) Encourage Open Communication: Create an environment where open communication is encouraged. Let the individual know that they can approach you at any time if they have questions, need clarification, or require additional support. Being accessible and approachable fosters trust and ensures they feel supported throughout their journey.

    d) Recognize Efforts and Progress: Acknowledge and celebrate their efforts and progress along the way. Positive reinforcement is a powerful motivator and encourages continued growth and improvement. Take the time to provide constructive feedback, recognize milestones, and highlight their achievements. This reinforces the value of the difficult conversation and reinforces their commitment to change.

    Remember, the journey doesn’t end with the difficult conversation itself. Following up and providing ongoing support demonstrates your dedication to their success and reinforces the importance of the conversation’s outcomes. 


    Difficult conversations present an opportunity for growth, understanding, and positive change. By preparing yourself thoroughly, you set the foundation for a constructive dialogue that can lead to improved relationships, increased productivity, and a healthier work environment.

    So take a deep breath, trust in your preparation, and approach the conversation with empathy and a genuine desire to find a resolution. You’ve got this!

    Ponder Points

    Want to level up your game and supercharge your conversations? Use the following ponder points for journal prompts. Writing down your thoughts, experiences, and emotions will give you incredible clarity and understanding of your actions. Plus, it’s a safe space to explore challenges and track patterns, setting you on the path to success.

    • How well do I handle difficult conversations in the workplace? Do I tend to avoid them or approach them proactively?
    • Am I mindful of the language I use during difficult conversations? Do I focus on behavior and impact rather than making it personal?
    • How effectively do I express genuine intent during difficult conversations? Do I make it clear that my goal is to help the other person reach their full potential?
    •  Am I patient and allow the other person to express themselves without interrupting or filling the silence?
    • How well do I check for understanding and action at the end of difficult conversations? Do I ensure that the other person fully comprehends and agrees to the necessary changes?

    Make a commitment to have impactful conversations and GROW!

    Do you have tips for difficult conversations or comments about this article? Please share in the comments!

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