Cultivate the Qualities that Make Hard Conversations Easier

Conversations where the stakes are high and the relationships are important can be challenging.

Some conversations are harder than others. Whether it is negotiating a deal that the company is relying on, asking for a raise, addressing the problem behaviour of an employee, telling a boss we think they are making a mistake, bringing up a problem with a spouse, or disciplining a child, there are some conversations that get our hearts racing.

Conversations that are challenging typically have one or more of three components:

  • The relationship is important.
  • The outcome is important.
  • Conflict is expected.

The more of these components involved, and the more important either the relationship or the outcome are to either party, the more difficult the conversation is likely to feel.

Because all of our relationships are created through the conversations that we have, our ability to talk about the important things determines the quality of our relationships. So, getting better at these conversations will improve the quality of all our relationships.

Whether you initiate a hard conversation or it takes you by surprise, the most valuable thing you can do to assure a good outcome is to manage your own fears and your own emotions. Many people think that if they have the right skills and the right words they will be able to manage these conversations, but the truth is both easier and harder than learning communication skills. How you are in these conversations is much more important than what you say.

Cultivate These Four Qualities in Your Relationships to Make Hard Conversations Easier

There are two main challenges: finding the courage and willingness to have the conversation in the first place, and staying when it gets rough.

Many people go through life avoiding conflict at all cost and never cultivate the courage required to have these conversations. Others manage to start the conversation, but disengage when a certain threshold of discomfort is reached.

To have important conversations despite fear and discomfort requires courage, commitment, compassion, and patience. These are all qualities we can cultivate within ourselves.


Introducing the topic of a hard conversation requires the courage to face one’s fears and a willingness to be uncomfortable with whatever comes. With practice, you learn that you will be able to handle whatever the outcome of the conversation is. That knowledge becomes the basis for courageous action. But before you have that experience, you may need to give yourself permission to be afraid, hurt, upset, threatening, and unskillful about having these conversations. Permission to be a beginner. And courage to dive in anyway.

Courage can be cultivated in many ways. A common tactic is to undertake skill training to increase confidence in one’s tactical skills in having effective conversations. You can also practice taking risks and celebrating handling whatever arises. In addition, courage can be bolstered by focusing on your commitment, especially to a given relationship or to important personal values.


Throughout history, parents who are committed to the physical safety of their children have overcome enormous obstacles in the face of danger. The same is true with less physical challenges. When we are more committed to a relationship or ideal than we are afraid, we act.

In the context of hard conversations, it helps to remember how many relationships are ruined by silence and hiding. When we convince ourselves that avoiding conflict in the moment is better than being real in a relationship, we betray the relationship. It is more effective to have the hard conversations in service of the relationship. The wonderful thing about choosing to serve the relationship instead of our fear is that when we focus outside ourselves, our fear naturally diminishes.


After we have found our commitment and mustered our courage to have a hard conversation, we must engage with compassion and empathy. We must have compassion for ourselves, for our fears, our imperfections, and our unskillfulness. As we practice having these conversations, we will start by doing them badly. We will lose our focus, overstate our positions, forget our commitments, and lose our courage. We must forgive ourselves for these missteps. They are simply speed bumps on the learning curve to better relationships.

We must also have compassion for the others in the conversation. They are probably as afraid as we are, maybe more so. We must have compassion for their vulnerability, the amount of courage it requires for them to engage in hard conversations, and their lack of skillfulness. We must have empathy for them, both in terms of the challenge of this present conversation, but also for how they got to this moment. This hard conversation may remind them of other hard conversations in their past that did not go well.


Patience is letting a conversation take as long as it takes to get to resolution.

Once a topic has been raised, people decide that a conversation is safe enough to engage in fully at different speeds. Some people are willing to make themselves vulnerable and share what is important to them quickly. Others are slow to lean in and need to test trust in micromovements. You are in control of how fast and how far you lean in, and you cannot control how far the other person does. Patience will keep you in the conversation as another person finds their courage to participate fully.

Cultivating patience through staying fully engaged in relationships through discomfort is a skill that can be developed and a practice that transforms the potential of any conversation.

Do you have conversations that you need to have? How can you cultivate courage, commitment, compassion, and patience in those conversations?

Let me know in the comments or on my Facebook page.


This post is part of the 2017 Blogging from A to Z Challenge.


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