Mastering difficult conversations in the workplace can be challenging. This is true particularly when delivering negative feedback to team members regarding their performance, behaviour, or skill set. These conversations often make individuals uncomfortable due to various factors.

However, managers must address negative influences and foster a positive work environment. This article explores the reasons behind managers’ reluctance to engage in difficult conversations and provides a systematic approach to handling them effectively. Additionally, it emphasises the importance of remote communication when holding such conversations and highlights the consequences of leaders failing to develop these essential skills.

Reluctance to Address Negative Influences

Managers often avoid difficult conversations at work for several reasons. Some shy away from confrontation, others prioritise politeness over addressing issues, and some hope problems will resolve themselves. Additionally, managers may doubt their ability to navigate these conversations successfully, fearing counter-accusations or potential disputes with employees. Unfortunately, this avoidance leads to the acceptance of substandard performance and behaviour, creating a culture of negativity within the team.

The Accumulation of Annoyance and Resentment

When managers fail to draw the line and avoid addressing difficult situations, the negative atmosphere at work tends to persist and worsen over time. The resulting layers of annoyance, frustration, and resentment can significantly impact team dynamics and overall productivity. Meanwhile, employees exhibiting poor performance or undesirable behaviour remain unaware of the unrest they cause, as they have been allowed to act in such a manner for an extended period.

Consequences of Neglecting Difficult Conversations

Leaders who neglect difficult conversations fail to realise the detrimental effects on their teams and organisations. Without addressing issues, they risk perpetuating a cycle of mediocrity, reduced motivation, and decreased productivity. Furthermore, failing to intervene can result in a lack of accountability and an erosion of trust within the team. Ultimately, the consequences of not mastering these crucial communication skills can lead to long-term damage to team dynamics and overall organisational success.

Holding Difficult Conversations Remotely

In today’s increasingly remote work environments, managers must adapt their approach to holding difficult conversations. Remote communication adds a layer of complexity, as non-verbal cues may be harder to discern. It is important to utilise video conferencing platforms to establish face-to-face interaction, fostering better understanding and connection. Active listening becomes even more critical in remote settings, ensuring that employees feel heard and acknowledged despite the physical distance. Managers should also consider scheduling conversations at appropriate times, considering employees’ availability and potential distractions in their remote work environments.

A Systematic Approach to Difficult Conversations

To effectively address difficult conversations, managers can follow a systematic approach. Firstly, it is essential to refrain from acting when feeling negative emotions such as frustration or anger. Remaining impersonal and unattached to the problem is crucial for a successful outcome. Gathering facts and documenting specific incidents or situations helps gain clarity and perspective. Clearly defining the expected standards and explaining the reasons behind them is vital. Managers should identify the desired change, set a timeline, and establish the consequences of not meeting expectations.

During the conversation, it is essential to state the facts objectively and own concerns without personalising them. Active listening plays a crucial role, as managers should attentively hear the employee’s perspective, keeping an open mind and demonstrating flexibility. Finding common ground and reaching an agreement on standards is ideal, but when agreement cannot be reached, managers must assert their position based on the research on the impact of the employee’s actions. Additionally, encouraging the employee to suggest resolutions and developing a clear plan going forward fosters a sense of ownership and commitment.

Benefits of Mastering Difficult Conversations

Numerous research studies conducted in the fields of organisational psychology and communication provide valuable insights into the importance of mastering difficult conversations in the workplace. Research shows that effectively addressing and resolving conflicts or performance issues leads to higher employee engagement, improved team dynamics, and increased productivity.

How To Get Difficult Conversations Right


1. Stay Focused on the Issue, Not the Person

Mastering how to hold difficult conversations involves distinguishing the person from the problem. Personalizing issues can escalate tensions. Instead, concentrate on the specific issue at hand. This objective approach prevents misunderstandings and keeps the conversation productive. Discuss the problem’s impact rather than attributing blame, fostering a more collaborative and less confrontational atmosphere.

2. Express Appreciation, Even in Difficult Interactions

Acknowledging each participant’s contribution is a crucial element in how to hold difficult conversations. Expressing gratitude, even when opinions clash, establishes a respectful and constructive environment. This approach encourages open sharing and can positively influence future interactions.

3. Control Your Emotions, Don’t Let Them Control You

Emotional intelligence is vital in how to hold difficult conversations. Recognize and manage your emotions to prevent them from dictating your responses. When feelings of frustration or anger arise, take a moment to understand their root cause. This self-awareness facilitates a calmer, more thoughtful discussion, crucial for resolving complex issues.

4. Prepare and Present Clear Objectives

Effective preparation sets the stage for how to hold difficult conversations. Clearly outline your objectives to provide direction and focus. This preparation helps in addressing the core issues efficiently and reduces the likelihood of the conversation veering off course.

5. Listen Actively and Empathetically

Active and empathetic listening is a cornerstone of how to hold difficult conversations. It involves fully concentrating, understanding, responding, and remembering what is being said. This practice demonstrates respect and openness to different perspectives, essential in resolving disagreements amicably.

6. Use “I” Statements to Express Your Views

Using “I” statements is a strategic approach in how to hold difficult conversations. This technique helps in expressing your perspective without sounding accusatory, reducing the chances of the other person becoming defensive. It’s a way to share your feelings and thoughts responsibly and respectfully.

7. Embrace Disagreements as Opportunities

Viewing disagreements as opportunities rather than threats is a progressive method in how to hold difficult conversations. This mindset allows for exploring diverse perspectives and understanding the underlying reasons behind differing views, enriching the conversation and leading to more inclusive solutions.

8. Balance Your Views with Others’ Perspectives

In learning how to hold difficult conversations, it’s important to balance your viewpoint with that of others. This involves acknowledging and considering different opinions and fostering a more inclusive and respectful dialogue. Such a balanced approach encourages mutual understanding and collaboration.

9. Manage the Setting for the Conversation

The environment plays a significant role in how to hold difficult conversations. Choose a setting that is private, neutral, and comfortable. The right atmosphere can ease tension, foster openness, and enhance focus, contributing significantly to the conversation’s effectiveness.

10. Acknowledge and Respect Differences

Acknowledging and respecting differences is crucial in how to hold difficult conversations. It involves understanding and valuing diverse viewpoints, which can lead to richer, more productive discussions. This respect for diversity paves the way for more harmonious and effective communication.

11. Be Open to Compromise and Collaboration

A willingness to compromise and collaborate is essential in how to hold difficult conversations. It shows a commitment to finding a mutually beneficial resolution rather than insisting on one’s viewpoint. This approach can transform challenging discussions into constructive problem-solving sessions.

12. Use Questions to Clarify and Understand

Asking questions for clarification is a key tactic in how to hold difficult conversations. It helps in deepening understanding and ensures that all parties are on the same page. Thoughtful questions can uncover underlying issues and open paths to resolution.

13. Acknowledge Emotions but Don’t Let Them Overwhelm the Conversation

In how to hold difficult conversations, it’s important to acknowledge emotions while keeping them from dominating the dialogue. Recognizing feelings validates the experiences of those involved but maintaining a focus on the topic ensures progress and resolution.

14. Follow Up Post-Conversation

Following up after a difficult conversation shows commitment to the outcomes and respect for the process. It’s a crucial step in how to hold difficult conversations, ensuring that agreed-upon actions are implemented and that the conversation has a lasting, positive impact.

15. Avoid Assumptions, Seek Facts Instead

Challenging assumptions and seeking facts are key in how to hold difficult conversations. Avoid jumping to conclusions and base your arguments on evidence. This approach promotes a rational

and fair discussion, essential for reaching a mutual understanding and resolving issues effectively.

16. View Others’ Actions Objectively: Beyond Their Conduct

In mastering how to hold difficult conversations, it’s vital to see past people’s behaviours to understand their motivations. By focusing on what drives their actions, you can address the core issues more effectively, leading to a more meaningful and productive conversation.

17. Prioritize Substance Over Style in Communication

When learning how to hold difficult conversations, it’s crucial to focus on the message rather than the delivery. Overlooking the style of communication and concentrating on the substance helps in understanding the real issues and navigating the conversation constructively.

18. Don’t Push Your View to the Exclusion of Others

In how to hold difficult conversations, it’s important to avoid dominating the discussion with your viewpoint. Encourage a balanced exchange of ideas, which leads to a more comprehensive understanding and fosters a collaborative atmosphere.

19. Don’t Let Bystanders Go Unheard—Draw People Out

Inclusive participation is vital in how to hold difficult conversations. Encourage quieter individuals to share their thoughts, as they often provide valuable insights. This approach ensures that all perspectives are considered, enriching the discussion.

20. Establish Ground Rules for Effective Communication

Setting clear ground rules is a proactive measure of how to hold difficult conversations. These guidelines help in managing the flow of the discussion, ensuring that it remains respectful and focused on the objectives, thus enhancing its effectiveness.

By implementing these strategies, you can enhance your ability to hold difficult conversations, leading to more effective and positive outcomes in a variety of settings.

Mastering difficult conversations is crucial for effective leadership and maintaining a positive work environment. By addressing negative influences promptly and effectively, managers can enhance team performance.

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