Otis McGregor – Service, Passion, Guidance | Conversations with Coaches | Boxer Media

Share on:

Otis McGregor | Conversations with Coaches | Boxer Media

Otis’ passion lies in helping people succeed. He’s used this passion as fuel through years in Army Special Operations and coaching rugby. It now drives him to create better leaders. He believes that better leaders create better organizations, better organizations create better communities, and better communities will create a better world.

In getting to chat with Otis for even our short time together for today’s episode, it’s clear that he’s the real deal. We get a chance to discuss his service to our country, how he found his passion for rugby, and all the ways in which this passion and service have translated to his coaching business.

One of my favorite parts of our conversation is when we touched on our shared love for both the “aha” moments and the “hmm” or “huh” moments in coaching – sometimes small new questions are just as powerful as the big answers.

To learn more about Otis:

Share on:


Kevin Stafford 0:00
Hello everyone and welcome to another fine episode of the conversations with coaches podcast. I say it’s gonna be a fun episode because I have complete confidence that it will be. Because I’ve just had a chance to get to know Otis McGregor a little bit and I get to help you get to know him a little bit as well. Oh, is his passion lies in helping people succeed. He used this passion as fuel through yours in Army Special Ops and coaching rugby. It now drives him to create better leaders. He believes that better leaders create better organizations, better organizations create better communities, and better communities will create a better world. i What first time I read that sentence when I was looking at your bio, I was like, oh, that’s just that’s it. That’s everything. And so I was like, I wanted to recreate it perfectly here, Otis, it’s great to meet you. And I’m glad to have you on the pod.

Otis McGregor 0:44
Hey, thanks for having me, Kevin. It’s good to good to chat with you and have a little fun in the green room before we jumped on the recording button. So yeah, it’s always good.

Kevin Stafford 0:55
And you never know. You never know if the chemistry is not going to be there. You know, I like to I like to go I have a little bit of back and forth do a little small talk is to make sure that you know we like each other and I’m completely unsurprised that I think we like each other. So let’s, let’s jump in and talk. Let’s not go all the way back to the beginning. Because that’s we don’t have that kind of time. But let’s start with how you got your star how you got your beginning, as a coach, how did you sort of get your powers get your superhero powers? How did you discover or realize or kind of grow into coaching? And how has that evolved as you’ve kind of grown your coaching practice to today?

Otis McGregor 1:27
Well, I had a moment. Here in my home office, I had been retired from the Army after 25 years, retired for seven years. And I’ve worked I bounced around from job to job and every one of them I just wouldn’t sit and write. And that moment, interestingly enough, it’ll be seven years this next month, seven years next month sitting in my home office here feeling sorry for myself wondering what’s wrong with me? What what’s going on? Why can’t I find that job? As I sat here, I reflected back on my life since leaving the Army. And I realized that only two things have been consistent in my life. My family and Boys High School rugby. And yeah, very ironic that those were the two things. But as I as I looked at it was like, Well, why Boys High School rugby because I didn’t play rugby growing up. I’m gonna Texas boy, I played football. Yeah, so looked at this volunteer thing that was, I mean, truthfully, a second full time job. Why was I spending so much time with it. And I took that, that, that thing that that commitment that I made, and I looked at it in three different parts. Number one, the game of rugby, love it. Now. You see, those of you on video can see the ball over my shoulder. The boys, you know, we were a club. So our house was the clubhouse, which meant our house was full of teenage boys all the time. 35 Extra sons in and out of our house, love those boys. But the third element is what real I realized was what was really fueling me and that was their coach, challenging them, holding them accountable, pushing them further than they thought they could be teaching, guiding and mentoring them to be not just good rugby players, but great young men in life. And I took that and I started to explore that concept a bit more and I got introduced to something I’d never heard of executive coaching, leadership coaching. And I I took my what was then a business development consulting business, and I pivoted into executive coaching and that’s that’s what I’ve been doing ever since and man it is just so much more fulfilling. I mean, you read my my purpose statement, man that that that’s my fuel. That’s the thing that gets me up in the morning is to change the world. And I believe that everybody has that opportunity to do it you may not think it but man you don’t know an action what action that might be. And this just popping into my head when my favorite things say hi to somebody smile at somebody you pass with somebody in the aisle at Walmart, you give them the the two finger country wave as you’re driving down the road, right? Those sort of things you never know that that might be the difference in that person’s life that might stop them that might stop them from spiraling down into the pits of despair and depression. And that’s changed in the world we can all do it and just little simple things.

Kevin Stafford 4:36
And doing it with intention to that’s something that I’ve often I don’t want to say struggled with but have embraced the challenge of is you know, out in the world, getting into my own head I’m in my own thoughts I’m doing running my own errands. I’m doing my job I’m you know, I’m with Family. I’m with friends. I’m by myself, I’m in the grocery store. I’m at the mechanics I’m saying you know, I’m just living my life. And I’m thinking my own thoughts and maybe stuff put my head, maybe I’m dwelling on something, maybe I’m thinking about the next thing I’m supposed to be doing. And I forget to be kind or be polite, or just engage with the human beings who are around me. And I am lucky to have been helped through that at a young age by a key mentor, like kind of in my in my mid 20s, to just basically kind of like, give me some tough love and be like, do get out of your head, get out of your way. And just remember that there are a lot of people out there, who could use a smile, who could use some eye contact, who could just use just some kindness in the smallest possible increments all the way up to every other large opportunity for kindness we get. And I love, I love that that’s at the heart of why you do what you do. Because that really is at the heart of why I mean, anybody who cares about the world, why we all do what we do, we might not be able to articulate it that way. But we just want to help people be better. And knowing that that will also help us be better, you know, that it’s like, it’s such a beautiful, I think of it as like, whatever the opposite of a vicious circle is it’s a virtuous circle, you might call like that, but I don’t like to throw that word around there. But it’s just actually, you telling that story and explaining that kind of reminded me of how something that I got really good at, especially during the pandemic, where I’m constantly masked and public. And I’m, I’m losing half of my ability to really express like, that kind of kind isn’t Ashok I can make eye contact and so not that I, you know, had to work really hard for because I got some crow’s feet going on around the eyes. But I learned to really smile with my whole face, and smile with my eyes and forehead in my shoulders. And when I’m engaging with someone to really look straight at them and, and not in a creepy way at least hopefully, creepy way. But to really just be intentional about that. Knowing that I’ll never know what kind of benefit that might have been to somebody’s life, what kind of moment they might have been in weather, you know, however it landed. But just having that faith, having that belief that it is the right thing to do that it is helping it’s contributing. And building from there, sorry, reminded me of very personal decisions that got me excited.

Otis McGregor 7:03
But it’s so true. You know, I can remember when we first went to wear masks and everything we were doing, I did a little video just about what you said, you know, we can’t smile at people. But you know what, you know, because your mask is covering up your face your mouth. But you can do the you can do the wave, you can do the head nod, you can. Some people might not pick up the eye movement, those. If you’re a bit more into the body language, you will. But those little things make all the difference in the world. It reminds me of a good friend of mine heard flight time line told and he says this and he teaches us to elementary school kids kindness is free. And her played for the Harlem Globetrotters for 1010 12 years. So he knows about culture he knows about other people. And just you think about that, how simple that is, and how much truth there is to that. Kindness is free. Yeah.

Kevin Stafford 8:07
And it’s, yeah, I could talk about that, for that alone, I could talk about for hours. But there was something else to that. Yeah, as you were speaking about your origin stories that really struck a chord with me. And it’s how a for a lot of people, even these days, even as coaching has just exploded into all sorts of areas and become much more on top of people’s awareness. And as they move through their professional lives in their personal lives. A lot of times we think of coaching in the context of Youth and Sports are really like where the first thing that comes to a lot of people’s minds. And it gets gets me thinking about something that I know a lot of coaches focus on too. And that’s sort of identifying those gaps, where it’s like, we’re in these in these areas of our lives, where there our education, and our growth is very structured. And there are there are coaches and teachers and mentors all over the place. And then we get to a certain point in our life, and it’s just kind of like you know, we’re just kicked out the door. It’s like, Alright, enjoy the next, you know, if you’re lucky, 5060 years, however long it goes. And I feel like there’s such a not just a need, but like a hunger for more. For more coaching as you move through your life, I don’t think you ever really outgrow the need for a coach, or at least the benefit you can get from a coach. I just think that we just don’t have at least we haven’t in the past had people who are filling those gaps, executive coaches, leadership coaches, career coaches, across all sorts of industries, hyper specific, more broad, you know, corporate entrepreneurial, and everything in between. There’s so much good work to be done. And there’s such a hunger for it to such a recognition of the value of it and I feel like there’s a good a good forward momentum right now in the coaching industry in general that I’m like, I’m really, really pleased to be a small part of it. It’s really it’s great to watch and great to experience.

Otis McGregor 9:50
Yeah, it is it is and you know, every professional athlete has a coach, and I’m not just talking about the ones on the team. I spent some time with golly, just drew a blank on his name, plays linebacker for the Philadelphia Eagles. Last summer spent some time in his house a big dude has a place in Texas and we’re hanging out there. He’s got a personal trainer coach. They’re in the offseason. I mean, we were there hanging out in May. And his personal trainer coach is there. I mean, here’s a guy at the top of his game. I mean, he’s, he’s an NFL All Star pro pro bowler. Gotta get my words. Right, right spores, right words, you know is he is that guy, and he’s got a coach, you think he’s been lifting weights. Since he was probably like, in sixth grade, he’s been, he’s been lifting weights. And he’s still got has a personal trainer, coach, that should tell you something right there. And then you look at all the other top athletes, every one of them, has coaches to make them better. And I think that’s something that that we should all learn from, I have a coach, I have a coach that I work with that that helps me grow and pushes me each and every time we talk in each day. And I cringe sometimes, because it’s like, no, I need to do them. I don’t want to do that. But you know, what that’s going to make me better is going to allow me to make more impact. Because that legacy, that legacy that we live for, is that that impact that we’re making in the world that change, whether it’s whether it’s the smile, or a direct impact to somebody’s life, by helping them have, even if it’s not an aha moment, because aha moments are pretty cool, right? But even if it’s not that, even if it’s just helping them move forward, just a little bit more, achieving something that yeah, they could figure it out and two years, five years, but helping them achieve it in the next couple of weeks. That’s what I’m talking about. That’s, that’s the kind of success that having a coach can bring into your career, your life, because somebody’s looking at the outside from the outside looking in, who’s who’s walked some of the same past and hears and listens deeply listens to what’s going on. And when I say listen, I don’t mean, I’m getting the word, but I’m getting the full picture. Right? Because I can hear the voice inflections. And even if it’s not a video call, I can still sense it. Ooh, that’s a touchy subject, right? Start to listen to those things. And you know, because you listen, you know, what you can do to help them overcome the burden, the obstacle that is holding them back, not that they couldn’t figure it out on their own, because I can tell you, I’m that guy right here. I’ve, I’ve figured out a lot of stuff on my own. There’s no doubt about it. But it was frickin hard. And, you know, what, I’d raise my hand and ask for, you know, whether it was in the teams when I was when I was agree Baray or, or even a little bit later in that military career or even in the business world? If I hadn’t been so prideful, in the sense of, hey, I need some help here. Who should I talk to? Can I Can you give me a hand? Because you know what, every one of them people would do it? And I’m glad you asked. Yeah, it’s the same thing. As we go forward in life, whether you’re the CEO, the junior manager, somebody who’s just at a college, and you’re not quite sure this is what you want to do. Well, guess what you can, you can trudge through it, and maybe figure it out. And 10 years later, 15 years later, look back on God, dang, that was that was not the right thing. Or you can hire a coach who will walk through it with you, who will guide you a coach is not going to tell you how to do it. They’re gonna guide you in mentoring. Right? It’s, it’s rigged and this is one reason I love rugby. Because rugby coaching is so much like coaching as an executive coaching, doing leadership coaching, even life coaching is so similar because, you know, with those with these coaching, with clients, you have a call, right? an hour, whatever, whether it’s a group call or individual calls, you have a call, and then that person has to go off and do those things. rugby’s the same way you practice all week. As a coach, you get that final say right before the first whistle. Hey guys, don’t forget the first whistle and guess what? God turns their ears off It happens, but God turns their ears off either that or there’s a sound barrier on the sideline. When they don’t hear anything you say, until halftime, you get 10 minutes at halftime, you get to say one thing, baby, I used to push it and say to that I wanted them to focus on the next half of the game. And then that’s it. It’s just like coaching, because I’m going to, I’m going to say here, we’re going to work on this, we’re going to build this capability, we’re going to build this process, this thought process in your head, I’m going to show you some skills that you might want to integrate into your life. So that you can live your life with intention and pursue your purpose to achieve your success. When you start to do that, you make those changes. You’re going to make slow improvements, but the coach is going to help hold you to that path. Whether he’s your he or she becomes your accountability partner or not. But that is, that’s where a coach helps you out. That’s where it makes the difference. It’s not just telling you, if you hire a coach, that behavior if you hire a coach, and they just say, okay, given you this, listen this, you’ll be successful. And I I’m very, very familiar with this, because I’ve worked with a lot of people in transitioning out of their career. And I do not tell them how to do it, I joke with him and say here, here’s your, here’s your 53 item checklist. You fill out this checklist, all 53 of these items in the proper order in the proper time you will live a happy life. And if you believe that I got some oceanfront property in Arizona, right to be in a coach’s job is to help you develop your plan your vision for your success. That’s why I say that phrase that you live with intention to achieve your purpose to achieve your success. That’s, that’s the secret sauce, man. It’s about what you want. And when it’s you what you want. And it’s the plan to achieve what you want. There ain’t no stopping you.

Kevin Stafford 17:20
That’s right. That’s right. And you know, what, if I just wanted a recipe, I could find one anywhere, you know, I’m actually looking for some help in the kitchen, I’m actually looking to prepare something a little bit special wants you to come in, let’s do this together. Because I kind of don’t you know, you can tell me like exactly how much of what goes into what but I know there’s there’s some, there’s more to it than that. And a coach is so much more helpful in that regard. And I love, love, love, love, love, love the way that you identified the difference between those aha moments, which are acknowledged are so great, especially when as a coach, you’re there for them. Some of the best moments of your entire professional career are those moments. But the ones I really like, are the moments that are something more like hmm, or, huh, sort of like this implied, I hadn’t quite thought of it that way before. Those are the moments so the daily work, you know, the the, the throughout the week, as you’re coaching them up, obviously, they can go out there and perform and some of those aha moments will happen, you know, in the, you know, on the training field, some of those will happen on the playing field, some of those will happen in between, some of those will happen in conversations afterwards. But those those ha moments I like, I mean, I like I love the aha moments, but I think I like the ha moments better because it’s, someone’s got a question that they haven’t quite thought of in that way before, and you help them find it. And they’re gonna, they’re gonna seek out that answer with you. And they’re gonna find it for themselves. And it’s just there’s, there are a few things more powerful than that.

Otis McGregor 18:40
Oh, yeah, you’ve planted the seed for them to nurture and grow in that direction. That’s, you know, it’s, they say, Well, I’d really like to Okay, well, how do we do that? What are the steps? what’s the, what’s that vision look like? What’s that theme out there? And then what does that mean? Define it? I mean, that’s one of my favorite things. I want to spend more time with my kids. Okay, what’s that? I love this Tony Robbins thing he he’s doing, you know, big stage of people when he stops and asks you to got Alright, what do you want, says I want to make more money. Don’t he pulls out his wallet and hands him a $5 bill and says congratulations, there you go. Right, because you know what, there’s more times my kids meet. Maybe it’s the same amount of time, but you’re not actually there. Maybe you’re all you’re thinking about all these other things. You’re not present in the moment. That’s, that’s where we start to make the difference. You know, and I’ll I’ll say my favorite thing about being present in the moment because what you do right now in the moment creates the future you want whether you want it or not. You can be intentional in This moment and what you do and how you do it, and whether or not you’re present. Or you can go through the motions and just have whatever comes to you. That’s what the present moment is all about. It creates your future.

Kevin Stafford 20:13
Speaking at the present moment I do, I can, I can have this kind of conversation with you all day I can tell this is this is the stuff that says this is the real, the real juice for me the secret sauce not but not so secret sauce. But speaking at the present moment, let’s talk at least a little bit about what your coaching practice looks like today. And I usually kind of two part this question. Who do you coach? Almost like? What did you know? When do you know it? Who do you coach primarily? Who do you focus on to be a certain stage of their development? A certain level and a certain organization? Certain industry? And then how do you coach them? Are you primarily one on one? Do you have group coaching or masterminds? Do you do keynote speeches? Do you have any books? Do you publish any courses? All of the above?

Otis McGregor 20:57
Answer? And we can. Yes. i i focus we focus tribe and purpose team. We focus on small business leaders 10 million to 100 million who are seeing success, because with success comes growth. Not not I’m crashing and burning, although we can help you too. But we want people who are seeing success and are going Holy crap. I’ve got success. Now. What do I do? How do I continue that success? Wow, we grew we grew 15% last year. Can we grow 20% next year. That’s what that’s who we focus on? Is that growth those teams or small business leaders who are growing and success, and we do it, we do it through our group coaching program called Greenbrae Leadership Program. Greenbrae leadership program is helping bring eight leaders within your team, not just people who have the position written on their door or on their business card. We’re talking everybody. Could you imagine leading a team of leaders? I mean, I did that in Special Ops. As a Greenbrae. Commander, every one of those guys were were awesome leaders. And you know what? Because they were great leaders. They made me a better leader. They challenged me each and every day. And wouldn’t you want that for your business? That everybody that’s that? Because in case you didn’t know, great leaders make great followers. Everybody in your business is a leader. They understand leadership, they know what leadership is, and they can lead themselves. That’s that that 20% You’re setting the bar too low, then? Yeah.

Kevin Stafford 22:44
That’s lit that up a little

Otis McGregor 22:45
bit. Oh, yeah. Yeah. That’s, that’s a great leadership program. And that’s a that’s our group coaching program that we run and it’s a it’s a combination of roughly seven hours of video, and then weekly group coaching sessions that we run it’s Yeah, I love that. I do also do a mastermind but it’s a Yeah, but it’s a give back to my veteran tribe. It’s a I call it the veteran business leader mastermind. So it’s a little special thing that I do to help out other veteran business leaders grow and move forward with their life, not just their business, but their life. And so that’s another piece that we do try and purpose in and we got a podcast. We also do Yeah, I do it with my son who’s one of my coaches and it’s called the camera notice show. And then yeah, like I said, I’d do it all i gotta book enable your team’s success. I got a bourbon video get to see the bourbon. But yes, it is a 70th anniversary commemorative bourbon. Yes, it’s it’s quite wasn’t I’m very happy with the way it came out. So is fun making this impact and creating great leaders around?

Kevin Stafford 24:15
I selfishly really want to just keep talking to you, but like I sort of thought we talked about a little bit before I hit record, I was gonna eyeball the Zoom clock and realize it’d be gotten a little long in the tooth, but I’ll just have to have you back on again in a few months. And we’ll just kind of continue this conversation because it’s, I mean, you’re doing the kind of work that I love, and you’re able to talk about it very eloquently, and with a great deal of passion. So I mean, why wouldn’t I want to talk to you again, this isn’t the good stuff. It’s like I love how transparently enthusiastic and passionate you are. It’s it is crystal clear that this is the like I jump out of bed in the morning to do this for you. And that’s just that’s lovely and very inspiring to see. So I mean, thank you for thank you for being here on the pod of course, but just thank you for doing the work that you’re doing and doing it the way that you’re doing it. Am I’m grateful that you’re out there doing what you’re doing. And I’m just glad to be like a tiny little part of it. And I’m glad to know you. So, thank you. Thank you Tripoli.

Otis McGregor 25:08
And thank you for the opportunity to express in on my passion and and get fired up. That’s why I always do show standing up because I get I get too excited to sit down when I’m talking about I started shifting

Kevin Stafford 25:21
my weight and sliding side to side leaning forward, I suddenly thought yes, that’s the best way to go for me. Well, oh, just thank you, audience. I’m gonna mean, thank you for listening. Do yourself a favor links to everything we talked about, you know, website, books, show notes, all that stuff down below. And if you have any questions for us, just reach out again, there’ll be links, I’m sure you’re reachable tribe and purpose, the website will be a good place. Are you are you especially active on any particular social media where you’d like to have people reach out to you?

Otis McGregor 25:50
LinkedIn, LinkedIn is a great place. We got a great presence there. And yeah, and check out our Monday moments newsletter posted on LinkedIn and sauce. Also, you’ll see it on all the social media just as an image, but you can read it on LinkedIn. And then you can also sign up for it at tribe desk. purpose.com. And, you know, get it first thing in the morning and it helps keep you kick your week off with a stoic quote and then not learn this week, which, you know, sometimes it’s like, Oops, other times, it’s like, deep philosophical, but you know, it. It is something that I learned that I’m sharing my lessons, my life lessons, each and every Monday morning, in our Monday moments newsletter.

Kevin Stafford 26:37
Excellent. All right, lots of lots of options for people to get to know you a little bit better, which is how we like it. So yeah, thank you. Thank you, everybody. Thank you, Otis. I’m gonna talk to you again real soon. I’m gonna have you back on LBC. I’ll be sliding into your LinkedIn, DMS and inviting you back on the show. Probably in a few months. I’ll make myself Wait until we get a little start seeing some warmer weather. But thank you and to the audience. Thank you once again, and we’ll talk to you again here very soon. Bye.

Think you'd be a great fit for the podcast?

Apply now to be our next guest!

Check Out Boxer Services

Be different

Enhance Your Brand

Most coaches struggle to explain what differentiates them from the next guy, let alone why your hot new prospect should pay you $10k more than your competitor who is seriously undercutting you.
Establish Your Authority

Establish Your Authority

Social Omnipresence allows you to meet your ideal prospects where they’re at by amplifying your authority across the same social media platforms where your clients are already spending their time.


Expand Your Network

What would you do with 300 new leads connected with you on LinkedIn each month? You’d probably build relationships with those prospects a lot faster, turn those relationships into clients, and make a lot more money!

Leverage Your Website

Elevate Your Website

You’ve established your brand and your authority. You’ve grown your social following and your LinkedIn following exponentially. People look up to you, they know you have answers, and they want to visit your website to learn more.

Before you go...

…how about another newsletter? 😉

In all seriousness, you’ll love this one. Five minutes each week with illuminating insights & amplifying spotlights from the world of business, branding, coaching, and marketing.

If that sounds like your speed, we’re more than happy to have you.