“Listening well is one of the most powerful skills you can bring to a difficult conversation.”
-Douglas Stone, co-author of Difficult Conversations and Lecturer at Harvard Law School

Conversation, by definition, is an oral exchange of information, as well as the expression of ideas, but true communication can not transpire without active listening. Your team can distinguish from your responses and other nonverbal cues if you simply hear them, but do not listen to them.

What is a difficult conversation?

A conversation becomes difficult when two people have different opinions and they are not in agreement. There is a feeling of negativity like you feel anxious, you feel you’re not heard; you feel hurt, and you feel angry. These are signs it’s a difficult conversation.

The person you are talking to is opposite from you, very different from you, operates differently, may be from another department and has different views. Some people are harder to understand; therefore it’s harder to get your point across.

This is where communication is very important because both of you have different communications styles.

As a leader, you can develop and master the art of difficult conversations, but you must consider many factors of the discussion before it even begins.

According to a study, one in four people “have been putting off uncomfortable conversation for at least six months.” And people are avoiding difficult conversations in different ways:

      • 50% of people would avoid talking to the other person;
      • 37% would dance around the awkward topic whenever they speak to the person in question;
      • 37% consider quitting their job or taking a different job; and
      • 11% quit their job.

How do you prepare for a difficult conversation?

Preparation is like a seed from which an outcome can blossom. The seed or message may be unpopular, but if nurtured in good soil can be cultivated to an acceptable outcome.

Being a leader means that you have to have this skill to deal with people when conversations seem to drive a wedge in the working relationship.

Here are five tips to note to effectively handle a difficult conversation:

#1: Set aside your biases and emotions

Take yourself out of the situation and look at it through a third-party lens. Understand what this person needs, what this person’s role is in the organization, and what is important to this person. Have that frame of mind where you want to understand that person despite the thought that this is a difficult person.

Before entering the conversation, it would be good to put everyone on the same page with the same goal in mind. You could start the meeting with: “In this meeting, we are going to be open to suggestions. We are not going to judge each other” or “In this meeting, we will listen to challenges and won’t be defensive.”

The people in the meeting might already know these, but starting the meeting with these sort of reminders can help everyone stay focused on the goal of the meeting. This is especially important when emotions come in and when triggers come in as people in the meeting might not be able to think objectively at that moment.

#2: Be aware of your triggers

It is important to know the people who, in any way, “trigger” your emotions. People can trigger you to be emotional. And when you are emotional, you might become reactive and unable to respond in a way that is best for you both and ultimately for the company.

So stay focused on the goal of the conversation to help you remain objective. Notice your emotions and reactions during the conversation. Do a self-check and recalibrate when you notice that your emotions are changing.

Prior to the meeting, profile that person who triggers you. This will help you prepare how to communicate with this person during the conversation.

#3: Be aware of your state

Sometimes a lot of things are happening in a day and you just came from a stressful situation. You need to check yourself and ask what your state is today before having a conversation with that person. Make sure that you are prepared to give your full attention to the person you are going to talk to.

#4: Be open and curious

Curiosity is important in difficult conversations. Leave your assumptions at the door. Instead of making assumptions about the person, stay open and curious. Keep an open mind. Stay focused on the goal. Try to find out ways where you can find common things together and to come up with a win-win solution for the person and the company.

Try to look at the conversation in another perspective and ask yourself: What is this person’s point? What is my point? How do we meet halfway?

#5: Have self-awareness

If things are getting too far, step back and recalibrate. Ask yourself: How am I feeling? Where am I at the moment? How am I reacting? Is my reaction helpful to the situation? Am I contributing to the situation?

Be reflective, rather than reactive. Reflect on your contribution to the conversation. How are you contributing to the problem that is making that conversation difficult? Should you change your tone? Or maybe change the way you ask questions? Should you be more curious and open?

What can you do when problems arise during a difficult conversation?

Sometimes in a conversation, things do not go as planned. You see no progress in addressing the issue at hand, which leads to a deadlock. It is important to note that coming up with a solution immediately is not necessary. Here is what you can do:

      • Call for a time-out. You must listen more than you speak. Pause, listen, and then pause again.
      • Set aside the issue and deal with it later. Let off steam.
      • Get a third party who is neutral in the matter to help mediate.

Understand that your role is not to enforce your message but to listen to the other person and craft a response that incorporates both your points of view. When the other person is obstinate and refuses to abandon his ideas, politely request a more detailed explanation of how they want things done to exhibit gaps in his understanding.

Using questions like “what if” and “could we” can break down the defense and spark creativity in the discussion.

What phrases to avoid and what to use instead

“Difficult conversations stem from different communication styles. You may have good intentions but the other party does not see it.”
— Anda Goseco, Global Executive and Leadership Coach

During a heated discussion, there are phrases and expressions that create triggers in the audience. It is best to avoid these words:

  • “Clearly”, “obviously” “without a doubt” communicate oversimplification and leave the audience feeling inadequate.
  • Exaggerations and instructions such as “should”, “you never”, “you always” should be replaced with “have you thought of” or “have you considered”.
  • Avoid saying “it is not personal” rather, prepare a list of phrases that sound less of an attack after all words have lasting impressions.
  • Practice phrases like: “this are inconsistent with our core values”, “this undermines the trust we have built” and “I will count on your support to champion all our values moving forward”.

Have you ever been in a difficult conversation?

“Defining your goals in the beginning, identifying what is good for the organization, and what is important to everyone can tone down the things that trigger a difficult conversation.”
— Anda Goseco, Global Executive and Leadership Coach

Reflect on these questions and check if you need to make changes.

  • What are those difficult conversations you have encountered before?
  • How did you contribute to that?
  • What do you need to do now and in the future to change the outcome of those difficult conversations?

Remember that in a conversation, there are always two people. When it becomes difficult, there’s no one to blame. As Douglas Stone said, “The single most important thing you can do is to shift your internal stance from “I understand” to “Help me understand.” Everything else follows from that.