Episode 88: Win Win or No Deal
27 Aug 2026 · 19 min
In this solo episode of the Stand Sure Coaching Podcast, host Rob Anderson explains his foundational business principle – “win‑win or no deal” – and how it shapes every aspect of his coaching practice. He frames his life in three chapters (military service, 25 years of corporate leadership development, and his current role as a full‑time life and leadership coach) and uses this backdrop to illustrate why authentic, pressure‑free offers are essential. Anderson describes the circumstances under which he will make a coaching offer: only when he genuinely believes he can help, and he does so transparently, outlining the work, investment, and expectations without manipulation or artificial deadlines. He discusses his stance on pricing and discounts, emphasizing that specials are only used for specific barriers, not to coerce sales, and that trust is eroded if clients discover missed discounts. He is equally comfortable hearing “no,” viewing it as a sign of a non‑fit rather than a failure, and he will refer prospects to other professionals when appropriate. The episode stresses that the right coaching relationship, not the volume of sales, is the objective, and that prayerfully seeking the right client aligns with the win‑win ethos. Anderson also notes that sometimes the best outcome is no deal, challenging conventional sales pressure. He concludes with a clear invitation: listeners can schedule a discovery call via StanSherardCoaching.com if they feel coaching might help them, while also asking for a podcast rating and share.
Chapters
Hey, if I have to pressure you to hire me, I probably shouldn't be your coach. And if I have to undervalue what I do to just get you to say yes, you're probably not the right client for me either. And that's going to sound harsh, that's going to sound strange, and may not be what you're used to when someone is running a business. But I believe the best coaching relationships start with one simple principle: win-win or no deal. Hey, welcome to the Stand Sure Coaching Podcast. I'm Rob Anderson, and I think of my life in 3 chapters. The first one, my service in the military in some of the most challenging environments of my entire life. The second chapter, 25 years of designing and delivering leadership development in both Fortune 500 and mid-sized companies. And now I'm in my third chapter as a full-time life and leadership coach where I help people who feel stuck to rediscover who they are, transform how they live, and move forward with purpose. And that's what this podcast is all about. Welcome to Stand Sure Coaching. So there's a principle that my coach, Justin Janowski from Faith to Influence, talked about. I heard this about 2 years ago, or I'm sorry, about a year ago, that it just really stuck with me. And it's win-win or no deal. And the more I think about it, the more I realize that's exactly how I approach and how I want to continue to approach my coaching business. So in this episode, I want to explain what win-win or no deal actually means to me. And I want to talk about why I'll make an offer when I genuinely believe that I can help someone. And I also want to explain why I'm completely comfortable with hearing no. I mean, if we've been— if we've had a relationship for a long time, we've been friends, we've worked together on businesses, we dive together, whatever it is, right? I'm okay. I mean, if I feel like I'm— I can help you and you say no, dude, I'm, I'm totally cool with that. And, and there's no hard feelings, or, you know, it doesn't have to be weird afterwards or anything like that. But before we finish, I'm going to give you a simple way to have a conversation with me if you're wondering whether coaching might be the right next step for you. Here's something that you need to understand about me. If we're having a conversation and I really believe that I can help you, there's going to come a point where I'm going to make you that offer. And I'm not going to apologize for it. I'm not going to pretend I— I'm not going to pretend I don't have a business. And I'm not going to hide what I do because I'm worried somebody might think I'm trying to sell them something. Coaching is my profession. I am a professional coach. It's what I do. It's how I put food on the table. If I was an electrician and you told me that you had an electrical problem, If I was a plumber, if I was a carpenter, you know, I would probably tell you that I can help. If I was an architect and you needed my help designing a building, I'd offer my professional services. Same thing as, you know, if I was a doctor and you came to me because something was wrong, I wouldn't hide the fact that I practice medicine. I am a coach. So when somebody comes to me and talks to me, About feeling stuck, about trying to make a transition, struggling with a direction. If I see someone out there that's trying to figure it out and trying to figure out what's next, if I know— if someone's in my circle and I get that feeling through conversation that they want something different, they know they want something different, but they don't know How they're going to move forward. I'm listening. And sometimes I hear enough to think, hey, you know what? I can help this person. I'm in something I feel that I was called to do. And, you know, when I truly believe that, I'm going to tell them. But there's an important distinction. An offer should always come from a place of genuine service. I don't ever want it to come on as pressure. Or manipulation or out of fear. It shouldn't come from creating some artificial deadline just to force somebody into making a decision. I mean, there are times I do run specials and there's a business reason why I will run specials, but I'm not going to run a special just to get someone to say yes. Because if I'm not worth the full price, That they're willing to pay full price for. It just doesn't make sense. It should never come from someone feeling guilty for saying no. You know, I can make the offer clearly. I can explain what I believe coaching could help them accomplish. I can explain what working together looks like. I can explain the investment. And then they get to decide. Because no has to be just as acceptable to me as a yes. And it is. I mean, sure, I would love to get your business because it's not just the business. When I make an offer, it's because I'm genuinely excited about working with that person. There are people out there— I have turned down coaching opportunities because it's just not the right fit, or I don't want to get excited, or I don't feel like that I can help. I've had people come to me with stuff I know that that is way out of my wheelhouse, and I just— and I won't even give the offer. If they ask to work with me, then it's kind of a little more— it's actually a little more of a difficult conversation of telling them why. That it's not good. But again, I mean, I can explain the investment. I can explain what working together looks like. You know, I've had people in my life who've been, you know, lifelong friends, business partners, neighbors, family members, and I'm completely comfortable if any of those people decide that They don't want to enter into a coaching relationship with me. We're still good. Friendship doesn't need to create an obligation to become my client. Family doesn't create an obligation to become my client. Knowing me personally, having a good conversation with me, that doesn't mean that you owe me your business. Sometimes the answer is just simply no. Sometimes the answer is not right now. And sometimes the answer is they don't feel like I'm the right coach. I'm totally cool with all that. So sometimes, and again, this is where I've turned business down. Someone's approached me for coaching. It's like, you need therapy or counseling. Or you need somebody who works in that area. And that's totally okay. If I believe somebody needs support, but I don't believe I'm the right person to provide it, I would rather refer them to somebody else who is. Because getting the client is not the objective. Creating the right coaching relationship is the objective. Now, I'm a praying guy. What my prayer always is, it's not, God, send me clients. Now, I'll tell you, one time it was. But really now, it's, God, Send me the right client. And that's where the other side of win-win becomes important. Win-win doesn't just mean the client feels good about the decision. I have to feel good about it, you know, as well. I never want somebody getting ready on one of our Zoom calls and either one of us Really regretting. Them regretting buying it, me regretting that I sold it. I don't want somebody looking at their bank account, looking at the statement, looking at if they're doing it by credit card or withdraw and resenting the decision that they made. You know, I don't want somebody feeling like they were baited or pressured, coerced, guilted, talked into something that they don't really want. That's a terrible foundation for coaching. And it makes that coaching conversation that much more difficult. Coaching requires trust. It requires honesty. It requires somebody being willing to show up. Think deeply. Go do the work. But it's a trusting relationship. Right now, I have a deal that's going on until the end of August. I had a customer that— it's the right relationship. We've already been working together. We're going to continue to work together. And as they were about ready to pull the trigger on my 1-year transformation, I had to stop them and say, wait, wait, wait, wait, wait, hold on. I have a special going on right now, and I need to give you the discount code before you click purchase. You know, they would have bought that anyway, but You know, and yeah, it would have been extra money in my bank account, but here's the deal. One, let's say they found out 3 or 4 months later, hey, I paid you an extra $500. You had a discount going on. Why didn't you tell me about it? There's a lack of trust there. 2, as an ethical coach, I can't live with myself knowing I have a special going on or had a special going on And let that person pull the trigger anyway, sitting there knowing that they could save $500. Now, I don't run those specials often, but when I do, I do it for a very specific reason. Coaching requires trust and requires honesty on both sides. And when you don't have it, it becomes much harder when the relationship starts out with resentment. And again, the opposite matters too. I don't want to walk into a coaching relationship feeling resentful either. I don't want to be sitting there thinking that I discounted myself so heavily that I'm no longer feeling good about the agreement. And I don't want to feel like the value I bring isn't being respected. And that's my responsibility too. If I agree to a coaching relationship, I need to believe that the exchange is fair. Have I done deep discounts for people in the past because of whatever situation was? Yes. Most of the time I do it because I'm the one who really wants to coach that person and there is a barrier to it. And I honestly am getting— I feel like I'm getting more out of that relationship than what they are. But I want the client to be able to say, what I'm receiving is worth that investment. And I should be able to say the value that I'm providing is being appropriately recognized and compensated. And that's the win-win. And honestly, sometimes the best deals is no deal. Say it one more time. The best deals is no deal. And there's a strange pressure in business to close everything. Every lead is supposed to become a prospect. Or every prospect is supposed to become a client. Every conversation is supposed to end with a sale. And I just don't believe that. I don't even believe in the percentages. I know people talk about closing rates, professional salespeople. I'm not a professional salesperson. I'm a coach. I just have to do the sales so I can get the opportunity to coach people. Sometimes a successful conversation ends with, Hey, I don't think that this is the right fit. And that's not failure for either one of us. That's clarity. Maybe another coach would serve that person better. Maybe a different client would serve me better. Maybe they're not ready. Maybe the financial commitment doesn't make sense. It's not— to me, it's not a financial commitment. It's an investment. It's an investment in yourself. It's an investment in your future. But maybe that financial commitment doesn't make sense for them. Maybe the personalities don't click. Maybe what they're looking for isn't actually coaching. And there are 100 reasons 2 good people can decide not to work together. And it's cool. No one's wrong. No one has to be offended. No one has to feel rejected. No one has to feel minimized. No one has to feel guilty. Sometimes there just isn't a win-win. So there's a no deal, and, and I'm perfectly fine with that. If you ever have a conversation with me about coaching, I want you to know something before we even begin, and that's if I don't believe that I can help you, I'm not gonna make an offer. If I know somebody who I believe can serve you better, I'm gonna point you right towards them. But if I listen to what you're dealing with and really, really in my heart believe that coaching, coaching with me could help you move forward, I'm, I'm gonna make you an offer. Not because I think I can fix you and not because you think that you owe me anything and not because every conversation needs to become transactional. I'm going to make the offer because I believe that I have something that could help and it's my profession. I talked to a coach the other day who wasn't going to make an offer and decided at the last minute to go ahead and make the offer. With that, with that potential client. The client accepted. That client went on to write a book that is a New York Times bestseller that's helping hundreds of thousands of people, if not millions of people. And they credit it back to that coaching or the coaching conversations that they had. Now, who knows if they would have went on to write the book? And who knows if all those people would have found help anyway? But because one coach who wasn't quite sure made the offer anyway and changed not just their client's life. So I have to ask myself, if I don't make the offer, what's sacrificed for my client? I'm gonna make the offer because it's my profession and I believe I have something that could help. Then you're the one who gets to decide, and I get to decide. Do we both see the value? Do we understand the commitment? Do we, do we both believe that this relationship makes sense? Can we both walk away from that? That, that, that talk, that conversation, that interaction, feeling good about what we agreed to? And if the answer is yes, awesome. Let's go to work. Let's get started. Man, I'll tell you what, there's nobody that gets, gets a client going faster than me. You say yes immediately. Immediately. Once that contract is signed, once we got the payment in, right away. You're getting your content. You're getting your material. If the answer is no, dude, it's cool. It's all good. And that's the kind of business I've wanted to build and I continue to build. That's the kind of coach that I wanted to be and I continue to be. And that's the kind of coaching relationships that I have now and will continue to have. It's win-win or no deal. Hey, if you're listening to this and something in, in your life or your business feels stuck, uncertain, or ready for change, let's have a conversation. Not a pressure-filled sales call, not a conversation where you've already committed to buying something, just a real conversation about where you are, where you want to go, And whether coaching might help get you there. If I believe I can help, I'm going to tell you. If I don't, I'm either not going to make an offer, or I'll tell you, or I'll refer you. And if we both believe working together makes sense, then we can talk about the next step. And that's a win-win. Again, if you say no, totally cool. Man, if you say yes, that is phenomenal. I want to get started with you and I want to go do cool stuff with you. I want to take you to that next level. Hey, if today's episode helped you think differently, do me a quick favor. Give it a 5-star rating on Apple Podcasts or whatever app that you are using to listen to the show. Share this episode with a friend. And if you're ready to go beyond listening and it's a real transformation, visit me out on StanSherardCoaching.com to explore my current offerings. Would love to just book a discovery call with you and see how we can work together.
