Leading Conversations Around Difficult Issues

Navigating difficult conversations…we know the terrain well in supply chain and sustainability —complex stakeholder relationships, competing priorities, and tough tradeoffs that demand honest dialogue. The first quarter of 2025 has been challenging for some clients and colleagues. Behind every successful initiative lies countless challenging conversations.I wanted to share this list that captures what I've learned (often the hard way) about handling challenging discussions: 1. Lead with empathy - acknowledge feelings before diving into issues 2. Stay calm - pause and breathe when tensions rise. Cooler heads prevail. 3. Prepare but remain flexible - rigid scripts rarely survive contact with reality 4. Ask genuine questions - "help me understand your perspective" 5. Give authentic appreciation - recognize effort before suggesting changes 6. Own your emotions - acknowledge feelings without manipulation 7. Respect others' viewpoints - validation doesn't require agreement. You can disagree and still find a happy path. 8. Be specific - vague criticisms like "you always" rarely help 9. Collaborate on solutions - problem-dumping without brainstorming fixes nothing 10. Set clear boundaries - know what you can and cannot commit to 11. Listen actively - not just waiting for your turn to speak. Read this again… 12. Apologize sincerely when needed - take responsibility, not half-measures. Accountability helps build trust. 13. End with concrete next steps - clarity prevents misunderstandings. Playing back throughout tough conversations with key points and actions shows active listening and understanding. 14. Reflect afterward - what worked? what could improve? In my experience leading global teams, the conversations I've handled poorly weren't failures of strategy—they were failures of approach and understanding context. For example, a recent negotiation with a supplier facing severe capacity constraints could have deteriorated into finger-pointing. Instead, by focusing on understanding their challenges first (point #4) and collaborating on creative solutions (point #9), we found a path forward and workable compromise. Staying calm helped too ;) What's your experience? Which of these principles has been most valuable in your leadership journey? Or is there a 15th point you'd add to this list? ___________ 👍🏽 Like this? ♻️ Repost to help someone ✅ Follow me Sheri R. Hinish 🔔 Click my name → Hit the bell → See my posts. #SupplyChain #leadership #sustainability

“What elephants are we ignoring in this room?” This question, suggested by my executive coach Ben Anderson, transformed how our leadership team communicates. I decided to start making space for my leadership team to bring up any elephants in the room at the top of meetings: company logistics, hiring processes, and more. Then our board observer Jessie Woolley-Wilson helped me take it to the next level by introducing the idea of “benevolent friction” - the art of intentionally creating safe spaces for uncomfortable conversations that are the catalysts for growth. By practicing benevolent friction, we minimize potential resentment or frustration and build up trust and respect. As a result, we no longer just acknowledge the hard topics. We actively seek out these friction points. Each leadership meeting starts with team members sharing their top 2-3 areas of healthy disagreement that we then debate. And what we’ve learned is that the most innovative solutions often emerge from constructive conflict. Recently, I challenged our team’s thinking about recruiting success. Instead of celebrating hire counts, we discussed deeper metrics. How do we really know our recruiting strategy is working? How well do new hires thrive after they join? These tough questions are guiding us to better hiring processes. The key to this success was in creating a culture where we not only tolerate friction, we welcome it as a tool for continuous improvement. Where disagreement isn’t seen as disruption, but as dedication to getting things right. Great leaders don’t just spot elephants in the room. They proactively look for them.

Real conversations at work feel rare. Lately, in my work with employees and leaders, I’ve noticed a troubling pattern: real conversations don’t happen. Instead, people get stuck in confrontation, cynicism, or silence. This pattern reminded me of a powerful chart I often use with executives to talk about this. It shows that real conversations—where tough topics are discussed productively—only happen when two things are present: high psychological safety and strong relationships. Too often, teams fall into one of these traps instead: (a) Cynicism (low safety, low relationships)—where skepticism and disengagement take over. (b) Omerta (low safety, high relationships)—where people stay silent to keep the peace. (c) Confrontation (high safety, low relationships)—where people speak up but without trust, so nothing moves forward. There are three practical steps to create real conversations that turn constructive discrepancies into progress: (1) Create a norm of curiosity. Ask, “What am I missing?” instead of assuming you’re right. Curiosity keeps disagreements productive instead of combative. (2) Balance candor with care. Being direct is valuable—but only when paired with genuine respect. People engage when they feel valued, not attacked. (3) Make it safe to challenge ideas. Model the behavior yourself: invite pushback, thank people for disagreeing, and reward those who surface hard truths. When safety is high, people contribute without fear. Where do you see teams getting stuck? What has helped you foster real conversations? #Leadership #PsychologicalSafety #Communication #Trust #Teamwork #Learning #Disagreement

🔥 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.

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.

Stop dreading tough talks. Master them with these 21 phrases instead: I once snapped when a colleague questioned my timeline. My defensive reaction created a week of tension. That day I realized emotional responses solve nothing. They only create new problems. We've all been there: Feeling defensive Reacting without thinking Watching a simple disagreement turn into a lasting conflict But I've learned the shift from reactive to constructive changes everything ✨ 21 ways smart people handle difficult conversations: 1) Lead with Curiosity ↳ "Tell me more about your perspective on this" ↳ Questions defuse tension faster than statements 2) Name the Energy ↳ "I notice there's tension here, let's address it" ↳ Acknowledgment creates safety 3) Find Common Ground ↳ "We both want what's best for the project" ↳ Alignment before action 4) Set Clear Expectations ↳ "Here's what I need, what do you need?" ↳ Clarity prevents future conflict 5) Pause the Escalation ↳ "Let's take a step back and break this down" ↳ Breathing room creates solutions 6) Mirror Their Language ↳ Use their exact key words when responding ↳ Matching builds instant connection 7) Acknowledge Impact ↳ "I see how this affects your priorities" ↳ Understanding beats defense 8) Own Your Part ↳ "Here's where I could have done better" ↳ Accountability creates trust 9) Focus Forward ↳ "How can we prevent this next time?" ↳ Solutions beat blame 10) Check Understanding ↳ "Here's what I'm hearing - am I getting it right?" ↳ Clarity prevents escalation 11) Create Space ↳ "Let's revisit this when we're both fresh" ↳ Time transforms tension 12) Stay on Topic ↳ "Let's focus on solving this specific issue" ↳ Boundaries keep talks productive 13) Express Confidence ↳ "I know we can figure this out together" ↳ Belief shifts energy 14) Share Context ↳ "Here's what led to my decision" ↳ Understanding reduces resistance 15) Invite Solutions ↳ "What ideas do you have for this?" ↳ Collaboration beats control 16) Set Timelines ↳ "When should we check in on this?" ↳ Structure creates safety 17) Validate Concerns ↳ "That's a legitimate worry - let's address it" ↳ Recognition reduces defense 18) Stay Factual ↳ "Here's what the data shows us" ↳ Evidence beats emotion 19) Close with Action ↳ "Let's clarify next steps together" ↳ Progress prevents repeat issues 20) Follow Through ↳ "As we discussed, here's what I've done" ↳ Action builds credibility 21) Document Growth ↳ "Here's how we'll work differently now" ↳ Learning beats repeating Difficult conversations aren't obstacles to success. They're the moments where true connection happens ✨ Which strategy will you try in your next challenging conversation? -- ♻️ Repost to help your network transform difficult conversations into opportunities 🔔 Follow Dr. Carolyn Frost for more practical tools to succeed with confidence

From a former Google Director and now VC on difficult conversations: “Regarding hard conversations, I have one trick which I use over and over again.  It's transparency and bringing people around to the same side of the table. For example, in the past, when I needed to have conversations with staff who were performing very poorly, I'd say: ‘So and so, it's not working out. We had this goal for you. You haven't hit the goal, and we've come to the end of the road.’ It's a terrible conversation. It's awful. But I got used to it. However, what I discovered is much more effective is to flip the conversation to something like the following: ‘Here's the problem that we're trying to solve as a group, and you know this. This is what the result has been. We're not getting there. What is your analysis of what's going on?’ Usually, they start seeing things from your POV and the results are better in every respect, from the discomfort of the conversation to the results.  Often employees will reflect on the issue and almost fire themselves. Or, if they shouldn't be fired, you may come out from the conversation like, ‘Huh, this person's actually really thoughtful. Had a great idea. We set this up poorly.’ I think the same kind of approach works with so many things,  i.e., just letting somebody else in on what you're grappling with. Then amazingly, there's limited conflict and they help solve your problem. In each of these situations - conflict, management, hard lessons, leadership presence - they're all basically different UIs on top of the same underlying stack.  That stack is built out of bringing the people into your planning and thinking process as transparently as possible.”

In one of my leadership experiences, I encountered a situation with an employee who, at first glance, seemed difficult and uncooperative. It would’ve been easy to label her as a “toxic” employee and move toward termination. Instead, I chose to take a different approach—one rooted in curiosity and conscious leadership. Here’s what I learned: Behavior is a signal, not a conclusion. What looks like negativity or resistance is often a sign of unmet needs or misalignment. Instead of assuming the worst, I opened a dialogue with the director. This allowed me to understand the dynamics she was struggling with, including frustrations she hadn’t felt safe to express. Address the issue directly, with respect. When a high performer exhibits challenging behavior, the default reaction is often avoidance—either tolerating the behavior or quietly planning their exit. Instead, I leaned into the conversation with transparency and goodwill. Sharing my perspective candidly, while also being curious about hers, helped us uncover the root of the tension. Create alignment. Through open communication, we discovered that her skills were being underutilized, and her passions weren’t aligned with her role. By realigning her responsibilities to better match her strengths, we created a win-win scenario that elevated both her performance and team morale. Lead with curiosity and responsibility. Instead of reacting defensively, I took responsibility for my own stories and assumptions about the situation. This shift—from judgment to curiosity—created space for productive dialogue and lasting change. What was the result? That director became one of our most impactful team members, stepping into a role where she thrived and supported others in doing the same. The takeaway? Toxicity isn’t always what it seems. By addressing behavior with compassion, curiosity, and integrity, you can transform conflict into connection and underperformance into opportunity. If you’re dealing with a difficult team dynamic, ask yourself: What story am I telling about this person? What if their behavior is an invitation to lead more consciously? Remember this: every challenge you face in leadership is an invitation to grow. When you approach difficult dynamics with curiosity and a willingness to learn, you’ll uncover solutions that benefit everyone involved. You have the power to turn resistance into collaboration and frustration into transformation. Keep leading with purpose and heart—you’re exactly where you’re meant to be. #ConsciousLeadership #LeadershipDevelopment #LeadWithPurpose #TransformationalLeadership #LeadershipMatters #WorkplaceCulture #TeamDynamics #ConflictResolution #EmployeeEngagement #CareerGrowth #PurposeDrivenLeadership #ScalingImpact #HumanCenteredLeadership #FutureOfWork #LeadershipWithHeart #LeadershipJourney #InspirationForLeaders #MindfulLeadership #LeadershipTips #GrowthMindset