Importance of Difficult Conversations in the Workplace

🔥 Radical leaders don't avoid difficult conversations. They transform them. The most courageous act in leadership? Not the big presentation. Not the tough budget call. Not the strategic pivot. It's sitting across from someone and speaking truth with kindness when every instinct tells you to run. I've coached C-suite leaders who'd rather resign than have a five-minute conversation about performance. I've lived this personally. The conversations I feared most became the moments that defined my leadership. Truth: Psychological safety isn't built on avoiding hard truths. It is built on how we deliver them. 3 principles that transform difficult conversations: 1️⃣ Lead with curiosity, not conclusion. "I noticed X and I'm curious about what's happening" opens doors that "You did X wrong" slams shut. This works across differences. When we're curious, we create belonging. 2️⃣ Honor the whole human. Before addressing what someone did, acknowledge who they are. The most inclusive teams remember: Performance is just one dimension of a multidimensional human. 3️⃣ Make it safe to be uncomfortable. The best leaders don't minimize tension. They normalize it. "This conversation might feel uncomfortable, and that's okay. We'll navigate it together." Your team isn't waiting for a perfect leader. They're waiting for a real one. 👇 What difficult conversation are you avoiding right now? What might be possible if you transformed it instead? In Community and Conversation, 🧡 Jim P.S. My August calendar for "Courageous Conversations" has three spots remaining for leaders ready to build truly inclusive teams. Message me for details. Book an introductory meeting at the link in my Bio.

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

🔥 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

This week I met Joseph Grenny, co-author of "Crucial Conversations", and it reminded me of a lesson most managers forget. 🎯 We don’t talk about hard things enough. We pass it off as too "small" to address: ↳ That nice teammate who keeps missing deadlines ↳ That person in a meeting who constantly interrupts you ↳ The tension with your boss you can’t quite place Meanwhile these small moments kill motivation, morale, and performance. The first step to fixing a slugging team isn’t always "work harder". It’s having the damn conversation so you can create a shared path forward. If you haven't read this incredible book (link below) here are the basics: ⭐️ Crucial conversations are where leadership is tested––the stakes are high, opinions differ, and emotions run hot. 1️⃣ WORK ON YOURSELF ↳ Get unstuck: Check in, what do you need to have this conversation? ↳ Start with Heart: Clarify what you want and don't want from the talk. ↳ Master my stories: Check the stories you’re telling yourself 2️⃣ STATE YOUR PATH ↳ Share facts ↳ Tell your story ↳ Ask for others’ paths ↳ Talk tentatively ↳ Encourage testing 3️⃣ CREATE SHARED MEANING ↳ Learn to look: Watch for signs of silence or aggression. ↳ Make it safe: Pause the convo and rebuild trust as needed. ↳ Explore others’ paths: Listen deeply to their viewpoint. 4️⃣ MOVE TO ACTION Only when you've created shared meaning, can you: ↳ Decide who does what and by when ↳ Follow up and ensure accountability It sounds simple, but crucial conversations is the hardest skill to learn. It's also probably one of the most important factors for team success. A huge thank you to Kerry Patterson, Joseph Grenny, Ron McMillan, Al Switzler for writing one of the best books in leadership development. --- Have you ever avoided or addressed a conversation? What did you experience? What conversations are your managers avoiding? Let me know in the comments, and let’s talk about it! Did this resonate? Share it with your LinkedIn audience! We're always looking to spread great knowledge and information. ♻️ And follow me (Yen Tan) for more manager dev and L&D shenanigans.

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.

Many of you know I coach leaders to be inspirational, and part of that formula is understanding this: some of the most impactful moments come from the conversations we’d rather avoid. I remember early on in my career a situation where I had to tell a General Manager that he needed to address a poor-performing Executive Committee member who wasn’t aligned with our core values. It was uncomfortable, especially because the GM was hesitant to act, fearing it might disrupt team dynamics. But core values aren’t negotiable—they’re the foundation of trust and integrity within any organization. By leaning into the discomfort, I explained why accountability was essential, not just for the individual’s growth but for the entire team’s success. After a series of honest and transparent discussions, the GM took the necessary steps to address the issue. The outcome? The team felt a renewed sense of clarity and alignment, and the organization as a whole benefited from reinforcing our commitment to living our values. As leaders, our greatest impact often comes not only from what we say but from our willingness to address challenges directly. The courage to have these difficult conversations isn’t optional—it’s essential for growth, both individually and collectively. #difficultconversations #Leadership #Hospitality #Growth #ServantLeadership

After my post yesterday about the importance of assessing team dynamics, I had someone reach out and ask me what to do if, as a team member, you are having team dynamic issues with someone you have to work closely with. I am someone who LOVES harmony with the folks I work with. I actually crave it. However, I am also not afraid of conflict, as long as it is healthy. I think teams that operate in pure harmony are, at times, avoiding the difficult stuff. So my advice to folks who are experiencing team dynamic issues is: 1. Determine if the issues are a result of healthy friction or if there's something more underlying. 2. If it is between you and one person, rip off that band-aid and have that uncomfortable conversation. It can go something like this: "I've noticed during this conversation, it felt like there may be friction between you and me (give specific example). Our relationship is very important to me, so I was wondering if there's something I can do differently in my communication approach." Or something like that.... but whatever you do, don't avoid having the conversation. 3. If you do not feel comfortable having that conversation, consider speaking with your manager or a trusted partner to get advice on how to approach it. It is essential to remember that there are always two perspectives to consider: yours and the other person's (and likely more if these dynamics are playing out publicly). Years ago, I was given this phrase by my executive coach: "approach conflict with curiosity". If you enter a conversation thinking you're right, you'll likely end that conversation still divided and possibly with more conflict than you started with. Our reminder for today: approach conflict with curiosity...and don't let team dynamic issues linger. The quicker you tackle them, the stronger you'll be for it.  What else would you add? 

I've noticed... Through our hybrid ePrograms and consulting work, I spent a great deal of time coaching front line leaders. Over the years, I’ve noticed a common theme when it comes to confronting disruptive employees. These leaders… Tend to avoid conflict, don’t want to hurt their employee’s feelings by confronting them about something negative, and they so desperately want their employees to “like” them. Knowing this about these leaders makes me love them even more. However, it’s my job as their “coach” to remind them… Most humans avoid conflict because conflict is painful. And, as a survival technique, we are designed to avoid pain. 𝗜𝘁’𝘀 𝗼𝗸𝗮𝘆 𝘁𝗼 𝗯𝗲 𝘂𝗻𝗰𝗼𝗺𝗳𝗼𝗿𝘁𝗮𝗯𝗹𝗲 – 𝗵𝗮𝘃𝗲 𝘁𝗵𝗲 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻 𝗮𝗻𝘆𝘄𝗮𝘆. Your job as a leader is to help your team and each individual become…better. You can’t become better if all you hear is the good stuff. It’s the “bad” stuff that helps us grow. 𝗧𝗲𝗹𝗹 𝘆𝗼𝘂𝗿 𝗲𝗺𝗽𝗹𝗼𝘆𝗲𝗲𝘀 𝘁𝗵𝗲 𝘁𝗿𝘂𝘁𝗵 – 𝘁𝗵𝗲 𝗴𝗼𝗼𝗱, 𝘁𝗵𝗲 𝗯𝗮𝗱, 𝗮𝗻𝗱 𝘁𝗵𝗲 𝘂𝗴𝗹𝘆. Most humans want to be liked by other humans (I know I do). However, it is far better to be respected by your employees than liked. 𝗜𝘁’𝘀 𝘄𝗵𝗲𝗻 𝘆𝗼𝘂 𝘀𝗵𝗼𝘄 𝘆𝗼𝘂𝗿 𝘁𝗲𝗮𝗺 𝘆𝗼𝘂 𝗰𝗮𝗿𝗲 𝗲𝗻𝗼𝘂𝗴𝗵 𝘁𝗼 𝗯𝗲 𝗵𝗼𝗻𝗲𝘀𝘁 𝘄𝗶𝘁𝗵 𝘁𝗵𝗲𝗺 – 𝘁𝗼 𝘁𝗲𝗹𝗹 𝘁𝗵𝗲𝗺 𝘁𝗵𝗲 𝘁𝗿𝘂𝘁𝗵, 𝘁𝗵𝗮𝘁 𝘁𝗵𝗲𝘆 𝗴𝗿𝗼𝘄 𝘁𝗼 𝘁𝗿𝘂𝘀𝘁 𝗮𝗻𝗱 𝗿𝗲𝘀𝗽𝗲𝗰𝘁 𝘆𝗼𝘂. It’s okay to want to be liked! But not at the expense of being respected. #leadershipdevelopment #healthcareleaders #difficultconversations #effectivecommunication #culturechange #healthyworkculture

Companies require #antiharassment training. So why not training on speaking up, advocating for self, and handling tough conversations too? As a woman engineer previously working in male-dominated environments, I’ve experienced harassment before. And I’m grateful that anti-harassment training exists. 👉🏼BUT if I had to choose? I’d 1000% rather know how to speak up for myself AND have everyone in the organization learn how to communicate with respect, clarity, and confidence. Because I didn't know how to do it, and the majority of my leaders didn't either. 📊 66% of business leaders experience miscommunication at least once a day. 📊 100% of employees say they experience miscommunication at least once a week. 👀 Here’s the gap: We shouldn't reduce anti-harassment training... ...but we need to add mandatory training on #communicationskills for #hardconversations, #assertiveness, and #selfadvocacy. It shouldn't be optional. Because: 🚨 Employees are told to speak up, but not how to. 🚨 They’re encouraged to advocate for themselves, but not taught how to do it without fear of backlash. 🚨 They’re expected to handle conflict, but don’t get trained on navigating difficult conversations effectively. 👉 We’re required to learn what NOT to say. But why aren’t we trained on HOW to say it? Real inclusion isn’t just about avoiding harm, it’s about equipping people to communicate with confidence and respect. 💬 What do you think? Should companies make communication skills training mandatory just like anti-harassment training? 👇 #CommunicationMatters #LeadershipDevelopment #WorkplaceCulture #SpeakingUp #WomenInTheWorkplace #CareerGrowth #Assertiveness #WorkplaceInclusion #DiversityAndInclusion #ProfessionalDevelopment