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Preparing for Difficult Conversations


August 19, 2014  Min to Reads


We all know that if we are going to interact with people then we are going to have difficult conversations. Even more self-apparent is the fact that if we serve any leadership capacity difficult conversations are not only inevitable; they are necessary. The question is how to get good results out of these conversations.

In my leadership journey I am learning a lot about what works and what doesn’t work. One crucial lesson that I am in the process of thinking through and absorbing is the need to be prepared for the unexpected before entering into these types of conversations. We are dealing with human emotions, ours and the other party’s, so the course of the conversation can move down a multitude of different paths, most of which we don’t prefer or expect, but expect them we should and prepare for their eventuality we must.

I recently failed to make such preparations and found myself caught off guard by the response I received from the other person involved in the conversation. Needless to say, the conversation wasn’t the success I planned. I really knew better, but I only prepared for one response and therefore wasn’t in a position to shift my course appropriately.

My suggestion is that we should plan for multiple courses and have contingency plans in place for such shifts in direction. Ultimately we want to steer the conversation to our preferred end, but we must also prepare for the real possibility that the final destination point may be far away from where we had planned. The key is that if we arrive here because we took a different path for which we were prepared, we at lease arrived somewhere that we understood was a possibility and we now know where to go next. If the destination is a surprise, we will be lost and frustrated, and the way forward will be vague and difficult to discern.

The advice to prepare for multiple paths in whatever journey we take is good advice, but in difficult conversations it may be the difference between leaving with our integrity in tact or leaving embarrassed and upset. I’ll leave you with three specifics tactics for preparing for difficult conversations.

  1. Rehearse the conversation following the different paths you believe it may take, and guide it in your mind to a fruitful conclusion.
  2. Prepare a variety of questions that you can ask to keep directing the conversation. Write them down and rehearse them imagining the different responses you may receive, thus keeping you from surprise and the emotional turmoil that often accompanies surprise.
  3. Prior to the conversation, think about the various positive attributes that you see and appreciate about the person you are getting ready to engage. Write these down too so that you don’t loose sight of them. This will help you speak with compassion even while being direct, and it will help you avoid turning your emotions negatively toward the person.

What about you? How do you prepare for difficult? What other tips can you share? Please share your comments as others will benefit from the collective wisdom.

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