How to Train Managers to Have Difficult Conversations

One of the most important skills for a manager to possess is the ability to have difficult conversations. For managers to train to have these conversations, they need to first understand what they are and what they’re not. Managers shouldn’t see difficult conversations as a way to win an argument, but rather as a way to get results. They also need to be aware of their own emotions and how they might affect the conversation. 

Professional woman concentrating on writing notes with a laptop on desk.

To prepare for a difficult conversation, managers should gather all the relevant information and set clear goals. They should also prepare for potential roadblocks and have a plan for how to address them. During the conversation, managers should remain calm and focused on their goals. They should also be willing to listen to the other person’s point of view.

Training managers to have tough conversations is vital to the growth of any team, as well as for the personal and professional development of the managers themselves.

In this article, we’ll discuss types of difficult workplace conversations and how to better manage those discussions. 

The Types of Difficult Conversations at Work

Difficult conversations happen all the time, and most team members would rather avoid them if possible. Brushing the situation under the rug will only make it worse in the long run, however. It’s best to handle the conversation efficiently, and with empathy, so everyone can go back to the task at hand.

To provide some insights for managers, we’ve compiled a list of several difficult conversations at work examples.

The types of difficult conversations your managers need to have at work include:

Resolving conflicts between team members: A lack of communication or poor teamwork can lead to conflict between coworkers, which can be resolved by talking about the issue openly with the parties involved. If your managers don’t address the issue directly, it may fester and grow worse.

Addressing poor performance: Managers need to understand what steps to take if one of their employees isn’t performing well in their job duties. There are options for addressing this situation effectively—such as giving them feedback on their performance or setting up a meeting for further discussion about their work habits and potential for improvement.

Discussing sensitive topics with employees: These types of conversations may involve sensitive information, such as an employee’s salary or health issues, so they’re often fraught with emotions and hard feelings—but they’re still important topics that need addressing.

Terminating a position: This type of conversation is tough because it involves letting go of someone who’s been part of the team. Staff might have gotten close with them and shared personal stories, or they may even be friends outside of work. It’s hard when these relationships end, especially when they’ve been positive ones.

Giving negative feedback: Negative feedback can come in many forms, such as giving an employee constructive criticism or pointing out a mistake they made on their last project. While negative feedback can be uncomfortable for both parties involved, employees need to receive this kind of feedback regularly so they can grow professionally and improve their performance in the future.

Admitting their mistakes: One way managers can humanize themselves is by admitting their mistakes without making excuses or blaming others. This is a great way to show their team members that they’re not alone in struggling through difficult situations at work and that everyone makes mistakes.

Managing Difficult Conversations in the Workplace

A workplace is a place where people interact with one another. Some conversations are easy, and some are hard. But no matter how difficult the conversation is, it needs to be managed properly to avoid misunderstandings.

There are many ways to manage difficult conversations at work. Here are several tips that can help managers handle these types of situations:

1. Preparation is key

Before managers go into any conversation involving heightened emotions, it’s important they prepare. Your managers should play the conversation in their heads ahead of time to help them predict how employees might react and how to best approach the situation. This exercise also helps identify moments in difficult conversations where redirection might be needed to move past those emotions and focus on facts.

2. Provide context

At the beginning of a difficult conversation, it’s important to explain the context. This isn’t a time for the managers to be vague. They need to be direct and respectful, outlining points that can be seen with an objective eye and steering clear of heightened emotions.

3. Listening is one of their best strengths

A difficult conversations training will teach managers that listening is a leader’s strongest ally. Staying open to what the other person has to say allows managers to process with their employees on their level.

4. It’s not a competition

Having difficult conversations isn’t about who’s right or who’s wrong. Heading down that path will get managers nowhere fast. To build trust and move the conversation in the direction it needs to go, leaders will need to leave their competitive nature and pride at the door.

Difficult Conversations Training for Managers with KnowledgeCity

According to the result of several studies, when a staff member was the higher-ranking employee in a challenging dialogue, they were more likely to be happy about the results. More than 75% felt satisfied with the outcome of a conversation with a direct report, compared to 46% feeling somewhat or completely satisfied with the results of a discussion with a supervisor.

How can difficult conversations training help your managers? It can prepare them for challenging employee or peer conversations, which is half the battle. The training can also empower them to see difficult conversations as a starting point for learning and a growth catalyst for both manager and employee.

KnowledgeCity has training available to help you encourage your teams to tackle difficult conversations in the workplace head-on. All of our courses are offered online in a variety of languages, offer real-world solutions and efficient skills training.

Your managers can take our Communication Best Practices course or any of the thousands of Communication and Business courses available on our platform.


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