Handling Difficult Conversations With Senior Leadership

Imagine this: you become aware that a senior leader doubts your skills, competence or doesn't realize your true contributions. They simply have the wrong perception of you. How do you change that perception without looking defensive or wasting time? I partner with a large leadership development firm as a fractional consultant where most are measured on delivery days and client billable hours. I wasn't the "traditional" consultant and was originally brought into the firm with the expectation that average utilization rates don’t really apply to me. I would deliver other strategic value such as advising on new product development, hosting thought leadership events and more given my unique experience as a tech leader, founder of an ed-tech startup, angel investor and coach. This arrangement was fine with previous leadership - but they all left. When new leadership came in, I needed to re-establish my value. Then I heard an off-hand comment. Due to inaccurate internal reporting, my utilization dashboard severely undercounted my billable hours. The new leader (my ‘skip-level’) had looked at my name and squinted, wondering how much value I truly provide. Not a good sign. Here are the key things I did to change her perception: (1) 📊 Manage up with data: I proactively set up time to speak with the new leader and came armed with data on what I did actually deliver - hours billed, hours forecasted, new revenue pipeline unlocked, etc. (2) ⏰ Focus on what they care about now: I honed in on the things I knew would matter most to her in her new role but did not shy away from outlining my arrangement with her predecessor. (3) 📢 Call out their concerns: I named the dynamic directly - "This is our first meeting and based on inaccurate data, you may think I'm not delivering enough value or working as hard as others. Let me share the facts." (4) 📖 Own the narrative: I took the opportunity to combat misconceptions with data and frame my value in a way that aligned with her priorities. (5) 📐 Understand how they measure success and reframe your value: I dug to understand exactly how she would be evaluating her team moving forward, offered suggestions and sought feedback on alternative ways for me to deliver value The key is to take charge of the situation when you know a senior leader has the wrong impression. Don't shy away from the hard conversations. Be proactive, listen between the lines, focus the dialogue on their priorities, and make your case. This is a critical skill for anyone, but especially consultants and those who fill "non-traditional" roles in their company. Don't assume leaders will just figure it out. Go make the case for your value directly and shift their perception. #managingup #executivepresence #coaching

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

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.

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.

These 4 words can make anyone anxious: "We need to talk." The problem isn't having hard conversations: It's how most people approach them. I used to wing these conversations and wonder why they went sideways. Then I studied how the top 1% of leaders handle conflict. The difference? They have a system. Most leaders wing difficult conversations and create more problems. Smart leaders use proven frameworks that build trust while addressing issues. Here's the approach that transformed my leadership: ✅ Phase 1 - Foundation Setting: "Thanks for your patience. I've thought things through so we can have a productive conversation." This immediately signals you're not reactive: You are thoughtful and solution-focused. ✅ Phase 2 - Trust Building: "I trust you and that's why I'm being straight with you." You lead with respect, making it clear this isn't about their worth as a person. ✅ Phase 3 - Context Setting: "I want to be transparent. This impacts our success." Connect the conversation to shared goals, not personal frustrations. ✅ Phase 4 - Reality Acknowledgment: "This might be hard, but I want us to work through it together." You acknowledge difficulty while committing to partnership. ✅ Phase 5 - Problem Focus: "Something's affecting your results. Let's handle it together." Action-oriented language that invites collaboration. ✅ Phase 6 - Preparation Time: "Let's meet tomorrow to review data. Bring your take." Respectful timing that allows for thoughtful responses. ✅ Phase 7 - Solution Mode: "We've been falling behind. How can we fix this together?" Partnership language focused on forward movement. The result? Conversations that could have ended relationships actually strengthened them. Hard conversations need not take a negative turn. They are investments in better outcomes. What conversation framework will you try first? ♻️ Repost this to help leaders navigate difficult conversations strategically. 🔔 Follow Dr. Oliver Degnan for more strategies on Burnout, Productivity and Leadership.