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How To Approach Difficult Conversations


Ugggghhhh….the dreaded difficult conversation!!  They are a part of life, connection, love, respect but so many of us avoid difficult conversations as if they thwart these things. 

We are terrified of hurting someone’s feelings or causing a fight, but it’s more hurtful to everyone involved when we live in a grey area of half-truths or lies. 

Difficult Conversations Often Lead to Positive Change.

A difficult conversation doesn’t have to be a catastrophic event that tears down the foundation of a relationship. In fact, even the most uncomfortable conversations can lead to positive outcomes — if you approach it in the right way. It takes some clarity about what you want from the conversation and some simple language tricks that make it easier for everyone involved to feel loved and heard.

Without further adieu, here are 7 tips on how to have difficult conversations. 

1. Know Your Intention for Having the Conversation

Furthermore, if it’s a loved one, approach your conversation WITH LOVE

Crazy concept, I know. 

If it’s your boss, again, approach your conversation with understanding rather than contempt.

Seriously though, identify your purpose for bringing it up. 

Are you looking to “show them” or prove them wrong? 

Is it validation that you’re seeking? 

Do you have difficult news to deliver? 

Are you asking for a raise or feedback?

We often go into conversations with our defenses up and have rehearsed all the ways the conversation can go sideways. But getting really clear on why this conversation is important and how you want it to go will help you not flounder when you actually approach the topic. 

2. Be clear on what Outcome You Want From the Conversation

It’s easy to get wrapped up in our feelings and burst into difficult conversations like a volcano of emotions erupting. 

Even \wWhen the other person listens, responds and tries to offer solutions we aren’t receptive because we have no idea what we even want!! 

How can you expect another person to know what you want from the conversation when you don’t even know? 

  • Get crystal-freaking-clear on how you want things to look moving forward before even starting the conversation. 
  • Be honest and direct. 

Let’s say for example you have taken on too much and you are afraid of asking for help because you don’t want to disappoint anyone. 

You go to your boss or significant other exploding with emotions of overwhelm with a tinge of resentment onto the other person. They feel confused and question if, in a way you are insinuating they are responsible for your breakdown! 

Even if they offer you a solution,no one really feels good about it. 

Versus, saying something like, “I realize that I’ve taken on too much. I was hoping to deliver and be of service to you/the company/our family but I’ve overcommitted and it’s causing me to feel overwhelmed. Is there anything you can take off my plate or help me delegate?” 

This is much clearer, less emotionally charged, the solution is already on the table, and no one feels attacked or blamed. This shows that you’re owning your shit, taking responsibility, and also in leadership by knowing when it’s time to delegate out. 

3. Be open-minded and give yourself permission to be wrong or misunderstood

I know this one is hard. If your mind’s made up, you are 100% right and there is no room for the other person’s perspective or experience, there is a good chance this difficult conversation will be a fight. 

Yes, your perspective and experience is valid and should be shared, as is theirs. 

Also, understand that we all hear things through a filter of our life experiences, insecurities, hopes & fears, which means that we often misunderstand the intentions of others. 

So, if you are misunderstood, acknowledge & validate their feelings and then clarify what you meant. 

This can look like, “It’s totally understandable that you took it that way, considering past circumstances and the stress you’re under but my intention is to bring us closer together by sharing my feelings with you so that there isn’t any additional stress added.”

4. Be honest & apologize

This one kind of piggybacks on the last one. Sometimes we are wrong, and that’s okay. It’s human, but own it. 

Oftentimes when we realize we are wrong we are terrified of what that might mean about us so we go into protection mode. We try to cover up where we’ve been wrong, or we try to somehow make it right so no one finds out, or we find a way to blame the other person for something because if they hadn’t done blah, blah, blah then we wouldn’t have been wrong. 

This does not help your relationships! 

Not friendships, not co-workerships, not romantic relationships, not family relationships – none, it’s a bullshit tendency and it’s important that we work on it. 

Example, “You are totally right and I projected my own fear onto you, I am really sorry and I take full ownership.”

Does it suck to say? YES. Does it need to be said to maintain trust, honesty, integrity, safety, and vulnerability in a relationship? YES.

5. Take responsibility for how you’ve contributed to past difficult conversations

I know, more yucky stuff. 

Owning how you’ve shown up before shows that you are working to be better. Sometimes in stressful situations we aren’t the best version of ourselves.

Additionally, if the other person starts to bring up old stuff they are probably still hurting from it. Denying it or fighting about it isn’t going to get you closer to what you want from the conversation nor is it going to heal their hurt. 

Keep your eye on the prize, whatever outcome it is that you’re working towards and don’t let this derail you. Owning it helps to diffuse the situation. 

“I know I did that in the past and I am sorry. I am working to be better and act differently, what I’m hoping for moving forward is….”

6. Listen And Paraphrase To Show That You’re Really Paying Attention

This is a form of mirroring, which is an effective way of building rapport with the person you’re talking to. 

Repeating back what you heard the other person say shows them that you are listening and processing what they are saying. It also gives them an opportunity to clarify any misinterpretations. We may think we fully understand what someone is saying but when we repeat back to them how we heard it there may be a disconnect. 

Example, “I’m hearing that you’re really upset about xyz and that you want me to help. Here’s what I can do… or when do you need a solution so I can take some time to think about it?”

Objectively think back to the Yanny vs. Laurel argument. Typically we are not audibly hearing different things in an argument, however, we do emotionally hear things differently. Which brings me to my next point. 

7. Don’t jump to conclusions or make assumptions 

As I previously mentioned, we mentally and emotionally process things through subconscious filters. These filters are picked up from past experiences and/or from what we’ve been taught to believe.

This is another area where mirroring really helps. For example, let’s say I have to have a difficult conversation with my husband about my mother-in-law’s care. He snaps back out of frustration and it goes like this:

Me: delivers difficult change in care

Him: Why is that happening? Did you check with her doctor on this? This is ridiculous!

Me: *filtering his response through fear of not being good enough, wanting to assume that he is blaming me*

Me: The situation is very frustrating and I did check with her doctor on this. Your questions are valid but just for my own understanding, are you questioning my ability to care for your mom?  (I mirrored & acknowledged his frustration and questioning, then sought clarification to keep me out of reacting to assumptions.)

Him: WHAT? No. I’m just frustrated with the situation, I know you are doing your best and I appreciate you.  

Interpretations and assumptions often get us into trouble. Seeking clarification helps us stay out of the conclusions drawn by our shitty committee. 

Don’t Expect A Quick Fix — Take Time For A Healthy Resolution

This compassionate communication stuff takes work! It takes practice! 

I’ve had the same conversations with my sisters and husband many times and they’ve had the same conversations with me. It takes time for healthy resolutions to become second nature

Try to be compassionate with yourself and others when navigating difficult situations. Understand that we will backslide into old behaviors sometimes but don’t let that erase the work that you and they have done. 

Ready to work on yourself to create compassionate and empowering relationships?

These tips are helpful and provide perspective on how to be a better communicator but if you are ready to do the work and show up powerfully for yourself (and in turn those around you) let’s chat about coaching! I would LOVE to support your growth in this area. 

  1. Tracy says:

    So good! This is valuable for ANY relationship.

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HOt Topics

Reading suggestions

How to Set a Boundary 

Compassion Fatigue...It's a Thing!

8 Ways to Cultivate More Self-Love

tell me more...