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Essentials for the Inevitable Difficult Work Conversation

June 28, 2019

3,000. That is the number of results that come up on Amazon.com when searching for “workplace communications” books. Clearly, appropriate and effective communication and conversation are essential to almost any job in any industry and in any country. So fundamental is this behavior that it is often taken for granted and believed to be as natural and intuitive as taking a breath.

For some, in fact, it is. History is filled with skilled communicators. Those for whom capably conveying a message or having a conversation is effortless. According to USC Annenberg School of Communication and Journalism, Winston Churchill and Martin Luther King, Jr. fell into this category. Each understood how to communicate in difficult situations. Churchill understood the value of messages that are short and to the point while Dr. King’s famous speech included the words “I have a dream” eight times, demonstrating the importance he placed on repetition to impart an idea.

But what about the rest of us? How do we have difficult conversations in our career, jobs and business life? These tough work conversations may be about performance (or the lack thereof), change, new responsibilities, diminished responsibilities and the list goes on.

To begin, it is critical to realize that what is defined as a difficult conversation is subjective and personal exchanges that are felt to be awkward or touchy vary from person to person and even within the same person over time. This depends largely on a person’s personal history, personality traits, communication style and even emotional intelligence. Your current state of mind and personal circumstances can also impact what is perceived as a difficult conversation and as we know this shifts frequently. Your seniority and level within an organization can also be a factor in how and what you perceive to be a difficult conversation.

No matter what we personally designate as a difficult conversation, the reality is that we all must be a party to them from time to time. Implicit and important here is the idea that these conversations best not be avoided. Kicking the proverbial can down the road or sticking one’s head in the sand will not make matters go away. In fact, one can argue that procrastinating allows an issue to fester and may make it worse and ultimately even more difficult to discuss. So, rule number one is to avoid avoidance. Determine your own best way to approach a difficult conversation but approach it you must.

Approaching a difficult conversation does not imply a scattershot approach. Rather we must have the self-awareness and awareness of circumstances to calibrate our message to unique circumstances. For example, discussing an unpaid invoice with a client necessitates a different approach than informing a member of your team that their performance requires improvement. To the extent possible, adopt a situation sensitive approach.

Keep your goal in mind. Difficult conversations can get…difficult. Reactions are unpredictable. It can be easy to get distracted and caught up in the moment and the emotion. As such, when preparing for the dialogue it is essential to determine the goal or desired outcome. This will help keep you on track.

It is also important to try to set some time limits on the conversation. Without this, there is a risk of an endless exchange. It can become a drawn-out and unproductive. Limitless analysis and examination of the situation will undoubtedly allow emotions and distraction to creep in; a succinct and sensitive approach is optimum.

When thinking about the difficult conversation you need to have, it is advisable to think about the reaction you will get. The other person will have his or her own unique circumstances, views and reactions. He or she will surely have at least minimal difference of opinion and/or assessment of the situation or problem at hand. Try to take this into account. Be prepared to accommodate and adjust but without losing track of your goals and the objective of the conversation. Remember that the other person’s unique point of view may be impossible to anticipate.

This next suggestion may be obvious, but in difficult conversations it’s best to avoid blame and disparagement. The other may be at fault however criticism has the effect of putting people on the defensive and instead of receiving your message they will be focused on objecting. Keep it productive and non-confrontational. This will make it easier for both of you and also increases the likelihood of a positive resolution, whatever the issue may be.

Finally, practice is helpful. This may come from experience with these types of conversations themselves or from a practice session with a trusted friend or family member. Iron out your message, get feedback about your style, tone and even body language. Be open to reflection and improvement.

You may never look forward to or enjoy a difficult conversation in your workplace, but some forethought and planning can certainly reduce discomfort and improve outcomes. Avoidance may be easy in the near-term but not ultimately effective.