Navigating workplace dynamics can be complex, especially when it comes to challenging conversations such as performance issues, feedback or personal matters. Despite our very best intentions, these discussions often go off track. The good news is, by understanding why they go wrong, you can learn to handle them with confidence and clarity.
Here are the top five most challenging conversations in the workplace and why we often get them wrong:
- Delivering Constructive Feedback
One of the most common yet challenging conversations in the workplace is giving feedback. As managers, team leaders or colleagues, we are often called to address areas where others may not be performing to their full potential. The goal is to help the individual grow and improve, but delivering feedback poorly can have the opposite effect, leading to defensiveness, frustration or disengagement.
Why We Get It Wrong:
The key to giving effective feedback lies in how it’s delivered. We often focus on what went wrong, but fail to balance it with positive reinforcement or constructive suggestions. This can create an unbalanced, negative conversation that puts the recipient on the defensive. Additionally, feedback is often given in a rushed or impersonal way, leaving the other without the tools they need to improve. People also sometimes avoid giving feedback out of fear of confrontation, but this can lead to bigger issues down the line when problems escalate.
How to Improve It:
Frame feedback in a way that is both constructive and empathetic. Keep the conversation focused on specific actions, not personality traits. And most importantly, make sure to offer support and a path for improvement, allowing the recipient to feel motivated rather than defeated.
- Asking for a Raise or Promotion
The conversation around salary and promotions is one of the most difficult conversations in any workplace. It’s a highly personal conversation, and asking for a raise or promotion can feel intimidating – especially if you’re uncertain of how it will be received. It’s easy to feel vulnerable or even undervalued, and the fear of rejection can make the conversation even harder.
Why We Get It Wrong
Often, this conversation isn’t approached strategically. It may be brought up at the wrong time or without adequate preparation. Sometimes an employee will focus on why they deserve more money based on personal needs (e.g., paying bills, supporting a family), whereas employers are – of course – more interested in understanding the value someone brings to the company. A lack of clear, quantifiable achievements or a failure to understand market rates can also weaken an argument.
How to Improve It:
Approach this conversation with preparation and confidence. Before discussing a raise or promotion, gather evidence of your contributions and how they align with the company’s goals. Understand your market value and be ready to present your case. It’s important to remain professional and avoid making it an emotional conversation. Practicing beforehand and staying calm and collected during the conversation can make a significant difference.
- Addressing Poor Performance
When an employee is underperforming, addressing it early can help prevent more significant problems in the future. However, discussing performance issues can feel like a confrontation, which can be uncomfortable for both the manager and the employee.
Why We Get It Wrong:
Performance discussions often focus on the negative aspects of a person’s work without offering clear solutions or support. Managers may become frustrated or assume the employee knows where they are falling short, which can lead to ambiguity. Employees may not feel heard or understood if the conversation is one-sided, and they may leave feeling alienated or unmotivated. Additionally, performance issues are often addressed too late, when the problem has already become more difficult to resolve.
How to Improve It:
Make sure to approach performance discussions with clarity and empathy. Be specific about what aspects of the job are not being met, but also acknowledge any positives to maintain balance. Work with the employee to understand any challenges they may be facing and offer support, whether it’s additional training, resources, or more frequent check-ins. Establish a clear action plan for improvement and set follow-up meetings to track progress.
- Dealing with Personal Issues at Work
Sometimes, personal issues – whether related to family, health, or emotional well-being – spill over into the workplace. While we want to be supportive and compassionate, these conversations can be delicate. Balancing professionalism with empathy can be tricky, and many managers and colleagues struggle with how much to involve themselves in a co-worker’s personal life.
Why We Get It Wrong:
Often, these conversations are avoided out of fear of overstepping boundaries or making the employee feel uncomfortable. When they do occur, there can be a tendency to either be too distant and impersonal or too involved, making the person feel as though their personal struggles are being “used” to judge their professional abilities. Moreover, if the employee doesn’t feel comfortable sharing, it can result in misunderstandings.
How to Improve It:
Create a safe space for employees to discuss personal issues, emphasizing confidentiality and support. Approach the conversation with genuine care and without judgment, and offer assistance in finding appropriate resources, if necessary. Be clear about professional expectations, but show you’re willing to work with them during difficult times.
- Managing Conflict Between Colleagues
Interpersonal conflict in the workplace is inevitable. However, addressing it can be one of the most uncomfortable and challenging conversations for managers and employees alike. Whether it’s a disagreement between colleagues, a personality clash, or a larger team issue, unresolved conflict can quickly undermine productivity and morale.
Why We Get It Wrong:
Conflict is often avoided out of fear of exacerbating the situation, but ignoring it only allows tension to build. Sometimes, we also fail to approach the issue with neutrality, unintentionally taking sides or addressing it too late. Furthermore, conflict resolution requires both active listening and emotional intelligence, skills that many of us aren’t taught but are essential in guiding the conversation towards a constructive resolution.
How to Improve It:
Take a proactive, neutral stance when managing workplace conflict. Allow each party to share their perspective without judgment, and focus on finding common ground. Encourage open communication, and provide clear expectations for behaviour going forward. Follow up regularly to ensure that the issue has been resolved and doesn’t resurface.
Conclusion
Challenging conversations in the workplace are inevitable, but they don’t have to result in conflict or discomfort. With the right preparation, empathy, and approach, even the toughest discussions can become opportunities for growth. By understanding why we often get these conversations wrong and implementing more effective strategies, we can foster a more supportive, transparent and productive workplace environment.
At 1948, we specialise in communication skills training and run masterclasses on Navigating Challenging Conversations in the Workplace. Visit our website here to learn more or get in contact for further information.
