The Difficult Conversations Every Leader Needs to Master – Part 1

A difficult conversation is any conversation in which there are strong differences of opinion between two people, and which has the potential to become emotional.

In Part 1 of this article we’ll explore what makes a difficult conversation difficult. In Part 2 we’ll consider a few practical steps to take to make a difficult conversation more effective and less stressful.

Why are some conversations difficult?

People enter almost every conversation with certain expectations and opinions/positions. Those expectations are based on the relationship between the people, and the circumstances surrounding the conversation. When it feels like those expectations or positions are being challenged, human nature often reacts initially with emotion. For example, seeing a coworker with a smile on her face after a holiday weekend approach you and ask you about your weekend, you expect a pleasant conversation. Conversely, if you made a sizeable mistake and your boss asks to meet with you, you enter the discussion with a degree of apprehension.

What are the emotions that often characterize a difficult conversation?

People are by nature emotional creatures. Emotions tend to influence the direction of most conversations. Having too much emotion often leads to bad outcomes, while having too little emotion can make the conversation seem fake. Unless one is intentional, emotions can take over a difficult conversation.

Difficult conversations are often characterized by emotions such as fear, anger, frustration, conflict, and other strong dividing – not unifying – emotions. The emotion is often pent up and can be released rather strongly. Because emotions can run high on both sides, the conversation may become quite heated. It’s normal to have fear and worry that a person initiating a difficult conversation might offend the other person or that something might go wrong.

Emotions can be strong, and when they become strong enough to overcome a person’s natural inhibitions against acting on his or her emotions, the behaviors driven by strong emotion may not be appropriate. A natural tendency when reacting to emotion is to “shove back” when emotionally shoved. Of course, this often brings a shove back from the person and the situation can escalate quickly without ever being the initial intent of either party.

Call to mind the last difficult conversation you had, and answer these six questions:

  • What was the issue that precipitated the conversation?
  • How much time did you prepare for the conversation before having it?
  • What were the emotions you were feeling?
  • How clearly were you or the other person thinking during the heated portions?
  • What there any relational damage-control that had to be done afterwards?
  • Did the issue addressed get blown out of proportion at all?

Human filters create some of the difficulty

Human filters occur on both sides of a difficult conversation. For us as the listener, a natural response to something we don’t want to hear is for us to insert filters in order to lessen the discomfort of hearing it. The filers can cause us to miss the substance of what is said, and we come away with only a sense of how badly we felt (and the baggage of negative emotions like resentment).

For us as the speaker, when we need to confront an issue, it’s likely for us to filter what we are saying in order to soften the message. We may dance around the issue in such a way as to be confusing or never get to the real issue. Or worse yet, we might simply avoid the difficult conversation and hope that the issue goes away. For any sizeable concern, avoidance is never an effective solution.

It’s more costly to avoid the difficult conversation

According to research by CPP Inc. & Accenture, each US employee spends 2.8 hours out of each workweek dealing with workplace conflict caused by people who should have taken part in a difficult conversation. About a third of these situations result in personal injury or attacks, while 22 percent of employees said that it led to illness and workplace absence. Unaddressed conflict is cited as a reason for quitting a job about in about 35 percent of the quits.

THus avoiding the difficult conversation will likely cause even more problems than finding an effective way to hold the difficult conversation.

Bottom Line

A difficult conversation is any conversation in which there are strong differences of opinion between two people, and which has the potential to become emotional. Difficult conversations are part of every organization in every country and every culture in the world. Leaders must be prepared to lead effectively more then ever when the conversation turns difficult.

In Part 2 of How to have the Difficult Conversation we’ll consider a few practical steps to turn around the difficult conversation and make it more effective and less stressful.

This article was in part excerpted from module 27 of my acclaimed leadership training program, Leading Through People™, which has made a positive difference for more than 10,000 supervisors, managers, and leaders worldwide.

I love working with people and organizations who want to improve their effectiveness! Here are several outstanding resources that can help you and your organization to go to the next level:

About me: I work with some of the world’s top employers by helping them get the most out of their talented people. My company’s extensive leadership development course catalog provides effective skills-building for everyone in the organization, from the new / developing leader to the seasoned C-level executive. My company’s coaching programs produce significant results in compressed periods of time. I also help job seekers, higher ed, and employment services connect people to better jobs faster. My company’s acclaimed career development tools help people navigate the ever-changing landscape of conducting a successful job search. To find out more, please visit us at, email us at, or call us at 215-942-0982.


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