How to Navigate Key Conversations

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?

Starting a difficult conversation at work can feel really intimidating and overwhelming. You know it’s necessary, but where do you even begin without causing more issues? 🤔 Thing is, having these conversations is crucial for a healthy workplace. As much as you may want to avoid them, we need them. The good news is, there are ways we can navigate these conversations in a healthy and productive way. So, here are tips to initiate challenging convos: 🎯 Prepare yourself. Before diving in, take some deep breaths to calm your nervous system and a moment to reflect on your goals for the conversation. What is your intention and the ideal outcome? What other ways could this turn out? How can you cope with an outcome that is different from your vision? Going in with a level of clarity in your own mind can lead to a more focused and effective discussion. 🕒 Choose the right time and place. Timing is everything. Find a private, neutral setting where both parties feel comfortable and are less likely to be interrupted. 🗣️ Be clear and direct. Clearly and calmly state the issue but do so with respect and understanding. This can help lower guards and reduce misunderstandings. 🤝 Focus on solutions. Approach the conversation with a solution-oriented mindset instead of just showing up with more problems to call out. I always like to have some ideas of my own and make sure I open the door to hear theirs as well. When you can listen actively to their side, rather than pointing fingers, it encourages a more productive and less defensive dialogue. 🌱 Follow up. After the conversation, check in with the other person. This can help show you’re committed to ongoing support and resolving the issue together. Difficult conversations are part of growth personally and professionally and help us to create a psychologically safe workplace. By approaching them thoughtfully, we can turn challenges into opportunities for understanding and collaboration. 👇 Have you had to start a tough conversation at work? How did you approach it? Share your experiences and tips! Creating norms around difficult conversations tends to come up in our Psychological Safety training programs. DM me to learn more! 🖤 Create a great day! #MakoMindfulness #MindfulnessTraining #StressManagement #PsychologicalSafety #TrainingAndDevelopment #StaffDevelopment

This is hard to admit: even though it's a big part of my work as a COO, I still get anxious before a difficult conversation with a teammate. But, I've learned a few tricks over the past 25 years that have helped me feel more confident in the effort, even if it still isn't any fun.... 1. BUILD A CONVERSATION MAP What context can you provide for how you've come to this conversation? What is your end goal or the next step and can you clearly articulate it? This is no time for passive language. 2. BE CLEAR UP FRONT I don't slowly wade into the conversation - I start off by stating it's going to be a difficult conversation. It takes the pressure off of me at the beginning and, again, avoids passive language. 3. APPROACH THE CONVERSATION WITH CURIOSITY After I identify the purpose of the conversation (the problem) and detail the context (the evidence), I create space for the other person to share. If there is one thing I've learned in leadership, it's that you can't make assumptions about 'the why'. Difficult conversations open up space for YOU to more fully understand the systemic pressures of their work. 4. REMEMBER: IT'S NOT THEIR JOB TO MAKE YOU FEEL BETTER ABOUT THE CONVERSATION How often do you apologize in a difficult conversation? In what other ways do you try to show empathy, by shifting the focus to how you feel badly? It's not their job to make you feel better about it. Approach the conversation with confidence and compassion - and, remember that the best you can gift them in that moment is clarity and space. reminder: The Big Lil is launching a monthly newsletter full of strategy and partnership for leaders of mission driven start-up's, small businesses, and nonprofits. Sign up here: https://lnkd.in/gf9Dt4c8

You’re not stuck. You’re avoiding a hard conversation. And the longer you wait, the worse it gets. Most “stuck” teams aren’t under-resourced. They’re under-communicated. I've seen it firsthand..and been guilty myself. I've let  ↳ The team carry one person’s slack ↳ Morale quietly erode due to inaction ↳ Needed decisions get delayed to "process further" Hard conversations aren’t mean. They’re leadership. They protect your team from burnout. They create alignment and momentum. They stop resentment before it spreads. If you've been avoiding something hard, start here: 1️⃣ Name what you've been dodging. → What needs to be said, but hasn't? → What decision have you been sidestepping? 2️⃣ Acknowledge the cost of inaction. → What has your delay cost the team? → Who’s picking up what shouldn’t be theirs? 3️⃣ Stop carrying what’s not yours. → Don't cover for someone out of fear. → Your protection may be their limitation. 4️⃣ Say the hard thing, clearly and kindly. → Don’t bury truth in soft language. → Clear is kind. Vague is exhausting. Dragging your feet helps no one. And it’s costing you and your people. Leadership starts with honesty. And honesty creates healthy teams. What conversation have you been avoiding? ♻️ Repost to help more leaders lead courageously. For more:  🔔 Follow me, Paul DiCicco.  ✉️ Try the Lead Well, Live Well Newsletter: https://lnkd.in/e-8fvs8d

Even as a seasoned executive, I still feel that knot in my stomach before a #tough_conversation. With a team member whose performance is slipping. A peer creating friction. Or a partner across the table when I have to deliver bad news. I’ve learned that avoiding it only erodes trust. A while back, I had to tell a long-time partner that a key project milestone would be missed due to an interconnection delay beyond our control. I knew it would land hard - it meant financial strain for both sides. I could’ve sent an email. Instead, I picked up the phone. I acknowledged their frustration, laid out the facts, and - most importantly - offered options for moving forward. It wasn’t an easy conversation, but it preserved the relationship because it became a negotiation, not just bad news. Here’s what works, whether you’re talking to a subordinate, a peer, or a counterparty: - Lead with context, not blame. Show why the conversation matters and connect it to the bigger picture. - Be specific—and bring options. Don’t just drop the problem. Share what’s at stake and what’s possible. - Invite dialogue, not just agreement. Pause. Ask, “How does this feel to you?” or “What’s the best way forward from your perspective?” Even after decades in leadership, I still feel a flicker of discomfort before these talks. But that discomfort is a signal - you’re about to build trust, not lose it. How do you handle the tough talks?

Early in my career, I needed to tell a senior executive that his behavior was harming morale. I 𝐀𝐆𝐎𝐍𝐈𝐙𝐄𝐃 over how to have this tough talk without endangering my job. There was no easy way around it. This was going to be 𝐇𝐀𝐑𝐃. Ultimately, we sat down together in a neutral setting. I focused on my desire to see the team thrive. The executive, while surprised, appreciated my honesty. We had an open dialogue, and things improved. It was a growth moment for both of us. 𝐒𝐔𝐂𝐂𝐄𝐒𝐒! 𝘏𝘖𝘞'𝘋 𝘐 𝘋𝘖 𝘐𝘛? Here are three things that have always worked best for me: 1. 𝐁𝐞 𝐜𝐥𝐞𝐚𝐫 𝐚𝐧𝐝 𝐟𝐨𝐜𝐮𝐬 𝐨𝐧 𝐭𝐡𝐞 𝐢𝐬𝐬𝐮𝐞, not the person. Make it about solving problems, not attacking character. 2. Listen first, then speak. 𝐒𝐞𝐞𝐤 𝐭𝐨 𝐮𝐧𝐝𝐞𝐫𝐬𝐭𝐚𝐧𝐝 before asking to be understood. 3. 𝐅𝐢𝐧𝐝 𝐜𝐨𝐦𝐦𝐨𝐧 𝐠𝐫𝐨𝐮𝐧𝐝. Align on shared goals and good intentions to prevent discord. Courageous conversations require emotional intelligence, empathy, and care. With the right mindset and approach, you can express yourself effectively while minimizing defensiveness in others. 𝑾𝒉𝒂𝒕'𝒔 𝒎𝒂𝒅𝒆 𝒚𝒐𝒖𝒓 𝒄𝒐𝒖𝒓𝒂𝒈𝒆𝒐𝒖𝒔 𝒄𝒐𝒏𝒗𝒆𝒓𝒔𝒂𝒕𝒊𝒐𝒏𝒔 𝒔𝒖𝒄𝒄𝒆𝒔𝒔𝒇𝒖𝒍? Share one tip below for constructively having necessary but tough talks. I look forward to learning from your experiences!

Dreading that Difficult Conversation? Sometimes the most Difficult Part of a Difficult Conversation is getting it started. Here are 3 Techniques from 3 Thought Leaders. 1) Acknowledge Responsibility - Mel Robbins State your responsibility for the cause of the conversation - "I recognize that I should have shared these misses with you sooner" This is my most common go-to. In nearly all conversations I address how I could have done more first. This allows me to diffuse the other person's emotions. And as Mel puts it: Set a more level playing field. 2) "I am going to say this in a kind way, but at the same time I want to be 100% clear" - Josh Etress ⚡️ Josh directs us to - Say this, in a low, slow, and direct voice. Braces the person for what is to come. Add "I know this isn't going to be easy" at the beginning to prepare the person emotionally. I have used this a few times recently and it is a great starter. For myself and my nerves and the emotions of the person receiving. 3) "I need to have an uncomfortable conversation with you." - Simon Sinek Allows them to be prepared and less defensive. And if you do not trust your skills for having the conversation, the next bit of advice is fantastic: "I am afraid of having this conversation because I'm afraid I'll say the wrong thing or it'll come out the wrong way and make things worse. So please be patient with me as I fumble through this but it is more important to me that I have the conversation and try to address this situation than to avoid it because this relationship matters to me and I want to go through this with you. Can we have this conversation now? Here I have acknowledged that the conversation may be clunky. I also ask for permission - to ensure that the person is ready for the conversation as well. By acknowledging these things up front, saying the wrong thing can be addressed immediately and not derail a conversation. In any Difficult Conversation, having the conversation is most important. And I hope 1 of these 3 ways helps you to get it started. Move towards Conflict. Make Growth happen.

Hard conversations don’t have to be quite so hard if you understand how to approach them — and what to say. Preparation is important. Before the #conversation, give thought to what you want for the relationship. I once had a boss I didn’t fancy all the much (haven’t we all!) When I stopped to consider what I wanted for the relationship, I realized we didn’t have to like each other—but it was important that we respect each other. With that in mind, I started the conversation with a statement of mutual respect and a curious mindset. If you are approaching someone about a behavior, you’d like them to stop, this wording might be helpful: “(Name) I really appreciate X about you. There is one thing I’m curious about though. I’ve noticed you often do Y. Help me understand how Y helps you do Z.” A statement like this mitigates defensiveness and gives insight into why the other person does what they do. You can then share how the behavior impacts you and move to brainstorming a solution. My boss and I never warmed up to each other. But I did get her to stop looking at her watch & rolling her eyes when I arrived at the office at 9:30 am each day implying I was late and lazy. She had never before realized that when she left the office at 3:00 pm, I was still there. And would be until 7:00 pm. Preparation = managing nerves = mutual respect = an easier ‘hard’ conversation. #toughconversations #crucialconversations #courageousconversations