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Life would be so much easier if we just didn’t have to have “the talk”.

Some of us have made dodging difficult conversations an art form while others dive into them like a bull in a china shop. There is no easy way of having a conversation with someone that may very well hurt their feelings, put them on the defensive, or make you feel uncomfortable. However, depending on your approach, hard conversations with others can actually lead to personal breakthroughs, mutual understandings, and can even strengthen relationships rather than destroy them.

It seemed like every conversation I was having was a difficult one. From hashing out a communication problem with my work partner to telling a dear friend about her habitual lateness, I was constantly in the position to deliver a confrontational message.

In the past, my way of dealing with difficult conversations was quite simply not to have them. I had a nasty habit of putting them off or I would go into them on the defensive. I’ve also been on the receiving end of a difficult conversation and it’s just as tortuous. Earlier in my career, when I was laid off, I vividly recall the troubled expression my manager had when she delivered the news. I could visibly see how difficult it was for her to let me go.

When it comes to handling difficult conversations, we either:

  • React passive aggressively
  • Go into battle mode, or
  • Avoid them all together

By that logic, the risk of tarnishing the relationship is too great. When difficult conversations are not handled with care:

  • Relationships are ruined
  • Feelings go unexpressed and are pent up
  • Resentment ensues
  • We miss opportunities for genuine connection

There is a better way. Here’s what I’ve found works when having a difficult conversation:

1. Always have them face-to-face.
In our technology-driven world, it’s easier to shoot off a text or email to say what we can’t say in person. The problem with this approach is that online communications can be taken out of context and be completely misinterpreted. Without human components like tone of voice, body language, and personal presence it’s hard to get the complete story.

Here’s what to do: If you find an online or text conversation is leading into an uncomfortable space, stop and redirect. You could say something like: “I sense this conversation is going in a direction that might be better spoken about in person. It’s important to me that we continue this. Can we find some time to talk more in person?” If an in person conversation is not possible, speaking by phone is your next best option.

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2. Check your intentions.
Your intention for the conversation is the most important thing to consider. Founder & CEO of, Tanya Ezekiel has a great list of pre-requisites to have in place before having a difficult conversation. She advises that you make sure your intention is not to prove your point or get something off your chest. As a matter of fact, if you come into any conversation with an “I’m right your wrong and here’s why” approach, it’s a surefire way for things to go badly.

Here’s what to do: The trick is to get clear on your intentions for the conversation. Be sure to check-in with yourself first beforehand to make sure your intentions are to:

  1. Understand the other person and
  2. Improve the relationship.

You can accomplish this by setting aside your ego, being empathetic, and being open to co-creating a solution to move forward.

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3. Get centered before the talk.
When you feel upset or otherwise emotionally charged about a situation that involves the other person, it can make having a difficult conversation feel that much more difficult. Emotions can takeover leading to a total breakdown of the conversation and leave the situation completely unresolved. You may say things you don’t mean, feel like you weren’t being heard, or cause the other person to get defensive.

Here’s what to do: Put some space in between you and the conversation. If you need time to process and clear your mind, take it. If you find yourself getting tense in the midst of a difficult conversation, take a pause and excuse yourself until you can collect your thoughts, work through your emotions, and return to it with a clear mind. Some people need more time to process things than others. Honor whatever time you need to center and prepare yourself but do set yourself a firm time to come back to the conversation and stick to it.

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4. Be empathetic and consider the other person’s POV

Sometimes we may come into conversations with our own one-sided point of view. This can be limiting and doesn’t take the other person into consideration. There are always two sides to a story but if we don’t put ourselves in the other person’s shoes, we will never get the full picture.

Here’s what to do: Look at the big picture. Maybe the communication breakdown was because you didn’t give clear directions. When you are willing to see the other person’s perspective, you learn what you can do to improve and move the relationship forward.

You could also talk it over with someone who is detached from the situation and holds no personal interest in the outcome other than to help you see the bigger picture. This can be a trusted friend, mentor, or coach. Ask this person to help you see things in a different way.

We don’t have to dread difficult conversations and confrontation. When entered with care, they can have the capacity to heal and deepen relationships.

This article originally appeared on Live in the Grey.


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