Andrea Wedell

Whether you use the term difficult conversations, assertive communication, or nonviolent communication, we all find ourselves in situations where we have to talk about something that makes us uncomfortable and involves calling out another person. These conversations are always difficult, but become especially challenging when they can’t take place in person. How can we introduce a tricky topic in a thoughtful manner, especially in a virtual environment? 

If you’re a manager, you might feel anxious about giving constructive feedback to your direct reports. In fact, this is quite a common cause for anxiety — according to Harvard Business Review, 68% of managers said that they’re often uncomfortable communicating with employees and 37% said they’re uncomfortable giving direct feedback about their employees’ performance if they think the employee is likely to respond negatively.

Of course, managers aren’t the only ones who need to engage in difficult conversations. Research published in SHRM found that 62% of employees reported being treated rudely at work at least once a week. Given that statistic, it’s not surprising that employees might need to share feedback with peers or their own managers, and anticipating a conversation like this can cause fear and anxiety.

In my 25+ years as a communication coach, I’ve learned that we tend to build these conversations up in our minds. They take on an outsize role in our thoughts, causing us to ruminate and stress outside of work. But when we make the commitment to engage in these difficult conversations, we have the ability to move forward, both in the specific situation and in our careers in general. In my course, Dread-Free Difficult Conversations, I share how to reframe the very idea of having a difficult conversation, shifting from a feeling of dread to embracing the productivity these conversations can bring. Here are a few tips for you and your employees to keep in mind.

Dread-Free Difficult Conversations: Speak Up with Courage

Last Updated April 2020

  • 30 lectures
  • Intermediate Level
4.6 (128)

Overcome your discomfort and assertively lead productive, empathetic conversations with win-win outcomes. | By Andrea Wedell

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5 tips for handling difficult conversations

1. Understand when it’s time to have a hard conversation

How do we know that we need to have a difficult conversation? If you’re spending a whole lot of time thinking about something, especially if it’s beginning to take over your personal time outside of work, that’s a good sign that it’s time to have a conversation about that topic. I recommend keeping tabs on your feelings and your focus — do you feel that your concerns about this topic are preventing you from moving forward? 

Here’s an activity that can be very useful: Imagine that you weren’t focused on this problem right now. How could you be using your time and energy instead? By understanding the impact this situation is having on your productivity, you may be more motivated to engage in a difficult conversation. You may realize that it’s taking a larger toll on you and your wellbeing than you had previously noticed.

Another point to note here: It’s very common to worry about what will happen when we call someone out or tell them that their behavior is upsetting us. But having a difficult conversation is all about sharing whatever is triggering or troubling you. It’s irrelevant what they might be thinking about the situation.

2. Work with anxiety and fears about the conversation

As I’ve mentioned, it’s very common to have fear and anxiety leading up to a difficult conversation. For example, many people are hesitant to engage in difficult conversations because they’re afraid they will progress into full-blown conflicts, which could be even worse than the current situation. Another common fear is that even after going through the trouble of having a difficult conversation, the other person won’t change their behavior and all that awkwardness won’t lead to any significant change.

If you or your employees are feeling any resistance toward difficult conversations, I recommend working through these fears and worries. First of all, it helps to identify exactly what we’re feeling. In my course, I’ll outline a number of the most common fears, and it’s very likely that these will resonate with learners. Seeing that your fears are common can help to de-dramatize them.

In the course, we’ll also dig into common causes of anxiety and fear-based thinking. Generally, there’s a pattern people follow when experiencing these emotions: there’s a situation that triggers specific emotions, which in turn trigger a particular behavior. Developing self-awareness helps us understand what triggers us, whether it’s a particular situation or type of person. And once we know what triggers us, we can do different exercises to counterbalance or reframe anxious thinking.

Similarly, if you or your employees are afraid that difficult conversations won’t lead to any change, it can help to level-set expectations. There are things that are within our control and things that aren’t. We can’t control other people’s actions, but we can control our ability to speak up about them. It is possible that speaking up won’t lead to any change in the other person’s behavior, but it will change their understanding of how you are feeling.

In my course, Dread-Free Difficult Conversations, we’ll look in-depth at other common fears and how to overcome them.

3. Understand who you’re talking to

To increase the chances that the other person will really hear what you or your employees have to say, it’s important to think about who they are and how you can clearly articulate your needs to them.

Each person will have their own needs and priorities, and it helps to consider this before having a difficult conversation. For example, talking to a peer is different than talking to a manager. A peer might think of success in terms of their own career and advancement, while a manager might think more about the team’s overall performance or the top-line goals outlined by executive leadership.

Taking a step back to look at the whole picture and understand who you’re talking to means your message is so much more likely to land.

4. Practice assertiveness techniques

Once you or your employees have gone through the first three steps, you’re almost ready to have a difficult conversation — but not quite. Before actually sitting down to have the conversation, I recommend practicing assertiveness techniques. There is certain language that can be used to communicate more directly, but this doesn’t come naturally to everyone.

To begin, it helps to understand our default. What type of language do we tend to use when we’re uncomfortable? For example, some people become more bluntly direct while others may go into “people-pleasing” mode. They may find themselves apologizing or hedging their language with a lot of softening words. 

Once we understand our tendencies, we can start correcting them and adopt an assertive style. We can practice sharing thoughts in a more direct yet fact-based manner. For example, using “I language” can be incredibly helpful. Let’s say you wanted to confront a peer about their disruptive behavior in a meeting. Using “I language” involves describing the situation and the impact it had on you: “At the last meeting when you joined late and looked at your phone the entire time, it was really disruptive and I’m very uncomfortable with that.”

“I language” helps you state the problem clearly, but it does more than that. When we describe our own reaction to a situation, no one can really argue with our own point of view. People are less likely to get defensive when we describe the effect their behavior had on us. Again, this doesn’t always mean that they will change the behavior, but using assertive language helps ensure that they’re aware of the effect that behavior has on us.

5. Deliver effectively despite being remote

Without the option for in-person conversations, sensitive messages need to be crystal clear, direct, and delivered live over video. Taking the time to do videos, or multiple videos shows your commitment to your people and strong leadership. It demonstrates that you want to connect on a visceral level on important issues.

Delivery skills are essential. Communicating remotely comes with an increased sense of distance between people. That means we need to work a little harder to come closer. Use excellent delivery, imagine people are in the room with you, and really connect. People are impacted over 90% by the way a message is delivered, and 7% by the words themselves. Body language and facial expressions are what we humans tend to trust.

Once you have your message keyed up, rehearse it in front of a mirror so you can see how it might land. Better yet, film yourself and watch. Sometimes we think we’re projecting an image that matches our intentions, but it comes across very differently when we put our voices and gestures to words. You may discover, for example, that your facial expressions are much more intense than you previously realized!

In this post, I’ve just scratched the surface of how to handle difficult conversations, based on my 20+ years of one-on-one coaching experience. In Dread-Free Difficult Conversations, we’ll focus on transforming feelings around hard conversations. My goal is to help you and your employees stop dreading these interactions and begin to embrace them for all the productivity and upgrades they can bring to your lives.

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