How to Conduct Difficult Conversations
The ability to conduct difficult conversations is an inevitable part of leadership, yet it is one of the most challenging skills for new managers to master. How leaders handle these interactions can significantly impact team morale, trust, and overall performance. Research underscores that effective communication in difficult situations not only improves employee engagement but also reduces turnover and fosters a culture of accountability.
The Top 7 Most Dreaded Conversations for New Managers
Data from people manager assessment centers consistently reveal that certain conversations provoke the most anxiety for new managers. These interactions test both confidence and communication skills, yet they are critical for building credibility and trust within a team. The seven conversations new managers most often struggle with include:
- Compensation Discussions
Talking about pay is inherently sensitive. Whether addressing raises, bonuses, or salary adjustments, these conversations require transparency, fairness, and tact to maintain morale and motivation.
- Addressing Inappropriate Behavior
Confronting unprofessional conduct — whether harassment, insensitivity, or breaches of policy — can be uncomfortable. Managers must act decisively while remaining objective and respectful, ensuring that boundaries and expectations are clear.
- Navigating Difficult Personalities
Conflicts with strong-willed or challenging team members test a manager’s diplomacy and patience. Handling these personalities effectively requires empathy, consistency, and skill in setting behavioral expectations.
- Managing Poor Performance
Providing constructive feedback about performance deficiencies is essential, yet stressful. Managers must clearly define the gap between expectations and outcomes while outlining actionable steps for improvement.
- Promotion and Advancement Decisions
Conversations about promotions — or lack thereof — can create disappointment or resentment. Managers need to communicate decisions clearly, explain the rationale, and outline pathways for future growth.
- Owning Mistakes
Admitting personal errors may feel risky, but apologizing with accountability models integrity and fosters a culture of psychological team safety. Employees respond positively when leaders acknowledge missteps and demonstrate learning from them.
- Addressing Lack of Accountability
When team members fail to take responsibility for their work, managers must intervene to clarify expectations and reinforce consequences. This conversation is crucial for maintaining high standards and a culture of ownership.
Recognizing and preparing for these high-stakes discussions equips new managers to approach them with confidence, empathy, and clarity — turning moments of discomfort into opportunities for growth.
Top 7 Field-Tested Tips for New Managers on How to Conduct Difficult Conversations
Here are a few field-tested tips on how to conduct difficult conversations better as a new manager:
- Prepare Thoroughly
Preparation is the cornerstone of any successful difficult conversation. Before engaging, clarify your objective — what outcome are you hoping to achieve? Collect relevant facts and examples to support your points, avoiding hearsay or assumptions. Preparation also involves anticipating potential reactions and thinking through how you will respond calmly and constructively.
Managers who enter conversations without a clear purpose risk escalating tension or causing confusion.
- Choose the Right Setting
While it may seem trivial, the environment in which you hold a conversation matters. Private, quiet spaces signal respect and discretion, while public or noisy areas can amplify stress and defensiveness. Scheduling the conversation in advance rather than addressing issues spontaneously allows both parties to mentally prepare and signals that the discussion is important but manageable.
Timing matters too — avoid starting difficult conversations during moments of high stress or immediately before critical deadlines.
- Don’t Procrastinate
Delaying a tough conversation never makes it easier. In reality, avoidance amplifies the problem — your anxiety grows, the issue festers, and the eventual discussion becomes even more complicated. Take the time to prepare, get clear on the outcome you need, and allow any immediate emotion to settle. But once you’ve done that, address the situation promptly.
Timely conversations prevent small concerns from turning into larger performance, morale, or cultural problems.
- Establish Ground Rules and Stay Focused
As with any important meeting, ground rules can provide helpful boundaries for an effective discussion. Agree that there will be no personal attacks, no interruptions, and no blaming. Difficult conversations should emphasize resolution rather than blame. Encourage dialogue by asking open-ended questions and inviting the employee to contribute ideas for improvement.
Collaboratively identify solutions and agree on measurable steps and timelines. This approach reinforces accountability while demonstrating that the conversation is meant to support growth rather than punish.
- Be Open and Empathetic
Your job as manager is to be direct, calm, and objective. State your concern and then ask your team member if there’s more you should know about the situation. Sometimes there are behind-the-scenes explanations that can help your understanding.
Then, use your best active listening skills. Ultimately, you want the situation to improve. To make that happen, you need the cooperation of your direct report. Show empathy but, at the same time, don’t reduce your expectations for acceptable behavior and performance.
- Agree Upon a Path Forward
After addressing the issue, shift the conversation toward shared ownership of the solution. Collaborate on a clear, step-by-step plan that outlines the specific behaviors or outcomes required, along with realistic milestones and check-ins. If others are affected by or connected to the issue, ensure they are aligned with the plan as well.
Your role is to coach and guide — reinforcing progress, calling out setbacks early, and keeping the individual focused on the agreed-upon direction. As the manager, you set the cadence of accountability and create the structure that supports meaningful, sustained improvement.
- Follow Up Consistently
A single conversation is rarely enough to sustain change. Schedule follow-up discussions to review progress, provide ongoing support, and reinforce expectations. Follow-up signals commitment to employee development and accountability while helping to solidify behavioral changes over time.
The Bottom Line
For new managers, the ability to conduct difficult conversations is an essential component of building a high performing and high functioning team. By preparing carefully, approaching discussions with empathy, staying clear and solution-focused, and following up consistently, managers can turn challenging conversations into opportunities for growth, trust-building, and team alignment. Mastery of these skills sets the foundation for sustained organizational performance and stronger employee engagement.
To learn more about how to conduct difficult conversations, download Effective Communication Skills – The Essential Ingredient in Any Interaction
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