Today we spoke with Coach Roger, an executive coach, entrepreneur, international speaker, and former math teacher. As the founder of The School of Reinvention, he pulls from his experiences in various educational roles, as well as having made the leap from corporate America to freelance, to empower others to reinvent themselves and determine what a successful life means for them. Tune in to hear Roger’s approach to his work, why he believes coaching is important, and how he inspires clients to start a new chapter of their lives.
Transcript:
Roger Osorio [00:00:01] Veteran teachers were telling me, “this is awesome what you do with these students and the parents are requesting you, like they want you, not someone else to work with their kids.”
Sam Jayanti [00:00:12] Welcome to Ideamix radio. I’m Sam Jayanti, and every week I chat with entrepreneurs, solopreneurs, career changers, experts and enthusiasts for insider tips that you can apply to turn your idea into a business. So sit back and enjoy today’s show.
Sam Jayanti [00:00:34] Sir Roger, you have this really interesting background where you trained to become a coach, but you actually went into teaching and then returned to coaching. So tell us about that arc and that journey and how you made that progression.
Roger Osorio [00:00:48] Yeah, so when I made the decision to pursue a master’s in Psychology, which was focused in executive coaching, I actually didn’t know what coaching was at the time. The driver for that was working with math students prior to that and just falling in love with the process of unleashing their confidence on a subject that they felt they were not meant for, they were not born for. And in the process of doing that, I learned that what math students needed help with was not the actual math, but it was more the confidence, breaking down living beliefs, all those kinds of things. And once you did that, get out of their way. The math takes care of itself. It’s actually not that hard once you remove those barriers. And so I fell so in love with that process and I was only doing that maybe six to ten hours a week after my daytime, like, my day job.
Sam Jayanti [00:01:36] And what was the day job at the time?
Roger Osorio [00:01:37] So I was a national account salesperson. My acount was actually in Anheuser Busch.Wwe had a special beer cooler that brought beer down like ten degrees below its freezing point, believe it or not. And then I got to go to all these great events with them because this was like a premier product for them that they could bring into all their clients. And then after doing that by day, I would go work with these students learning center that was about five minutes away from my apartment and I just fell in love with it, it was like six to ten hours a week, and at some point it it hit me like, there’s something out there that I think I could be better at than what I’m doing right now. It’s not that I wasn’t enjoying what I was doing right. I worked for great people. So I know some people say like, you know, “screw corporate, I’m out of there”. I wasn’t really, I didn’t feel that way either, so I didn’t really agree with that movement either, what people were saying there. I go, “actually I work for great people,” people who many of them were old enough to be my parents and they, you know, really took me under their wing and helped me out a lot. But then something about these six to ten hours, I realized I’m doing something special here. I was getting a lot of great feedback from experienced teachers. I mean, veteran teachers were telling me, “this is awesome what you do with these students and the parents are requesting you, like they want you, not someone else to work with their kids.” So from there I just made this decision that, you know what I think I need to explore this, and I decided to take this leap and begin my first reinvention. And I didn’t call it a reinvention then, but I knew that I needed to take this leap and figure it out. And I knew that I needed to learn more about the science of helping people break through and unleash what their potential is. And that’s where I found this master’s in Psychology. I actually thought it was going to be a master’s in Education. I figured that makes sense. I mean, if I wanted to do it–
Sam Jayanti [00:03:22] That’s what you were doing.
Roger Osorio [00:03:22] Right. I’m teaching people so I think it should be in the School of Education somewhere. And it wasn’t there, I looked through all those programs I go, none of this looks like a recipe for helping someone grow up. It’s a lot of, you know, here’s how you teach math. I already know that part, that’s not so hard. The hard part is breaking through. So as I continued to look, I looked into the School of Psychology and some of the master’s in psychology programs and I found this one called Executive Coaching. Well, these are not executives but this coaching thing sounds interesting. I read through it, when I saw the curriculum I go, “that’s a recipe for growing humans.” And so I enrolled and got into it and since I needed a place to practice, I was already tutoring math students. So I figured, this is a great way to practice coaching while I’m learning about it. I’ll just practice on my math students.
Sam Jayanti [00:04:10] Hundred percent. So how hard is it to coach–and I’ll be curious to hear from you, which are which are tougher–is it harder coaching middle schoolers and high schoolers, or is it harder coaching adults?
Roger Osorio [00:04:23] Ah, middle schoolers and high schoolers for sure. Oh my gosh.
Sam Jayanti [00:04:25] I was expecting you to say adults!
Roger Osorio [00:04:27] No, adults are easier. And the reason is because one of the underlying assumptions of all coaching is that the client wants to be there. And when you’re working with students, you’re already in an environment where they didn’t necessarily sign in/sign up for this on their own. This is, you know, mandated, they have to be there. So you have to break through that first in order to really unleash the power of coaching with them. So I had to create an environment that they wanted to come to the classroom, that they wanted to be a part of, even though they felt math is not a subject. So that’s what you’re up against. With adults, they’re paying you to be so, obviously you must want this on some level. I don’t have to convince–
Sam Jayanti [00:05:06] It’s a conscious decision.
Roger Osorio [00:05:07] Exactly, I don’t have to convince them. So I would say working with, coaching high school and middle school students was a lot more difficult.
Sam Jayanti [00:05:12] Okay. When you described what you do, a phrase that really stood out to me was “school of reinvention.” And I think you said in the video, by accident, “40 is the new 60,” but meant it as 60 is the new 40. But tell us a little bit about how you work with people in their 40s, 50s, 60s, many of whom are displaced out of the roles that they’re in, due to whatever set of modern economic phenomena we all live with. How do you help them find the next thing and find their source of reinvention?
Roger Osorio [00:05:52] So, it’s interesting. You mentioned the 40 is the new 60, that was actually intentional because I really I believe there’s an opportunity to make that stage of life so exciting that someone in their forties is going to want to do that. “Ugh, I wish I was 60,” I want to create that. So I actually flipped out on purpose because I know that’s what I want to do. If I can only say in a couple of few words, I would say 40 is the new 60 is what I’m trying to create, not the other way around where you look at it the other way. So, but you know, in terms of your question, and how do I help men do something like that? Well, first I have to acknowledge some of the barriers and some of the challenges. You know, I’m learning so much about age discrimination that they’re facing–layoffs, and during COVID, this was only accelerated and because it was an opportunity, unfortunately. People saw it as an opportunity to lay off people who were older. And I was caught up in one of those layoffs and when I looked at all the people around me, they were old enough to be my parents. And I’m like, this doesn’t seem like just a random coincidence. This almost seems by design. And so between that or forced early retirement, people are finding themselves in this position at that age in their 60s where they are…what do I do now? And the question that they ask us, “what now” or “what’s next?” These are the most common questions I was getting from this group. And so a lot of it is really one, helping them understand what they already have within them. Because a lot of times I found that people were kind of just, “well, I did this work and that was it, and I wasn’t even passionate about it. So did it count for anything?” And my answer to that is “absolutely,” it counted for so much. You just have in mined for the right things, you have extracted the right values from that work. But it’s there. The good news is that, don’t worry, and if you didn’t find it yet. It hasn’t disappeared. It didn’t go away. It’s just under a few layers. We just got to get it out of there. [00:07:52]Once we get it out of there, you can take that and repurpose that to help launch a new chapter, something completely different. We look at your old work in a very different way. We don’t look at it as “well I’ve been doing marketing for the last 20 years.” That’s cool. You don’t have to do marketing anyway. There are a lot of other things you got from that. And then I want to help you reframe that work. [22.4s]
Sam Jayanti [00:08:14] So for our listeners who are interested in coaching, you know one of the things that they struggle to do is understand the concrete impact of a coach, right? So give us an example of someone that you’ve worked with who is in this situation, right, laid off from a job and spent a bunch of years doing this one thing. How do you help them sort of unpack, or mine, as you said, what was useful about that and how they recombine that with, you know, perhaps an area that they’re passionate about or interested in to sort of retool for the next phase of their career.
Roger Osorio [00:08:52] So one particular kind I’m thinking about, when we started this process, I asked for a lot of stories about her career. I wanted to hear some of the highlights. I might go back as far as you want, wherever.
Sam Jayanti [00:09:04] And you’re trying to get at like the most enjoyable moments there, like what gave her pleasure, what made her really excited and interested about that role?
Roger Osorio [00:09:11] Exactly. Plus, I also figured these are probably going to be things that she remembered, right? Because they stood out for whatever reason. But I also spent time like, “what were some of your biggest challenges?” Some of those moments feel like, Wow, that was really tough, I struggled a lot. Even if it didn’t end positively, tell me about that. And what I’m doing is I’m listening for patterns, I’m listening for key words, places where she might emphasize something, but not even realize she’s emphasizing the words. She uses a lot, things like that, parts of the story that she might go back to a lot. And I’m trying to help her hear what she is not hearing herself. And this is perhaps one of the most important things I do as a coach. And when I teach coaching how I used to teach coaching at IBM, this is what I would teach a lot. What you have to listen for what they can’t hear. They may actually say it. I mean, it might sound so obvious, but not to them. And so we need to be listening for that when we find that we can grab on things and start digging a little deeper: “Tell me more about that,” “I noticed, like, you sat up a little bit more when you said that part of the story,” “I noticed you smile and just like, popped on your face,” and it didn’t look like even subtle. Like it was just like *gasp* and I want to hear more about that. And I don’t, you know, saying, like, tell me what was so good about it, no just tell me more. And then it’s like, Wow, gosh, you know, “that was a really interesting day because…” and then we’re hearing that. And I’m really just trying to understand like, what was it about, what were some of the things about the job, the experience, maybe the ways that she behaved, things she did. And if I can extract those and separate them from the profession or function like marketing or whatever, maybe then we can take those and like, where else could we experience that? What other places could you experience something like that? That’s the starting part. It’s really like mining for all of those really magical moments in your past. And then from there, we’ve got something we can move forward. Plus, the person is in a much better state when you’re talking about even the challenges, because then it’s like you can find the things to be proud of.
Sam Jayanti [00:11:10] Totally, makes a lot of sense. One of the questions that I feel comes up a lot in conversations with coaches is this concept of coachable clients, right, like when are clients ready, in a sense, to receive coaching? How do you ascertain that? Sometimes they don’t even know if they’re ready. How do you ascertain that?
Roger Osorio [00:11:35] There’s a couple of things that I do. The first is I’ve learned not to sell too hard because I noticed that I know if I sell too hard and I don’t mean too aggressively, I just get too excited. If I get so excited, I might accidentally inspire or motivate that person to say, “yeah, maybe I should do some coaching.”
Sam Jayanti [00:11:52] It’s almost as though you’re excited for them.
Roger Osorio [00:11:55] Exactly, and it spills–
Sam Jayanti [00:11:55] And they need to feel that excitement themselves.
Roger Osorio [00:11:57] And it’s contagious, right? You know, when we’re around excited people who are excited, we feel that, too, for the moment. But then it’s time to sit down and have sessions, and all of a sudden you need to have that excitement. I can’t continue to bring that every moment, and that’s when I want to be very careful how I talk about it. Two, once we’re in the sessions, you know one client I’m thinking about, it’s many years ago, you know, after two or three, really I notice it after the second but I thought let me give it three or four sessions and just realized the work wasn’t getting done. And that was and I felt that in the end, this person was just not ready to even embark on those, on this new path or whatever it was. He was definitely upset or not satisfied with what he was doing, but at the same time he was also apparently not unsatisfied enough to.
Sam Jayanti [00:12:50] To work toward the change.
Roger Osorio [00:12:50] To begin taking that action, exactly. And I realized in a few sessions in and we had to “break up,” I guess, if you will. So and I explained it to him, I go, you know, this is really not going anywhere and it doesn’t make any sense for you to pay me for basically just hanging out. And so this is just not worth it anymore for you, I guess, you know, but I want to help you if at any point you find yourself ready. So that’s another thing that I notice. I don’t let it go past too many sessions because I just want to make sure that at the end.
Sam Jayanti [00:13:21] It’s serving the client.
Roger Osorio [00:13:22] Exactly. And I’m not enjoying it either, so I’ll be selfish here I’m like, I’m just not having fun and I’m doing this because I want to make an impact. So if it’s not happening, it’s not happening. So that’s, see, that’s the other thing. But then there’s this, I would say, like so one, if I sell too hard I can try to mitigate that a little bit upfront. If someone’s just not taking action at all, I realize maybe they’re just not ready, like it’s not bothering them enough to take action. But then there’s the other case where someone always has an excuse. Like there’s always an objection to why this can’t work. Like, well, and with those situations, I always give the benefit of the doubt. I always think, let’s see if I can break that down. I mean, so let me go and do some objection busting here. Let’s go through and break through as many as I can. But if it continues to happen and we’re just never getting to it, right now this is not the right thing, this is not the right solution. There might be something else. Maybe it’s actually something working with a counselor or a therapist. Maybe there’s something else or someone else, another professional that’s more qualified. And then I’ll refer.
Sam Jayanti [00:14:32] So you raised a really interesting point, right? The distinction between coaching and therapy or counseling, where do you draw that line? I think different different coaches draw that line in different ways, beyond the ‘coaching tends to be forward looking and sort of problem-solving oriented or goal oriented” and therapy can often be somewhat backward-looking. Where do you draw that line?
Roger Osorio [00:14:59] You know, I always keep it really simple [00:15:01]coaching, looking forward; everything else, looking backwards. [2.9s] And I feel one: I’m very strict about that because I feel like, I mean, I know that as coaches, we have a responsibility to not go backwards and be very careful with the clients not to go backwards. And so for me, if we have to start digging into the past and all of that, and I recognize that, I always say ‘this is now within the realm of somebody else and another kind of expert, not what I do.’ I’m here to help you look forward. You know you have to already be at a point where you’ve decided ‘I’m ready to be moving forward’ and I’m going to help you accelerate that path forward. But if we have to go backwards too much, I mean, it’s different going backwards a few months, that’s not so bad. But if we’re going way back, one, I’m not qualified. So I will not help you here. And some people are like, ‘no, no, no, let’s keep this going. I love the chemistry we have, I feel so comfortable, and there’s a lot of trust’ and I go, ‘I hear you, but trust me, this is not going to end well because I’m just not qualified to do that.’ I may have some understanding of that because I have a master’s in psychology that does not qualify me to do that work. I don’t practice this. And so I have to be very clear, like, I think that there’s now you might want to work with both of us. That’s an alternative. That’s something that could work. But I cannot address the backward-looking issues. I address the forward-looking issues.
Sam Jayanti [00:16:23] That makes a lot of sense. One of the things you talked about in your work with your math students was convincing them of getting to ‘good enough’ instead of ‘perfect’. There’s so many people in so many different contexts who hesitate to do something because they don’t feel they can be perfect on it. And really, you know, most things in life require a level of mastery, but not perfection. Tell us about how you convince clients of that distinction. You know, there are different ways to do it, especially with adults versus students.
Roger Osorio [00:17:07] Well, they’re…the ways are not that different. They’re not that different. Because I talk–actually to both of them, I talk a lot about the neuroscience and science of learning. And I talk about the science of mastery. And this is something that I studied a lot and I actually teach them both the same exact stuff. Like I don’t say that there’s a version for students or version for, so I actually treat it the same. And when I talk about is, you have to make a decision how good you want to be at something. You don’t have to, by default, be great at everything that you do. And I get we, many of us, have been brought up to believe that, that everything has to be an “A” because that’s it. Whereas in reality, life, we are an “A” in a few things, a “B” in a few, a “C” and a “D” and others. And that’s cool. And plenty of things we’re an “F” in. And that is ultimately how life works out. But again, when you’re a student, there’s a lot of pressure, parents, the school teachers, system, so I’m not going to go and bash all of that. And same for adults, like I’m not going to go against all that but, we still have responsibility for how we approach things. And I promise if you approach it in a way where you are OK with setting a different target capable of being good at something, being good enough at something, being great is just a different level and that’s going to require another set of steps and a commitment. One example I always use and this is the same for students and for adults, but I love the student one because I always think of one particular student who I had this conversation with. And she said, “you know, I just feel like I’m never going to be good as this other girl in class.” And I would ask her, “how much time you spend on your math every day?” And she goes well, and I knew the answer to this because I knew how much time she spent in ballet: every afternoon. You know, to and getting ready for it, going all the way to the class, getting back. By the time she sat down to do the homework it was already 9pm. So I knew that there wasn’t a lot of time for math. And basically, she said “yeah, just maybe 30 minutes, maybe an hour or something like that.” Well, that student spends a lot more time on math, I know this. It’s not a secret that she’s really into it and all of that. You’re really into dance. You know, you are an “A” student in dance because this is your jam, this is what you do and it’s where you spend most of the time. And so I use this as an example to understand like this is how you learn to set your expectations.
Sam Jayanti [00:19:23] Your relative prioritization, in the end.
Roger Osorio [00:19:25] And that’s going to reflect your performance in all of these things. So you can be very proud of a “B”, like super proud of a “B”. I’m super proud of you getting “B’s” because that shows me like, wow, you have levelled up. By the way, you went beyond those “D’s” and “C’s” and you’re at a “B”. That’s insane. Don’t worry about what others are saying and all that, and I’ll talk to your parents. That’s why we have parent-teacher nights, and with clients and adults it’s a little different. We don’t have the “parents” part of it, but you know, [00:19:50]in a way, you are dealing with the parent inside of them who is telling them, “no but I really have to be great,” you [5.7s] know? But when we talk about the science learning and make that objective, it starts to become okay, I see what you’re saying. I guess realistically, I can’t do what it takes to master that. And that’s OK. Do you need to master that? Like, what level of mastery will make a difference? And then we start to realize, but these two areas right here, you need to be a master of those. Like that you should obsess over being the A plus plus student on that.
Sam Jayanti [00:20:21] Yeah, that makes a ton of sense. So, Roger, we’re going to shift gears a little bit.
Roger Osorio [00:20:25] Cool.
Sam Jayanti [00:20:25] And I’m going to ask you to pretend that I am a new client of yours. And we’re going to do sort of a mini, like, coaching session. Not too long. So I’ve just come in, we’re meeting for the first time. Over to you.
Roger Osorio [00:20:44] Awesome. So what brings you to coaching? What drove you to hiring coaching.
Sam Jayanti [00:20:50] I have just left my current role and I am not sure what to do next.
Roger Osorio [00:20:58] OK. How did you go about leaving that role?
Sam Jayanti [00:21:03] I was let go.
Roger Osorio [00:21:07] OK. And how did that make you–well how do you feel about the work you were doing prior to that, just before that, getting that news?
Sam Jayanti [00:21:16] It didn’t love it. You know, I don’t think that I was necessarily a fit with the culture of the organization. I think that my own skills were not a perfect fit or there wasn’t, there just wasn’t a structure within which I felt that I was unlocking them maximally. And I think it was in a culture where there was just too much of a care or attention being paid to sort of development of individuals. You know, everyone was sort of moving forward in some fashion, and it was so much about the velocity of moving forward that the people were almost of incidental.
Roger Osorio [00:22:09] What were some of those skills that you felt were just not, I guess, being expanded or utilized as much as they could have?
Sam Jayanti [00:22:17] Yeah, I think my role there was basically in sales and business development and it was hard to be, you know, we were an enterprise software company. So you were acting as a bridge, effectively, between a customer who may not be technical and a bunch of software engineers who are highly technical and a product that was highly technical. And so it was, you know, in some ways, an interpreter’s job, but it was also a very iterative and kind of interactive role where you had to sort of communicate but also enable both sides to understand each other and give both sides a little bit of what each one did, right, effectively because one person wanted to tackle a problem one way and the other people might want to tackle it a very different way. And those weren’t always the same.
Roger Osorio [00:23:26] What was a moment where you would say that skill really came out? Maybe it didn’t come out a lot, but one where it probably came out the most in you and you probably went home and thought, “wow, I was awesome. Like I was pretty awesome that day.”
Sam Jayanti [00:23:42] It was, I mean, there were a number of moments like that, and it was always when we were interacting with the people leading and driving a business who had a very different view of their business and a very different set of performance objectives and market objectives and strategic objectives from the technical staff, who then was seeing sort of a piece of the puzzle and much more involved in the micro, right, and I think being able to take that set of what are the business requirements and translate them into the technical piece of what we needed to do was more like great moments.
Roger Osorio [00:24:30] Now that you find yourself on the spot, what’s your number one question?
Sam Jayanti [00:24:35] Where are my skills best utilized and where will I thrive?
Roger Osorio [00:24:39] Where are your skills best utilized and where will you thrive. And when you work, when you think about those questions, what are some of the answers that come to mind?
Sam Jayanti [00:24:48] Yeah, that’s a great question. I think for me, I am a problem solver by nature, so I love thinking about the solutions to problems and trying them. But then when the solution becomes established and we just have to deploy that solution a hundred more times, I’m less interested in that piece of it. So I’m more interested in the creation of the solution and making sure it works in the ideation than I am and the OK now we just got to deploy the solution a lot of times.
Roger Osorio [00:25:27] And do any places come to mind where you’ve seen or perhaps colleagues or friends that you’ve seen doing this kind of work? Maybe you’ve thought, looks pretty cool.
Sam Jayanti [00:25:36] Startups and entrepreneurship.
Roger Osorio [00:25:38] Startups and entrepeneurship. And where in that have you maybe even envisioned that you might offer them like your superpower? Where you could really flex your superpower the most.
Sam Jayanti [00:25:54] I think either by partnering with someone who has an entrepreneurial idea or pursuing one myself.
Roger Osorio [00:26:00] OK. Have you thought of any?
Sam Jayanti [00:26:03] Yes. And that is Ideamix and we’re here today.
Roger Osorio [00:26:06] I love it. I love it.
Sam Jayanti [00:26:08] But that was amazing. Thank you for indulging me in the role play. But you know, it’s great for our listeners and viewers to have a sense of what your coaching style is like. So it’s kind of hugely useful to do these many sessions.
Roger Osorio [00:26:26] Yeah, no I love these demos. When I used to teach at IBM we did this all the time, and I would always get asked, “can you do one of your demos?” And I’m like, “Yeah, let’s go what do you want to throw at me?” And then, you know, it was always just a lot of fun because it gave us an opportunity to, you know, where I could run the session and zoom out to the class and look around at everybody and say, OK, what did I just do there and all that and people start dissecting some of the things that I do, whether I need them or if I need back, or where I was making eye contact. If it’s a difficult question and I see a person struggling, I might look away for a moment, grab my glass of water, give that person space. These suddle little things, that’s awesome to see how the class notices those kinds of things. But then they become aware how powerful that can be. And it seems — was that by accident? Did he get his water on purpose or by accident? But it seems like the timing was so good and those are kinds of things that make sense, they create space for the person. And honestly, I learned this teaching math. This is where I learned all of these skills. When I go back in and I’m running the lesson, I give people examples, I think because the last– where did you learn how to do that, how’d you practice that I go “the classroom”. When I worked with middle school girls, I had the lowest track, or whatever you want to call them, and they were struggling the most. So imagine all of these students I have in the room are all thinking, “I’m not a math person,” so I’m up against an entire room of that there’s no mix
Sam Jayanti [00:27:45] A very reluctant set of students
Roger Osorio [00:27:47] Absolutely. And the first thing I had to do was create a safe space and I had to learn how to create a safe space so that someone could make a mistake and say something that maybe they weren’t sure about. Just like a client, we have to make our clients feel comfortable saying something because it will iterate on that. But if I can’t get you to say the first thing, we’ll never get to version 17, which might be the one.
Sam Jayanti [00:28:10] Totally.
Roger Osorio [00:28:10] Oh my gosh, I really where it’s gone, like how it’s developed and evolved, but I’m got to get you to version one first or otherwise, we don’t get it.
Sam Jayanti [00:28:17] Absolutely. Version one is always the first step. Well, Roger, thank you so much for your time today. It’s been a pleasure chatting with you.
Roger Osorio [00:28:24] Likewise, I really enjoyed this. And great questions. They got me reflecting and thinking about my own journey.
Sam Jayanti [00:28:31] Great, I’m glad! Thanks very much. Thank you.
Sam Jayanti [00:28:36] Thanks for listening today. You can subscribe wherever you get your podcasts. And while you’re there, please do review the show. We love hearing from you, so email us at info@theideamix.com or Instagram DM us. Our episode this week was produced by the incomparable Martin Malesky, with music by the awesome Nashville-based singer-songwriter Doug Allen. You can learn more about Doug at DougAllenMusic.com.