Don't shy away from tough conversations, they're the only ones that actually matter. I spent three weeks avoiding a conversation with a key customer who'd gone quiet after our last demo. I kept telling myself they were "just busy" or "evaluating internally." Finally, I called them directly: "I get the sense something didn't land right in our last conversation. Can you help me understand what happened?" Their response changed everything. "Honestly, your solution is impressive, but it solves a problem we had six months ago. Our priorities have completely shifted, and we didn't know how to tell you." That five-minute conversation saved us weeks of follow-up emails and gave us crucial market intelligence about how customer needs were evolving. Here's what I've learned about tough conversations: The longer you wait, the tougher they get. That awkward silence after a proposal isn't going to resolve itself. Address it directly. Most "tough" conversations aren't actually tough. They're just uncomfortable because we're afraid of what we might learn. The information you get is always more valuable than the comfort you preserve. Even brutal feedback moves you forward faster than polite silence. Three conversations I stopped avoiding: "It seems like this isn't a priority anymore. Should we pause?" (Usually reveals the real timeline and decision-making process) "What would need to change for this to be a clear yes?" (Gets to actual objections instead of vague concerns) "Who else needs to be convinced, and what are they worried about?" (Exposes the real decision-making structure) The pattern: Every tough conversation I've delayed has gotten easier once I actually had it. The counterintuitive result: Customers respect directness. They'd rather have an honest conversation than continue a polite charade. What conversation are you avoiding right now? What would happen if you had it this week instead of next month?
Why I stopped avoiding tough conversations with customers
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Your comfort zone might be costing you. Whether it’s politics at the dinner table, tensions at work, or exchanges online, many of us have gotten a little too cozy avoiding discomfort. But the conversations that make you want to shut down or run in the other direction are often the ones you most need to stay in. Overcoming division and polarization isn’t just about finding common ground. It requires learning to stay engaged even when you want to bolt. Real connection across difference almost always involves some level of tension, defensiveness, or moments when you’re tempted to change the subject. The goal isn’t to eliminate discomfort; it’s to develop the skills to move through it productively. This builds genuine empathy and stronger relationships, instead of fragile harmony. 3 ways to stay engaged when conversations get uncomfortable: 1. Stay Curious – When someone says something that activates you, pause before defending or dismissing. Ask: “Help me understand your perspective on this.” 2. Notice What Pushes Your Buttons – When do you shut down, get defensive, or dismiss other perspectives? This awareness helps you identify and interrupt your patterns. 3. Repair, Don’t Retreat – When a conversation goes sideways (and it will), focus on getting back on track. Try: “I think I missed something important you were trying to tell me.” That knot in your stomach during a tough conversation? It’s what growth in real time feels like. Despite all the division around us, most of us still crave real connection—even with people who see the world differently. The key is learning that the path there runs directly through discomfort, not around it. What helps you to engage productively across difference? Please share your strategies in the comments.
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No one likes a difficult conversation... These 8 reframes make them easier. Credit to Scarlett McCabe. Follow her for more content like this. Original post below: _____ No one likes a difficult conversation... These 8 reframes make them easier. The biggest myth in difficult conversations---that the right words will magically appear in the moment. They won't. But these practical swaps will help you navigate them with confidence: 1. Instead of: "We need to talk..." Say: "I'd like to share some observations and get your perspective." Why: Reduces immediate defensive reactions and shows you value two-way dialogue. 2. Instead of: "The problem is..." Say: "Here's the situation as I understand it..." Why: Creates space for different viewpoints without assigning blame. 3. Instead of: "You always/never..." Say: "I've noticed that recently..." Why: Focuses on specific instances rather than character judgments. 4. Instead of: Starting with complaints Say: "My goal for this conversation is..." Why: Sets a constructive tone and clear direction. 5. Instead of: "You made me feel..." Say: "When [situation happens], I feel..." Why: Takes ownership of your emotions while clearly linking them to specific actions. 6. Instead of: Avoiding silences Say: "Let's take a moment to consider this." or “Lets come back to this” Why: Gives both parties time to process and respond thoughtfully. 7. Instead of: Pushing for immediate solutions Say: "What options do you see for moving forward?" Why: Invites collaboration rather than forcing outcomes. 8. Instead of: Ending vaguely Say: "Let's agree on next steps and check in [specific time]." Why: Creates accountability and clear path forward. These phrases are particularly relevant where there is a power dynamic at play. Remember---difficult conversations become easier when you focus on clarity over comfort. _____ ♻️Repost to help someone in your network. 🔔Follow The Success Method by Luke Tobin for more. 📈Join 60,000+ High-Performers, Getting Stronger, Smarter, and More Successful Every Week. 🎯Click here to subscribe to my FREE weekly newsletter: https://lnkd.in/e_Bv9r2i
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A Difficult conversation is any discussion where stakes are high, opinions differ, and emotions run strong. These often involve sensitive topics like performance issues, personal conflicts, boundary-setting, or delivering bad news. Here are some key points to handle them well: 1. Prepare Yourself First Be clear about your purpose: What do you want out of this conversation? Anticipate the other person’s perspective and emotions. Regulate your own emotions—go in calm, not defensive. 2. Start with Respect Use a neutral and non-accusatory tone. Begin with something like: “I’d like us to talk about something important, because I value our relationship/work together.” 3. Focus on the Issue, Not the Person Describe facts, not judgments. Example: “The report was delayed” instead of “You’re careless.” 4. Listen Actively Let them share their side without interruption. Show empathy even if you disagree: “I hear that you felt…” 5. Seek Common Ground Ask open-ended questions: “How do you see this?” Aim for problem-solving together instead of blaming. 6. Stay Solution-Oriented End with actionable next steps. # Difficult Conversations by Douglas Stone / Bruce Patton / Sheila Heen
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What’s one piece of advice you’ve been known to ignore? I’ll go first. “Just get over it.” Receiving this type of feedback — especially in the work place — is akin to being told to calm down. Ima do the opposite. Damn near every time. This is not good advice to give someone. I don’t care how close you are to the receiver. You’ll be closer to being throat punched than thanked for offering such “sage” advice. The reasons are pretty obvious, but I’ll restate for the people in the back: 1. If your goal is to shut down communication entirely, congratulations! You’ve instantly succeeded. You’ve not opened any space for communicating real feelings, you’ve closed them down; and likely indefinitely. 2. If you think everyone feels / processes pain the same way you do, I pity your loved ones. You’re the person that minimizes others’ experiences and makes them question their sanity. You should be in charge of nothing. 3. If you block the complexity of a situation with the “simple” solution of getting-over-it, you’re goal is really to make yourself feel safe. Again, well done! You will never be the person others go to for support or guidance. You will always be that guy / gal with whom people avoid having any kind of meaningful exchange. If most of your interactions start / end with polite nods in passing or pointless chats about the weather, think about the why. It’s not always because of this terrible advice, but if you’ve given it you may recognize a lot of the above. Do better. Most people can get over just about anything. In their own time. In their own way. Be a bridge to that place, not a boulder blocking the path.
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Your Tone Speaks Louder Than Your Words We’ve all been there receiving a message or having a conversation and immediately sensing something beyond the words. In work, your tone of voice can: ✔️Build trust or erode it ✔️Show confidence or uncertainty ✔️Motivate or frustrate Consider this: A client asks for an update. You respond, “I’ll get to it.” Flat, rushed, or indifferent tone? They feel ignored. Warm, attentive tone? They feel prioritized. A colleague sends feedback. You say, “Noted.” Cold and curt? It may spark tension. Calm and appreciative? You strengthen the relationship. Even in emails, calls, or virtual meetings, your tone sends signals that words alone can’t carry. The same sentence can be received as helpful or harsh depending on how it’s delivered. For those of us in customer support, virtual assistance, or executive support, mastering tone isn’t optional, it’s a superpower. Pro tip: Before sending a message or replying to a client, ask yourself: "If I were on the other side, how would this make me feel?" What’s one time your tone (or someone else’s) completely changed the outcome of a conversation at work? Share your experience in the comments,I’d love to hear it too! Happy Mid-Week❤
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I’m reviewing a transcript of a “difficult conversation” a leader had that could have gone better. Their angle on the conversation was good and they learned a few things... But I noticed a few of things that needed to be tweaked, all to improve her ability to get to an outcome that the "other side" could agree to. Here are 5 things I’m fixing. Might help your own difficult conversations too: 1. 𝗦𝘁𝗮𝗿𝘁 𝘁𝗵𝗲 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻 𝘄𝗶𝘁𝗵 𝗮 𝘀𝗵𝗮𝗿𝗲𝗱 𝗽𝘂𝗿𝗽𝗼𝘀𝗲: shift from “I wanted to talk to you about last week’s hand-off” to “I want to make sure our two teams are successful together” → This is a strong signal you’re here to work WITH them and not work ON them 2. 𝗕𝗲 𝘁𝗿𝗮𝗻𝘀𝗽𝗮𝗿𝗲𝗻𝘁, 𝗻𝗼𝘁 𝗷𝘂𝗱𝗴𝗺𝗲𝗻𝘁𝗮𝗹: move from fixing (“you’ve got to stop doing X”) to describing “When you do X, it has Y impact”) → “Fixing” raises defenses, “describing” lowers them 3. 𝗦𝘄𝗮𝗽 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝘄𝗶𝘁𝗵 𝗹𝗶𝘀𝘁𝗲𝗻𝗶𝗻𝗴: instead of peppering them with questions (“why X” “what about Y”), listen to what they’re saying instead (“you didn’t realize the impact this had?”) → Questions make people explain themselves, listening makes them feel understood 4. 𝗠𝗮𝗸𝗲 𝗿𝗼𝗼𝗺 𝗳𝗼𝗿 𝗿𝗲𝗽𝘂𝘁𝗮𝘁𝗶𝗼𝗻: Go beyond the facts (“This is best practice”) and consider feelings and reputation (“Will this make you look bad to your customer?”) → Most disagreements are fueled by emotional concerns. If you’re not talking about them, you’re not solving the whole problem 5. 𝗔𝗴𝗿𝗲𝗲 𝗼𝗻 𝗽𝗿𝗼𝗯𝗹𝗲𝗺𝘀 𝗯𝗲𝗳𝗼𝗿𝗲 𝗳𝗶𝗻𝗱𝗶𝗻𝗴 𝘀𝗼𝗹𝘂𝘁𝗶𝗼𝗻𝘀: When you think you’re ready to start solving, double check (“So, sounds like this is mainly a communication problem, right?” “Exactly!”) → Agreeing on the problem is the start of working as partners Teams that do these five things know how to turn their problems into partnerships. How do you make sure your difficult conversations are win-win?
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Handling “intrusive” questions at work👇 We all have different limits on what we feel comfortable sharing, and just because someone is curious doesn’t mean we owe them personal information. Questions like “Do you have a boyfriend or a girlfriend?” might seem friendly to some, but for others they can feel intrusive or inappropriate, especially in a work context. If someone oversteps your boundaries, you don’t have to answer. You can respond calmly and respectfully, then redirect the conversation. You might say: “Thanks for showing an interest, I prefer to keep personal things private.” “I’d love to talk about [X topic] though, shall we talk about that?” This keeps the tone kind but firm, and helps you maintain control of the conversation. It’s not necessarily wrong to ask personal questions, but it is important to read the room and respect when someone sets a boundary. 💬 Have you ever been in a situation like this, on either side? Share your experience & advice in the comments 👀 📌 Please note the advice in this post is general and won’t fit every situation. Use your judgement and adapt it to your context. ➕ Follow Claire Benjamin for more strategies on navigating tricky situations at work
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A quiet blind spot that wrecks good conversations: "We judge others by the impact of their communication. We judge ourselves by our intent (which is invisible)." Think about your last hard conversation or disagreement. When someone hurt you, you felt the sting of their words. Impact was undeniable. When you hurt someone, you probably defended yourself: “That’s not what I meant.” “You misunderstood.” "I was just trying to help." Intent felt obvious to you. That’s a communication paradox. We give ourselves the benefit of the doubt we rarely extend to others in conversations. At work, “constructive feedback” can land as criticism. Your team doesn't see your intent, only the stinging impact of the review of their work. In sales, “helpful questions” can feel like pressure to a prospect instead of curiosity and genuine desire to solve their problems. At home, “problem-solving” can make your spouse or kids feel unheard when all you were trying to do was offer a winning solution. The fix isn’t complicated, but it may be uncomfortable at first. Stop defending your intent. Start owning the impact. Try: “It sounds like that landed differently than I meant. Can you share what you heard?” When you acknowledge impact first, people become curious about your intent. When you defend intent first, they stop listening entirely. Where have you seen this gap between intent and impact? What phrasing helps you bridge it?
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Ambushed in a Meeting? How to Bounce Back as the Adult in the Room It’s happened to me more than once. You walk into a meeting thinking you’re here to discuss X. Then, out of nowhere, someone lobs Y at you — a criticism, a surprise decision, a loaded question — and suddenly the whole conversation shifts. Your heart rate spikes. Your brain scrambles for a comeback. And afterward, you replay the moment thinking, “I should have said…” Here’s what I’ve learned about recovering — and reclaiming your footing. 1. Pause Before You React In the moment, silence can be a superpower. Take a breath. Jot down the key point you just heard. Pausing signals composure, not weakness. 2. Park It, Don’t Dodge It If you need time to think or get facts, say: "That’s an important point — let’s set it aside for a moment so I can get you a solid answer." This moves the conversation forward without letting the ambush derail you. 3. Reframe After the Meeting Follow up — in writing or in person — with a clear, concise response. This lets you address the issue when you’re prepared and keeps you in control of the narrative. 4. Focus on the Relationship, Not Just the Point An ambush often says more about the person delivering it than about you. Ask yourself: Was this a misunderstanding, a power play, or a genuine concern? Your long-term strategy should focus on keeping communication channels open — even with challengers. 5. Learn, Don’t Linger Instead of replaying what went wrong, use it as a diagnostic tool: Could I have anticipated this? Do I need better data at my fingertips? Do I need allies in the room next time? The “adult in the room” isn’t the one who never gets rattled — it’s the one who gets rattled and still chooses to respond with clarity, control, and grace. Think of it like walking onto a stage mid-performance. You didn’t write the first act. You don’t control the lighting. But you can still deliver your lines with such poise that the audience remembers your presence — not your surprise.
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12 Phrases That Kill Work Conversations (and What to Say Instead) High emotional intelligence isn’t about being the loudest, it’s about keeping dialogue open. 1. When You’re Wrong ❌ Defend yourself → ✅ I was wrong about that. 2. When You Need Support ❌ Struggle alone → ✅ I need some help. 3. When You Don’t Know ❌ Pretend to know → ✅ I don’t know enough to make that call. 4. When Someone Disagrees ❌ Argue your point → ✅ You might be right. 5. After a Mistake ❌ Blame others → ✅ That’s on me. 6. When Making Decisions ❌ Assume you know best → ✅ Let’s hear your perspective first. 7. When It’s Tough ❌ Hide the issue → ✅ This isn’t working. 8. Too Many Tasks ❌ Take on everything → ✅ I’ll need a hand with this. 9. Unrealistic Deadlines ❌ Agree blindly → ✅ Let’s set a more realistic date. 10. Need More Time ❌ Respond quickly → ✅ Let me think and get back to you. 11. Against Your Values ❌ Say yes out of fear → ✅ Not for me, thank you. 12. When You Disagree ❌ Stay silent → ✅ I disagree, and here’s why. Small shifts in language = big shifts in trust, collaboration, and respect. Which one do you see most often at work? Positioning the Top 1% as Industry Authorities on LinkedIn while Generating 3-5 Warm Leads Monthly
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Global Customer Success Leader | Advisor | Former Apple, VMware, CloudHealth, InfoScout, Watsco, Motorola, Leanpath
1moWhile I generally agree with you, just be mindful of cultural differences. Americans highly value direct communication, but it can be viewed as insulting in some cultures.