How to Communicate Difficult Messages

Have you ever felt your heart race while facing the challenge of delivering bad news to a customer in a live chat? If so, you are in good company. This is one of the most daunting aspects of customer support and can often lead to heightened emotions and escalated situations. But what if I told you there’s a proven, structured approach that can empower you to handle these tricky exchanges with confidence? I’ve created a four-step framework called CARE, specifically designed to help you convey bad news effectively: **C - Clearly Explain the Issue**   **A - Acknowledge the Impact**   **R - Respectfully Listen**   **E - Explain the Next Steps** This method isn’t just about softening the blow; it’s about upholding professionalism, demonstrating empathy, and steering the conversation toward a constructive conclusion. When it comes to explaining the issue, be concise and assertive. Cut out any fluff or unnecessary apologies. Speak with clarity and purpose, while ensuring your tone remains respectful. By acknowledging the impact of the news, you show genuine empathy, which greatly enhances the likelihood of the customer accepting your message. A simple phrase like, “I understand this isn’t the outcome you were hoping for,” can make a world of difference. Engaging in respectful listening—yes, even in written form—builds trust and alleviates frustration. It’s about grasping the intent behind the customer's words and recognizing their concerns. Finally, by explaining the next steps, you guide the conversation toward resolution. Provide alternatives, share useful links, or offer tips that can still add value for the customer. Countless teams have transformed their customer interactions by adopting this approach. One of my clients reported a significant reduction in escalated chats and a remarkable improvement in customer satisfaction scores. Imagine navigating even the toughest conversations with composure, equipped with a reliable technique that leads you forward. It’s not merely about delivering bad news; it’s about doing so in a way that respects both the customer’s feelings and your company’s standards. Delivering bad news is undeniably one of the toughest challenges in live chat. Are you ready to discover more powerful techniques like this to elevate your live chat support skills?

🔥 How to Handle a Difficult Conversation as a Leader 🔥 Difficult conversations are one of the toughest parts of leadership but also one of the most important. The key isn’t just delivering bad news and walking away, but staying engaged, even when it’s uncomfortable. I recently wrote about this in my Harvard Business Review article, “How to Talk to an Employee Who Isn’t Meeting Expectations,” where I shared strategies to turn these moments into opportunities for growth. As an executive coach and advisor, I work with leaders navigating these conversations every day. Here are four things to keep in mind to make the discussion more productive: 👉 Set the stage for collaboration Approach it as a partnership. Start with alignment: “My goal is to provide clear feedback and ensure we are collectively working toward your development.” 👉 Encourage self-reflection Invite them to assess their own performance. “Looking back, what’s working well? What would you improve?” This helps shift the mindset from blame to growth. 👉 Deliver feedback with clarity Be specific and avoid ambiguity. Focus on observed behaviors, not assumptions. Instead of “You’re not engaged,” say: “I’ve noticed you’re quieter in meetings, and team members think you are disconnected.” 👉 Reset expectations and look ahead Frame the conversation around the future. Instead of focusing on what went wrong, ask: “How would you handle this situation differently next time?” Difficult conversations don’t have to feel like confrontations. When approached with preparation, empathy, and a focus on growth, they can be transformative strengthening both performance and trust. Please share in the comments, what strategies have helped you navigate tough conversations? ⬇️ 📖 Read my full HBR article here: https://lnkd.in/eMuV9eWp #Leadership #Coaching #Feedback #FutureOfWork #GrowthMindset #Careers #Thinkers50 #Coach #Professor #Advisor #MG100 #BestAdvice #JennyFernandez

Please, for the love of your reputation, stop saying this at the beginning of difficult conversations. I mean it! Promise me you will never again say: “Can I give you some feedback?” or any of it's cousins, like, "Can I offer some coaching?" @DavidRock, the father of #Neuroleadership, likens that phrase to ‘hearing footsteps behind you in a dark alley.’ 😱 When you say it, you instantly put their brain into a ‘threat’ state. (If you enjoy putting people into a threat state, you have a bigger problem!) Depending on their personality, their next move will be fight, flee, or freeze. You’ve doomed the conversation before they spoke a word.💣 You've backed them into a corner. You’ve given them two choices: 1. Say, “No, thank you.” (With a dose of passive-aggressive snarky energy), or 2. Sit silently as you describe something you disapprove of...😡 With one sentence, you've just told your conversation partner that you are not a safe person to talk with. If you’ve been taught to start feedback conversations this way, I’m not surprised. Much of what we were taught pre-dates the integration of brain science and influence. I ONLY teach techniques that help you do two things every time: • Feel calm & curious before any ‘difficult’ conversation • Speak and respond in a way that maintains or improves your relationship and reputation Here is one brain-safe way to start a corrective feedback conversation with ANYONE: “Hi, I’d love to connect about that meeting this morning with the development team. We probably need just 15 mins or so. What time works best for you today?” Then you prepare. Between now and that conversation, you fill out a short 5-step template to help you organize your thoughts, so you can say all you need to say in less than 45 seconds, then turn it over to them. Writing down your thoughts ahead of time helps you avoid trigger words and closed-ended questions… or anything else that could sabotage the conversation and sour your relationships. The best teams are led by leaders who create #PsychologicalSafety. What’s your biggest fear or pet peeve about giving or receiving corrective feedback? ----------------------------------------------------------------------------------------------------------------- I'm a certified Executive Coach who transforms brilliant but overwhelmed ‘Worker-Bees’ into influential ‘Queen-Bees’ who earn more, work less, and finally enjoy success and ease in all parts of their lives. Find my featured section for: • A free Influence the Boss eBook • Client success stories • Link to a free masterclass for female leaders who want to work & stress less and more 💰 If you’re tired of doing your best, but having it backfire on you, and are ready to unf*ck your career now, book a call to see if my program can help you: https://calendly(dot)com/denisegreen/book

Starting a difficult conversation at work can feel really intimidating and overwhelming. You know it’s necessary, but where do you even begin without causing more issues? 🤔 Thing is, having these conversations is crucial for a healthy workplace. As much as you may want to avoid them, we need them. The good news is, there are ways we can navigate these conversations in a healthy and productive way. So, here are tips to initiate challenging convos: 🎯 Prepare yourself. Before diving in, take some deep breaths to calm your nervous system and a moment to reflect on your goals for the conversation. What is your intention and the ideal outcome? What other ways could this turn out? How can you cope with an outcome that is different from your vision? Going in with a level of clarity in your own mind can lead to a more focused and effective discussion. 🕒 Choose the right time and place. Timing is everything. Find a private, neutral setting where both parties feel comfortable and are less likely to be interrupted. 🗣️ Be clear and direct. Clearly and calmly state the issue but do so with respect and understanding. This can help lower guards and reduce misunderstandings. 🤝 Focus on solutions. Approach the conversation with a solution-oriented mindset instead of just showing up with more problems to call out. I always like to have some ideas of my own and make sure I open the door to hear theirs as well. When you can listen actively to their side, rather than pointing fingers, it encourages a more productive and less defensive dialogue. 🌱 Follow up. After the conversation, check in with the other person. This can help show you’re committed to ongoing support and resolving the issue together. Difficult conversations are part of growth personally and professionally and help us to create a psychologically safe workplace. By approaching them thoughtfully, we can turn challenges into opportunities for understanding and collaboration. 👇 Have you had to start a tough conversation at work? How did you approach it? Share your experiences and tips! Creating norms around difficult conversations tends to come up in our Psychological Safety training programs. DM me to learn more! 🖤 Create a great day! #MakoMindfulness #MindfulnessTraining #StressManagement #PsychologicalSafety #TrainingAndDevelopment #StaffDevelopment

I have a passionate hate for the word “but.” It slips into our conversations with the best intentions and ruins them. Especially when we’re trying to give feedback. I hear it constantly when I coach my Stanford University Graduate School of Business students through role plays of tough conversations: “You’re a valuable member of our team, but...” “You did a great job on that presentation, but…” The second that word enters the conversation, the first half of the sentence vanishes. It’s no longer praise—it’s a prelude to disappointment. And it’s hard to believe that it was true in the first place. The same goes for our personal moments. “I love you, but you need to empty the dishwasher.” Ok, do you really love me? Or is your love conditional on clean dishes? We think “but” softens the blow when something difficult needs to be said. It doesn’t. Instead of sparing someone’s feelings, it confuses the message and muddies our intent. That’s why I tried an exercise for the first time this year with my students—BUT BUSTERS. Here’s how it works: Roleplay a tough feedback conversation. Try to do it without saying the word “but.” Tally the number of times you still say it. The direction is to say what you mean. Then stop. Use a period or use “and” if the ideas truly connect. For example: ✅ “You are an incredibly valuable member of our team..” ✅ “Lately you haven’t been meeting your deadlines. I’d like to understand if there are any obstacles you’re facing to getting work done on time.” I ask my students to track how it feels to not say “but.” Is it hard to stop yourself? Does your demeanor feel different when you don’t use it? They say it changes everything about their conversations. They feel more clear, respectful, and effective. It helps them start from a place of belief in what’s possible. All of that impact from the removal of one simple word. We don’t need to bury constructive feedback inside compliments, and we don’t need to cushion clarity with contradiction. It takes practice, and I still work at it, too. Try it for a day or two, and let me know how it feels. — Like this post? Follow me for more insights on leadership, team building, and the future of work. Subscribe to my LinkedIn newsletter Leadership is Everywhere: https://lnkd.in/g_VETsRY

How do you deliver bad news effectively? It’s never easy, but at times it’s paramount to take control of your time and your schedule. Over the years, I’ve navigated partnerships that didn’t work out—whether due to misaligned schedules or a vision that no longer matched. Here are three principles I’ve found invaluable for making those tough conversations more constructive: 👉 Make it quick  Don’t draw it out. If someone knows a difficult conversation is coming, their mind is already racing. Deliver the news promptly to ease anxiety and minimize discomfort. 👉Be compassionate  Put yourself in their shoes. Be honest, but kind. It’s not about sugarcoating—it’s about finding the cleanest, clearest, and most empathetic way to communicate. 👉Don’t over-apologize  Apologies can confuse the message or make it seem like you’re unsure of your decision. Be calm, clear, and confident. These moments are challenging, but they’re also an opportunity to show empathy, leadership, and integrity. How do you approach delivering difficult messages?

I thought I had nailed the audit— until the room went cold. You could feel the tension. Ever been there? It was one of my first big audits, and I was ready. I had all the facts, findings, and recommendations. But as I delivered the report, I watched the room shift— arms crossed, faces tightened. My confidence melted. What went wrong? I had the facts, but not the TACT. Delivering tough news is about more than just the data. It’s about how you communicate it. Since then, I’ve followed this simple framework to deliver difficult issues without damaging relationships: (too much 😀) T - Transparency Be upfront, but clear. Don’t sugarcoat the facts, but don’t overwhelm them either. A - Active Listening Give people space to respond. Listen, and show empathy— it can turn defensiveness into openness. C - Constructive Approach Always offer solutions. Frame the issues as opportunities for improvement, so it’s not just about what went wrong. T - Thoughtfulness Consider the timing and tone. Present the issues in a way that shows respect for their position and challenges. The right delivery can shift the entire conversation. 👉 How do you handle delivering tough messages?

I can still feel that dread in my body. The kind I used to get before having any kind of “difficult” conversation at work. Giving less than stellar feedback. Delivering bad news. Asking for help with my workload. Telling someone I couldn’t take another project on. I still feel it sometimes - because I’m human. But what if I told you it was possible for those kinds of conversations to feel easier? I’ve been talking about how to make that happen this week. Yesterday, we talked mindset when it comes to difficult conversations. Today, it’s strategy time. Combine these with the mindset shifts covered yesterday: 💡Plan Without Overplanning. Have a plan but do not overly prepare or overly script because that can work against you. (1) If things go off script or something you didn’t plan for happens, you may panic or get overwhelmed! It’s hard to show up how you want when feeling strong emotions. (2) If you’re fixated on thinking about your script and what you’re going to say next, you’re not going to hear what the other person is saying. Outline the points you want to make, but leave it at that. 💡Engage in Active Listening. Listen to understand, not to respond. Ask lots of questions. Don’t interrupt. Don’t judge or jump to conclusions. Channel your empathy to understand how the other person might be thinking and feeling. The better you are at active listening, the better you are going to show up, and the more likely you are to get a better response from your counterpart in the conversation. 💡Plan for Next Steps. Think about what you want to happen after the conversation--keeping in mind that you may need to adjust in real time. What makes sense to move the conversation forward? What are the likely next steps? Be prepared to propose the next steps or a solution where possible, or ask for input on a solution and brainstorm together. What was the last difficult conversation you had (or maybe avoided having) in the workplace? Any other strategies you’d add to the list? What mindset shift do you want to make for your next difficult conversation?