Retail Leadership with Steve Worthy
You’ve earned your position. Now let’s make sure you lead like it.
Retail leadership isn’t what it used to be.
And if you’ve been doing this long enough, neither are you.
The job gets bigger. The expectations get louder.
But the guidance? That usually disappears right when you need it most.
And most leaders are left figuring things out quietly while still being expected to have all the answers.
This podcast is for experienced retail leaders who’ve already proven themselves
and know there has to be a better way to lead than just carrying more.
I’m Steve Worthy. I’ve spent over 30 years working across retail — from boardrooms to regional and district markets, through restructures, reinventions, and the parts of leadership no one really prepares you for.
I’ve coached thousands of retail leaders and advised teams that support the retail industry, and this podcast exists for one reason:
To give you the perspective and clarity most leaders are expected to figure out on their own.
Now let’s make sure how you lead actually matches it.
Retail Leadership with Steve Worthy
What Happens When You’ve Outgrown Your Role?
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What Happens When You’ve Outgrown Your Role?
In this episode, I sit down with Ryan Holm from Helzberg Diamonds, and we get right into the real tension many retail leaders feel but rarely talk about — the moment you know you’re ready for more, even if you haven’t said it out loud yet.
Ryan’s journey from Dunkin’ Donuts to leading innovation in a Berkshire Hathaway company is filled with the kind of insights leaders need right now.
In this conversation we cover:
- How to know when the spark is fading
- Why targeted upskilling outperforms “learn everything” development
- The advantage of speaking both store and HQ fluently
- How to approach AI with a practical mindset
- How to evaluate whether you’re truly ready for the next step
This episode gives leaders a clearer view of where they stand today and what they may need to consider for tomorrow.
If you’re in a season of transition, this one will give you something real to think about.
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So today on the show, we have Ryan Holmes. He is the divisional vice president of operations and innovations for Hellberg's Diamonds. This conversation, gosh, it was long overdue. I did a couple of podcasts on the differences between HQ and stores, but never had anybody on that actually has been going through it. So super excited to have them on the show today. So get ready for an amazing episode of Retail Leadership with Steve Worthy.
SPEAKER_00Welcome to Retail Leadership with Steve Worthy, where we go well beyond the corporate playbook to unpack major opportunities, hidden challenges, and critical issues that senior retail leaders face every day. So let's get started right now.
SPEAKER_03Well, Ryan, I'm I'm super excited to have this conversation with you. Um we we had a call, a Zoom call, and we were talking about your journey. And I was like, okay, we gotta, we gotta, we gotta turn this into a podcast episode. We gotta do this. Um, because there are a lot of people who need to hear and learn from you about what you've um what you've been able to accomplish in your in your retail journey, which has been a lot. So I am going to allow you this opportunity to uh introduce yourself and then we'll get into some of the questions.
SPEAKER_01Yeah, well, I mean, thanks so much for having me. I really enjoyed getting to chat with you. And yeah, so my name's Ryan Holm. I'm the divisional vice president of retail innovation and operations at Helvberg, which, if anyone's not familiar, is a retail jewelry chain. We are owned by Berkshire Hathaway, um, been in business since 1915, and we were the first national jeweler to market with lab grown diamonds, which is super exciting, uh, especially right now, more than ever. Um, but yeah, my my journey, I mean, I started out in food service, spent 10 years all through high school and college at uh at Dunkin' Donuts. And then I got into jewelry and um kind of a tagline that stuck. I was I was interviewing to make that shift. And this guy, super witty guy without missing a beat, said, Oh, you're moving from sprinkles to sparkles. And uh it gets a laugh everywhere. Uh kudos to him for just off the cuff. But um, yeah, last 11 years I've been in the world of jewelry and now uh mostly in operations and now on the innovation side.
SPEAKER_02Sprinkles to sparkles. I love I love that. That may be the that may be the um the title of this episode.
SPEAKER_01Um I grow up and have more wit, I will be able to do something like that. Uh that's my dream one day.
SPEAKER_03Yeah, that's so that's that's that's so awesome. That's so awesome. Um, well, yeah, you had you did go from from from sprinkles to to sparkles. So talk a little bit about that shift, right? Because I think there are a lot of leaders who are going to be listening to this, but also, you know, those who are in corporate, right? I think part of our initial conversation was this idea around make a move, right? Uh, you know, with over here on Worthy V Tell, we have this um programs and coaching and training around make a move, um helping, helping uh individuals make a move up on or out of the organization, which is the premise for this conversation. Ooh, I got bars. I just rhymed. I I didn't even realize I had I can I can rap. Um but um I wanted to talk a little bit about that initial move, right? Because I think that's important for people to understand what was your thought process from from going from sprinkles to sparkles, and then we'll definitely talk more about um your your current role.
SPEAKER_01You know, it it's interesting. Sometimes there's that mix of like you you fall into something, you know, it's that um what's the phrase? It's the difference between finding what you love and loving what you found. And and for me, it was just this like, I, you know, I felt like I was as high as I was gonna go, right? I had I had really developed from an associate working at a Dunkin' Donuts in high school to being essentially a like a district manager role for a franchisee, and I wasn't gonna be the owner. And so, you know, at at 26 years old, it was like, well, I'm not just gonna sit here. I I'm hungry for more and something different. And so I knew I needed to pivot and I didn't know what that looked like. And, you know, I just kind of fell into jewelry. I had friends that that worked in a major jeweler's um home office, and I thought, I could try that. I know operations. People are people, I know how to run a you know, a busy food service store. Let me just step it up a notch and get out of a uniform and put on a suit and we'll see how this is, and immediately just fell in love with certain aspects of the world of jewelry. I mean, it's it's really just an elevated retail where a big part of your job as a store manager is recruiting, right? Is recruiting really empathetic people who are good at selling jewelry because day in, day out, they've got to meet people on the sales floor who are celebrating one of the most meaningful moments of their lives and make them feel like they've got their full attention and they want to hear that love story and sell them an engagement ring. And it's just, it's an incredible industry.
SPEAKER_03Nice. How how did you get to how how did you get to that point where you realized that you had reached your limit? Right. You you, you know, you you knew that you weren't probably growing from a positional standpoint, but you were probably you probably weren't growing either from a a leadership standpoint. Like what triggered in your mind, like what was the mental process that you had to sort of go through? Because I I I you know I've experienced something very similar. Okay, this is it, this isn't it. And I've probably chronicled sort of my decision-making process, but I want to get your thought process from like uh, you know, really come to that um um that self-reflection of, man, I want more, but I don't know what that more is. And then also the second part of that is like, what's missing in my in my toolkit that's actually going to help me get to whatever that next may be?
SPEAKER_01Yeah. It's a great question and one I've thought a lot about. And I think, you know, the simple answer is you kind of feel it in your gut. To elaborate a little bit more though, for for me, it was that when a challenge pops up and I'm really engaged and I love what I do, it feels like a spark. It feels like, oh, this is gonna be hard. I know I'm gonna be tired, but I want to figure this out. And I think I had reached a point at that point in my career, at the end of my time in in food service, where the challenges that would pop up didn't feel like they lit a spark anymore. It felt like, oh, this is frustrating. I've done this before. I know what that work looks like. I'm not gonna be breaking any new ground in in, you know, my view of the world. And so I think that's really what made me feel like I want that spark back.
SPEAKER_03Yeah, that's that's so good. That's so good. And I think I I think also the temptation too is the is is the is the fear associated with trying to find out what that next spark is. It could be. Did you did you experience any any trepidation with with going and trying to figure out what that next spark was going to be?
SPEAKER_01Totally. I had so much self-doubt going into jewelry because at that point in my life, you know, I owned I owned one suit, right? It was like a suit I had for a wedding and a funeral, right? It probably didn't fit very well. I didn't feel super comfortable in one. And I wasn't a jewelry person, right? Like I wore a garment, a running watch, and that was it. I just wasn't a jewelry person. Um, so it felt like a huge risk. And yeah, I wasn't sure it was the right thing, but at the end of the day, it was I knew I needed to do something different and just take that initial leap. And if I got it wrong, I'd do I'd try again, right? But it was time to do something different.
SPEAKER_03Yeah, I love that. I love that. So you you take this, you make, you make a move, you decide to make a move, and now you're now you're in this this world of of of sparkles, right? Um, which is uh contrasting very different than where you where you came from. Um what were some of the things that you were able to take with you um from the one world to the next? And then what were some of the things that you had to unlearn, possibly because you're just like, well, maybe this just doesn't translate well here, because I th I I would assume that there were there were several things that you probably had to unlearn about yourself.
SPEAKER_01Yeah. At the end of the day, people are people, right? And so that element of like, you know, being a leader and you know, whether it's managed in a store location or or multiple, which I did a lot of in my my jewelry career, it was, you know, finding the right people, building a team, and making sure everyone is is focused on achieving that same goal. And that that was really the same, you know, between industries. As different as the the setting was and the goals were, that um listening and making people feel heard and making sure that you know you're addressing the, you know, giving recognition and also addressing poor performance was was the same between them. As far as what to unlearn, I I think one of the biggest things was learning to slow down, right? In in the world of of food service, it's you it's just all about hustle, go, go, go. And in jewelry, it was more about let's slow down and and listen to our clients because there's so much more valuable in uh value in that than trying to just move on to the next.
SPEAKER_03Oh, that's so good. That's so good. And I think and I and I I could imagine that that was extremely hard. Um, you know, coming from a very fast-paced uh, you know, world to uh even retail, so even you know, Hellsberg and selling jewelry is fast-paced um in a in a different way, right? Um still the the the listening, but then there's also the taking in what you're listening and then translating that into some measure of communication to help out um to help out the customer. Um one thing that uh I I I wanted to to talk about was that so now you've you uh you did you did multiple units within with within Hellsburg, but now you you're sort of on the on the on the corporate side. Could you talk a little bit about that transition?
SPEAKER_01Yeah, it that's an interesting one. So it was really similar to what we were just talking about with that that move from food service um into jewelry. It was kind of the the same thing. I um early on just developed a, it was kind of a best practice, right? We had this method for for setting goals for a new month for associates. And I thought there's a better way to do this. I'm watching people break out calculators and pencils and papers. Now, granted, this is probably 10 years ago, but still even then it was it was jarring to see that. And I thought, you know what? I've got enough Excel skills. I could, I could build something to make this a little tighter and share it out with my peers. And it was kind of an eye-opening moment when I realized the satisfaction that I got from developing a process and rolling it out to peers and helping them do their jobs better and them share excitement and thanks for it. That reward, that sparked feeling was so much greater than me being successful as a store manager. And it just turned into something that I realized I needed to cultivate and keep, you know, leaning into that spark of. Feels great to be able to develop a process for the organization. And eventually, it really just the scope of that kept getting bigger until the point it felt like, all right, these little side projects of process improvement I'm taking on are to the point where I'm putting enough time and energy and sometimes even you know, after hours time and energy into these because of the satisfaction from it, that it's making it up to the opening level.
SPEAKER_03Yeah. You know, I you know, I love that because here's here's what I'm hearing, right? Um, and you've and you've probably heard this and seen this throughout your your retail career when individuals want to leaders want to make a shift from whether it's one store to the next, one market to the next, or different things like that. Um what you I've what I'm hearing is that you you you started something, you you realized that there was a an opportunity or a gap that existed. And you didn't exploit the gap. You say, you know what, I can actually do something about this. I can actually probably create something that one, I feel really good about. And two, is it gonna make my life easier? And then three, it's actually going to help communicate something to and to my peers and actually help them out. So you it's almost like you you you created your your your own role and started owning it. And then people started to recognize what your your your contribution and your and your value. I always talk about um having a valued opinion, right? Talk about having a value opinion on yourself, your team, and the and the business. And I almost feel like you did all three of those um when creating that that spreadsheet and that communication tool. Um what were you what were your thoughts about that and when you when you rolled that out and then when it started to take off, where did uh where did it go from there?
SPEAKER_01Yeah, I and what's interesting about that is is I don't think that you can pick and choose from those three things you just mentioned, right? You kind of need all three to make it to make it work. But but to answer your question, for for me, the you know, the place where it really took off was was actually during the pandemic, right? It was something that I I knew I liked pre-2020. Um, and I would always kind of take on when an opportunity arose. And when I had that time, you know, to to slow down when the stores were shut and really reflect and think about what am I enjoying about this career that I've got. I I just thought, hey, it's time to upskill a little. I'm gonna use this downtime to build out, you know, some skills in that area I'm feeling a satisfaction from. And it must have been within less than a year after stores reopened from COVID that I was then suddenly juggling a dual role. So I had both a regional manager role. So I was covering a territory of stores, and then I also had this kind of store ops and IT integration side role. And and really that that shift was so natural. Every week became this conversation with my supervisor going, here are the things on my plate in both roles, right? And that secondary store ops and IT role just kept growing and growing and growing to the point where I'm like, this has become a full-time job. And you know, trying to juggle both and figure that out.
SPEAKER_03So yeah. That's so good. That's so good. So I I w I want to talk about that um here in a second, but you said something that I I I can't let I can't let go because I think there's a lot of individuals who need to understand the the what you said about upskilling, right? You you you you realized that you had some more time on your hands, but you said, you know what, I need to upskill, you know, myself. And talk a little bit about that because what I tend to see sometimes are is that, you know, a lot of leaders within retail, they're they have amazing operational prowess, right? But then they may lack some of the people, leadership, you know, you know, skills and uh emotional um uh intelligence and maybe some communication and some self-awareness and certain things like that. Um when you when you made the decision to to upskill, how did you know what you what you lacked? And then how did you realize that um this is what I need to actually upskill in myself? Because I would I would almost assume that it wasn't just a a technical upskill, it was more of a of an interpersonal sort of decision-making process that you had to go through.
SPEAKER_01It it's a little bit of both. And here's it it's interesting. I see the same thing you see, and what I see a lot of kind of frustrated leaders do is upskill broadly. And while there's nothing wrong with that, I say, Oh man, that's so good. Yeah, it and and look, there's value in that, right? If if going back and just getting a general business degree or getting the MBA or anything is going to make you feel satisfied, by all means go for it. For me personally, it was it was very targeted upskill. It was here's something that I know I want to accomplish and I feel passion when I do. Let me just take a couple certificate programs, and then that will unlock the doors to understand in even a little bit broader terms. And so letting that, you know, where I want to get dictate what the upskill is.
SPEAKER_03That's so good. That's so good. I couldn't control myself when you said that because I I really couldn't, because I I I I firmly believe in that, right? Um, I I think the tendency is that you you want to cover all your bases, right? So you you go out and you learn all, you know, this myriad of different things, and then none of those things tend to stick. And I think it's it's um it's extremely valuable for for leaders to really understand what those gaps are, the very specific gaps that will actually that they need to address. And sometimes they're very singular in the most in the you know in for the for the most part. I think the other part too is that, and this is for somebody just I'm just thinking about this, the whole Pareto bull, for the whole Pareto principle, the 80-20 rule, right? The tendency is that when we think about upscaling, we think about, you know, covering the 80%, which covers the, you know, will cover the 20%. It's uh completely opposite. Pareto principle says that if we focus in on 20%, it will give us 80% of our return. And so I think when you think about upscaling and understanding where you are, there's probably only one or two things that you need you as a leader will need that will actually give you the biggest return on your investment of your time. So I'm so happy you said that, Ryan Moore. Uh, we can probably stop the interview here, but we won't. Um because I think that part was someone's gonna get an extreme amount of value out of this, but they're gonna get even more value out of this next topic. You have you you you man, you have the ability now to speak like two languages in retail. You have the ability to speak store, and you also have the ability to speak corporate. Uh not a lot of not a lot of leaders have that ability to do that. Um, and I I really want to dig into this uh and this into that ability. Could you talk a little bit about sort of that um that idea of what I just spoke about, the ability to be able to speak both languages because and how important that has been, you know, for you throughout your journey.
SPEAKER_01Yeah. First, first of all, anyone who hasn't listened to your HQ and and store that that you have two kind of dueling, you know, stores from HQ perspective and and um vice versa should go listen to that. Because I got a ton out of it. And it was like, I was like cheering in my car when I was listening to that. I was like, yes, exactly that. Because it that's the world that I I live in. And I so what I think happens in a lot of organizations is there is just simply misunderstanding of what each group is is facing, right? Neither group has usually, not always, but usually not lived what the other has. And so I think there is there's perception that's wrong on both sides, right? So from a headquarters perspective, I think often there's frustration with the stores. They're going, I don't get this. I spent forever putting together this, you know, visual merchandise change that I want to roll out to the stores. And I made it really detailed, and I had someone vet the communication and I was clear, and you know, I consulted the stores when I developed it, and we rolled it out, and it didn't get 100% adoption, and I'm frustrated. On this, on the store side, what you're seeing is someone going, they they rolled this out, and I don't get it. They go into an office, they don't have customers and call-offs and people distracting them. They get 40 hours a week to sit in a chair and focus on this and boundless resources. It should be perfect. And and neither side is right at all, right? The person who went into headquarters is is dealing with way more than the storks realize. There are definitely not limitless resources, right? They had to work cross-functionally in a situation in which not everyone's goals are aligned with theirs and buy for resources and work with a vendor to develop whatever thing they're rolling out to the stores, right? And and they had other competing meetings and things pulling their time away from that project and probably a deadline where they had to push it out a little earlier than they wanted. And on the flip side of that, the people in headquarters rolling out the stores aren't thinking about the fact that, okay, yeah, you didn't get 100% adoption, but some of the stores you rolled out to, you know, someone in that store, you know, left the week before. Someone else is just found out they're, you know, they're really sick and are going to be on leave of absence, and there's tons of reason. You need to give that store so much empathy and patience and pause with what you're asking them to do.
SPEAKER_03That's so good. That is so good. And um I I I often I often feel that um, I mean, I mean maybe you and I were having this conversation before, and I I've probably told this story several times where you know. Whenever there was a new initiative that was rolling out, part of the thing that I would do for my markets was like I would raise my hand and say, hey, let's do it. Let's do it. And I think my my team initially, they used to always get pissed off at me. You know, well, that's just you just add it to the workload, Steve, and you're just not, you don't understand it because you're not dealing with the day-to-day. And then as we would get into the throes of the initiative and um and the the different ideas that corporate would want to see happen, and I would bring in leaders, store leaders, and they would have a seat at the table, and they were actually creating, helping to create the conversation, then allowing the conversation to be thrusted upon upon them. And they started to see what corporate does in a different light compared to like, oh, hold it for a second. Now I'm actually, I can I could understand their timetable compared to my timetable. And so anybody who's listening to this, if if you have the opportunity to to take on initiative, something from a corporate standpoint, I highly recommend it. Your team will probably get pissed at you. Don't don't don't don't tell them Steve told you to do it, um, because I still want them to listen to the podcast. But yeah, you can tell them I told you. But I think there's a lot of value in in in in sort of this um, I don't know if you want to call it reverse mentoring type of type of perspective that uh that that needs to take place. What are your thoughts on that, Ryan?
SPEAKER_01I I totally agree. That that repeated communication with someone in the you know, in the whether it's HQ or stores, that you have respect for and interest in what they're doing is so important. Because I think a lot of retail leaders today are rightfully saying, hey, we need to do more, we need to do more store visits, right? We need to start, you know, mixing these cultures and understanding our stores better. But there is something that you gain from that repeated communication versus a singular store visit that um I just don't think one is a substitute for the other.
SPEAKER_03Yeah. No, that's so good. That's so good. Uh a couple more things that I want to chat, um, chat about. I I cannot have a conversation with you without talking about AI. Right. And and it's and it's impact or, you know, it's person, it's it's lore, if you will, um, over over the over the retail space, um where the where the narrative is some not even the narrative, it's more the reality of what we see where a lot of retail companies, the corporate aspect, and they're running with it. They're they're all they're they're going after it. They're like, hey, we need to do this. You know, I got competition over here that's doing it, and I got my I got the stakeholders and the shareholders in my ear over here saying we we need to figure out how to implement and infuse AI into this process, but then you have the stores and the field leaders who are like, we don't need it, or um what does this mean for us? Being the fact that you can speak both languages, and um, are you currently dealing with anything associated with AI within your current role or any initiatives? And how are you dealing with that and communicating um that to the team?
SPEAKER_01Yeah, I most all of my projects right now have some level of AI involved. Some of it's more machine learning than than AI, but it gets branded that way nowadays. Agreed. Um But I I think it there's a lot of um both excitement and hesitancy around the term AI today. And what's what's really interesting is uh and we talked a little about this in our last conversation, that that walk, you know, crawl, walk, run with AI. And I think to your point, there are the run phase is what gets the hype on, you know, you go on LinkedIn, you see people talking about their tech stack, and you know, the thing with the run phase is it it's not free. It costs a lot of money and it takes partners, right? The the crawl phase, it is fairly simple, even though I think there's still people avoiding that crawl phase. And the crawl phase is is fairly easy, right? Everyone has an example of um, you know, they pulled up chat GPT and you said, well, what are you interested in? Oh, I'm interested in health and nutrition. Great. Ask Chat GPT to make you a meal plan. And then, you know, people are blown away. And you can respond and say, Well, I'm a vegetarian. Can you, you know, and it'll it which is great. The walk phase is what's getting left out of the equation because I think what's fundamentally different about AI than any other tech revolution is email can't teach you email, Excel can't teach you Excel, but AI can teach you AI. And so there's this mindset shift that has to totally break through for you to start walking with it, right? And I think it if I were to give one practical piece of advice for people who want to try and figure out, who are sitting there and they've tried cool things, they've crawled with AI, they've been like, oh my gosh, that's amazing. You know, I asked it to write me a poem in the voice voice of a pirate and it did it. That's cool. And then they sit in front of the prompt box and they're like, how do I take this to the next level? The one piece of advice I would give is tell whatever large language model of choice, I am a and give your role. And what do you need to know about me to help me be better at my job? So ask it what questions to ask you, and it you'll be amazed at what it responds with and says, Well, I'd like to know this, this, and this. And it'll give you a laundry list of questions and it'll start learning about you and how it can help you.
SPEAKER_03That's so good. That's so good. Um, the run phase is not free. Um I love I love that part. There's so many, there's so many things I'm writing down, and we're gonna clip for for uh you know, for from this podcast. Stick it, sticking, sticking to AI for um for a second, right? Because I I I I a hundred percent agree with you, right? But I here's one of the things that um when we start talking about from an upskill standpoint to kind of go back to that um uh aspect. Yes, there are AI can help you learn help you learn AI, but I I I want to I want to ask you about like your strategic thinking now, right, associated with AI, because I I I think it it it has changed the way that we need to think strategically about the inputs. You and I we probably had this conversation prior to you, right? About the inputs and you know, the inputs prior to, you know, uh using AI and then the outputs that AI generates for us, right? Have you how have you had to change up, or if you had to, change up in sort of your strategic mindset when it comes to AI and how you and how you think and how you see things?
SPEAKER_01Yeah, the the tough part is it's it's tempting to move fast with AI because one, I to your point, I think everyone's feeling behind the ball. And it's tempting to move fast because oftentimes turning on an AI feature is really flipping a switch and saying, Yeah, I'm gonna, you know, feed this in. But what you you need to be thinking about is am I feeding it outdated data, right? It it just in an example would be um we've got a a communication um vendor that is rolled out an AI tool, right? In memory, it'll crawl your whole company's resource library and return answers to the end user, which is incredible. But if you have an outdated resource library that you haven't been maintaining and pulling down outdated content, it's gonna do more harm than good. So I think just the getting the, you know, cleaning up your your inputs. Um AI is only as good as the data you give it. Yeah, that's so good.
SPEAKER_03That's so good. I'm we have um we're working with uh with a couple of sponsors and they do they do sort of um AI data um um categories or you know, um categorization, you know, at the very beginning, right? Because they you know, while they have the AI for the output, right? But their main thing is like, well, how do we help organizations organize their data to begin with? Because you have and you know you know this as well as I do. Like retail is not short of data. We are not, we are not short of data. There's there's so much, we are a data-rich industry, and I think the tendency sometimes is that we we hide behind that data, and you we either don't do anything with it or we or we make a decision and use the data to justify the decision that we've made, regardless if it's right or not. Right? And so I think that's you know, it's like we're gonna go this way. The data says for us to go this way. And I was like, well, why? Well, the data says it. So well, that our customers don't care about that. Doesn't matter. What data says we're gonna do this, we're gonna sell like it was Hellsberg, we're gonna sell like, you know, um uh uh, you know, uh, you know, big pink diamonds. The data says that we should do that. We should we we'll we'll be ahead of the game. AI told us to sell big pink diamonds, and you're like, well, I don't know if our customers are asking for it. Um you know, so here's the I here's the thing. I don't want to see in like six months' time Hellberg, Hellsberg selling big pink diamonds, right? I'm gonna say Steve. I'm gonna come for them. I'm gonna come for them. Um I I wanna uh the the the last piece that I wanted to I want to move into and is is to sort of go back into this um being ready for what's next. Um you have dealt with a a lot of leaders who um you know want to get promoted because you know you know what Ryan, I've been with this company for 15 years and I've seen somebody else come in and they gotten promoted ahead of me, or um you even yourself, you you you came in, Ryan, and you just you you came from ducking donuts and now you're now you're doing all of this stuff. And um, you know, how how does that supposed to make me feel? Because I've been here for this this period of time. Um you know, uh we we hear that, but we also hear and we also see the individuals who are silently not sort of equipping themselves for for for what's next. How how can you how have you been able to identify those individuals who are are ready for what's next compared to the individuals who just talk a good game about being ready for what's next?
SPEAKER_01Yeah, it's that difference between like performing well today and the role that you're in and feeling like that means I should have a what's a what's next, right? Yeah. I I have a good friend that that's going through this right now. And here's the thing I think he is gonna make the leap, uh, but he hasn't narrowed it down yet, right? He's been upskilling generally, you know, and and I think he can do more. He's got the, you know, a capacity to do it, but it it it's clear to me he hasn't targeted what that next thing is. Like he hasn't gotten granular with it and said, this is what I want to go after. It kind of feels like buckshot and it it's tough as it's it's apparent he's ready for something new and he's done with the current role and he's performing in it, right? But um I think he'll get there. It's it's just a lot of he, you know, he's working with that uh coach right now and he's trying to figure out, well, what is it broader that is next for me? And so I think if I had one piece of advice for people, it it's find a space that you feel that spark in and chase that. Don't just chase something new.
SPEAKER_03Yeah. And I and I here's here's the one part that really I I latched onto because it's exactly what I do, which is coaching, right? I love and I am is and it's not just because I do it. Um I I have been a strong advocate of of executive coaching for like the last 20 years. Um because I've been very fortunate to always have a uh a coach and someone that I could prov that that will provide me this unbiased perspective of who Steve is, um, my thought processes and how I see the world. Um and I I gotta tell you, it is probably one of the best things that any leader when you start talking about upscaling. So certifications and school are are great, but I think the other upskill that your friend is actually doing is this self-evaluation, self-awareness aspect and the coaches helping them see themselves differently than how you see yourself. Because when you're in the role, yeah, man, you could you're a rock star. You a rock star. But man, when you go to the next level, you're starting over. Nobody knows you, nobody knows you, and you're literally starting from square one. Yes, you may think just because I I used to I used to tell this to my team all the time. Um, they would, you know, I get them promoted to like a district manager or a regional manager, and they and they go off to another market. And I would always say this, listen to me, you're not the leader when you get there. There's all there's there's someone else that everybody else is already listening to. And and they're like, and they would call me, they would call me, I hate you, Steve. You're so right. There's all there's already somebody there, and it's not that's all that they're that everybody around that they're listening to, that they're following, you are, you're gonna have to sort of grab that position from them when you when you go there. And if and I just and and it sounds sounds quirky, but it's so true. Just because you take on that initial next role, there's already already somebody there that is assume that role. So you have to sort of start from square one, build, um, build connection, build um uh alignment, um, uh authenticity and buy-in with who they are. Because I can imagine, Ryan, that they were like, well, I don't know who this Ryan person is. You know, what what were some of your thoughts? What were some of your things that you that you did to sort of move your way into that position of leadership?
SPEAKER_01Yeah, I I think the biggest thing is um, you know, no one no one likes to know it all, right? So when you find that person, and and I by the way, I have to say, I I think you're dead right. There are people already in any market or what whatever it is, you know, we call it a district or whatever, that people are already viewing as the leader. So, regardless of the fact that you might have a track record and someone that put you in the position, um, there are going to be people looking going, what about this person? We've all been the silent leader who's sitting here. And so I think the big thing is it don't try to diminish that, right? Like that there's a reason for that. Embrace it and say, Hey, talk to me. Do and a lot of times this person that is that silent leader may may have no desire to move up, right? Correct. Sometimes they want to move up and there's something holding them back. In fact, at another company I worked for, one of my proudest moments was there was that person in this store that I was managing that had been passed over for a store manager promotion. I no less than half a dozen times in in the last 10 years. And we sat down and had a heart to heart and you know, had to give some feedback about, hey, this is the perception around what you're doing that's holding you back. And this is going to be difficult for me to challenge you on that, but let's let's talk about that and let's change it. And I will put my neck out and say, if you can, you know, take this feedback, um, we will make sure that you don't get passed over for that promotion. And to this day, she is a store manager and has been since I left that store. And I never miss a birthday, you know, a work anniversary, a holiday. We always text each other and check in. Uh, it's one of the highlights of my career. So I would say just don't treat that person as an enemy, right? They are, they are someone that you should embrace and befriend and celebrate because they're viewed at as a leader for a reason. Awesome.
SPEAKER_03Let me let me let me ask you this question. Have you ever had, have you ever had any any regrets? Right? Any regrets in like, you know, a potential opportunity that that you were like, oh, I wish I would have, I wish I would have done that. Or, ooh, man, that actually over there looked really good. Have you ever ever felt any regret?
SPEAKER_01Definitely. I think the biggest thing for me is um long, long time ago, I ended up in a a position that wasn't a fit for me. And I knew that where I was at was not a cultural fit. And for whatever reason, I latched on to success in this place that was not a fit for me. And I knew that I needed to leave for a variety of reasons. Um, most of which was my own mental health and well-being. And I felt like a failure to walk away without having achieved success there. Um, and when I I gave in and said, hey, it's time for me to find something that is a cultural fit, um, it was the biggest relief I've ever felt in my career. So yeah, uh r regret would be just just sitting in a place that I I well knew was not a cultural fit for way too long.
SPEAKER_03That's so good. That's so good because I think, you know, I I've I've experienced that, you know, so many times in those in in uh in in my career. And there's somebody out there that's experiencing that right now. They're they're possibly in a role, they're possibly in this, in this situation where, while, you know, the money may be good, right? The money may that's another thing too, right? I've I've I've I've been in opportunities where I knew I needed to move on, but the man, that money was good. Um and I was like, okay, I'm I'll I'll figure it out. And and then, you know, actually my move out of retail, um, out of out of retail was the the toughest decision that I've had to make, but I felt very similar to you in the context of that while I was there doing it, man, I just knew that there was something more for me to do. There was something, there was a bigger voice and purpose and intent and intent that I needed to actually accomplish, and I was able to sort of you know finally make that decision and pull the trigger. It was it was extremely hard. Um last question for for for a leader who's who's thinking about you know making a move, who's who's who's sort of frustrated, who's um sort of in that place where you and I were, um give them give them some you know pieces of advice, inspiration, or whatever it is that you may want to share with them to help them, you know, make a move and think about where they are differently and also to help them and give them the the encouragement to move forward.
SPEAKER_01I think the biggest thing is is listen to your gut. If you aren't feeling that spark and excitement about what you're doing, don't ignore that. Don't tamp it down. Don't try and convince yourself you just need to work harder. If it doesn't feel right, there's there's a reason. When you're in the right role and the right place and a big challenge comes your way, it'll energize you, not make you feel defeated. Um and then the second piece of advice I'd add on to that is if you're feeling that and you know you need to make a move, go go get a coach. Maybe Steve Worthy is your next coach, but but find someone to talk to, right? Find a mentor. There's tons of resources out there and and find someone to to talk to about, you know, what's next and and help be an accountability partner for you.
SPEAKER_03Oh man, Ryan. I I'm so I'm so happy we we uh we connected um on on uh on LinkedIn. And then I'm sapped we had that opportunity to have that first conversation. Uh I'm excited for everyone to uh to listen to and to watch this episode. They're gonna get so much out of this in understanding uh where they are and uh and understanding that where they are is not their final destination or it doesn't have to be their final destination. There's so much more out there for people to understand about themselves, but also with the the career within retail that they've that they've chosen. Um you and I both love the industry, and uh um we know that everyone out there who you know who realizes that they have the potential, they can reach that potential. So thank you so much for for being on the on the on the podcast.
SPEAKER_01Steve, thanks for having me. And and thanks for the work you do. I look forward to all the episodes you put out. And uh yeah, it's been a great conversation. This was a ton of fun. Thank you.
SPEAKER_03Awesome, man. Awesome. Good stuff.
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