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Mediating Conflicts with Compassion and Civility


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After nearly 20 years as a litigator, Winter Wheeler decided it was time to pursue her passion for mediation. She left her senior position at an Atlanta law firm and pursued her dream.

In today’s episode of Motivational Mondays, we discuss how Winter resolves disputes by focusing on civility and compassion. It begins with meeting people where they’re at and mastering the art of uncomfortable conversations.

Winter shares a unique point of view that you don’t want to miss!

Winter’s journey from litigation to mediation

Winter knew within a year of graduating law school that she wanted to build an empire and leave a legacy for her children. She wanted to be in a position to hit the ground running and quickly climb to the top, earning respect and gravitas.

To accomplish that, she knew she needed years of litigation experience behind her. It’s near impossible to book high-paying clients without it. 

Winter enjoyed being a litigator which she describes as putting puzzle pieces together. She got to solve problems, help people, and the job allowed her to use her skillset to the fullest.

If you’ve considered mediation as a career choice, she says to look at your life and what you can afford to do and what you want to achieve. She won’t advise someone to spend $300,000 on law school—you have to decide if that’s what you want yourself. She notes while you don’t need to be an attorney to succeed as a mediator, it makes the road to success easier.


Mastering the art of uncomfortable conversations

The technique that Winter uses in mediations—The Four Cornerstones of Mediation™—focuses on communication, cultural distinctions, empathy, and approaching each individual as an individual

f you can approach someone and understand the lens with which they view life you can have a better conversation. But you must step away from your lens and be willing to adjust your communication accordingly. 

Winter isn’t saying you can’t have feelings about a situation. But when you want to get your point across, you can’t say the same thing five times and think they’ve heard it. You have to change the way you approach a conversation and say things in a way they’ll understand.

View yourself as a translator or an interpreter. When you find common ground and make sure everyone has what they need, it can feel like they have what they want. Once you get to that place, they feel like they won that day and everyone can move on.

One of Winter’s favorite quotes is “Stop expecting yourself from other people.” They don’t have your experience and cannot be you. Give of yourself because you want to and don’t expect anything in return.

When you let go of those expectations, you let go of the burdens you’ve put on yourself. You relieve yourself of pain you didn’t know you were putting yourself through.


Meeting people where they live

Winter helps people resolve their differences by listening. She’s there to help them get the emotion out of the way so they convince themselves to resolve their situation.

Each human being knows what’s best for themselves and their families and they will make decisions accordingly. They don’t want to do something because she told them to. 

Winter will ask each party, “I want you to tell me why you want this. What is it about this that you need? What do you think this looks like in real life?”

The Dad in a scenario may want full custody of his children but he works 12 hours a day. Wouldn’t it be better for the kids to have their Mom pick them up from school because she can? Winter helps people move away from operating out of spite. 

In this episode, we also delve into another one of Winter’s TEDx Talks, “Confessions of a Mom Who Has it All.” Winter shares what led to writing the talk that left her in tears as well as the struggle of balancing a career and a family. Don’t miss her heart-warming and powerful story.


Listen to this episode to learn about...

  • [1:29] Winter’s journey from litigation to mediation
  • [5:33] Mastering the art of uncomfortable conversations
  • [10:43] Meeting people where they live
  • [13:58] Confessions of a mom who has it all
  • [21:59] Women can have careers and be mothers


Listen to the bonus episode to learn about Winter’s Four Cornerstones of Mediation and how years of legal practice can make you a stronger mediator.