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January 04, 2020

Prerequisites for Having a Difficult Conversation

Having a difficult conversation typically involve sharing a frustration, giving critical feedback, working through a disagreement, or making someone aware of how they’ve negatively impacted you or the team. We encounter these at various times in our professional and personal lives. [Go here for a quick caveat about difficult conversations]

Once you’re clear about why you want to have a difficult discussion, and you’re committed to initiating it, I’d encourage you to first consider some important foundational orientations.

Part of what leads to an effective discussion has to do with addressing these prerequisites first:

Clarity and self-awareness. Whatever the situation is that you’d like to discuss — Are you clear about how you’re feeling about it and why? Can you name the emotion? Can you describe what situation or behavior triggered it? Knowing the answers to these questions will help you communicate clearly when discussing the situation with another person.

Being out of the emotional trigger. Before having a difficult conversation, it’s best if you’re not in the height of the emotions that were originally triggered. Find ways to process or release the emotion first before attempting to have a discussion. That way, you can remain more grounded, objective, and open during the conversation.

A goal of connection, not winning. Ask yourself—what’s my goal in having this discussion? Is it to win the argument, prove the other person wrong, or make the other person feel bad? Whatever your intention is, it will inform how you show up and what you say, even unconsciously. See if you can connect with a genuine desire to build connection and strengthen the relationship.

Courage. Courage is not the absence of fear or vulnerability, but the willingness to step into it for the sake of something important. As John Wayne said “Courage is being scared to death and saddling up anyway.”

Genuine curiosity and openness. This is an important starting point for any attempt to share differing views with the desire to create mutual understanding. As Edgar Schein points out in his book Humble Inquiry, “The more we remain curious about the other person rather than letting our own expectations and preconceptions creep in, the better our chances are of staying in the right questioning mode. We have to learn that diagnostic and confrontational questions come very naturally and easily, just as telling comes naturally and easily. It takes some discipline and practice to access one’s ignorance, to stay focused on the other person.”

Seeing the other with compassion. I find it helpful to focus on the humanity of someone with whom I’m about to engage in a difficult discussion. They have their own stresses, challenges, and woundedness. Their own story and journey. Having some compassion for those aspects can help set the stage for positive connection.

Now, go here for a playbook of strategies and phrases you can use for having a difficult conversation.

A caveat about difficult conversations: the discussions I’m referring to in this article aren’t the same as those that would address incidents of discrimination, racism, harassment, or abuse. Conversations about these situations would require a different approach, likely aided by advice or mediation from professionals in human resources, psychology, social work, law, or otherwise.  

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