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Restoring Impossible Relationships with Greg Stephens

Million Dollar Relationships

Release Date: 12/30/2025

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What if restoring impossible relationships just required knowing what's on the other side?

In this episode, Greg Stephens shares how 24 years as a master trainer for Crucial Conversations taught him that breakthroughs aren't permanent until they're practiced over and over. That realization led him to shift from training to coaching, creating a six-month program where executives and emerging leaders have conversations they never thought possible. His specialty? Seeing relationships like some people see music, orchestrating conversations where people show up as their best.

Greg also reveals why his mentor Bill Solomon intentionally made his welding job miserable before college, teaching him the resilience he'd need to push through Baylor surrounded by wealthy students. Most powerfully, he explains "emotional accounting": why putting off a Friday conversation until Monday doesn't just ruin your weekend, it costs you exponentially more on the back end.

 

[00:04:44] What Alignment Resources Does

  • Company goal: everyone eats at the trough (trainers train, coaches coach, sales people sell, speakers speak)

  • Greg's specialty lives in areas of difficult relationships, everyone has at least one

  • Works with relationships that seem impossible

  • Application of Crucial Conversations tools for talking when stakes are high

[00:05:40] Twenty-Four Years Teaching Crucial Conversations

  • Was master trainer in Crucial Conversations, taught it for 24 years starting in 2001

  • Before the book was written, it was called "Path to Dialogue" then "Dialogue Smarts"

  • One of first master trainers, stayed until January this year when he released his book

  • Got to travel the world, train on stage, do keynote talks

[00:06:00] Why Breakthroughs Need Practice

  • People would take class, have great experience, have aha breakthrough moments

  • Found that breakthroughs aren't permanent until they're practiced over and over

  • If you want permanence around a breakthrough, you've gotta go do something

  • That piece was lacking, so decided to shift business to coaching

[00:06:20] The Six Month Coaching Program

  • About six month program, 20 different weeks

  • Teaching executives and emerging leaders (ages 21-28)

  • Wanted to teach younger generation what executives said "I wish I'd learned this 20, 30 years ago"

  • Most people say "I've had a coach before, this is nothing like it"

[00:07:00] Building Up and Completing Relationships

  • Build people up in relationships, let them go back and improve, clean up, or complete relationships

  • Complete doesn't mean never see person again (could, but doesn't have to)

  • Can work next to person and have completed relationship around an issue

  • It just doesn't show up for you anymore because you know where you stand, said what you need to say

[00:07:40] The Skills Most People Don't Have

  • Coaches and mentors say "you need to go have this conversation," but how?

  • There are skill sets you need, the application of them, and how to make adjustments

  • People talk about psychological safety but don't know how to create it

  • What to do when your emotions take hold or other person's emotions take hold

[00:08:20] How to Really Listen When You Disagree

  • How do you begin to really listen when you disagree with everything being said?

  • How do you get on the right topic?

  • Most people don't know how to dissect and break down conversations

  • Greg helps dissect it and break it down for people

[00:08:40] Executives on Retainer

  • Some executives don't want to learn all skill sets, just want someone to do it for them

  • Working with groups on retainer where they call when they have big problem

  • They lay out background, what they've done, then Greg lays out plan for conversation

  • Role plays exactly what might happen, clients say "it was like you were right there"

[00:10:00] When People Don't Show Up as Their Best

  • Sometimes people have breakdown, don't show up as their best, come back saying "I really blew it"

  • Great learning point, it needed to be this way

  • Limiting belief: thinking it's over when conversation goes badly

  • When you know these skills, you can go back over and over and reset

[00:11:20] What Drives Greg Most

  • Watching people restore relationships they thought were just not possible

  • Worked with police captains on issue, individual conversations showed no one thought it could be done

  • Scheduled for four sessions, had breakthrough after first session

  • One person took responsibility for their part, allowed everyone else to take responsibility

[00:13:00] It's Still Hard Even With Skills

  • People say "you have the skill, you should be able to do it"

  • Greg still doesn't like having difficult conversations

  • Doesn't want to have the conversation, but wants what's on the other side

  • "Stop looking at the conversation right now. Let's look at what you want beyond that."

[00:14:00] Work is Easy, Personal is Hard

  • When working with businesses, always eventually get to their personal lives

  • Those are the much more difficult conversations

  • Work is easy, we all want to make more money and enjoy work

  • Hardest ones are family businesses with so much emotion and unspoken hierarchy

[00:16:00] Bill Solomon Changed Everything

  • Gentleman who wrote forward to Greg's book, had heart transplant before writing it

  • Bill told Greg "I'm so glad you asked me to write the forward because I couldn't stop writing"

  • Two months later Bill had book of his own called "Losing Control" (in his seventies)

  • Was the person who pointed Greg toward something more in his life

[00:17:20] The Welding Job That Taught Resilience

  • Bill gave Greg job before college as welder's helper (Bill was CFO of company)

  • Told the guys "You're gonna like this guy I'm bringing in, but treat him like crap"

  • "Tear him down every day. Make him feel stupid. You're gonna begin to like him. Make it hard on him."

  • Never told Greg this was happening

[00:18:20] Breaking the Golden Handcuffs

  • Wouldn't have business today without Bill Solomon

  • Getting through Baylor, getting great job, then getting out of job and breaking golden handcuffs

  • Starting own business in 1999, none of that would've happened

  • Bill took interest, made it difficult on purpose, said "you're gonna be a great leader one day"

[00:21:40] Greg Reynolds Called Every Day

  • After Greg's divorce, Greg Reynolds called him every day for three months

  • All he said was "How you doing today? How you doing today?"

  • One of hardest times Greg ever went through

  • Showed Greg the power of that, he's done same thing for friend of his

[00:22:20] Taking Interest in People

  • If you really want to take interest in a person, find out what they're doing every day

  • Every one of these gentlemen shaped how Greg mentors others

  • Having conversations he never would've had, saying what he never would've said

  • Taking interest like Bill Solomon did, being there like his coaches

[00:24:40] "What Do You Want to Do?"

  • Woman was looking at situation from the past when she didn't have skills

  • Now she does have skills

  • "Question isn't what they want or what I want to do. It's what do you want to do?"

  • She got quiet: "I want to have the conversation."

[00:25:00] Over 20 Resets to Stay on Track

  • They practiced again, she went and had conversation

  • Wrote amazing email about how each time she had to stop herself and come back

  • Get conversation back on track by sharing your best intent

  • Had to do that more than 20 times

[00:28:20] Investing Upfront vs. Costing on Back End

  • If you add skillset and knew how to address it, you'd say "I'm not wasting my weekend"

  • Have conversation, no matter what outcome, it's out of you

  • Have entire weekend to problem solve whatever that was and learn about what you did

  • Used time wisely by investing upfront rather than it costing you on back end

[00:31:40] Marcus Newcomb Connection

  • Marcus Newcomb is special person, they hit it off

  • Greg has gotten to meet so many great people networking and marketing his book

  • Kevin is "the real deal"

 

KEY QUOTES

"Breakthroughs aren't permanent until they're practiced over and over. So if you want permanence around a breakthrough, you've gotta go do something." - Greg Stephens

"If you really want to take interest in a person, find out what they're doing every day." - Greg Stephens

"My life is built on the shoulders of all my friends and people in my life that have shown me so much." - Greg Stephens

CONNECT WITH GREG STEPHENS 

๐ŸŒ Website: https://www.alignment-resources.com 

๐Ÿ’ผ LinkedIn: https://www.linkedin.com/in/gregstephens2 

๐Ÿ“š Book: Build New Bridges: The Art of Restoring Impossible Relationships (Amazon) 

๐ŸŽ™๏ธ Podcast: A Shot of Inspiration 

โฐ Office Hours: Weekly coaching forum (details on website)

 

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