Managing Challenging Conversations

One of the toughest tests of your leadership isn't how you handle success. It's how you navigate disagreement. I noticed this in the SEAL Teams and in my work with executives: Those who master difficult conversations outperform their peers not just in team satisfaction, but in decision quality and innovation. The problem? Most of us enter difficult conversations with our nervous system already in a threat state. Our brain literally can't access its best thinking when flooded with stress hormones. Through years of working with high-performing teams, I've developed what I call The Mindful Disagreement Framework. Here's how it works: 1. Pause Before Engaging (10 seconds) When triggered by disagreement, take a deliberate breath. This small reset activates your prefrontal cortex instead of your reactive limbic system. Your brain physically needs this transition to think clearly. 2. Set Psychological Safety (30 seconds) Start with: "I appreciate your perspective and want to understand it better. I also have some different thoughts to share." This simple opener signals respect while creating space for different viewpoints. 3. Lead with Curiosity, Not Certainty (2 minutes) Ask at least three questions before stating your position. This practice significantly increases the quality of solutions because it broadens your understanding before narrowing toward decisions. 4. Name the Shared Purpose (1 minute) "We both want [shared goal]. We're just seeing different paths to get there." This reminds everyone you're on the same team, even with different perspectives. 5. Separate Impact from Intent (30 seconds) "When X happened, I felt Y, because Z. I know that wasn't your intention." This formula transforms accusations into observations. Last month, I used this exact framework in a disagreement. The conversation that could have damaged our relationship instead strengthened it. Not because we ended up agreeing, but because we disagreed respectfully. (It may or may not have been with my kid!) The most valuable disagreements often feel uncomfortable. The goal isn't comfort. It's growth. What difficult conversation are you avoiding right now? Try this framework tomorrow and watch what happens to your leadership influence. ___ Follow me, Jon Macaskill for more leadership focused content. And feel free to repost if someone in your life needs to hear this. 📩 Subscribe to my newsletter here → https://lnkd.in/g9ZFxDJG You'll get FREE access to my 21-Day Mindfulness & Meditation Course packed with real, actionable strategies to lead with clarity, resilience, and purpose.

Most of our interactions—especially the difficult ones—are negotiations in disguise. In their book Beyond Reason, Roger Fisher and Daniel Shapiro highlight how success in these conversations often comes down to addressing core concerns—deep, often unspoken emotional needs that shape how people engage. These concerns are: Appreciation, Affiliation, Autonomy, Status, and Role. Ignore them, and you’ll likely face resistance, disengagement, or frustration. Acknowledge and address them, and you create the conditions for stronger relationships, better problem-solving, and more win-win outcomes. I’ve learned this the hard way. Appreciation A senior leader I worked with was frustrated by pushback from his team. The problem? He was so focused on driving results that he rarely acknowledged their efforts. Once he started genuinely listening and recognizing their contributions, engagement skyrocketed. The team felt heard, and collaboration improved instantly. Affiliation A new CEO walked into a fractured leadership team—siloed, political, and mistrusting. Instead of pushing quick solutions, she focused on rebuilding connections, creating shared experiences, and reinforcing that they were one team. The shift in culture transformed their ability to work together. Autonomy A department head was drowning in tactical decisions because his team constantly sought approval. By clearly defining goals, setting guardrails, and empowering them to make decisions, he freed up his time and saw his team step up with more confidence and accountability. Status A high-potential leader felt overlooked and disengaged. His boss didn’t give him a raise or a new title but started including him in key strategic meetings. That simple shift in visibility changed everything—he became more invested, more proactive, and took on bigger challenges. Role A VP was struggling, not because of a lack of skill, but because she was in the wrong seat. When her boss recognized this and shifted her to a role better suited to her strengths, she thrived. Sometimes, people don’t need a promotion—they need the right role. Before a tough conversation or leadership decision, check in: - Am I recognizing their efforts? - Making them feel included? - Giving them autonomy? - Acknowledging their status? - Ensuring their role fits? Addressing core concerns isn’t about being nice—it’s about unlocking the best in people. When we do, we create better conversations, stronger teams, and real momentum. #Conversations #Negotiations #CoreConcerns #Interactions #HumanBehavior #Learning #Leadership #Disagreements

In my mission to empower #1MillionWomenBy2030 to sit at the table of their dreams, I hear stories of Black and Brown women facing toxic behaviors in the workplace far too often. One of my coaching clients recently stood up to a toxic, sexist sales leader, and in a heated moment, let her emotions get the best of her—putting her career and reputation at risk. We’ve all been there—facing prejudice, bias, and bullying. It’s frustrating, it’s exhausting, and it feels personal. But as women striving to break barriers and rise into leadership, how we handle these situations matters. And we CAN do it in ways that protect our careers and our dignity. Kamala Harris has shown us how to master this in public debates, but her approach offers valuable lessons for the workplace and boardroom, too. ➡️ Here are 5 powerful takeaways from Kamala’s approach that can help us navigate these challenges: 1️⃣ Stay Composed, Stay Powerful: When Kamala faces opposition, she doesn’t lose her cool. She remains calm, collected, and controlled—and that’s exactly how we own the room. When emotions take over, we give away our power. Hold onto yours by staying composed. 2️⃣ Shift the Story: Don’t let a toxic person define the moment. Reframe it by focusing on YOUR value and strength. You are more than their bias, their assumptions, or their behavior. You belong at the table—and you define your story. 3️⃣ Deflect With Grace: Kamala uses humor and calm deflection to shift the narrative. When faced with offensive comments, sometimes a smile or well-placed question is enough to disarm them. You don’t need to feed their fire—show them it’s not even worth your energy. 4️⃣ Address the Behavior with Precision: Call out toxic behavior, but do it wisely. Focus on the issue, not the person. This keeps the conversation professional and shifts the power in your favor. Strategic words can cut deeper than emotional outbursts. 5️⃣ Lead with Solutions: Kamala doesn’t just counter chaos—she presents herself as the alternative. In the workplace, we can lead by showing that WE are the solution, that professionalism and inclusivity drive results. This elevates us beyond the fray. To the women out there facing these battles every day: You are strong, you are capable, and you belong at the table. Don’t let anyone push you off your path. How we navigate these challenges isn’t just about today—it’s about the legacy we build for future generations of women leaders. What strategies have helped you rise above toxic workplace environments? Share your insights and let’s empower each other to keep breaking barriers. #WomenInLeadership #ExecutivePresence #CareerGrowth #LeadershipDevelopment #Sales

🔥 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

A lot of Black women have been taught to lead with an apology in professional spaces. To seem less “intimidating.” To be more “palatable.” But let’s be clear: you don’t have to dim your light just to make others feel comfortable. Being direct isn’t rude. Being confident isn’t aggressive. You’re not doing too much, you’re doing what’s necessary. Let’s change the language: ❌ “I’m sorry, I know you’re busy but…” ✅ “When you get a moment, I’d like to discuss [topic].” ❌ “I hate to be a pain, but…” ✅ “Circling back to make sure this stays on track.” ❌ “Just wondering if you had any thoughts on…” ✅ “Do you have feedback on [specific item]?” ❌ “I hope this makes sense…” ✅ “Let me know if you need anything clarified.” ❌ “I don’t mean to overstep, but…” ✅ “Here’s a suggestion I believe could add value.” You’re allowed to speak up without softening every sentence. You deserve to take up space without over-explaining why you’re in the room.

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.

Over the past 5 years I learned how to make confrontation a conversation. For years, I avoided confrontation. It was uncomfortable, and I wanted to be liked. I was very immature in my thinking. So, I’d ignore the tough topics, let things slide, and convince myself that keeping the peace was worth more than speaking up. But here’s the truth: that mindset held me back, both personally and professionally. When I stopped avoiding confrontation, I started seeing massive growth. Here’s why addressing confrontation is smart and GOOD for business: 🟢 Prevents Miscommunication: Avoiding confrontation can cause misunderstandings to fester. When you address things head-on, you clear the air and ensure everyone’s on the same page. 🟢 Fosters Trust: People appreciate honesty. Even if the conversation is difficult, addressing issues with integrity shows you respect both yourself and your colleagues. 🟢 Drives Progress: Problems don’t disappear when we ignore them. In fact, they often get bigger. By addressing them directly, we create opportunities for real solutions and growth. Now, let’s talk about how to do this tactfully. Cause the HOW is huge when it comes to this. When I talk about confrontation, I don’t mean a heated debate so you have to be thoughtful in your approach. Here are 5 ways to turn confrontation into a productive conversation in the workplace: 1️⃣ Start with Empathy: Understand the other person’s point of view first. Approach the conversation with curiosity, not blame. 2️⃣ Focus on the Issue, Not the Person: Address behaviors or outcomes, not character flaws. Keep it solution-focused. 3️⃣ Use "I" Statements: Own your feelings. For example, “I feel frustrated when…” vs. “You always…” 4️⃣ Stay Calm & Collected: Keep your emotions in check. If needed, take a breather before speaking. 5️⃣ Offer Solutions: Confrontation without a path forward is just complaining. Be ready to suggest ways to move forward. Other things to consider are the when, where and with whom. Try to time the conversation well and determine the best medium. Maybe Slack isn’t the best mechanism for this type of conversation. Lastly, think about who’s in the room. Think about whether or not this should be a private conversation or if it’s better suited for and with a group. Next time you’re facing confrontation, remember: it’s not about winning, it’s about growing. Don’t shy away from these conversations—they’ll make you, your team, and your business stronger.

Don’t avoid the hard conversation. Use these 8 steps instead: Like many people, I used to avoid hard conversations until it was too late. When the stakes and emotions are high, and opinions differ, silence breaks trust. Tension builds. Trust erodes. Opportunities are lost. I learned this time and again. What if you could handle these moments with clarity and kindness? Use these 8 steps to navigate difficult conversations: 1. Ask to Understand: - Help me understand your perspective. - Can you walk me through your thinking? 2. State Only the Facts: - Here’s what I’ve observed [..]. - What’s your take on this situation? 3. Focus on Shared Goals - We both want [shared goal]. Let’s figure this out together. - How can we ensure the best outcome for everyone? 4. Stay Calm Under Pressure - I can see this is important to you. Let’s talk it through. - I’m committed to finding a solution with you. 5. Acknowledge Their Perspective - I hear what you’re saying. - It sounds like [paraphrase their perspective]. Is that right? 6. Address Misunderstandings - Can we clarify what you meant by [..]? - What do you think I might not be seeing? 7. Find a Path Forward - What’s the best way for us to move forward? - Here’s what I propose. What are your thoughts? 8. Recap & Align - We've agreed on [..]. Anything else to consider? - Let's check back in [specific timeframe]. Difficult conversations aren’t the problem. It’s how we show up for them that makes the difference. With the right approach, you can turn high-stakes moments into shared understanding. ➕ Follow me, Melody Olson, for Leadership, Tech & Career Insights. ♻️ Repost to help your network navigate difficult conversations with trust.

The Double Standard of Emotion in Leadership It’s a massive issue how society holds women and Black people to an impossible standard of calmness and composure, especially when advocating for justice or speaking truth to power. We are told not to be "too emotional" or "too angry," as if passion discredits our arguments or invalidates our points. Yet, when white male leaders display the same — or even more — emotion, it's reframed as strength, conviction, or passion. Consider this: Donald Trump has built an entire career on being angry, shouting grievances from podiums. Justice Brett Kavanaugh wept and raged through his Supreme Court confirmation hearing, yet his outbursts were excused, even praised, as evidence of his humanity. These displays of unchecked emotion don’t cost them their credibility — instead, they are often rewarded for it. But let a Black woman raise her voice, let her show frustration at systemic injustices, and the labels come fast: "angry Black woman," "emotional," "intimidating." Let a Black man speak with urgency, and he's "threatening." And let’s be clear: the issue is not that Black women or Black men are intimidating. The issue is that some people have chosen to be intimidated, projecting their own fears, biases, and perceptions of who they think Black people are. Their discomfort isn’t about us — it’s about the stereotypes they carry. Their response to our presence and our voices reveals more about them than it does about us. This double standard isn’t just frustrating; it’s designed to silence us. It says, "Stay quiet, stay pleasant, or we won’t take you seriously." It’s a control tactic to keep women and people of color in line, preventing us from wielding the same force of passion and emotion that white men are not only permitted but encouraged to display. Let’s be clear: emotion is not a weakness. Anger is not a flaw when it comes from a place of truth and justice. Passion is what drives change. If our voices make people uncomfortable, perhaps it’s because they shine a light on injustices too long ignored. Join me in rejecting this double standard. Embrace our voices — loud, passionate, emotional, and unapologetic. The world doesn’t change with silence; it changes when we demand it, even if our demand shakes the room. If it’s good enough for them, it’s good enough for us. #SpeakYourTruth #ShakeTheRoom

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