Join Now

5 Tips to Improve Difficult Conversations

2 Women sitting at a table, communicating. Grayscale.


My family, some members in particular, are notorious for avoiding difficult conversations.


Having tough conversations is not something I learned growing up and it certainly was not modeled for me by my parents or family. Instead, I mostly remember my mom saying, don’t tell your dad this, or don’t tell your dad that. I also remember my dad telling my mom how things were and her crying. But never do I remember them talking things through from different points of view.


I have brothers that will skip town instead of breaking up with a girl or leaving a job. I’m not kidding.


It’s not that my family is cruel or mean, we are scared. We are scared to disappoint, to disagree, and we are certainly afraid to have any kind of serious or difficult conversation. 




We are not self-confident. We are insecure about where we fit in and who we are. We struggle to believe we are as good as others. We, all in different ways, experienced trauma throughout our childhood, I suppose. I know so many of us do, some in huge earth shattering ways and for others in repetitive little doses. We all have our demons, our personal row to hoe, I guess.


I think most people do, I don’t think I’m unique in my insecurities. I think most of us could benefit from increasing our skill or strengthening our muscles when it comes to confidence and having the tough conversations. 


How do we do it and how do we get better at it?


First and foremost you have to do it. 


You can’t leave town, avoid, or ignore things forever. This is literally what my brother does, he simply leaves town, always living like a gypsy.


My insecurity manifests more in people pleasing.


I give in, I don’t ask for what I want, or I give more of myself than I should. I don’t really get what I want, but I don’t have to do the tough conversation either. Eventually this builds a life that is not authentic to me and my dreams and I end up unhappy. 


I know many of you may not be as extreme as my brother but I bet many of you are at least a little like me. People pleasing at your own expense in order to avoid the difficult conversations creating a life that is not making you happy.  


Unfortunately, so many situations require difficult conversations. In our personal lives, between partners, parents, children, and other family members.


At work, we may have to ask for a raise or promotion, or maybe we are the boss having to give feedback to an employee.


Difficult conversations are required if you are determined to build a life that ideal for you.


Here are 5 ways to improve your confidence having difficult conversations.


1. Set a date and time with the other person.

You have to set a date and time for difficult conversations so you aren’t constantly putting it off until some later date that never actually comes.

Another benefit of setting a date is that it will signify to the other person that the topic is important to you. 

If you don’t make this conversation a priority, something unexpected will always come up, so be sure to stick to it.


2. Clearly state your case, feelings, or plan. 

Whatever it is that you want to discuss, clearly outline it. Have a clear plan of what you want to express to the other person, know what it is you want, and clearly tell them.

Be sure to remember that you are in charge of how you feel. Be careful not blame others for how you are feeling. 

I feel X because I think X. 

Not you make me feel X when you X.

Make sure you fully express what is on your mind.


3. It takes two.

Be sure you are listening as well as talking. Try to see their side of things, and appreciate what they are thinking and feeling as well.

Ask them, what do you think about this? Do you see something I am missing? What are you worried about? 

Have a goal in mind but brainstorm solutions together.

Listen to the person you are talking to. Don’t sit there waiting to argue your case, be sure you are actually hearing what they are saying.


4. Agree to disagree.

Feel free to table a subject if things start to get a bit heated or you or your partner are not in the right frame of mind to have a calm discussion. 

Just be sure to set up another date. Let’s take a break and pick this back up next week at this time.

Remember you may not ever totally agree, but at least everything is on the table. Don’t leave someone in the dark or do things behind their back.


5. Act as if you know nothing about the topic. 

Adar Cohen talks about this in his TedX talk about having difficult conversations. 

This is a tool we sometimes use in coaching in order to hold space. Which means, not to pass judgement based on what we think we already know. 

This is a really great way to get the other person talking about how they feel and what they are making the situation mean. 

When we are faced with an issue we automatically take all our knowledge and beliefs and judge the situation. We decide quickly how things are and what needs to be addressed. We believe we are right. 

It’s natural for us to do this.

The problem is that we don’t see our own blind spots and filters.

When we are not open to others perspectives on the same situation we may assume things are one way and they may assume they are the opposite entirely.

We have to be open-minded and this is easier said, than done.

When we look at a situation or topic from a blank slate we are trying to see it from new eyes, no filter, no preconceived notions of what it’s about. We look as if it’s the first time we are seeing it.

We may actually learn something, we may even change our perspective.


Using these five strategies you will find yourself having the conversations you need to be having in your life instead of avoiding them. Start by scheduling the conversations; if you did only that suggestion you will be so much further ahead because  you will at least , be having them.


And adding in the rest of these strategies will be a total game changer for your life. All the sudden you are being authentic, getting more of what you want out of life, and having more open and honest relationships with others.


It’s a win for you and everyone around you.

Join Life Made Simple and begin to Re-Invent your life today!

Click Here for Wait List - Opens 2023