How to Negotiate Like Your Career Depends On It — Insights from a Top Sports Agent

Hey, I'm Kwame Christian, and you are about to step into the world of Negotiate Anything, the number one negotiation podcast in the world, where we teach you how to make difficult conversations easier while getting more of what you want in the process. Each episode is packed with practical tips and strategies from the experts. We delve into negotiation, conflict resolution, and leadership skills that are crucial in both business and in life. Whether you're closing a deal, managing a team, or navigating personal relationships, Negotiate Anything provides you with the tools you need to succeed. Our conversations are real, relatable, and most importantly, rooted in practicality. So if you're ready to transform your conversations and elevate your negotiation skills, join me on Negotiate Anything. Subscribe and listen on Apple Podcasts, Spotify or wherever you love to listen. Let's make every conversation a winning negotiation. Henry, thanks for joining us today.

Kwame, thank you so much for having me.

Hey, man, it's my pleasure. So how about you get us started by telling us a little bit about yourself and what you do?

Yeah. My name is Henry Oregon. I'm the founder and NFLPA certified agent here at Disruptive Sports Agency. We run a fully minority owned sports agency that specializes in representing NFL athletes, coaches and NBA players.

This is great. And listeners, Henry is a man of great discipline and restraint. He is in Las Vegas, Nevada and he told me he was doing nothing fun. So I was very impressed.

Absolutely, man. Gotta be focused. It's game time, season's upon us. So the clients aren't partying right now. Why would I be partying?

There you go. There you go. This is great. And listen, I always want to make sure I give you the opportunity to shout out, you got a new book, man, that's really exciting.

I appreciate that. I've been working on it for two years now. The book is called the Informational Interview Playbook. And it's just really, it's all about mastering the informational interview. It's the book that I wish that I had when I was coming out in undergraduate and graduate school. So it just gives over, goes over some of my tips and tricks of how to conduct informational interview. It really, it helps you figure out what you're trying to do in life. Right. When you go to college, unless you're a doctor, a lawyer, or an accountant, college is not very linear. Exactly what the next path is to getting a job. Right. And so in order to figure out what you want to do, what you're passionate about and how to do that, you need to go to the person that's done what you're trying to do, you need to talk to a lot of people and figure out how they got there. So this book just discusses the strategies to master an information interview and the tactics I used to get to where I'm at today.

This is great. And I think one of the cool things about the way that you're approaching it is because it's not just the standard informational interview book. You're coming at it with a perspective that is very business focused because of your experience, your extensive experience negotiating high level deals.

Absolutely.

Yeah, man, this is great.

Yeah. I mean, negotiating high level deals for me is it was landing those conversations to get those clients and converting those, you know, into opportunities to be able to negotiate and make money was all a negotiation itself in the first place. So you're always negotiating. No matter what it is, whether it's get on your podcast, whether it's to go have coffee with somebody, take a girl on a date, take a guy on a date, you know, whatever that may be, you're always negotiating.

This is great. This is an awesome place to start, Henry, because you negotiate high level deals, but I love the fact that you still have this negotiator's mindset permeating throughout your life. Because you're right. Every. Every single conversation we have, we can look at it through the lens of negotiation and it helps us to be a lot more intentional. And I think it would be really cool to give the audience an idea of kind of the life cycle of the negotiations that you have. So, for example, you have to negotiate to get the client. And then once you get the client, what types of negotiations are you doing on behalf of the client?

Yeah, you're negotiating for football clients, basketball clients. Let's just start there. Coaches clients, you're negotiating marketing deals. You know what their brand endorsements looks like, how much they're getting paid. Just for simple, simple simplicity terms, you know how much you're getting paid per signature for memorabilia, then you're negotiating their split language in their contracts. If they're rookies or drafted rookies, you know, when they get paid, as far as the lump sum payment and their signing bonus, there's a tons of different nuances that you're negotiating. You're negotiating with the client's parents, you know what he's going to get them, what he's not going to get them. You're negotiating with his brothers, his siblings, his girlfriend, his wife. And I think that negotiations at times has a negative connotation. Right. Because people associate negotiations with oh, he's going to get over on me. But no, it's always negotiation. You know, hey, if I get two pieces of pizza, it's usually cheaper than getting one slice of pizza. And so everything is always negotiation. So it's just understanding that and just for the client, just negotiating everything for them.

Now, when you think about all of these types of negotiations you're having day to day, we have personal life, we have business life, we have the. Throughout the entire lifecycle of your clients, what would you say for you are the most challenging negotiations that you have to do?

I mean, they're all challenging. None of them are easy. It's just about how many reps you've had maybe at that specific conversation. And then the ones that are toughest are the ones that you, you don't have leverage or you don't have an out or you don't have another option to select. And so when you have no leverage, you really can't negotiate. You have to just take what is given and not continue to try to push. I see people push a lot and they have nothing to stand on. Well, you want this amount of money, but nobody else wants to give it to you. So if nobody else wants to give it to you, that person is not going to give it to you.

Absolutely.

It's just really simple. Like why would I give you $10 when everybody else only wants to give you one?

You're right, man. And I think, you know, we could, we could do a big societal deep dive on this. You know, when we think about, hey, participation trophies, everybody kind of feels entitled to, to whatever it happens to be because they are special and the only version of themselves. But what if nobody else wants that version of you? Then you don't have leverage because you don't have options. And I think that it's interesting because I've seen in the negotiation world just the concept of power and leverage almost falling out of favor and focusing more on the interpersonal aspect of it and the empathetic aspect. And I think those are really important. I mean, I talk about in the books and everything like that. It's critically important. But I think sometimes the pendulum have swung so far to the other side that we feel like we can almost empathize our way to an incredible deal even if we don't have leverage. And that's just not the case.

Well, in some instances, people don't even use empathy. People just come in there and just demand this. And I mean they, sometimes they get laughed out the door respectfully, oftentimes in my space, they get laughed out the door disrespectfully. And, like, they're telling you, hey, like you're an idiot, and great, have a good one.

Exactly. Yeah, man. Let's. Let's get deeper into leverage. So let's just start off with the fundamentals. When you think about leverage, how do you define it? And then let's talk about how we can actually use it.

Oh, that's great. Okay. When I think about leverage is having something that if one person does, it's on a very simplistic level. It's this one person I'm in talks with about getting something done. This person also wants what this person has. The goal is to keep both of them not knowing which either side it has or is offering and to leverage the two to make the market value go up. Just like, let's say an auction. Right. 2500 here. Do I got three? Do I have three? Do I have three? Going once, going twice. I got three over here. And they just keep going up and up and up and up. Right. But each side who's bidding on whatever they're bidding on, they have a number in their mind that they're going to stop at.

Absolutely.

And your goal is still to get them to exceed that.

Bingo. So this is really good. This is really good because I was doing a presentation, a LinkedIn Live event yesterday, talking about when, knowing when to walk away. And I know that's one of the things that you cover, so we'll get to that in a second. And one of the questions that somebody asked is, it was, hey, should I be. I've always only negotiated with one person, one entity, one organization at one time. Is that a bad decision? And based on the way that you're describing it, one of the major sources of leverage is the competitive market that you can create for yourself, your product, your service, whatever it happens to be. And if you can create that bidding war, then you can leverage one party against another to increase the value of the deal.

Correct. And just as we're talking about leverage, and that's the main focus point right now we're talking about, in my space at least, you have to create marketability. Right. If nobody knows your name, well, then you may not have leverage because just nobody knows who you are. So I think from my background being a marketer, you know, working at Nike, working at Coca Cola, working at Procter and Gamble, marketing is something that is extremely important to increase somebody's value. Right. We see people all the time get jobs that are, you know, not Qualified enough or they don't know what they're talking about or people say that even about me or you. Right, but I market myself, therefore you know who I am. Therefore we're able to have a conversation. But if nobody knows you, you can be the best person in Idaho. Right. But if nobody knows you, nobody's calling you for that service. So you have to market yourself and market your clients in order to create leverage.

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Yeah, yeah, it's going to be difficult. Something that I've never seen anybody talk about before. But. Right. Your brand is what introduces yourself before you even walk in the room. Right. So that's important. And there can be negative and positive stigmas based on your brand and the negatives can help you just as much as the positives at times. So doing it in an authentic way. You know, I am from the Bay Area and we're not a very, we don't like to do it, we're not very showy. We like to get things done and let people talk about it. We're not really like self braggers, you know. So marketing yourself can be difficult. But for me, marketing yourself and creating your brand, it's just putting yourself in Uncomfortable situations which puts you in rooms or allowing people to hear you that may never have heard you or talked about you at all. Agreed that that helps create your brand for sure.

Man, this is great. And let's now talk about walking away because you're in these high stakes negotiations. Not all deals are meant to be made. And so first I want to talk to you about how you come to that conclusion. When do you know it's time to walk away?

Well, I mean, rejection is God's protection at times, right? It's, you know, so I live on that. I've been rejected by many clients or many clients or many deals haven't worked out. And when it becomes something that you're just not going to take or you're, you're comfortable with or okay with walking away from it, then you walk away. I mean, I think that's. It's very hard to go into it and make it so that everybody can understand it or it can be applied to everybody in your situation. Because every situation is different. Right. I wasn't willing to walk away from creating this book. Right. I got rejected by 26 publishing companies and I did not want to do self published. So I found a way to walk away from self publishing completely that was off the table, that wasn't an option. And the publishers that told me this would never work, I said I'm going to make this work. I'm going to prove you wrong, I'm going to send you a copy and I'll make sure all your managers get it. Because you're stupid.

Right.

And I talk like that. I do. And it's not always the most greatest, but we all have a little bit of underdogness and sometimes it's good. So I found a hybrid publishing company that believed in the concept and I put my own money up behind it to. I wanted to put it out. How, how I want people to be able to take that knowledge and be able to use it to the best of their ability so that they can succeed. So I was. That you can walk away from things in many different facets.

Absolutely. And first of all, I love that story because as a fellow author I know how hard it is and like, kudos to you because I didn't even like, I didn't even try to go traditional publishing the first, the first time around, you know, so kudos to you. And I love the hybrid route because I've had a number of friends who have been successful with that and like seeing that, that dog you have in you, I know I have no doubt you're going to be successful with it, too. And you bring up a really, really good point too, because there's no way for us to sit here on this podcast as negotiation experts and tell people this is how you know when to walk away with precision in your precise scenario. It's not possible because we don't know exactly who you are as a listener. And the thing is, what might be a good deal for one person could be a bad deal for another person. And so you have to really take the time to look within yourself to figure out what it is you want and need and why, and then stand firm in your convictions, in your values, your beliefs, and recognize when it's time to walk.

Yeah, absolutely. But into kind of to the next segment, trying to, like, help people, give them the tools in whatever facet of life that they're in, and trying to figure out how to walk away from a deal. Right. You have to manage expectations with yourself and you have to figure out what the number is, what the, you know, ultimatum is of, you know, when you're going to walk away, what you're just not going to tolerate, what you're going to work with. That is the most important thing is managing expectations with yourself in those deals.

100%. And I want to talk about that too, because we understand that we need to manage our expectations. And I think it's a lot easier for us to see it in other people. Like, hey, listen, what you're thinking is possible, that's ridiculous. We can see it really easily. But for us inside of ourselves, we have this self serving, buy it. So we're saying, oh no, I deserve something that might be astronomical. And so when we're thinking about managing our own expectations, how can we do that in a way that is objective and firmly rooted in reality? Because a lot of people struggle with that.

Yeah, it's knowing your comps, knowing what the competition is, and going to the person that's done what you're trying to do and seek advice from them. You know, if you've never seen somebody get a $50 million deal for this specific position group and it's 80% higher than the closest paid person, well, then you're not managing expectations correctly. And I'll give credit right now to all of my competitors and counterparts in the running back market. I think all those agents are doing a phenomenal job right now. There's a holdout, not a holdout, there's a gang of running backs that are really, really good players that are not accepting deals that are not fair to their position, the beating that their bodies are taking. So they're not. They're trying. They're attempting to hold out on the deals they've been offered and take the franchise tags that they've been offered and just play with that embedded on themselves to increase the value of the overall market. So some of them may have been offered, let's say, 4 for 40 million with 20 or 30 million guaranteed, and they're accepting only the 10 million right now that they're going to get this season, or 10, 10 million, some change. And they're just. They're doing. I mean, they're doing something that's very risky, but it's very necessary for change.

That's so cool. For a number of reasons, because we think about the relationship you have with your clients, but then you also have to think about the relationship that you and your client have with each individual franchise. And then, especially when you think about the concept of leverage, we recognize that a lot of times we're competing with other franchises and other individuals, so we often look at them as competitors. But now we're seeing how those same negotiation skills could be utilized, even with competitors, to say, hey, we listen, I'm being treated unfairly. Are you being treated unfairly? Yeah, you are, too. We should gather our resources, because independently, we're not strong enough to create this change. But if we come together, we can.

And so they created their own leverage. Bingo.

Oh, that's great.

So it all ties back into one another. There's multiple ways to skin a cat. So in this scenario, there's numerous ways to create leverage, and they're creating a few different, you know, unique way.

Absolutely. And I think that gives us a great segue to this next point, talking about creating a framework for the deal. And so when you're. When you're thinking about the way that you're approaching these. These big negotiations, what type of frameworks do you put into place?

Yeah. Or a lot of people. Right. It's. What is the. The client's expectations? Right. What is like before we talk about framework. I'm sorry, Ambassador, I hear you a little bit.

You're good.

But before you're talking about framework. Right. And what are the confines of the deal? You have to manage the expectations. Hey, what are you guys. Look. What. What is the client looking for? Right. What are. Me as the agent, what am I looking for and why am I looking for? What is the team looking for and what are they looking for? And then you create that pot, and you see if everybody's in the same page or have the same or in the same vicinity of what we're talking about. Then you create the framework of the deal. Okay, you guys want to do no signing bonus, but you want to increase the guaranteed dollar value. Okay, this is the amount of years we're looking for. This is between the ballpark of range of the amount of money you want the deal to look like. These are the things we're not willing to accept. These are some of the things we're willing to accept. And then you come up with the framework of the actual confines of the different buckets you're placing money into or that you're coming up with for the deal. Then you're trying to increase that and they're trying to decrease that. Right. And so that's how you're creating framework and managing the process of a deal.

It is absolutely, because it starts with the internal conversation. Internal within your team, you and your clients, they might have astronomical expectations that you need to manage. And so you need to negotiate with them to get on the same page with regard to those expectations. And then you need to figure out what is a type of deal within which framework we can offer to the other side and start the negotiations while understanding that they're going to try to chip away at that value and you're going to be trying to hold your own, keeping that value together. But you don't just come to the table with the franchise and say, so what you thinking? Then let the conversation meander without some direction. I think it's really important for people to understand, like we're getting an understanding of what the topics are, what are our upper and lower bounds on those topics, and then you use that preparation to guide your negotiation 100%.

So, I mean, you continually prepare. So once you kind of figure out what you and the client want and what the team's expectations are, I mean, for me, we're always gathering numbers and data and different statistics to figure out where our clients are kind of at any given point in time as far as their trajectory to get paid. I mean, it starts from when they get drafted and where they get drafted, or where they get placed as free agents or where they don't. I mean, you're always creating leverage and then going back to the drawing board and trying to figure out the framework of what that next deal will look like or what the team may be coming to you with to try to either get you to restructured, and oftentimes your restructure is going down, you're being paid less and why you're coming. So you need to combat that and always be ready for, okay, this client's not doing well. This could potentially happen. But here are some of the things in the clause in the contract that we have to enable them to restructure. Or we could walk away and just take the guaranteed money that we already have.

Yeah, that makes sense. And I want to wrap up with when. When we are walking away, what does that conversation look like with the other side?

It can be very, very positive. Hey, I really appreciate your time. I don't think we can get a deal done at this price. Always still closing. Let's recircle back at this date or a later time to try to figure out if we can come closer to grips with a fair number that we both can agree upon. So that's one way to walk away. That's one of the better ways to keep the conversation, keep the door always open. Or it could be, hey, we're going to move on to another team. Thank you so much for your time. We have another deal on the table. This is your last and final chance to match this number we're talking about, or beat it. Or it could be. Sometimes it can get a lot more emotional than that, depending on the situation. I've been in a number of PFA or free agency conversations. When a player goes undrafted and there's not a lot of rules, they can get very heated at times, and they can try to use some very tough or brash for negotiation tactics, but those usually only work on people that lie or that don't know their leverage or are affected by emotion. I'm going to see you again. I'm going to be here. And if I have a player you want to, well, you're going to call me. So there's no need to necessarily walk away from a deal with anger towards one another because you're going to see each other again every year. So I wish I had a great sound bite for you to finish this off with, but I think that your podcast is amazing, and I think what you're providing us is you are interviewing people that have been to where other people want to go, and they're providing that information and giving those messages for free to others, which is amazing. Right. Something I wish I had when I was a kid, before technology got to where it's at today.

Thanks, man. I appreciate it. Yeah, that's. That's what we're trying to do. Just pay it forward. And that's what you've been doing with. With the work that you do with your clients, but now you're putting it out into the world with this new book. I'm pumped for you, man. It's. It's so important. And listeners, we're going to put a link to Henry's company, to the book and everything else, and LinkedIn as well. You're active on that, too, so you can keep in touch and get the book. But, Henry, man, really, really appreciate you coming on the show today out from Vegas. Making time for us, man, means a lot. Thank you.

I appreciate you, brother. Have a blessed one. I got to go catch a flight.

Thank you. I'll see you. You crushed it, man. Thank you. Congratulations. You've just joined an elite club by listening to a full episode. You're now officially on the Negotiate Anything team. So welcome aboard. What most team members do is they subscribe to the podcast because that allows them to automatically get the latest episodes of the show. The best things in life lie on the other side of difficult conversations. Keep learning, keep practicing, and keep getting better. Your relationships will improve, your career will soar, and you'll have the confidence you need to get the most out of these crucial conversations. Again, thank you for joining the team. We're excited to have you, and I will see you in the next episode. I'll catch you later.