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The Art Of Coaching

E418 | How to Get Better at Having Hard Conversations

The Art Of Coaching

Brett Bartholomew

Business, Education, Health & Fitness

4.9648 Ratings

🗓️ 16 March 2026

⏱️ 29 minutes

🧾️ Download transcript

Summary

For myself and a lot of other people, it seems like folks are getting more and more unprofessional. Not just individuals — organizations too.    People hide behind screens. They don’t want to have real conversations, and it chews up time and wastes energy.   You’ve got to find a way to get past that in today’s world.   So today we do a broad ranging Q&A on how to be assertive when you need to be — whether you’re dealing with a lazy contractor, a business that didn’t deliver, or just trying to get out of your own head.    How to frame conversations whether they’re over email or in person, so you decrease the likelihood of things escalating. How to take the governor off, say what you need to say with a clear, assertive message, and maintain your composure in the process.   What You’ll Learn:   ∙ How to say the hard thing without over-explaining, apologizing for it, or walking it back   ∙ Why most people mistake conflict avoidance for kindness — and what it's actually costing them in their relationships, career and credibility   ∙ How to deal with people who are unprofessional or hide behind screens instead of having a real conversation   ∙ How to stop overthinking   ____________________     Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Transcript

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0:00.0

One of the newest things we're doing this year is in October I'm hosting what's called the non-superficial bullshit conference. This is something that started out as a joke, but now has become very real here in Phoenix, Arizona, October 3rd and 4th at the new Art of Coaching compound. Now, the gist.

0:29.5

Many... Now has become very real here in Phoenix, Arizona, October 3rd and 4th at the new Art of Coaching compound. Now, the gist. Many of us have heard about all of these conferences and maybe attended some of them where it's all about, oh, you gotta be a world beater. This is the truth about marketing or this is the secret of training and fitness and this is how to 10X your life and all this other stuff. What I wanted to build, me and my friend Jason Miden, actually, is something that spoke to people

0:48.8

that are actually dealing with struggles that are more real world every day, right? You've built and rebuilt businesses from the ground up. You want to hear from people that have done that. You want to hear from people that have struggled through failing relationships. Change cities, uprooted their lives, taken a risk on themselves, pivoted careers. How do you figure it all out when your previous playbook failed or changed? The through line for everything we're gonna discuss at this conference, at this summit, at this gathering is all things that are real. Because we don't think people need more secrets or hacks, they need strategies to navigate hard conversations, brutal setbacks, and the chaos that comes with building literally anything that lasts. So all of the outputs, what are you gonna get? As always with our events, actionable solutions. We're not doing a bunch of nonsensical theory, direct unfiltered access, who is speaking myself, my good friend Jason, Missy Mitchell McBeath gunner Peterson stew Mcmillan Kelly and Juliet star red great friends of mine Jess Ellis Sanjeev Javier Jen Wheater strum and we are going to have so many more special guests all of these folks have dealt with these things all of these saying all of these folks have had to change their brand change the way they speak about certain topics in a different landscape, move, deal with managing kids and managing relationships, all of it. We have three different tiers and you can get a discount by pre-ordering my new book, The Anti-Hero Advantage with Penguin Random House. Just go to artofcoaching.com slash no BS. Literally artofcoaching.com slash NOBS. If that doesn't work for you, just go to artofcoaching.com slash events. We are gonna keep this at about 20 to 50 people. This is something special that we're doing. You're gonna be on our property. It's gonna be be a lot of fun and it's like nothing we have ever done before. So check it out again, artofcoaching.com slash no BS. Welcome to the Art of Coaching Podcast. I'm Rev. Otholomew and at a young age, poor communication nearly cost me my life. Now, I help others navigate the great area of social interaction, power dynamics and communication so they can become more adaptable leaders,

3:25.3

regardless of their profession, age, or situation.

3:28.8

This podcast is for everybody who is fascinated with solving people problems.

3:34.2

So if you're in the no-nonsense type who appreciates frank conversations, advice you can put

3:38.7

to use immediately, and learning how others navigate the messy realities of leadership,

3:43.5

you're in the right place.

3:44.7

I'm glad that you're joining us. Let's dive in. [♪ music playing in background, music playing in background, So today I wanted to do something that was near and dear to my heart, near and dear to my heart because as many of you know, I have been dealing with construction will just say fun for the last six months, eight months, maybe even a year that as we build out the art of coaching compound, which is set to finish here soon. Now, I've also been dealing with a lot of other things as our business grows and continues to evolve. And with this comes this balance of how can I be assertive when working with contractors, when working with people, when working with colleagues even, anything like that, without being rude. Now we've done episodes on assertiveness before. This is going to deal more with, you're dealing with other people, whether that is contractors or whether you've gone to a hotel on vacation. What do you do when you're not happy with the service? What do you do when you feel like somebody's showing up in a really unprofessional way? How do you find that line between not just going pure dark energy and also just being kind, right? Because it is a balance. You don't want to be railroaded. Nobody wants to be railroadaded and that's very easy. It can happen when we,

5:06.0

which as many of you guys as the listeners, can over-index on feeling like we've got to be the ones to say the perfect thing. We've got to be the ones to be more professional. And so how do you reconcile that? Another thing that we are going to talk about because we are going to do a a little bit of a grab bag episode on this one,

5:25.6

is how do you deal with, how do I phrase this? How do you get better at having hard conversations face to face? This is something we've talked about as well. And then how do you balance oversharing? Cause these were comments and questions that we got from an audience as well. And that one might be an actual deeper die because this has been one that we've gotten

5:47.2

a lot.

5:48.2

All right.

5:49.2

First and foremost, and I don't, I want to get right to the point, right to it for you guys.

5:53.7

How do you find that balance between being assertive when, and I think about my contractor,

5:58.2

I love him to death.

5:59.2

He's a facilitator of our, sorry, not a contractor.

6:01.8

I was getting ahead of myself in the notes. Cory Berrios, Cory helped us do a workshop recently with the Texas Rangers. He led a full day at Orca Performance. He's a wonderful, wonderful human. They're doing an addition to their home, right? And they've had some construction issues. I've had construction issues. And you wanna be empathetic to the people that are, you know, working on these things. You to be understanding, but also sometimes you need to put a foot in the ass. There's no diplomatic way that you can really say that sometimes. So I think what I wanted to say is, all right, I tend to know your baseline response in first and foremost. I am somebody who tends to lead with assertiveness. I'll say, hey, this is not acceptable, what's going on. So I have to dial that pack. That said, something I've been guilty of doing. Definitely the last three to five years is over indexing and over, almost over compensating, you know, trying to, I've almost become too nice. I've almost become too nice. And I've talked about this before. And so I think about like, how can I manage this even with something's costing me money, something's costing me time, something's costing me my sanity? The first principle is thing you have to do, whether you like it or not, is you usually have to start creating a paper trail.

7:25.0

Right? If there is something with a contractor, especially when it's construction or it's a big project or you're paying tens of thousands of dollars, it helps to start a paper trail. Because unfortunately, should that ever become a legal issue, you're going to have to go back and say, Hey, here's what was agreed upon. Here's what we talked about all of these saying, now, this is not me saying that you go into it with that intent.

7:48.5

I don't like how we live in this gotcha society. You know, so if you're dealing with something, let's say you have a personal coach of your own and it doesn't matter if they're a business coach, it doesn't matter if whatever they are. All right, if you're not happy with the service at a micro level, you just reach out to them. I mean, I've done this with my CPAs.

8:06.5

I've said, hey guys, I've been with you three to four years. I really value our relationship, but I have to admit, it feels like something's been different over the last year. I'm not getting as much proactive communication. It's now tax season. Much to my surprise, I saw a lot of things miscategorize, how can we reconcile this?

8:25.5

Right? I don't want them to feel like I'm coming at them.

...

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