Difficult Conversations


This past week at work we had a class on having “Difficult Conversations.” It couldn’t have been timed better; we had just been on a long photo-shoot where not only do we have to work with our team for an extended period of time, but we have to work with other teams as well. So many personalities together for 10 days straight you are bound to have some conflicts!

I do not like confrontation, I don’t like to make a big deal out of little things, and it takes a lot for me to get to the point where a conversation is necessary. I am one of those people that feel other people’s embarrassment. I don’t like to make anyone uncomfortable it makes me uncomfortable; I would rather be uncomfortable than make others uncomfortable. I have a hard time watching a movie where someone is embarrassed! I cringe and my face gets a little warm… but if there is one thing I have learned, you can’t always avoid confrontation. In my professional life, family life, and even with my closest friends, no matter how laid back you are, from time to time a difficult conversation is necessary.

I have recently discovered that the people I value most in my life are the ones that I can have a difficult conversation with and we can come out of it better and stronger than before! If someone really cares about the outcome they will come into the conversation looking at the big picture rather than just looking at their point of view. Which is the perfect beginning to a difficult conversation.

Here is what I learned from our Difficult Conversation Class:


Share Your Positive Intent

First things first, do not have a conversation with someone just to share your frustration with them, know what you hope to accomplish. Ask yourself, what is my intention for having this conversation? Enter the conversation and open with that, your positive intention.

Some examples of positive intentions:

-Improve a situation or working relationship -Clarify feelings, avoid repeating a situation -Support an environment of trust and accountability

Some not-so-good intentions, if these are your reasons, it may be best NOT to have the conversation:

-You’re making negative assumptions. You may fell ignored, disrespected, or marginalized, but you are assuming that was their intention? Remember, impact does not necessarily mean that is what they intended. (Another class we had at work was Positive Intent. It was super helpful as well and the key take away, was in any situation always assume the other person had positive intentions.)

-Win, get even, prove “I’m right” or have another person admit they made a mistake -Assign blame or cause guilt/embarrassment/ shame

If your intention is one of these reasons, don’t let the emotions festers. You need to work through it, but not with the other person. Go home and talk to your spouse or your best friend, someone not involved in the situation. Write about it in your journal, work through those emotions, so you can come back at the situation with a different view.

When you approach the other person you should be able to address the situation in 60 seconds or less! Get straight to the point. One thing we were told not to do is start with something positive, insert the negative feedback, and end with something positive, that’s apparently called a “feedback sandwich,” and either your message gets lost, or whenever you compliment that person going forward they will be waiting for that negative feedback to follow.

The opening statement should be your positive purpose, and then that person knows why you have chosen to speak with them and what you hope to accomplish.


Share Your Perspective

Describe a specific situation or example that illustrates the behavior you want to address, but only focus on the facts, don’t let your emotions get the best of you or make assumptions, only share what you have observed or observations that have been shared with you. If you come at them with assumptions they will either get defensive or they will shut down.

Use “I” statements to let the person know how you felt or how you feel. (I remember learning, “I” statements in I think 7th grade, so that still holds true even at 28.)

Let the person know what’s at stake. Why is it important for you to have this conversation and what could happen if you don’t?

Invite a response, this one is the hardest one for me, I want to hear what people feel and what they have to say, but sometimes I wish I could just say what I feel and then walk away from the situation. I guess it’s not fair to just drop a bomb and walkaway, but again I’m not good with conflict! The point of having a conversation is to get both side’s point of view, not just share your own. So step outside yourself and see the situation from their perspective. One thing I loved that they said was to “cultivate an attitude of curiosity and focus on learning as much as you can about what the other person has to say.” I think we have all been in those conversations where people think their way is the only way and that’s it. They don’t really care what you have to say. (If they care about how they feel, and you care about how they feel, than no one is caring about how you feel.) I think it’s important that both people care enough to see both sides of the situation.



Listen to what the other person has to say and ask questions. This makes sure you are clarifying what you think they are saying and let’s the other person know that they are being heard and understood. When people feel misunderstood that is when the conversation can go south fast! Don’t sit there and think what you are going to come back with next, take time to actually process what they are saying. Let the other person talk until they are completely finished and don’t try to interject. This time is called “Silence or Questions Only.” (That can be very hard for some people!)



Share your ideas and explore the other person’s suggestions for how to resolve the situation. I have been in conversation where our opinions were deadlocked. She wasn’t going to cave and I wasn’t going to cave, so we agreed to disagree. That’s not really a resolution. The entire purpose for having a difficult conversation is to resolve a problem; you don’t want to leave the conversation without knowing what that resolution is, or with the intention of figuring out a solution. Maybe you don’t think of it in the moment and you both take some time to think about resolutions and revisit it. (If you are like me once that conversation is over you don’t want to have to ever enter the subject again, and you just want to resolve it and move on, but that’s not always realistic.) Rome wasn’t built in a day! Resolutions may take time, but the good thing is that you are both working to get the situation sorted out.

After learning these steps I had a few questions,

How do you deal with people that get defensive?

How do you deal with people that automatically blame you for something unrelated to the topic at hand? (Have you ever approached someone with a topic and they come back at you with things from years past or something completely unrelated? It drives me crazy!)

How do you deal with people that compare apples to oranges? They compare the situation you both are in to something that was completely different or taken out of context. (I have a hard time with people that tell you how you feel or tell you how you should feel in any situation.)


As you can see by my questions I struggle with defensiveness or blame when you approach someone with a hefty conversation. If the other person gets defensive or tries to blame me for a non-related situation I tend to shut down, which is something I need to work on. (And is a major reason for why I don’t enter into a lot of difficult conversations in the first place!) They had some great responses however for dealing with “defensiveness.”

Defensiveness is usually driven out of fear or the need to protect one’s self. If the other person get’s defensive you can restate your positive intentions. You can try to clarify, like for instance if the person is comparing an unrelated situation, you can say, “It seems like we are talking about two different things, I am trying to address xyz.” Or “It seems like we have two different perspectives on this, let me try to explain it another way.” (I know this all sounds way to ‘professional’ and a little corny and of course the conversation can be much more relaxed, but you get the picture.)

After this class I felt much better about approaching people, some of it of course was common knowledge or seems like it would be, but it never hurts to learn different ways to resolve conflict.

If there is someone you have tried to resolve conflict with and you just can’t seem to see eye to eye (which is really unfortunate!) My suggestion would be to make sure that you don’t burn any bridges. Your feelings may be hurt and you may feel like you don’t want someone in your life, but for the sake of your relationships with others, and the uncertainty of the future I would just let it go. That person doesn’t need to be a major part of your life, but I would make sure that you never try to get a jab in, just for the sake of getting a jab in.

One of my favorite quotes comes from Cheryl Strayed, and Leah used it in her faces of Friday is, “be about ten times more magnanimous than you believe yourself capable of. Your life will be a hundred times better for it.” I actually had to look up “Magnanimous” when I first heard this quote and this is what I found:

Magnanimous comes from Latin magnus "great" and animus "soul," so it literally describes someone who is big-hearted. A person can show that over-sized spirit by being noble or brave, or by easily forgiving others and not showing resentment.

I whole-heartedly believe this to be true. In my own life, I have regretted holding grudges or saying something when I shouldn’t have. Sometimes I have let my pride get the best of me, and that is never good! I have had some of those difficult conversations with people for the wrong reasons. Sometimes I just wanted to be vindicated. However, I have never regretted forgiving someone being kind, even if the other person wasn’t.

I always want to make sure that no matter what happens every situation that arises I handle with grace. Some situations that takes far more effort than others! So I challenge you going forward to be magnanimous.

Well, I hope this helps you if you need to have a difficult conversation!

The class was based off the book "Fierce Conversations" by Susan Scott.

ADVICEKasey Taube