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Mastering Difficult Conversations: A Guide for New Managers


Difficult conversation

As a new manager, one of the most daunting aspects of your role might not be leading projects, setting goals, or even managing your time - it’s handling difficult conversations. Whether it’s providing feedback, addressing conflict, or delivering bad news, these conversations often trigger anxiety, both for you and your team members. However, they are also essential for maintaining a healthy work environment and achieving your team’s goals. In fact, research shows that 65% of employees leave their jobs because of poor management, and communication failures often play a key role in this.


So, how can you, as a new manager, navigate these tough conversations effectively? The good news is, it’s a skill you can learn and master with practice. In this guide, we’ll explore some of the most common challenging conversations new managers face and offer practical strategies, tips, and frameworks to help you approach them with confidence and clarity.


Why Difficult Conversations Matter

Before we dive into strategies, it’s essential to understand why difficult conversations are so important. These discussions can:


  • Prevent issues from escalating: Unaddressed problems tend to snowball. What starts as a minor misunderstanding can quickly turn into a much larger conflict if left unchecked. Having regular check-ins and addressing concerns early can stop bigger problems from arising.

  • Build trust: If your team sees you can handle difficult situations with fairness and clarity, they’ll trust you more. It’s also an opportunity to show that you care about your team members’ well-being and professional growth.

  • Promote growth and development: Whether it's a performance review or a feedback session, these conversations are an opportunity to help employees improve and grow, both professionally and personally.


Now that we understand the significance of these conversations, let’s get into how to handle them.


1. Preparing for a Difficult Conversation

Preparation is key to having a successful conversation. If you’re not prepared, you’re more likely to become emotional, miss important points, or let the conversation spiral into unproductive territory. Here are some steps to ensure you’re ready:


A. Be Clear on the Objective

Before initiating any difficult conversation, ask yourself, What do I want to achieve from this discussion? Are you addressing a performance issue? Are you delivering constructive feedback? Are you working through a conflict between two team members? Being clear on the objective of the conversation helps you stay focused and guides the direction of the dialogue.


B. Choose the Right Time and Place

Timing and setting matter. Avoid initiating a tough conversation when either of you is rushed, distracted, or stressed. Choose a private, comfortable space where you won’t be interrupted, and ideally, at a time when both parties are in a calmer state of mind.


C. Prepare Your Points, But Stay Flexible

It’s tempting to script the conversation to make sure you cover all points, but this can sound rehearsed and make the other person feel like they’re being lectured. Instead, focus on key points and be open to where the conversation takes you. You want to have a two-way dialogue, not a one-sided monologue.


2. The Art of Active Listening

One of the most crucial aspects of managing difficult conversations is listening. When emotions run high, it’s easy to focus on what you want to say next rather than truly understanding the other person’s perspective. But active listening is the foundation of constructive feedback and conflict resolution.

Here’s how to actively listen during a difficult conversation:


A. Be Fully Present

Put your phone away, close unnecessary tabs on your computer, and give the person your undivided attention. Non-verbal cues, like maintaining eye contact and nodding occasionally, show that you’re engaged.


B. Listen Without Judgment

Sometimes, we listen with the intention of judging or defending our position. Instead, focus on understanding the person’s point of view, even if it’s difficult to hear. This will help de-escalate the situation and keep the conversation on track.


C. Paraphrase to Confirm Understanding

Once the person has shared their thoughts, paraphrase what they said to ensure you've understood it correctly. For example, you might say, “So, if I understand you correctly, you’re saying that you’re feeling overwhelmed with your current workload?”

This simple technique can also help them feel heard and validate their emotions.


3. Keeping Emotions in Check

Difficult conversations often trigger strong emotions - whether it's frustration, disappointment, or anger. But as a manager, you have to remain calm and composed to ensure that emotions don’t derail the conversation.


A. Stay Calm and Centered

If the other person is upset, it can be tempting to react emotionally. But keep in mind that your role is to help resolve the situation. Take deep breaths, keep your tone neutral, and focus on the facts at hand. If you feel yourself getting upset, it’s okay to ask for a brief pause to regain composure.


B. Acknowledge Emotions Without Overreacting

If the person is visibly upset, don’t ignore their emotions. Acknowledge them by saying something like, “I can see that this is frustrating for you, and I want to understand more about what’s going on.” This shows empathy and opens the door to constructive dialogue.


C. Avoid Escalating the Situation

In some cases, the conversation may become heated. If that happens, try to defuse the situation by remaining calm, acknowledging their feelings, and steering the discussion back to the issue at hand. If needed, suggest taking a break and reconvening when both parties are ready.


4. Providing Constructive Feedback

As a new manager, giving feedback - especially negative feedback - can feel uncomfortable. However, constructive feedback is one of the most powerful tools for team development. It’s essential to approach it in a way that’s motivating rather than demoralizing.


A. Use the SBI Model

A simple yet effective way to structure feedback is the SBI model:


  • Situation: Describe the situation where the issue occurred. For example, “During yesterday’s team meeting…”

  • Behavior: Focus on the behavior, not the person. Avoid generalizations or labels. For instance, “You interrupted others when they were speaking.”

  • Impact: Explain the impact of the behavior. “This made it difficult for others to share their ideas, which delayed the meeting.”


This model helps to keep the feedback objective and focused on the actions, not the individual, making it easier for them to accept and act upon.


B. Provide Actionable Solutions

After pointing out the issue, offer specific, actionable steps for improvement. This could be things like practicing active listening or ensuring that all team members have a chance to speak. Clear next steps ensure that feedback doesn’t just feel like criticism but also an opportunity for growth.


5. Navigating Conflict Between Team Members

As a new manager, you’ll likely have to mediate conflicts between team members. These situations can be tricky, especially if you’re emotionally invested or if both parties have strong opinions. Here’s how to handle these delicate situations:


A. Listen to Both Sides

First, give each party the chance to explain their point of view. Make sure they understand that their input is valued and that your goal is to help resolve the issue, not assign blame.


B. Find Common Ground

Once you have a clear understanding of both perspectives, look for common ground. What do both parties want from the situation? What are the underlying interests at play? This will help you identify potential solutions that satisfy both parties.


C. Focus on Solutions, Not Problems

Keep the conversation focused on moving forward. Encourage both parties to brainstorm solutions together, rather than dwelling on past grievances. This can create a sense of ownership over the resolution, which is more likely to lead to lasting results.


6. Following Up

Finally, don’t forget to follow up after the conversation. This is especially important when addressing performance issues or conflicts. Follow-up meetings or check-ins show that you’re committed to supporting their development and ensuring the issue is resolved.

Send a summary email of what was discussed and the next steps. Reaffirm any action plans and provide additional resources or support as needed. This will reinforce the message and help both parties stay on track.


Difficult conversations are an inevitable part of leadership, but they don’t have to be overwhelming. By preparing effectively, listening actively, managing emotions, and focusing on constructive outcomes, you can turn these challenging moments into opportunities for growth and development - for both you and your team. Remember, practice makes perfect, and as you gain experience in handling tough discussions, your confidence and effectiveness will only improve.


So, as you navigate your new role as a manager, embrace these conversations as a chance to demonstrate your leadership skills and commitment to fostering a positive, productive work environment. With the right tools and mindset, you can master even the most difficult conversations with grace and success.


Are you a new manager looking to improve your leadership skills? Or is your company lacking an effective and affordable training program for new managers? Our innovative, fully self-directed, Emerging Leaders Program may be your solution. Visit www.leadwise.app to learn more.

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