Communicating Effectively with Challenging Personalities

When I'm negotiating, I tend to AGREE with the other side. Sounds counter-intuitive. But it's enabled me to close 7-figure settlements. Most lawyers think negotiations are about being tough, standing your ground, and not giving an inch. I take the opposite approach: tactical empathy. Here's how it works. When opposing counsel says something like, "That's a ridiculous settlement demand. We can never possibly pay that much," I don't fight back. Instead, I validate them: "I can see why you would say that. I'm sorry for that. What can I do to come up with an offer that makes sense for you? My client is unfortunately stuck here." Their reaction? Complete confusion. They're prepared for a fight. They've got their counterarguments lined up. But when I validate their feelings instead, their entire script falls apart. The best part? They start giving me information I can use to negotiate against them. When faced with validation instead of opposition, lawyers suddenly start explaining their real constraints, their client's actual position, and sometimes even what number they might actually be able to get approved. All because I didn't argue. I've found this approach works especially well on lawyers because they don't even know what's happening. They're so used to adversarial negotiations that genuine validation short-circuits their usual approach. The key elements: • Validate their emotions • Acknowledge their position • Ask questions instead of making demands • Keep validating even when they try to be difficult This isn't just about being nice – it's strategic. By removing the confrontation, you force them to either engage constructively or look unreasonable. Next time you're in a difficult negotiation, try validation instead of opposition. It feels counterintuitive, but the results speak for themselves. After all, the goal isn't to win the argument – it's to get what your client needs.

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.

As leaders, we often have to deal with more than just managing projects...we have to manage people, and not all of them are easy to work with 👀 Whether it’s a toxic colleague, a difficult client, or someone who thrives on conflict, these situations can derail progress if you’re not equipped to handle them effectively... 🟠 One technique to help you with this is the D.E.E.P technique. ➡️This communication strategy helps you stay composed, set boundaries, and avoid getting pulled into unnecessary conflict. ❊ 𝗛𝗲𝗿𝗲’𝘀 𝗵𝗼𝘄 𝘆𝗼𝘂 𝗰𝗮𝗻 𝘂𝘀𝗲 𝗶𝘁 𝗮𝘀 𝗮 𝗹𝗲𝗮𝗱𝗲𝗿 𝘁𝗼 𝗺𝗮𝗶𝗻𝘁𝗮𝗶𝗻 𝗳𝗼𝗰𝘂𝘀 𝗮𝗻𝗱 𝗽𝗿𝗼𝘁𝗲𝗰𝘁 𝘆𝗼𝘂𝗿 𝗲𝗻𝗲𝗿𝗴𝘆: 🔹 𝗗𝗼𝗻’𝘁 𝗗𝗲𝗳𝗲𝗻𝗱: When you’re dealing with someone who’s pushing your buttons—especially a toxic personality—resist the urge to defend yourself. In the workplace, defending every decision or action often just fuels the fire. Remember, toxic individuals often don’t care about your reasoning; they care about controlling the conversation. As a leader, your energy is better spent on moving the team forward, not justifying every move. Practice detachment and stay focused on your bigger goals. 🔹 𝗗𝗼𝗻’𝘁 𝗘𝗻𝗴𝗮𝗴𝗲: Difficult personalities thrive on drawing you into their chaos. It’s easy to get pulled into emotional battles, especially if it feels personal. But as a leader, you need to take a step back and ask yourself: Is engaging with this person productive, or is it a drain on my energy? Often, disengagement—keeping responses minimal and factual—takes away the power they have over you. By not engaging emotionally, you keep the conversation focused on solutions, not drama. 🔹 𝗗𝗼𝗻’𝘁 𝗘𝘅𝗽𝗹𝗮𝗶𝗻: It’s tempting to over-explain yourself, especially if you’re someone who values fairness and clarity. But toxic individuals usually aren’t looking for understanding; they’re looking for control. Over-explaining only feeds that need. Keep your responses clear, direct, and to the point. You don’t owe anyone a lengthy justification, especially when your leadership decisions are based on sound judgment. 🔹 𝗗𝗼𝗻’𝘁 𝗣𝗲𝗿𝘀𝗼𝗻𝗮𝗹𝗶𝘇𝗲: One of the hardest lessons I’ve learned as a leader is that not everything is about me. It can feel personal when someone’s being difficult, but toxic behavior often has more to do with the person causing it than the person on the receiving end. Don’t take it personally. Detach from their negativity, and remember: your leadership is defined by how you manage these situations, not by their opinion of you. •••••• The more time you spend defending, engaging, and explaining, the less time you actually spend leading effectively. Ultimately, leadership 𝗶𝘀𝗻’𝘁 𝗮𝗯𝗼𝘂𝘁 𝘄𝗶𝗻𝗻𝗶𝗻𝗴 𝗲𝘃𝗲𝗿𝘆 𝗮𝗿𝗴𝘂𝗺𝗲𝗻𝘁; it’s about knowing which battles are worth your energy and which aren’t. Difficult personalities will always exist, but they don’t have to shake your leadership 🙏🏻

Conflict is inevitable. How we manage it is both an art and a science. In my work with executives, I often discuss Thomas Kilmann's five types of conflict managers: (1) The Competitor – Focuses on winning, sometimes forgetting there’s another human on the other side. (2) The Avoider – Pretends conflict doesn’t exist, hoping it disappears (spoiler: it doesn’t). (3) The Compromiser – Splits the difference, often leaving both sides feeling like nobody really wins. (4) The Accommodator – Prioritizes relationships over their own needs, sometimes at their own expense. (5) The Collaborator – Works hard to find a win-win, but it takes effort. The style we use during conflict depends on how we manage the tension between empathy and assertiveness. (a) Assertiveness: The ability to express your needs, boundaries, and interests clearly and confidently. It’s standing your ground—without steamrolling others. Competitors do this naturally, sometimes too much. Avoiders and accommodators? Not so much. (b) Empathy: The ability to recognize and consider the other person’s perspective, emotions, and needs. It’s stepping into their shoes before taking a step forward. Accommodators thrive here, sometimes at their own expense. Competitors? They might need a reminder that the other side has feelings too. Balancing both is the key to successful negotiation. Here’s how: - Know your default mode. Are you more likely to fight, flee, or fold? Self-awareness is step one. - Swap 'but' for 'and' – “I hear your concerns, and I’d like to explore a solution that works for both of us.” This keeps both voices in the conversation. - Be clear, not combative. Assertiveness isn’t aggression; it’s clarity. Replace “You’re wrong” with “I see it differently—here’s why.” - Make space for emotions. Negotiations aren’t just about logic. Acknowledge emotions (yours and theirs) so they don’t hijack the conversation. - Negotiate the process, not just the outcome. If you’re dealing with a competitor, set ground rules upfront. If it’s an avoider, create a low-stakes way to engage. Great negotiators don’t just stick to their natural style—they adapt. Which conflict style do you tend to default to? And how do you balance empathy with assertiveness? #ConflictResolution #Negotiation #Leadership #Empathy #Assertiveness #Leadership #DecisionMaking