“We need to talk.”

The above phrase is often met with sweaty palms, racing thoughts and other symptoms of panic and anxiety. Whether the request to converse is coming from a manager, colleague, family member or partner, it’s usually a clear indicator that a difficult conversation lies ahead.

The ability to have effective difficult conversations is essential in building and maintaining positive relationships in and outside of the workplace. However, having tough conversations doesn’t come naturally to most people. A VitalSmarts poll found that more than 80% of employees are “cowering from at lest one scary conversation at work” that they know they need to have but are “dreading.” The majority of the poll’s respondents also said that they avoid difficult conversations because they “lack the confidence to speak up.”

From a business perspective, this is concerning: It’s critical that leaders can have candid conversations with employees when they need to. If they can’t, everything from performance to engagement and trust will suffer.

Before digging into the skills leaders need to have difficult conversations with team members, let’s first consider what constitutes a “difficult conversation.”

Difficult Conversations, Defined

In the most recent edition of their book, “Crucial Conversations: Tools for Talking When Stakes Are High,” authors Joseph Grenny, Kerry Patterson, Ron McMillan, Al Switzler and Emily Gregory define a “crucial conversation” as a discussion between two or more people with opposing opinions about a high-stakes issue in which emotions run strong.

Lori Mazan, co-founder and chief coaching officer at Sounding Board, Inc., a leadership coaching provider, agrees that difficult conversations are those that “raise emotions for one or both parties.” Thus, a conversation becomes “difficult” when the person on the receiving end or the person delivering the information feels nervous, hesitant, fearful, stressed or another combination of heightened emotions, she explains.

There are many types of difficult conversations that leaders will need to have with team members, and some are more difficult than others. Some common ones include giving constructive feedback, communicating that job roles and/or responsibilities have shifted and even having to lay off an employee, says Rashim Mogha, general manager, leadership and business portfolio at Skillsoft, author of “Fast-Track Your Leadership Career” and founder of empowered Women of the World (eWOW).

How Training Can Help

Having tough conversations “is all about soft skills,” says Laura Smith Dunaief, CPTM, a Training Industry Courses instructor and founder and chief learning officer at CareerCraft. Regardless of the message, leaders need to be able to articulate their message “in a way that others can hear them” and also be prepared to consider new perspectives.

For many leaders, these human-centric skills don’t come naturally. After all, Mogha says, for the longest time, the definition of leadership has been to keep your personal and professional lives completely separate, and to avoid bringing emotions to work.

Leaders might have gotten away with avoiding emotions at work in the past. But in today’s business environment — which the COVID-19 pandemic has drastically humanized — if leaders want employees to be invested in and committed to the organization, “they’re going to have emotions at work,” Mazan says.

To prepare leaders to navigate difficult conversations in the new world of work, start by training them on foundational soft skills, including:

Active Listening

Listening to understand is key to an effective difficult conversation, Mogha says. In fact, in most instances, leaders should be doing more listening than talking. Active listening also means asking thoughtful questions and considering the other person’s responses without judgement, Dunaief says.

Encourage leaders to give their undivided attention to the conversation by silencing their devices and focusing on understanding the other person rather than on what to say next. Non-verbal cues like nodding and making eye contact with the speaker are also important, especially in a virtual environment.


Empathy is a non-negotiable for human-centered leadership, especially when it comes to having tough conversations. Before having a difficult conversation with a team member, encourage leaders to practice empathy by putting themselves in the other person’s proverbial shoes. For example, if you’re speaking with a team member who dropped the ball on an important project, start by gauging whether there’s other factors at play that you haven’t considered: Are they burned out or even facing a mental health challenge you didn’t know about? Is their workload unsustainable? When leaders practice empathy, they are better able to provide the holistic support that employees need to perform at their best.

Emotionial Intelligence (EQ)

Because conversations become “difficult” when they are likely to evoke an emotional response, emotional intelligence (EQ) skills are critical for “keeping these conversations on the rails,” Dunaief says.

In a TrainingIndustry.com article, Scott Simmons, chief executive officer of Ariel, a leadership training company, outlines three practices to boost leaders’ EQ. They include: Being present and listening (i.e., listening to understand versus listening to solve), adopting an audience-centered mindset (i.e., instead of focusing solely on your own goals and priorities, consider your audience’s goals, challenges and motivations) and being authentic (i.e., practice vulnerability and “show who you are”).

Without adequate training and coaching on these skills, leaders “may find that others misconstrue their messages or that team members respond in unproductive ways,” Dunaief says. Perhaps even worse, leaders may avoid difficult conversations altogether, which Mazan says is like “leaving landmines everywhere” just waiting to blow up.

Although it might seem thoughtful to withhold difficult messages, “this is a disservice,” Dunaief says. “It robs the organization and individuals of opportunities to buy in to change” and holds employees back from “achieving their potential.”

Training can help leaders face tough conversations head on, which ultimately is to everyone’s benefit.

Was it Effective?

After having a difficult conversation, leaders may be left wondering … “How did I do?” To gauge whether or not a difficult conversation was effective, consider how the relationship feels afterward: Do you feel an increased sense of trust or psychological safety? Or do you feel more distant than you did coming in to the conversation?

It’s also important to look for behavior change after having a difficult conversation. Perhaps you spoke with a team member who was consistently late for a weekly meeting, only to find out that the meeting conflicted with their child’s day care drop-off. After adjusting the meeting time, are they on time and present? If the conversation resolved the issue you wanted it to, it means you were able to effectively communicate your message.

Lastly, don’t forget to ask for feedback: Was there anything you could have done differently that you should take note of for next time? Acknowledge that the conversation wasn’t easy for both parties, and make sure to say “thank you.”

Navigating difficult conversations is, well, difficult. But with a toolbox of human-centered skills like active listening, EQ and empathy at their disposal, leaders will be positioned to have them effectively.