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How to Have Difficult Conversations

You need to warm up before having a difficult conversation. Here is how.

One mayor barrier to success in business and happiness in life is our inclination to avoid conflict—which often means to avoid having a difficult conversation. Learning how to have difficult conversations at work or in a personal relationship boosts one's confidence, increases one's self-awareness, and the sense of being in control of one's own life.

We fool ourselves by thinking that the pain of not having that difficult conversation is lesser than the pain of having it. As a result, we use a variety of strategies to hold onto a problem. We might deny it, avoid it, resist it, rationalize it, or—which is a strategy we use so often—we blame someone else. Sometimes, we just submit to a problem and raise our hands. Whatever the combination of strategies is, we don’t self-author that part of our life. But our experience tells us that a problem doesn’t just go away, especially if it relates to a relationship. To the contrary, it tends to balloon and you might end up feeling caged, with your wings of freedom clipped.

What stops us from having that difficult conversation we should have? In one word, it’s fear. Fear of harming the other, fear of harming oneself, fear of losing the person we love or the consideration of a boss we want to please, a promotion, etc.. In other words, we fear the consequences of engaging in a difficult conversation.

There are several steps one can take to master difficult conversations. In this post I want to focus on how you can prepare to engage in a difficult conversation. I believe this is the most important component of an approach to difficult conversations and it’s one that is not often underlined enough. Like an athlete before engaging in a race, or an actor before stepping onto a stage, you need to warm up before entering into a difficult conversation.

Here is an exercise through which I like to guide my coaching clients and which produces great and often surprising results. It helps facilitating difficult conversations. Most recently, it has helped an executive, who was ready to resign, to realign with her principle and increase the performance of her team. It has helped a husband to have a conversation with his wife that had been postponed for years, beginning a very positive process of healing and reconciliation.

How to Prepare Yourself for a Difficult Conversation

The exercise consists of three steps.

First Step: Write a Letter.

Find a quite spot and a quite moment, sit down and write a letter to the person with whom you need to have the difficult conversation. Actually, it is a letter that you are not going to send to him or her, but writing it will allow you to put on paper your own experience, all your feelings, your personal perspective. While writing it, don’t censure yourself; don’t embellish your choice of words. Write down your raw experience and feelings. If you are bitter and angry, so be it. If you feel hurt, betrayed, misunderstood, just say it in plane language. Make sure nothing is left out. Once you are done, let it rest for a few hours or even a couple of days. Then, read it again and make sure your experience and emotions are captured in an accurate and comprehensive way. It helps to read the letter aloud as if you were reading it to the person it is addressed to. Edit the letter, if you need to.

Second Step: Step into the Other's Shoes.

Now that you have written the letter, put yourself in the shoes of the person that receives it. How will he or she react to your letter? How different will his or her perspective be? Sit down again, and draft the response to yourself as if you were the person who received the letter. Again, be as thoughtful and thorough as possible. What does putting yourself in the shoes of the other allow you to see of your own experience that you hadn’t considered before? This part of the exercise is very important because it helps you to gain some distance from your own experience and to consider how possibly the other interprets the same situation. Furthermore, it helps you to consider your own responsibility and your own contribution to the uncomfortable situation you are facing. In other words, you gain a larger perspective and this is important for the moment in which you will have the actual difficult conversation.

Third Step: Reevaluate.

Write again a letter in response to the one you received. Now that you have acquired a larger perspective, reconsider the experience again and write it in the form of response. At the end of the three steps, you will be more self-aware of your own experience and emotions, as well as more aware of the overall situation in itself. You will have gained perspective as well as clarity of what your responsibility is; you will see how the situation you are in is also the results of your own actions, emotions and thoughts. This, in turn, will help you to consider what changes you can make to ameliorate a given situation. You will have shift from a situation of avoidance or resignation, to one in which you are taking a constructive action.

All in all, these three steps will help you to get into the right state of mind. Now you are ready to focus on what is your desired outcome for that difficult conversation you have been putting off for some time.

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