How to Navigate Challenging Work Conversations

🔥 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

Every first time leader faces this moment: You know you need to give tough feedback. You need to call out underperformance. You need to have the conversation-the one that feels uncomfortable, personal, even risky. And yet, you hesitate. You avoid. You soften the message. Why? Because your brain is working against you. Your brain perceives conflict as a physical threat. - The amygdala-your brain’s fear center-kicks into fight-or-flight mode. - This triggers stress hormones that make your heart race, your palms sweat, and your mind scramble. - Instead of addressing the issue head-on, your brain tells you to avoid, delay, or sugarcoat.  The result? Leaders who dodge difficult conversations create bigger problems: 1. Unclear expectations → Performance suffers because employees don’t know where they stand. 2. Bottled-up frustration → Tension builds, leading to resentment and disengagement. 3. Loss of respect → Teams lose confidence in leaders who can’t address issues directly.  A great leader isn’t the one who avoids conflict-it’s the one who navigates it with confidence. How to Override Your Brain and Lead Tough Conversations Like a Pro ✅ 1. Reframe the Conversation → Instead of thinking, “This will be uncomfortable,” think: - “This is an opportunity to clarify, improve, and grow.” -Tough conversations aren’t about confrontation—they’re about alignment. ✅ 2. Master Emotional Regulation → High-stakes discussions require calm, clarity, and control. - Box breathing (4 seconds inhale, 4 seconds hold, 4 seconds exhale) slows stress responses. - Ground yourself-feet on the floor, slow your speech, control your tone. - Silence is a tool. Pause, listen, and let the other person process. ✅ 3. Lead with Clarity, Not Emotion → The goal isn’t to be harsh—it’s to be clear. - State facts, not feelings: “Your last three deadlines were missed” vs. “You’re not trying hard enough.” - Avoid the compliment sandwich. It dilutes the message—be direct but constructive. - End with action: What’s the next step? What needs to change? How will you support them? Tough conversations don’t break great teams-they build them. If you’re struggling with difficult conversations, ask yourself: - Am I avoiding this because it’s hard—or because I’m unprepared? - Am I prioritizing my own comfort over the team’s success? - What’s the bigger risk—having the conversation or letting the problem fester? What’s the toughest leadership conversation you’ve ever had? How did you handle it? Drop your insights below. 📩 If your leadership team needs to master high-stakes conversations, let’s talk. #ExecutiveCoaching #LeadershipDevelopment #DifficultConversations #HighPerformanceLeadership #EmotionalIntelligence #LeadingWithClarity

Stop fearing difficult conversations. Master them with these 21 phrases instead: I used to avoid conflict like the plague. Even with good intentions, I’d freeze up, shut down, or over-explain. That avoidance? It cost me trust. Clarity. Connection. Eventually, I learned: silence doesn’t protect relationships. Presence does. If you want to lead with courage, you have to show up—especially when it’s hard. 21 ways Emotionally Intelligent people navigate tough conversations: 1) Ground Yourself ↳ "Let me take a breath before we dive in" ↳ Regulating yourself regulates the room 2) Speak from the 'I' ↳ "I feel..." not "You always..." ↳ Language shapes energy 3) Ask, Don’t Assume ↳ "What’s most important to you here?" ↳ Curiosity over judgment 4) Honor the Human ↳ "I care about you—this matters" ↳ Connection before correction 5) Stay With Discomfort ↳ "This feels hard—and that’s okay" ↳ Growth often feels messy 6) Reflect Instead of React ↳ "Can I take a moment before I respond?" ↳ Response > Reaction 7) Use Silence Strategically ↳ Pause. Let things land. ↳ Space invites truth 8) Call Out Courage ↳ "Thanks for being honest with me" ↳ Vulnerability deserves recognition 9) Keep the Bigger Picture in View ↳ "Let’s remember why we’re here" ↳ Shared purpose realigns 10) Zoom In ↳ "What exactly are we solving?" ↳ Specifics defuse drama 11) Offer Reassurance ↳ "We’ll figure this out together" ↳ Confidence is contagious 12) De-escalate with Empathy ↳ "That makes sense—you’re not alone" ↳ Validation cools the fire 13) Ask for Feedback ↳ "How could I have handled this better?" ↳ Openness invites openness 14) Check for Emotion ↳ "How are you feeling right now?" ↳ Feelings often speak louder than facts 15) Break it Into Steps ↳ "Let’s take this one piece at a time" ↳ Simplicity calms chaos 16) Share What You’re Learning ↳ "This is teaching me a lot" ↳ Humility connects 17) Own the Outcome ↳ "Here’s what I commit to doing" ↳ Integrity builds trust 18) Repeat What Matters ↳ "Just to be clear, you’re saying…" ↳ Listening is leadership 19) Choose the Right Time ↳ "Is now a good time for this talk?" ↳ Timing shapes tone 20) Close With Care ↳ "I appreciate you talking this through" ↳ Endings leave lasting impressions 21) Keep the Door Open ↳ "Let’s keep this dialogue going" ↳ Safety means being available Tough conversations aren’t meant to be easy. They’re meant to be 'transformational'. Lead them with presence, not power. ♻️ Please repost to promote presence over avoidance. 🙂 Follow Marco Franzoni for more.

Want to stop triggering defensive reactions in critical conversations? Brain science reveals a simple technique that's transforming how top companies communicate: As an executive coach, this is the first thing I teach founders who are struggling with critical relationships. Why? Because it's consistently the most powerful tool for transforming toxic communication into productive dialogue. When you're fighting with your co-founder, your brain's threat response system activates. This shuts down the exact parts of your brain needed for effective communication. But there's a way to keep those neural pathways open. It's called speaking inarguably - using only facts that can't be disputed. Instead of "You don't care about this company" (judgment) Say "When you missed our last three meetings, I felt worried about our partnership" (fact) The first triggers defense mechanisms. The second creates psychological safety. There are two types of inarguable statements: • External facts: Observable behaviors, metrics, documented events • Internal facts: Your sensations, emotions, thoughts ("I feel frustrated") I've seen this technique help to transform toxic co-founder relationships into thriving partnerships more times than I can count. Here's how to start: 1. Pause before responding to emotionally charged situations 2. Strip away interpretations, focus only on observable facts ("You arrived 15 minutes late" vs "You're disrespectful") 3. Own your internal experience ("I felt anxious when that happened" vs "You're stressing everyone out") 4. Practice radical honesty about your feelings (This builds trust faster than pretending to be perfect) The hardest part? Letting go of being right. Your interpretations might feel true, but they're just stories you're telling yourself. This is where inner work meets leadership. When you master this, difficult conversations become growth opportunities. Your leadership emerges naturally from who you are, not who you think you should be.

I used to think that making my point loud and clear was the way to go. But I’ve learned that real communication isn’t about being right—it’s about being curious. Instead of saying, ‘You never listen to me,’ try: ‘Can we talk about how we’re approaching this?’ Instead of, ‘You’re not being fair,’ try: ‘Help me understand why you feel that way.’ Next time you feel tension rising, pause and ask yourself: Am I trying to win, or am I trying to understand? That shift changes everything. #Communication #Leadership #EmotionalIntelligence

Early in my career, I needed to tell a senior executive that his behavior was harming morale. I 𝐀𝐆𝐎𝐍𝐈𝐙𝐄𝐃 over how to have this tough talk without endangering my job. There was no easy way around it. This was going to be 𝐇𝐀𝐑𝐃. Ultimately, we sat down together in a neutral setting. I focused on my desire to see the team thrive. The executive, while surprised, appreciated my honesty. We had an open dialogue, and things improved. It was a growth moment for both of us. 𝐒𝐔𝐂𝐂𝐄𝐒𝐒! 𝘏𝘖𝘞'𝘋 𝘐 𝘋𝘖 𝘐𝘛? Here are three things that have always worked best for me: 1. 𝐁𝐞 𝐜𝐥𝐞𝐚𝐫 𝐚𝐧𝐝 𝐟𝐨𝐜𝐮𝐬 𝐨𝐧 𝐭𝐡𝐞 𝐢𝐬𝐬𝐮𝐞, not the person. Make it about solving problems, not attacking character. 2. Listen first, then speak. 𝐒𝐞𝐞𝐤 𝐭𝐨 𝐮𝐧𝐝𝐞𝐫𝐬𝐭𝐚𝐧𝐝 before asking to be understood. 3. 𝐅𝐢𝐧𝐝 𝐜𝐨𝐦𝐦𝐨𝐧 𝐠𝐫𝐨𝐮𝐧𝐝. Align on shared goals and good intentions to prevent discord. Courageous conversations require emotional intelligence, empathy, and care. With the right mindset and approach, you can express yourself effectively while minimizing defensiveness in others. 𝑾𝒉𝒂𝒕'𝒔 𝒎𝒂𝒅𝒆 𝒚𝒐𝒖𝒓 𝒄𝒐𝒖𝒓𝒂𝒈𝒆𝒐𝒖𝒔 𝒄𝒐𝒏𝒗𝒆𝒓𝒔𝒂𝒕𝒊𝒐𝒏𝒔 𝒔𝒖𝒄𝒄𝒆𝒔𝒔𝒇𝒖𝒍? Share one tip below for constructively having necessary but tough talks. I look forward to learning from your experiences!

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

Let's say an employee tells you they are struggling to get out of bed. They know that coming in late and looking unkept is not how they want to show up and this person feels embarrassed they’ve not been able to fix it. You as the manager or co-worker hearing this might feel overwhelmed because you are not sure what to say, what to do, or how to fix it. #1 Don't panic. Stay put. Breathe. Work through that "I want to flee" feeling which comes with fear, helplessness, and overwhelm. #2 You don't have to fix this. You can't. But you can listen with compassion and empathy. You are allowing the person to empty their head of chatter that has likely taken up a lot of brain real estate. What if they go on too long? “I want to hear what you have to say but you've shared enough that I feel concern for you. May I connect you with [this resource] to see what is available for employees? We can do that together." #3 Meet that person where they are. Allow for stretches of silence after a question or in the middle of the conversation. That person is likely processing. #4 Thank them for the courage to share this with you. They chose to speak to you because you are trustworthy. What an honor. #5 Do not diagnose a mental illness. You can say, "It sounds like you've felt depressed or down recently. Is that right?" #6 It's OK to be vulnerable about yourself but remember it's about them. #7 Admit that you don’t have all the info or answers but you can partner with them to find the right resources. This person had to be very nervous coming to you and being so vulnerable. They might be worried they'll be fired, passed over for future promotion, or deemed unworthy of future projects. Explain that this will be handled discreetly. Let them know of company policies, who they can talk to, and any EAP, ERG, or local resources. I always suggest that managers assign someone in the dept to find local resources--groups, nonprofits, crisis lines, warm lines, etc-- and put them in a pdf and also have a table with resources. #mentalhealth

Assistants, do you need to have a difficult conversation but aren’t sure where to start? Yep, I have been there. And here’s your reminder that staying quiet doesn’t mean we’re keeping the peace. It often just means we’re avoiding the discomfort. As an assistant, avoiding hard conversations can keep you stuck. Want to be seen as a strategic partner? You have to be willing to speak up, even when it’s uncomfortable. So what counts as a “difficult conversation” in our world? Here are just a few: 🗣️ Letting your executive know their last-minute changes are impacting your ability to plan effectively 🗣️ Telling a team member that you’re not their assistant just because you “seem available” 🗣️ Explaining why you can’t take on another project without compromising quality 🗣️ Pushing back on unrealistic expectations in a respectful, professional way Sound familiar? Yep, I thought so. Here’s how to get better at it: 1. Prepare, don’t rehearse. Be clear about your key points, but don’t over-script it. You want a conversation, not a performance. Go in with your message solid, but stay open to how the other person responds. 2. Lead with clarity, not apology. Stop over-explaining or softening the truth to the point it’s barely there. Try this instead: 🔸 “I need to address something that’s impacting my ability to support you well…” 🔸 “To meet that deadline with the quality you expect, I’ll need to shift some priorities. Can we discuss?” 3. Use data or impact, not emotion alone. Instead of “I’m overwhelmed,” say “In the past two weeks, I’ve taken on four new projects on top of my core tasks. Here’s what’s at risk if we don’t reprioritize.” You’re stating facts, not just feelings. (And one of my favorite messages to share is that feelings are not facts AND data always trumps passion). 😉 4. Practice active listening. Sometimes the real issue isn’t what was said. It’s what wasn’t understood. Give space for the other person to share their side too. That’s where trust is built. 5. Follow up. Document what was discussed, clarify next steps, and make sure everyone’s on the same page. No room for “I thought you meant…” confusion. You can’t evolve in your role without learning to navigate hard conversations. And you don’t need permission to advocate for yourself. You just need a little courage and a lot of clarity. What’s a difficult conversation you’ve learned to handle better? Drop it below because your insight might help another assistant grow.👇🏽 #evolvedassistant #administrativeassistant #executivesupport #administrativeprofessionals #executiveassistant

I got to train 75 managers in how to hold Tough Conversations and how to Lead with Emotional Intelligence this week. One of the hardest moments they identified was when a team member shared a situation with a strong emotion like, 💬 "I just applied for a promotion and didn't get it again." or 💬"I've been waiting for 6 months for a development opportunity and am still waiting." or 💬"I'm struggling with personal challenges at home." The initial reaction was to want to say, "How can I help you navigate this?" or "How can I support?" These are great responses motivated to 1) help the person and 2) find a solution. But, people feel relief not because of what you do but because of the connection you make with them. In fact, jumping to a solution without acknowledging how they're feeling can intensify the feelings of being misunderstood or not supported. This is where empathy is so powerful. By taking a moment to make a statement to acknowledge the person's emotion they are feeling in the situation, we can help them feel seen, heard, and connected to. This might sound like, 💬"That's a really frustrating situation. I know how hard it is to go after an opportunity and not get it." or 💬"I know how much work you've put in to be selected for this opportunity. I'm sorry you haven't gotten the result you wanted." or 💬"I'd love to hear more. Are you willing to share with me about your situation?" By identifying with someone's emotion or asking questions to give them space to share how they're feeling, we create connection, build trust, show them support, and can help de-escalate the feelings they are experiencing. Do you have any tips for expressing empathy when a team member shares a hard situation or emotion? #leadershipdevelopment #emotionalintelligence #empathy