Approaching, Beginning, and Working Through Difficult Conversations

Coach Jessica: BS, AAAI, ISMA

Jessica Peart is certified by both the American Aerobic Association International and the International Sports Medicine Association as a Master Personal Trainer, Master Group Fitness Instructor, Sports Nutrition Instructor, Pilates Instructor, Aqua Aerobics Instructor, and a Corrective Exercise Specialist. She also has a bachelor of science degree in business management. Jessica is a wife, mother, and dynamic leader who has made it her mission to help women live the life of their dreams. She is a national trainer of the year, entrepreneur and former business owner with more than 17 years of experience in health and fitness.
difficult conversation

How to Have Difficult Conversations & Stop Avoiding Conflict

As much as anything, I hate having difficult conversations.

Last week I was feeling frustrated and hurt and I took it out on others around me. The emotions were piling up just like the dust behind the TV. 

Tears were instantaneous, my patience was very short, and I’d wake up every night thinking about it. I was avoiding conflict and I knew the only solution was to talk about it… with the person, I was frustrated with. Not an easy thing to do. 

You’ve probably been there too, haven’t you?  Trust me, you are not alone. It is much easier to avoid uncomfortable conversations and conflict at all costs. But does avoiding the difficult conversations come with a cost? 


Avoiding conflict may seem like the best “out” from the uncomfortable situation, but the cost is internal turmoil, unexplored growth opportunities, and the feeling of having the emotions pile on top of each other like a large snowball picking up size and speed as it rolls down the hill. 

If these conflicts are left untouched it can lead to stress, poor sleep, depression, anxiety, high blood pressure, and weight gain.  

Learning to have difficult conversations is a healthy habit you need to start now. Don’t wait to make this change.

Start The Conversation

As a coach for over 17 years, I have had to have many uncomfortable conversations with clients who are trying desperately to reach their goals. 

I’ve also had to have difficult conversations with other people like my husband, kids, friends, parents, co-workers, boss … you get it, just about everyone in my life. 

Each and every time I’ve opened the lines of communication, good things have happened. 

That’s why having a coach in your life to push you to push past conflict in a positive way is so important. 

All of our LadyBoss expert weight loss coaches knowhow to have the difficult conversations that are holding you back. 

Are you ready to put a stop to the thing that is holding you back? 

Do I have your permission to coach you? 

Alright, let’s dig in and stop avoiding conflict!  

One Little Word

Let’s talk about a simple word… change. 

Even though “change” is easy to say, it is much more difficult to execute. When we are going through changes in our lives it brings up emotions that need to be addressed. As you work through these emotions by having uncomfortable conversations, you will see the growth and resolution that happens next. I’ve seen this countless times when a client wants to lose weight but:

  • Their support system at home isn’t cooperative
  • Their time management doesn’t reflect their goals 
  • People’s expectations are unrealistic
  • The thing they think is helping is actually holding them back. 

Have you ever been there before? You’re reaching for a goal but it feels like everything is stacked up against you? 

Lady, the changes you are making are SO WORTH IT!  Keep going! Understanding why you are feeling this way will help you conquer it. 

Phases of Change

conversation difficulty

There are 7 Phases of Change that we go through: 

  1. Denial
    You know when you know there is a problem but you’d rather sweep it under the rug?  Yup, that’s denial.
  2. Realization
    Something happens that makes you realize that there is something you need to talk about. You have been avoiding conflict and realize that change is needed. This is where, as a coach, I meet most women. They realize that something’s gotta change, but they aren’t sure just how. I get to help women start making the change.
  3. Resistance
    Oh, resistance. This, my friend, is where the change, the uncomfortable conversation, the difficult situations happen. Feelings of anger, blame, and defensiveness, come to the surface. Just like I was feeling last week. It is real and it is by far the most difficult phase to conquer. You feel like you are digging your heels in and letting your excuses take control. Not only are you avoiding conflict, but you are also avoiding the person that can help you resolve it. (Have you been avoiding your coach? Or do you need a coach?) Stay with me, because I’m going to teach you how to have difficult conversations that will make a change in your life possible.
  4. Letting Go
    Letting go feels like a relief, a weight that has been taken off your shoulders and a chance to actually breathe again. It is hope. You’ve had the tough conversation and you are letting go of all the anger, blame and defensiveness that has been holding you back.
  5. Searching
    You are searching for new answers and new solutions but with that comes with feelings of anxiety, uncertainty, fear, and frustration. Things like “can I really do this?” “How do I create a new normal?” might be running through your mind.
  6. Understanding
    Those new ideas are flowing now!
  7. Acceptance
    You’ve found the new normal all because you stood up for yourself in the Resistance Phase. Congratulations! 

Resistance, my friend, is part of change. Opening the lines of communication between your coach, your significant other, your kids, your boss, your employees, your teacher… whoever it may be, is the key!

How To Prepare For Uncomfortable Conversations

It’s been said that “Success is where preparation and opportunity meet.” (Bobby Unser) I want you to be successful. Let’s get prepared, stop avoiding conflict, and create the opportunity and how to have the difficult conversation that will (hopefully) change your life.

  1. Grab a notebook! Start answering these questions to gain clarity on the situation
    1. What is the challenge?
    2. How do you feel about it?
    3. What solutions have you thought about?
  2. The invitation. Ask the person for a “date or meeting” to talk about ____. Set a specific date, time, and location (more on that in a second). You don’t want to catch the other person off guard with your conversation. Giving them a chance to think about the problem too will help you both come to a resolution.
  3. The location. Choose a place where you will both be comfortable and that is non-threatening. My favorite places are: 
    1. Going for a walk. – When you are walking your body is able to release pinned up energy. Tension levels are instantly decreased. Because we typically walk side by side, we don’t’ have to look the other person in the eyes. Why would this be important?  It’s less threatening for both of you and it is easier to talk about your emotions. 
    2. Windshield time. – There’s nothing like being trapped in a car with somebody, looking out the windshield, and really talking. 
    3. Chairlift rides. – Some of the best conversations I’ve had with my kids have been on the ski hill riding up the chairlift. We are trapped for a few minutes to talk, then we each have time to think about the conversation while we ski down the hill, all to pick back up on the next chairlift up. You may not ski, but there are many other activities that you can do with somebody. Keeping your body busy is incredibly helpful.   

How To Have Difficult Conversations

The date is here! Now what?

Don’t worry, you’ve got this!

The conversation you are about to have is going to create solutions and allow your feeling to be heard. 

Your feelings matter!

The solutions you come up with are going to be life-changing!

That’s the first thing to do –pump yourself up! 

Speak positive words to yourself. It will not only impact the other person it will change how you feel about the conversation too. When you know why it’s so important that you have this conversation it will help you approach it with positivity. 


Speak calmly.

We automatically match other people’s energy. If you elevate your voice, so will the other person. But when you come with positive, calm energy, the other person will mimic you. You are in the driver’s seat. 


Find the common ground. 

Approach the conversation by acknowledging areas you both agree upon – the common ground. Openness and showing a true interest in problem-solving will help you actually find a solution. It isn’t a matter of who is right and who is wrong, it is about finding a common ground that you can both agree upon and accomplish.


Use facts, examples, and avoid placing blame. 

Use phrases like “I feel _____” instead of “you make me feel ____”. Stick to the fact and have examples of how situations have happened in the past. Remember, we are here for resolution. 



Keep the conversation equal. Chances are that you aren’t seeing the whole picture and the other person might have some ideas that might help you both in resolving it. 

There are always two sides to every story and by truly listening you will be able to see the other side. Avoid interrupting and really listen. 


Give thanks and take action. 

As you leave the conversation, thank them for their time and energy. Be gracious. Determine clear steps for both of you to take. This is putting your solution into action. I always find it helpful to schedule a follow up to the conversation. It may sound something like this, “Thank you for allowing my feelings and thoughts to be heard. I know it’s not easy to have uncomfortable conversations, and I appreciate your time. If it’s ok, can we grab a cup of tea next week and talk about how we’re both changing?” You might even want to text them a few days after the conversation too. 

You Will Feel Better

managing conversations

Trust me, I know how hard it is to have difficult conversations. Each time I feel the tips of my ears heating up and my chest turning red. 

But when I am prepared and I’ve created a positive opportunity, the tension is decreased. Over the years I have watched and coached hundreds of people through how to have a difficult conversation. I’ve also seen how these conversations and the communication that occurs completely change the trajectory of their lives. 

So many times, this conversation is the ONE thing that is holding them back. 

If it’s OK, can I coach you one last time? I’d like to ask you a series of questions that might unlock the next uncomfortable conversation you need to have. 

  • Where are you feeling pressure in your life? 
  • What triggers your negative emotions? 
  • Who are you avoiding? 
  • Who or what are you blaming?

If you were able to write something for one of these questions (or if you are human), it is a signal that you have an opportunity to change by having an uncomfortable conversation. 

You can do it!



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