Tips for Handling Difficult Conversations as a New Manager

It was unbelievably painful. When I became a first-time manager years ago, I made all the mistakes in the book. I thought I was on the right track. In reality, something had gone awry. By avoiding hard conversations about quality of work, I hadn’t setup my report for success. And when her presentation to senior leaders fell flat, I felt devastated. I knew it was my fault. Here’s 3 things I wish I knew as a new manager: 𝟭/ 𝗛𝗮𝘃𝗲 𝘁𝗵𝗲 𝗵𝗮𝗿𝗱 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻𝘀 𝘀𝗼𝗼𝗻𝗲𝗿 I focused on building rapport (good manager), but delayed giving candid feedback to my report about her work output (bad manager). I was avoiding confrontation—procrastinating until the “right moment” struck (never did). Since then, I’ve learned to lean into the discomfort. If there’s a performance concern, sit down privately with your report, explain the concern openly, point to specific pieces of work, share examples of what “good” looks like, and invite them to give their feedback. 𝟮/ 𝗔𝗱𝗮𝗽𝘁 𝗺𝗮𝗻𝗮𝗴𝗲𝗺𝗲𝗻𝘁 𝘀𝘁𝘆𝗹𝗲 𝘁𝗼 𝘁𝗵𝗲 𝗶𝗻𝗱𝗶𝘃𝗶𝗱𝘂𝗮𝗹 The beauty and curse of managing people is that each person is a unique combination of skills, motivations, and behavior. While I can “get out of the way” for certain skilled and motivated high-performers, the same approach would be a disaster for reports who are struggling due to weaker skills. The challenge is to listen and observe your report intently—so you understand which style to use to help them perform at the next level. 𝟯/ 𝗗𝗲𝗹𝗲𝗴𝗮𝘁𝗲 𝗺𝗼𝗿𝗲 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻𝘀 As a manager, my reports frequently raise concerns about other people. Early on, I would immediately jump into problem-solving mode. This got me overwhelmed. Fast. Later, I learned to first ask, “Have you talked to the person about your concern?” 80% of the time, the answer is no. Then I would make it my mission to coach my report to independently resolve their conflict. If I succeeded, they’d be empowered to handle a wider range of situations on their own. **** P.S. If you’re making a change, I coach tech professionals to make career transitions and build wealth abroad. Slide into my DMs and join my past clients at companies like Google, Meta, Square, & Stripe.

We all know this feeling: “A hard conversation is coming” As leaders, we need to EMBRACE this. But how? This is why I created the 5 Step Accountability Dial™, take a look: #1 - "The Mention." This is all about gently pointing out an issue without making a fuss, like tapping someone on the shoulder. It’s about making a verbal observation. Consider a colleague, Alex, who's consistently late for meetings. Rather than confronting him, you can say, "Hey Alex, I've noticed you've been coming in late for meetings. Everything okay?" It's a polite way to raise awareness. Moving on to #2 - "The Invitation." After mentioning the issue, extend an open hand for a structured dialogue. It's about fostering collaboration and understanding. So, after mentioning Alex's tardiness and giving him time, you might say, "Alex, let's sit down and discuss this further. How does your schedule look this week?" This sets the stage for a more in-depth conversation. #3 - "The Conversation" is where you get to the heart of the matter. It's about clarity and exploring reasons and solutions. During the conversation with Alex, you could say, "I've noticed you're consistently late for our meetings. Can we understand if there's an underlying reason causing this?" Keep the dialogue open and solution-focused. #4 - "The Boundary"   If changes haven't occurred, set clear guidelines and expectations. Make it clear that further missteps have consequences. If Alex's punctuality hasn't improved, you might say, "We need to work on a plan to improve your punctuality. Can we specify a date for this progress?" Setting boundaries reinforces expectations. Finally, #5 "The Limit" This is when previous steps haven't led to change. It's about implementing consequences and safeguarding team interests. In Alex's case, it could be, "Despite previous discussions, I haven't seen significant progress. The responsibility to improve lies with you now. Please understand the seriousness of this issue." Maintain professionalism while upholding standards (here’s where directness is critical). It’s all about clear communication, empathy, standards, and effective leadership (most things are!). What the authenticity dial allows is a clear path for leaders to engage with their team in a structured, effective manner.

What to do when your team is making a stupid decision. This thought, by itself, is a signal for you to slow down and seek better understanding. Thinking that people around you are stupid is a terrible way to enter into a discussion. First, you need to pause your own reaction. Ask open questions, restate what you hear, and test the assumptions beneath the current plan. This approach shows respect for other's thinking, surfaces gaps that might not be obvious, and softens any perception that you are challenging for the sake of challenging. As you listen, collect the facts, metrics, or customer feedback that best illustrate why a change might help everyone reach the shared goal faster. Once you have a clear grasp of both sides, turn your insight into a concise proposal that shows you have understood the situation fully. Anchor your message to outcomes the team already values (time to market, quality, customer delight, cost). Use evidence, small experiments, or quick prototypes to show how the alternative path removes risk or adds benefit. Invite teammates to create the solution so that the "new idea" is a collective win rather than a personal mission. Keep your tone calm and collaborative throughout the process. Choose settings that encourage thoughtful dialogue, such as one‑on‑one conversations or a short working session with the most relevant partners. Use “I” statements to own your personal perspective, and ask for reactions to keep the discussion balanced. If emotion rises, pause, summarize common ground, and suggest a brief break before returning to decisions. Finally, watch your own stress signals. Use preparation, breathing, or a short walk to stay steady. Remind yourself that disagreement is normal in creative work and that long‑term relationships matter more than winning a single debate. When the team adopts an improved approach, share credit freely; if they decide to stay on the original path, document your input, express confidence in the group, and stay engaged. Your composure and constructive focus will strengthen trust and increase the chances that your next suggestion lands even more smoothly.

Managers: if someone on your team comes to you with a concern, the worst thing you can do isn’t telling them you can’t give them what they want. It’s making them feel like they shouldn’t have come to you in the first place. So how do you prevent this from happening? Here’s my advice: 1 / Listen. 2 / Thank them profusely for bringing their concern to you. 3 / Repeat back to them your understanding of their concern to make sure you got it right. 4 / Ask if they have a proposed solution before you volunteer any you might have. 5 / Brainstorm solutions with them to see if you can figure out something that works. 6 / Agree on next steps. 7 / Proactively update them; don’t ever make them feel like their concern isn’t important to you or that you forgot about it. 8 / If you can solve it for them in a way that they’re happy with, do it. If not, tell them quickly and clearly, and explain why, and again hear them out. 9 / Thank them again for bringing the concern to you. Explain why you are so glad that they brought it to you, and that you always want them to do that. Is there anything you’d add? #management #honesty #communication

Managing Difficult Conversations Original Content Creator: Harry Karydes (Give him a follow) --------------- Do you find yourself avoiding confrontation at all costs? Here's a better way: 🟢 Step 1: Setting the Stage ↳ Prepare Mindfully: Prioritize introspection to align your intentions and desired outcomes for the conversation. ↳ Cultivate Empathy: Step into the shoes of the other party to grasp their perspective and foster genuine understanding. 🟢 Step 2: Navigate Emotions ↳ Maintain Composure: Stay poised and composed, refraining from impulsive reactions triggered by emotions. ↳ Validate Feelings: Acknowledge and validate the emotions expressed by both people, creating an atmosphere conducive to constructive dialogue. 🟢 Step 3: Active Listening ↳ Listen Intently: Devote your full attention to comprehending the speaker's message without interruptions or distractions. ↳ Seek Clarification: Pose clarifying questions to ensure mutual understanding and prevent misunderstandings. 🟢 Step 4: Choose Your Words Wisely ↳ Use "I" Statements: Express your thoughts and feelings using first-person language to avoid accusatory tones. ↳ Present Solutions Positively: Frame suggestions in a constructive manner, fostering collaboration and mutual respect. 🟢 Step 5: Finding Common Ground ↳ Identify Shared Goals: Explore common objectives or values to establish a foundation for agreement. ↳ Highlight Mutual Benefits: Emphasize the advantages of resolving the issue for both parties involved. 🟢 Step 6: Manage Expectations ↳ Be Realistic: Set attainable expectations for the conversation's outcomes, considering all perspectives. ↳ Clarify Responsibilities: Clearly outline the next steps and responsibilities to uphold accountability and progress. 🟢 Step 7: Focus on Solutions ↳ Adopt a Problem-Solving Mindset: Shift the conversation's focus from assigning blame to identifying actionable solutions. ↳ Foster Collaborative Brainstorming: Encourage input from all parties to cultivate innovative approaches to problem-solving. 🟢 Step 8: Follow Up ↳ Reflect and Improve: Evaluate the conversation's effectiveness, identifying areas for refinement and growth. ↳ Schedule Follow-Up: Plan subsequent discussions to monitor progress, address any remaining issues, and ensure the implementation of agreed-upon solutions. 📌 PS...Remember, the ability to navigate difficult conversations is a skill that grows with practice and patience. ________________ Original Content Creator: Harry Karydes (Give him a follow)

Saying "this might hurt" is not the best way to soften the blow of a difficult conversation. 📌 The phrase "this might hurt" can be confusing and misleading. It can make the other person feel defensive or anxious, and it can make it difficult for them to hear what you have to say. Instead of saying, "This might hurt," it is better to be direct and honest about what you need to say. State the issue clearly and concisely, and explain how it is impacting you. For example, instead of saying, "This might hurt, but I need to talk to you about your work performance," you could say, "I'm concerned about your recent work performance. It's not meeting my expectations, and it is impacting our team." It is also essential to be open to the other person's perspective. Be willing to listen to their concerns and try to understand their point of view. This will help you to have a more productive conversation. Here are some ideas to help you deliver difficult feedback: Set aside time for the conversation. Don't try to have a difficult conversation when you are rushed, stressed, or hungry. Instead, schedule a time to talk when you can both be focused and present. Choose a private location. Have the conversation in a place where you will not be interrupted and where you feel comfortable speaking freely. Focus on the behavior, not the person. Avoid personal attacks or generalizations. Instead, focus on the specific behavior that is concerning you. Be specific and provide examples. Don't just say that the person is "doing something wrong." Instead, give specific examples of the behavior that is problematic, as you want to give them a chance to find a solution. Be open to feedback, even if you think your needs and expectations are precise. It is possible that your message was misinterpreted or that the other person has a different perspective. Be willing to concede their point of view and be open to hearing their feedback. They may have some valid points that you did not consider. If you realize that you made a mistake, apologize. Remember, difficult conversations aim not to hurt the other person. It is to communicate your needs and expectations in a way that will lead to an improved outcome. By being direct and honest and by being open to the other person's perspective, you can have more productive and effective difficult conversations. 🧙♂️ Imagine that you have a magic wand that can make one thing about difficult conversations easier. What would it be? #management #humanresources #personaldevelopment #partnerships

“My teammate is a reserved person, and I find it challenging to get them to open up during our one-on-one meetings. Whether they're uncomfortable discussing certain topics or simply prefer to keep things brief, I want to create a more meaningful connection and draw out their thoughts.” A typical situation which happens quite a lot during the career of every manager. Hopefully, there are effective tips and tricks that can help me overcome this common situation and make our one-on-one meetings more productive and insightful. 🤔💡" 🔵 Avoid the Yes/No Trap: Instead of asking questions with one-word answers, opt for open-ended inquiries that encourage more elaborate responses. For instance, replace "Did you complete the project?" with "Tell me about your progress on the project and any roadblocks you've encountered." 🔵 Start with Neutral Topics: Kick off the conversation with light and non-threatening topics to build rapport. Casual questions like "How was your weekend?" or "What are your hobbies outside of work?" can set a relaxed tone and gradually lead to deeper discussions. 🔵 Show Empathy and Patience: Recognize that some individuals take time to open up. Demonstrate genuine empathy and patience during the conversation, reassuring them that their perspectives are valued. 🔵 Listen Actively: Active listening is a superpower! 🦸♂️ Be fully present during the conversation, maintain eye contact, and nod in acknowledgment to show that you're genuinely interested in what they have to say. 🔵 Use "What" and "How" Questions: Employ questions like "What challenges are you facing in your current project?" or "How do you feel about your role in the team?" These encourage detailed responses and deeper insights. 🔵 Allow Silence: Don't be afraid of silence during the conversation. Give your direct report space to collect their thoughts and respond in their own time. 🔵 Be Supportive: Ensure your team members know that you're there to help and support them. Show appreciation for their efforts and celebrate their achievements, fostering a positive and trusting atmosphere. 🔵 Reflect and Summarize: Throughout the conversation, paraphrase their responses and summarize key points to show that you're actively engaged and value their input. 🔵 End with Encouragement: Conclude the meeting by thanking them for their honesty and contributions. Express your commitment to their growth and well-being within the organization. By incorporating these strategies, you'll create a safe and empowering space for your quieter direct reports to thrive and shine! 💪 Remember, understanding and supporting our team members is a continuous journey that enriches both their professional development and your leadership skills. #LeadershipSkills #OneonOneMeetings #OpenEndedQuestions #CommunicationTips #EmployeeEngagement #TeamBuilding 🚀🤝

How do you handle difficult conversations at work? Handling difficult conversations at work can be challenging, but following these steps can help you navigate them successfully: #1- Prepare beforehand: Think about what you want to say and the purpose of the conversation. Consider your goals, facts, and any evidence or examples to support your points. #2- Choose the right time and place: Find a suitable time and private space to have the conversation. Ensure you won't be interrupted or overheard. #3- Stay calm and composed: Keep your emotions in check and remain professional throughout the conversation. It's essential to approach it with a level head. #4- Active listening: Give the other person a chance to express their thoughts and feelings without interruption. Demonstrate that you genuinely value their input and perspective by actively listening. #5- Empathy and understanding: Show empathy by acknowledging the other person's feelings and concerns. Be understanding, and validate their experience without dismissing or minimizing their emotions. #6- Be clear and concise: Present your thoughts and concerns in a clear and concise manner. Use "I" statements to express how you feel rather than placing blame on the other person. Focus on specific behaviors or situations rather than making generalizations. #7-Seek solutions collaboratively: Instead of focusing on blame or winning the argument, aim to find mutually beneficial solutions. Discuss and explore different options together, keeping the conversation focused on reaching a positive outcome. #8- Maintain professionalism: Even if the conversation becomes heated or emotional, remember to stay professional and respectful. Avoid personal attacks or derogatory language. #9- Follow up: Once the conversation is over, summarize the discussed points and any agreed-upon actions in an email or written note. This ensures that both parties are clear about what was discussed and any next steps. #10- Learn from the experience: Take time to reflect on the conversation, identifying what worked well and what could be improved. Learning from the experience will help you handle future difficult conversations more effectively. Remember, difficult conversations are an opportunity for growth and improvement. To learn more about how to handle difficult conversations or to schedule time to talk with Dr. Linda about training for your leaders or your teams, click the link: https://lnkd.in/gyD5HmZt

🔥 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.

From a former Google Director on difficult conversations, negotiation, coaching and transparency. "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 employee 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."