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Common mistakes people make when having a hard conversation at work

As a leadership expert, I help people negotiate these high-stakes situations frequently. These are the recurring issues I see.

Common mistakes people make when having a hard conversation at work
[Photo: fizkes/iStock]

There are times when having a difficult conversation at work is necessary. As a leadership expert for over 20 years, I often coach people, of various experience levels, through having these conversations effectively.

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Of course, difficult conversations can take many forms. It could be a discussion between two peers of equal level who disagree about how to move forward on a project. It could also be between a boss and an employee over a performance concern.

Although the subject matter may change, the stakes remain the same: Being ill-prepared for these exchanges can have an impact on your reputation and your role in team projects. Taking this a step further, poor communication can affect a company’s bottom line. And, in today’s work environment, strong interpersonal skills are essential in increasingly collaborative, networked organizations. When communication goes off course, it can affect goals and targets negatively, prompt high turnover, and result in low employee engagement.

When our company, Steinbrecher And Associates, Inc., set out to collect data on the behaviors of highly successful, emotionally intelligent leaders, we discovered that their goal when interacting with others was to come to “alignment,” which is not necessarily to reach an agreement or to end a discussion in disagreement. We found that their objective was to arrive at an understanding, or a meeting of minds, that moved them closer to accomplishing a common goal.

One of the ways they achieved this was by carefully preparing for important conversations and meetings prior to the engagement. (Of course, learning how to master these skills is equally important in the home and impacts relationships between partners, friends, and family.)

When preparing for these thorny conversations, take care to avoid these all-too-common traps:

Avoiding the conversation all together

This is probably the most common reaction when we don’t want to face a particular person or situation. People tend to avoid challenging discussions, as they do not feel confident or comfortable about having them. Of course, this almost never solves the problem.

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Putting off a necessary conversation just leads to further frustration and, often, resentment. Remember that if you work with this person again, there is a relationship to manage—as well as achieving a desired outcome. For example, if a conversation with a peer did not go well, the history of that experience will follow you into the next meeting with them. Avoiding the discussion will only prolong an ongoing issue.

Overestimating your abilities 

This is the exact opposite problem. While many people are afraid to raise difficult subjects, other people overestimate their current ability to manage difficult discussions. There are several reasons why and how this emerges: People often confuse their job competence and subject matter expertise with the ability to communicate, collaborate, and to listen to others mindfully. As well, many people tend to overestimate their level of emotional intelligence.

To avoid this, try some emotional regulation practices. These are habits to cultivate over the long term that may help you avoid the pitfalls of overestimating your ability to manage emotionally charged situations. While they won’t necessarily improve your emotional intelligence, they may keep you from making big mistakes. These practices include taking an intentional pause before responding when your emotions run high and focusing on your breath.

If things seem to be getting out of hand, try deflection techniques, such as asking the other person more questions instead of answering too quickly. And finally, you can always delay the conversation for another time if none of the other methods are working.

Not preparing

This is a chronic, habitual tendency of exceptionally busy people. Even the most emotionally intelligent person on the planet cannot expect to walk cold into one meeting after another and hope to accomplish anything resembling alignment on crucial issues. Without adequate preparation, successful alignment is not only unlikely, but in some cases, it is impossible.

To avoid falling into this trap, take some time before you sit down with the individual in question to think through the situation from both your own and the other person’s point of view. Some details you may want to consider are the best time and location for the conversation.

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For instance, where will your discussion take place? Believe it or not, the environment of your meeting can have a significant impact on the outcome. Think through specifics such as room temperature, noise level, lighting, furniture, comfort, and refreshments. Be sure to give yourself enough time to gather any information you may require for the conversation, and then consider the following:

  • How do you think the other person sees the situation?
  • What is the perfect outcome of this conversation for you?
  • How do you want to share information in order to provide your point of view?
  • What behaviors and emotions might the other person express?
  • How will you cover each step in your conversation?
  • How will you deliver your part of the conversation? (Try rehearsing it with a trusted friend and get their feedback.)
  • Visualize the conversation, as you would want it to unfold.
  • Do five minutes of mindfulness meditation right before having the conversation.

With practice, anyone can learn how to manage high stakes, stressful conversations while preserving relationships. When coworkers achieve a better understanding of one another and can become more aligned on projects, they make deeper connections, and organizations can experience constructive cultural shifts.


Susan Steinbrecher is the CEO of Steinbrecher And Associates, Inc., a leadership training and executive coaching firm. She is the coauthor of Meaningful Alignment: Mastering Emotionally Intelligent Interactions at Work and in Life, Heart-Centered Leadership: Lead Well, Live Well and author of Kensho: A Modern Awakening.

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