How to navigate difficult conversations at work

When you manage a team, the occasional difficult conversation is inevitable. You might need to deliver a negative performance review, talk to someone about unprofessional behavior, or step in to mediate a group conflict. Whatever the case, these chats are never easy. 

In this guide, we explore how to navigate difficult conversations at work while taking employees’ needs and feelings into account. We’ll also offer a few steps to follow and useful resources you can lean on.

Why getting difficult conversations right matters

“Difficult conversations at work” is a catch-all term for sensitive discussions you might need to have with your employees. 

Everyone handles tough news differently, and emotions can run high. The person on the receiving end of the chat may have a negative reaction, like sadness, anger, or shock. People depend on their jobs, so when they feel their livelihood is at risk, they can become defensive. While most employees stay professional, you’ll also need to know how to manage tears, standoffishness, rudeness, and even offensive language.

Here are a few common examples of difficult conversations:

• Delivering a negative performance review
• Intervening when an employee makes a big mistake 
• Firing someone or giving them a pre-termination warning 
• Addressing unprofessional behavior or misconduct
• Warning employees about upcoming layoffs
• Demoting a team member or removing certain responsibilities
• Explaining why you’re putting an employee on a performance improvement plan
• Setting boundaries if an employee breaks company policy

Difficult conversations are uncomfortable, but they’re a must

The temptation to avoid difficult conversations is pretty natural. After all, they’re uncomfortable and could lead to confrontation. But when you evade tricky discussions, the underlying problem driving the need for the conversation is unlikely to go away, and could even get worse. 

For example, if a manager avoids talking to an employee about an error they made, they're likely to continue making that mistake. It's better to face the problem head-on. When you lead with compassion and a clear plan for what comes next, you lay the groundwork for positive outcomes.

5 steps for handling difficult conversations

Preparation and expectation-setting are crucial parts of productive conversations. Following these five steps will help you plan your intervention and manage negative emotional reactions:

1. Identify the situation

Pinpoint the specific topic the conversation is targeted around, and avoid tackling several at once to keep from overwhelming the team member. If you don't already, consider building regular check-ins into your management approach. These smaller sessions are an ideal time to discuss growing issues or concerns, and help employees from panicking when they see a meeting suddenly added to their calendar.

2. Plan your talking points

Stay focused throughout the conversation by planning your talking points ahead of time. If things get emotional, a bullet point agenda can help you avoid getting flustered and losing your train of thought. It’ll also make sure that every aspect of the planned conversation is constructive and necessary.

3. Bring supporting information

When the difficult conversation is about something the employee has done, bringing relevant evidence to the meeting can help them see the exact issue and avoid them making excuses. For example, if a team member is routinely making a data entry error, show them where and how they’re going wrong. In many instances, they might not even be aware of the issue until it’s pointed out. 

4. Acknowledge the other person

If you suspect an employee will have a strong emotional response, address those feelings head-on. Ask them what they're thinking and how they're doing, and actively listen to their response. When the employee finishes sharing, respond empathetically, but don't rush to fix the discomfort. Kind words can ease the pain of a team member who's being let go, but promising to help them find a new role will give them false hope.

5. Create an action plan

When dealing with difficult conversations about performance issues or errors, create an action plan for how to improve at the end of the meeting. Without one, the employee might not know how to rectify the situation. Trackable objectives that explain how to boost performance will keep them accountable and give you a way to monitor progress. 

How to start a difficult conversation: 3 planning resources

These three useful resources will help make difficult conversations more manageable.

One-on-one meeting agendas

Regular one-on-one meetings are a great time to address any developing situations and have any tricky conversations. These weekly or bi-weekly chats with direct reports help managers streamline workflows, check in with how employees are doing, and monitor any objectives they’re working toward. 

Goal-setting template

Goal-setting templates are structured frameworks that help you define and track an employee’s targets. A well-written template will help you establish goals that align with business objectives and encourage employees to take ownership of the process, boosting accountability. It also clarifies their responsibilities and serves as a handy reference guide.

Pulse surveys

Pulse surveys are an excellent tool for gathering feedback from employees. Use them to gather unfiltered insights on things like the quality of training, leadership communication, tools, and the workplace experience. The information you gather could reveal issues preventing employees from doing their best work, helping you get ahead of things before they spiral out of control. Making the survey anonymous might even help you surface conflicts or insecurities that employees don’t feel comfortable talking about face-to-face.

Turn difficult conversations into clear actions with Workleap 

Learning how to have difficult conversations in the workplace takes planning, practice, and a willingness to actively listen. Taking a constructive approach enables employees to grow and feel more comfortable, helping you navigate tricky situations with much less hostility.

Difficult conversations are never easy, but Workleap can help. Workleap Officevibe empowers managers to make better decisions with more context. Gather valuable intel with Officevibe’s custom surveys and anonymous feedback, and learn how to improve employee engagement and performance with the platform’s AI-powered insights.

Demo Workleap today to see how it supports productive employee conversations. 

FAQs

What should you never do in a difficult conversation?

Never start difficult conversations when emotions are running high. If you begin a talk when you’re heated and not sufficiently organized, you risk reacting poorly in front of the employee and making the situation worse. You also won’t be able to deliver a clear, constructive action plan for improvements. Planning out talking points ahead of time will keep everyone on topic. 

You should also avoid backpedaling on your message in an effort to be “nice”. While it’s tempting to protect employees’ feelings at all costs, it’s essential that they clearly understand what they’re being told, without any cushioning or false hope. There’s plenty of space for empathy, and you should always remain respectful, but don’t avoid properly explaining an issue just because the other person may react poorly.

What skills are required for difficult conversations?

Empathy, clarity, a solutions-driven mindset, and active listening are all important skills for difficult conversations. Managers need to be able to share observations and map out ways to fix a problem while treating employees compassionately. Consider holding a difficult conversation training session to teach managers and leaders best practices when dealing with tricky topics.

What is the best way to have a difficult conversation?

The best way to have a difficult conversation is to properly prepare. Only engage with the employee after gathering your thoughts, pinpointing talking points, and prepping yourself to listen empathetically. Never start a tense chat if you’re actively upset with someone, even if they’ve made a big mistake. Employees deserve your respect and a professional approach to addressing the problem. 

You should also prepare for a strong emotional response from your employee. Everyone reacts to bad news differently, so make sure you know how to manage a range of different behaviors, including tears, harsh words, and bargaining.