How to Have Difficult Conversations

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We’ve all been there. We have a situation we need to deal with—involving our boss, a colleague, our spouse, our child, whomever—and because we realize addressing it will result in a difficult conversation, we keep postponing that “sit-down.” Meanwhile, the issue doesn’t go away, and it may even get worse, but our fear of that dreaded conversation outweighs our desire to get things out in the open.

Believe me, avoiding difficult conversations isn’t a unique occurrence; it’s almost human nature, since aren’t we programmed to protect ourselves from pain of any kind? But, this isn’t a question of avoiding physical pain—it’s just talking, after all—so why is it so darn hard? Here are a few reasons:

  • We feel like the potential outcome of a difficult conversation may create discomfort and we’re not prepared to deal with the consequences.
  • Avoiding the situation feels less stressful than confronting it, so we’re controlled by approach-avoidance or passive-aggressive behavior syndrome.
  • We tend to “catastrophize” and have irrational thoughts about uncomfortable situations. (The reality is never as bad as we imagined, right?)

The bottom line is likely this: we won’t initiate difficult conversations until we’re miserable enough to do so. Unfortunately, in some cases that may be too late, especially if the conversation results from a “trigger moment,” when it’s apt to spin out of control.

Ask yourself what price you’re paying by not having a tough conversation, and when you’re ready to be proactive, there are just two essential steps you need to take:

  • Thinking—deciding/making the difficult decision to have the conversation
  • Taking action—learning the skills you need to have the tough conversation and using them

Your thinking process begins by having a conversation with yourself: “discuss” what happened; explore intention, truth, and blame; and understand that the goal of the difficult conversation is to minimize hurt, anger, and guilt while allowing for as much integrity as possible. It’s important that your behavior be based on learning, rather than judging. These are some of the issues Marilee Adams, Ph.D., addresses in her insightful book, Change Your Questions, Change Your Life. Ask yourself questions like:

  • What do I want?
  • What are my choices?
  • What assumptions am I making?
  • What am I missing or avoiding?
  • What action steps make the most sense?

And, most importantly, “How can I turn this into a win-win situation for everyone?”

When you take action, be prepared to listen non-defensively, hear the other person’s perspective, and acknowledge it—even if you don’t agree. Avoid using global generalizations like “you always” or “you never” and don’t attack the person, instead describe behavior, provide objective data, and identify what your ideal outcome of the conversation would be.

There are two things to never lose sight of as your conversation moves forward: 1) your preparation won’t necessarily eliminate your discomfort, but minimize it, and 2) your behavior will affect the other person’s, so it will pay significant dividends to remain calm and focused on the matter at hand.

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