Success in Difficult Conversations

In our work lives as in our personal lives we encounter situations that demand initiating a difficult conversation. These conversations are not easy, but shouldn’t be avoided because that can often make things worse.

As much as the conflict avoider in us may want to run in the other direction, those who are able to courageously confront the situation are likely to push through the discomfort and grow from it. In addition, the relationship that is demanding the difficult conversation will most likely move forward.

A difficult conversation results when two or more people have: 1) a difference of opinion, perspective, needs or wants; 2) feelings or emotions are strong; 3) consequences or the stakes are high for at least one person. When you’re in a difficult conversation, you may find:

  • There is little safety between participants
  • Emotions are defining the conversation
  • Very little listening is taking place
  • Participants are aiming for a win/lose scenario
  • Participants may be playing a role: victim, aggressor, martyr, etc.

Obviously, this can result in a highly stressful environment. But it doesn’t have to be that way. Use the following steps to be at your best when initiating a difficult conversation:

Stay Calm
Breathe. Try to be present of what you are feeling and what it is you want. If possible, try to determine what the other person may be feeling and wanting. And when you begin the conversation, be certain to communicate your intent up front in order to provide safety for the other person.

Shift Your Perspective
Rather than focus on how difficult the conversation is going to be, try to think of it as a constructive conversation. By initiating this constructive conversation, you are demonstrating the value the relationship has for you. Keep in mind that this is an investment of your time and emotional energy that will benefit you as well as the relationship.

Make a Plan
Have a clear idea of the points you want to make, but don’t write out a script. You should be able to summarize both your perspective as well as the other’s. If you are uncertain of the former, you need to figure it out before initiating the conversation. If you are uncertain of the latter, you should provide ample opportunity at the beginning of the conversation to better understand this. Be careful of assumptions you are making as these can so often derail any conversation, and are especially dangerous when emotions are high.

Prepare to Actively Listen
This means listening to the other person in a way that ensures he or she feels heard. Being an active listener means you make a conscious effort to truly hear what the other person is saying—in their words as well as their body language. Practice holding off thinking about how to respond or interrupting until you have thoroughly heard what they are saying.

Be Compassionate and Demonstrate Empathy
Consider how it may feel to be on the other end of this conversation. Be respectful while they take in what may be very difficult for them to hear. Convey in your words, tone and body language that you truly care for how the other person feels about what it is you are saying. Try to get comfortable with the awkward silence that may result.

Seek a Win-Win Conclusion When Possible
In most cases a successful difficult conversation doesn’t result in a winner and a loser. Therefore, seek out an amicable resolution to the conflict in a way that is satisfying to both parties. This is not always possible, of course, but even when you have to convey bad news such as a job dismissal, see if there is a way to soften the news. Perhaps it is simply providing information about out-placement services, severance package, a solid reference, etc.

Reflect & Learn
When the conversation is over, take a moment to reflect on what went well and what not so well. What could you have said better or differently? There are certainly things outside of your control in a heated conversation and you will need to maintain your boundaries. Don’t take on guilt for the other person’s negative reaction to your news. This requires courage and you will likely be fortified the next time you need to have a difficult conversation.

In order to have a constructive difficult conversation, the steps above should help you navigate them more successfully. In most cases, your efforts are likely to improve the relationship and build your skill at navigating future difficult conversations.

“Twenty years of research involving more than 100,000 people reveals that the key skill of effective leaders, teammates, parents and loved ones is the capacity to skillfully address emotionally and politically risky issues,” according to the authors of Crucial Conversations: Tools for Talking When Stakes are High.

Start by rethinking your difficult conversation as more of a constructive conversation. Remember that whether it is with your family members, friends or co-workers you are directly confronting an issue that has stifled the relationship. Though it is not easy to do, the result of your efforts—in most cases—will move the relationship forward and build-up a powerful skill in you as a leader.

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