התמלול המלא של Empathy with Expectation: The Balance Great Leaders Master with Jeff Hill

face. Because they're they're incredibly different today than what they were six, seven years ago. And, you know, light years different than they were when I started in the industry. So we have to be aware of the challenges that our people are facing. I am I'm a bit of an old school kind of a guy, right? Not just because I'm old, but because you know, I I'm you know, I'm a five day a week in the office kind of a guy. And, you know, when, you know, when our city of Chicago was was shut down on, you know, roughly March 13th, and everybody was working from home, within about two months, I was back in the office five days. And initially my expectations were that's what it should be for everybody. And what I've come to learn and understand is You know, that environment isn't most effective for everybody. And there are those that need it and and it's helpful for them, and those that maybe it's more of a a hindrance for them. And and so re-looking at the job that we have to do it with the with the environment that we're currently in today, with the challenges that are is industry faces, but also with the opportunities that that brings us, I think is is how we balance that empathy and expectation side of it. The expectation really has not changed in our industry, right? How do we how do we develop you know successful programs for our advertisers to generate business for them and in turn revenue for us. That that aspect has never changed. Involving the creative process to do that has never really changed. It's one of the beauties of of this industry that I've enjoyed for nearly 40 years is being creative in the process. what has changed is, you know, the position of radio advertising and and we've addressed that through different digital solutions and other marketing ideas. But at the end of the day, the the task has not changed. But the challenge of how we go to market certainly has. And we just need to understand that and know that and help our team you know, overcome those those obstacles along the way. Jessy James: So keeping in touch with the changing times and really translating that not just in in into a vision, but also communicating and understanding the challenges that people are facing as a result of that. That's i that just sounds like, you know, the the the journey that you've been on in the last few years, particularly. And this kind of leads to my next question, which is can you share a time when you realize that your way of leading, living, no longer met the demands of your work and life? Right? And growth was needed. Jeff Hill: Yeah. There there's been so many of those times over the years from relocating, you know, when my wife and I were just married to coming back to Chicago and starting a family. I've always really tried to maintain a a very strict work life balance. and it, you know, sometimes meant the hours change because what I I've always tried to do, even though in our industry, entertainment is always a big part of it. So, you

know, whether you're entertaining clients out at a dinner, a sporting event, a concert, what have you, you know, there's a lot, there's a lot of time that goes into that. But I but I've always tried to maintain that when I walk into that door at my house, that I am dedicated and focused to my family. and try not in and spend it on the phone checking emails or tax it Obviously there's always going to be time where it's it's needed, but I've always tried to to maintain that. And and you know, it's I would say some of those specific challenges were always around times with senior leadership changes within the company. I tell everybody if you've been in this business long enough, you've gone through bankruptcy probably more than once. I am now in my third. so those types of challenges and discussions and things like that I think put a lot of different types of pressure and expectations that you know make you question or or or really put a strain on on that management style that you've had. I I've I have been very fortunate in my career that the leadership that I've had have really allowed me to manage my team. and that's, you know, for the most part from corporate leadership to local leadership, that they've they've really trusted me and allowed me to lead in a style and an with objectives that fit the fit the times, fit the products, fit the team. And so, you know, I've been very fortunate in that side. But when sometimes that leadership changes, especially at the senior level, sometimes you've gotta make some adjustments to that leadership style. Jessy James: And personally for you, what you know, especially when things kinda you know, at turning points, what were some of the fun what were some of the other fundamental changes that you had to make? Jeff Hill: y I think it is just that you know reanalyzing what my style has been and and what needs to get done now in a different work space environment. you know I I will tell you I I can recall, you know, thirty years ago when when digital was just starting to, you know, make space in in the radio world and probably a little bit more than thirty years ago. And You know, the mentality was, well, if it doesn't make you money, why do you even do it? And needless to say, we're we're far from that mindset today. So the integration of that, learning an entirely new advertising and marketing space while still maintaining and and growing the current space that I had been in probably for twenty years as we were making that adjustment, that that's probably one of the more challenging aspects. Man, you know, in radio, regardless for the most part of the product that you sell, you have a lot of different aspects to sell. Sometimes it may be sports franchises, sometimes it might be events, different talent you work with, things along those lines. But bringing in the digital space is an entirely separate industry, obviously, that you're folding into what you do. And how do you maintain that balance? How do you you

get those that are kind of non-believers in digital marketing, and there's still a few out there in the radio world, how do you get them to buy in and believe in this, as I said, while still maintaining and hopefully growing your core business of the radio space? Jessy James: Yeah. And so Jeff, from a leadership perspective, right, what did you have to outgrow or let go as you met all of these chan chal challenges and evolved your leadership style? Jeff Hill: Yeah, I think it you know, part of it is just that look not being afraid to learn, not being afraid to not understand products. you know, when you've been in the business as long as I have been. And listen, I I will still go on calls, especially in the digital space where I'm kind of just sitting back listening because the the digital tech heads are are way above my caliber. but not being afraid to jump into those calls and and, you know, and learn from them and take from them. And I and I think that those are the fears that we have as as leaders and especially long term of walking into a space where you're not the expert, where I can't sit there and pull from my, you know, years and years of experience and lead that discussion. as the expert in the room. And I think that again, getting into, you know, leadership styles and and learning and growing and things like that, that's okay. That that's something that you have to be comfortable with, not being the smartest guy in the room mentality. And that's not always an easy thing to do. when when you really can know and and and hold that role in certain conversations. And then you're bringing in this new space where you know, I've got half of my team that could w you know, run circles around me in conversations about digital marketing and digital advertising. Jessy James: Got it. You know, continuously growing it it requires a lot of commitment, right? So thinking about your journey over the past few years, what's been the most valuable investment that you've made in yourself for your own growth? Jeff Hill: time. You know, it's it's you know, not quantifiable from a dollar standpoint, but you know, I guess we could probably equate that. But I I think it really is just time and looking for those spaces to whether you know, to those spaces to learn, whether it is grabbing articles in LinkedIn, looking at industry trades, talking with experts. experts in, you know, the field of what I'm I'm trying to, you know, adapt to and and learn into. I think that, you know, it's really just making sure that you're finding the time to be able to do that, that you're dedicating the time to be able to do that, that it is a regular part of your routine of just making sure that, okay, am I dedicating time d daily really to learning more about what we can do, what we're you know, what we do do within different spaces of today's marketing field. Jessy James: And curious, Jeff, what does that look like? You said, you know, you you said that you dedicate time on a daily basis. Curious, what does that look like? Jeff Hill: I start my day, my my mornings every day with reading. You know, what's what's in my inbox from, you know, the industry, what's in our inbox from the company and and the training that they provide. really spending that time digging through, you know, the emails and the articles to make sure that I am, you know, really looking at not just updates on what I've been doing for most of my career, but information on learning about what can I do in the next stages of my career. I think it's also being I love taking meetings with new vendors with new opportunities because I think even if I may not have the budget to be able to do something, I can learn about something that's available to us in our industry. And so I may be learning about what are our competitors using and doing and things like that. So I think you have to look for those opportunities. Sometimes, you know, it's not as easy as just opening your emails and and reading what's in your inbox every single morning or at the end of the day. It's actually looking for those things and responding to those things that you think may help educate you. And if it's a, you know, sitting through a a, you know, half hour or one hour sales pitch just to learn about what the opportunity is, I I think, you know, you have to as a leader. within an organization, especially a sales organization, take the time to be able to find and and what's going on out there in the industry. Jessy James: Could you share a story of how, you know, reading every morning or talking to different vendors, how has that really shown up in your leadership style? Jeff Hill: Yeah, well, I'm my s my sales staff would would laugh and probably a few roll their eyes, but I'm you know, I'm kind of a let's try everything kind of a guy. Right? It's if hey, if you're gonna give me a trial on something, guess what? We're gonna try it. And you know, if a few years ago we we tried a prospecting tool that you know was was brand new to you know to me brand new to our team in in incorporating ai with kind of a a very high speed phone call approach where you know we built a list with this vendor and salespeople sat on their computer and had three three or four phone calls ringing at the same time and the first one that picked up, they had to be ready to go. And so I I think that they just see that I am willing to try new things to help push our business along. And I'm not, you know, I'm involved in two new concepts right now. one that we're a little further down the road on and one that that we're early on with and and just trying something brand new that, you know, most probably even my competitors would sit there and go, What really? That's what you know, you really want to do that? And I'm like, you you just don't know which of those opportunities might be the home run. And and in most of these opportunities, you know, we've generated a small business small amount of business. Maybe not to

keep it going, but I like I just I enjoy trying new things. I enjoy showing our team that we are open to new ideas, that we want to try new things, because in in our business, I think in sales in general, you can't be routine. You you can't, you know, what you did yesterday doesn't work today and sure as heck isn't going to work tomorrow. and you have to be adjusting, you have to be adapting and try to be ahead of that as much as you can. Jessy James: What's vision for your leadership, your legacy, or the impact that you want to have in the years ahead? Jeff Hill: it's funny. I I was just talking to somebody the other day and I said, you know, every pay every place that I have left, I have left it better than before. these days with the state of the industry, you know, I'm not sure financially that's going to be the case, but I think from a team standpoint that will be the case. And I and I think that I hope that my legacy, my reputation is that Exactly a lot about what we've talked about. That, you know, that I've been a very open and honest manager, that I've been a fair leader, that at times I was probably tough, but I was tough in a fair way and and I set those expectations and I held those expectations, and that I lived up to those expectations myself. That I hold myself accountable. as much, if not more so, than my salespeople. And I'm willing to do, you know, all the things that I ask them to do, I'm I'm willing to roll up my sleeves and and do as well. So no no job or task is too small. and you know, I I hope that that is how I am remembered when I, you know, someday retire. Jessy James: As you think about, you know, your legacy, what are the ways that you feel like you still need to grow personally in order to develop in order to create that, in order to leave that legacy behind, the way you imagine it, the way you envision it? Jeff Hill: Yeah, I I think it is You know, it's not just about the numbers, right? I mean, I I could sit here and say, I, you know, I want to grow and build our team to the point of where, you know, we've hit record numbers in Chicago or within the company or what have you. And and to me it it is more about the people that we have built, and the people that we have grown. and it is, you know, being better about connecting with each individual to help make them the best that they can be. And I think we're always I I'm never satisfied with Where I'm at in that process, I've always feel like there's a better, deeper connection that I can have with people, that there is a better way to help them be better at what they do. and I think that that's, you know, where I can still grow and where I can still help this team and and just become better individuals, as well as, you know, overall as a team. Jessy James: Yeah. And you know, given how much change your industry is going through, I'm curious, where do you feel most tested right now? Like what challenges are are stretching you the most in leadership and also in life? Jeff Hill: Yeah. I you know the radio industry you know has certainly gone through, you know, endless changes even, you know, in my career. Right. We're all we're always being challenged by the next technology and things along those lines. you know, we we fight every day the radio is dead mentality in spite of reams of of you know, data and and you know, information that will tell you the exact opposite. so I think the challenge that that I have is number one, maintaining the motivation and the belief within our team. And how do we continue to keep them, you know, we have amazing digital products and that's that's you know certainly where we are growing and people are learning and selling. But Our core revenue is still based on our core product, which is our three radio stations here in Chicago. but you know, like anything in life, when you are continued to you know, from you know, from clients to maybe in your home life being told that, you know, what are you doing? That industry is, you know, nobody listens to the radio anymore. How do you stay motivated in that? Right. And And I think that that is probably our biggest challenge is staying motivated as as a staff, mo and motivated as individuals that in spite of headwinds coming from everywhere, like I said, from from your clients to maybe your family, how do you how do you fight through that and still see the the opportunity that's in front of you? and I think that that's that's probably the the biggest challenge that we face here. Personally, I, you know, it's I would say sometimes the same. you know, is keeping that motivation alive and focused in in the right direction. you know, if if you've been in this industry long enough, you've gone through it probably two bankruptcies. I've gone through three. I'm currently in my third. so While in all of those times, very little has impacted the day-to-day operation of our individual markets and facilities. But you know, there there are struggles corporately and and battles you fight and and it is about maintaining that focus, maintaining that motivation, you know, blocking that out, you know, when addressing and working with your team to make sure that, you know. I can't expect them to come with the right attitude and and motivation if if they don't see me with, you know, bringing the the right attitude and motivation to the table every single day. Jessy James: And you know, resilience comes to mind, right, as you as you share the story. And I'm curious, how do you keep yourself motivated? where do you feel you need to grow and develop to meet these kinds of challenges? Jeff Hill: gosh. A stiff drink at the end of the day, maybe? No. No, I you know, I I will say, I I have always been a a relatively positive person throughout all aspects of my life. And I and I think that, you know, a phrase that I learned, you know, years ago, it's not a problem, it's an opportunity. And I think you really have to look at it like that. And and maybe the

opportunity, the the challenges are are obviously still there. The challenges may be greater than they ever have been. But we should look at that as then so are the opportunities. and you know, when I started out in this business, I had one radio station and I had just the market of Chicago to sell. And I had a certain audience and things along those lines. And that's all I could sell. Today I can sell any radio station in my company and I can sell a digital program to any person anywhere. So the opportunity is much greater. How do you harness that? How do you focus in on that? How do you, you know, make sure that you are mining in the right opportunities that can bring you the greatest return? Those are the things that that we're focusing on. And and so I I think really it it is about that. It you know, we're faced with challenges every single day, both personally and professionally. And if if you let all of those weigh you down, if if you allow that to sit on your shoulders, you you'll just never get out of it. And you have to look at the opportunity that that lies ahead when you when you solve to it. And i listen, half the time with You know, as a manager, my greatest joy still to this day is when a salesperson brings in a tough sale. those are those no it doesn't matter how big or small it is. When you when you've you had victory in a in a in a challenging situation, that is still my greatest reward in this in this job. Jessy James: Yeah, finally this last question is more of an invitation. You have this time and space to sh you know, to offer to our listeners whatever it is that is top of your mind, top of your heart for you. The floor is yours. Y take your time. Love to hear your thoughts. Jeff Hill: well thank you and and I I appreciate the opportunity you've given me today and hopefully we've been able to keep at least most of the people through to the end of this. you know, I I I think you know, leadership comes in so many different ways, so many different shapes, so many different sizes, so many different individuals. Look for those people, surround yourself by those people. As I said, you you have to be able to learn from everyone in your organization, those in your department, those out of your department, those with a title bigger than yours and and those with you know, without a title. And be open to that. Be open to, you know, as I said, surround yourself by those around those individuals. We know in life that when you You know, with your friends group, you know, we talk to our kids, you know, about, you know, don't, you know, don't build a fr friend group with toxic individuals. And and that is maybe truer in the workforce. You know, surrounding yourself by those people that that can help lift you up and not be afraid, you know, to you know be with people that regardless of title that can that can teach you and help you learn in in your leadership roles. Jessy James: Jeff, I appreciate the wisdom that you've shared here with us today. I've gotten so much out of this conversation. You know, going through three bankruptcies is no joke. And I love the fact that, you know, the most important one of the most important things seems to be focusing on the next opportunity and keeping yourself motivated. I mean, there were just so many nuggets out there, you know. wonderful listening to you. I'm sure anybody who's listening will take a lot out of this conversation. Thank you so much for being on the True Leadership Podcast. Jeff Hill: Thank you, Jesse.