Picture this: It’s Tuesday morning, and you’ve just received a complaint from a team member about their manager sending them an inappropriate comment on a Teams chat. It’s made them feel undervalued and even slightly offended.  It’s not the greatest start to your week, but you know you need to address this immediately. 

According to a poll, 80% of workers fear uncomfortable work conversations and put them off for as long as they can. The respondents said they bite their tongue because they lack the confidence to speak up, with 1 in 5 admitting they’re not at all confident that they’ll be successful in holding the needed conversation.

Yet avoiding these conversations only allows problems to fester and can lead to decreased morale, reduced productivity, and potential legal issues down the line.

With the right preparation and approach, difficult conversations can often become turning points that build trust, develop more empathy and build respect between managers and employees. 

Here are some ways to navigate those difficult conversations to keep your relationships intact and minimise awkwardness with your colleagues or employees.

1. Gather the right facts and evidence 

Before initiating any difficult conversation, ensure you have concrete evidence to support your concerns. This preparation phase is crucial because emotions can run high during these discussions, and having solid evidence and documentation helps keep the conversation focused and professional. 

If you’ve had previous conversations with this employee about similar issues, pull those records. Performance metrics, attendance records, and even screenshots of inappropriate communications can provide objective evidence that’s hard to dispute.

2. Choose the right time and place

Timing and environment can make or break a difficult conversation, yet these factors are often overlooked in the rush to address problems quickly. The timing of your conversation should allow for a full, uninterrupted discussion without feeling rushed. Block out at least an hour, even if you expect the conversation to be shorter – you never know when additional issues might surface or when the employee might need time to process what you’re discussing.

3. Keep the conversation solution-focused

Once you’ve laid out the specific issues and their impact, the most crucial part of any difficult conversation is shifting toward solutions. This transition from problem identification to problem-solving is what separates truly effective managers from those who simply point out what’s wrong. The goal isn’t to make the employee feel bad about their mistakes, it’s to create a clear path forward that benefits everyone.

Consider how you’ll explain the broader impact of their actions. Employees sometimes don’t realise how their behaviour affects others or the business as a whole. 

4. Anticipate responses and prepare your reactions

One of the most challenging aspects of difficult conversations is managing unexpected reactions from employees. By anticipating potential responses and preparing your reactions in advance, you can maintain your composure and keep the conversation productive, even when things don’t go according to plan.

Defensiveness can manifest as blame-shifting, making excuses, or becoming argumentative. When employees become defensive, acknowledge their feelings while redirecting the conversation back to the specific behaviours. You might say “I can see you’re feeling frustrated, and I want to understand your perspective. Help me understand what led to these interactions with your colleague.” This approach validates their emotions while keeping the focus on finding solutions.

Emotional reactions such as crying, anger, or complete shutdown require a particularly delicate touch. If someone becomes very emotional, it’s okay to pause the conversation and offer them time to compose themselves. However, don’t let extreme emotions derail the entire discussion. The issues still need to be addressed, perhaps just with additional sensitivity and potentially in a follow-up meeting.

Some employees will try to shift blame to others, their workload, or circumstances beyond their control. While it’s important to acknowledge legitimate concerns about resources or systemic issues, you need to keep the focus on their behaviour and choices. 

Remember, you can’t control how they react, but you can control how you respond to their reactions.

5. Document everything

Take notes during the conversation, including:

• Date and time of the meeting
• Key points discussed
• The employee’s responses and explanations
• Agreed-upon action steps
• Timeline for improvement
• Any support or resources provided

Difficult conversations are an inevitable part of people management, but they don’t have to be overwhelming. With proper preparation, the right approach, and consistent follow-through, you can address challenging issues while maintaining positive working relationships and a productive team environment.

The key is to act promptly, stay professional, and focus on solutions rather than blame. Your team will respect your willingness to address problems head-on, and you’ll create a healthier workplace culture where issues are resolved before they escalate.

At 1850, we help SME’s develop the communication skills necessary to address workplace challenges confidently and effectively. Contact us if your leaders need training on how to handle difficult conversations.