Loading summary
A
You're listening to the Sales Hunter podcast. My name is Mark Hunter. Hey, have you talked, have you ever thought about roi? I bet you have. But you know what? We're going to flip ROI on its side and we're going to talk about it in a totally different manner with me today. Jamie diglio, she is the founder of the Win Room. And, oh, by the way, the Win Room. Gonna have to ask her what WIN stands for. She spent time at Gartner. She spent time at Microsoft. Yes. She has her sales chops. Why am I talking. Let's get the show going.
B
Right now you're listening to the Sales Hunter podcast with Mark Hunter, where the focus is to help you as a salesman, sell with confidence and integrity. And now here's your host.
A
I want to know what my ROI is. So, Jamie, welcome to the show. Jamie diglio, founder of the Win Room. Let's unpack this roi. Go for it.
B
Hey, Mark, thanks for having me on.
A
Yes, I'm excited because you teased me as to what ROI and it doesn't mean what everybody. Return on investment. What's it mean?
B
ROI means return on interactions. It's how you make money instead of lose money in every conversation.
A
Okay, you got my interest because now we're talking about making money and that's what we do in sales. Right, Right. So, okay. Return on interaction. Yes, I, I, last time I looked, I think this AI thing is getting kind of big out there. So I, I have a feeling you have a spin on that.
B
So, yeah, it is big. And you know, us in sales, us in, in, in, in leaders, leadership. What is our competitive advantage in the age of AI, you know? Yes, using tools. AI tools, using it to help us with being more effective. But ultimately our competitive advantage when you can get information everywhere is how do we do this? How do we capitalize in this, these interactions? How do we be less predictable, more memorable in every conversation? And so that is what I teach sellers to do and leaders to do in how they're leading their team, how they're leading their, their prospects, their clients. How do they be more memorable? And it's in the interaction, breaking down the interaction.
A
Okay, so tell me, how do I become more memorable?
B
Well, I don't know.
A
Leaving me hanging.
B
So when we think about our interactions, how are we being number one, how are we being present? How are we being present in who we are, what we stand for, how do we have self leadership? And a lot of people don't know what they stand for, what they believe in. And so that's the first work that I do with the people that I coach and train. What do you value? What are your strengths? What do you, you know, where, where, what do you want to. What's your philosophy? What's your. So helping sellers to identify their leadership language, which is a combination of what they believe in, what they value, what they stand for, and then not just to be doing it, but speaking it in how they communicate with the people that they're talking with. Having a point of view. I mean, we've always said that, right? Like you have to have a point of view. You have to know what you're interested in for people to be interested in you. But really slowing down in our fast speed world. Slowing down and really being intentional about number one, what we want to say. But then also the biggest part about it is how to listen for the prospect or the clients listening. So breaking that down. Yeah. I always say that there's three sales conversations, right? There's always three sales conversations happening all the time. The first one is the one in my head. What do I think I'm going to say? Okay, you're laughing at me.
A
Yeah. Because. Because it happens to all of us, right. I mean, we all, we all have this, this voice in our head anytime we want to call. Yeah, right, Right.
B
Yes. And I call that, that's the war room voice. It's the sort of the questioning working. I call that the war room is working against results. It's the space where we doubt ourselves. We self sabotage, we focus on, you know, what should we say? We don't know what to say. And, or when I'm talking with revenue leaders, that's where we, when we're in that headspace, we're working against revenue. So that's what WAR stands for.
A
I like that, I like that. You, you've got. This is cool, you've got some cool acronyms. So that's good.
B
And so anyway, so back to the three sales conversations. They're always happening in every conversation. So the one in our head, right, the story we're telling ourselves, that's the first one. The second is actually the words that we're saying. Because what we think we say versus what we say are two different things. Right. And the third, though, and the most important is what is the person hearing? What are they listening for? And understanding that everybody listens from their own background. So you're listening. If I had somebody else in this, on this podcast, they would be what I'd be saying, but what they'd be hearing is different.
A
So true. Wow. Yeah.
B
So being able to understand and when you're in a conversation, number one, what is that person listening for? What did they hear? What did they hear? And so simple frameworks and tools to unpack that the simplest way to do that when you're in a conversation, like I tell all the people that I work with, the number one thing you want to ask at the end of a conversation was, was this helpful? Was this valuable? And the person's probably going to say yes. And you say, well, I'm, I'm curious. You know, I really value your feedback. What was most helpful that, that, that I talked about? I'd love your feedback. I mean, who doesn't want feedback or doesn't want to give feedback? So it forces the person to think about what we talked about and then they're going to say something, Whatever they say, that's, that's the, that's the answers to the test because that's the thing they care about. And then that's the thing, that's the thing that you're going to then follow up with. You know, what was it specifically that they, that they cared about? They liked your, your new approach, they liked your method, they liked how you talked about how I'm going to work with, you know, work with your team. It doesn't matter, whatever it is. So I mean, that's like one of the simplest things, tactics for. How do you listen for the buyer. For the buyer. Um, and really all this starts with is self awareness. Right. How, how are, you know, how you're showing up? Um, and then thinking of it as these interactions. This is like ongoing practice. You're just practicing. I'm practicing with you right now.
A
Yeah. Okay. I want to stop you right there for a bit because so many people, leaders included, and salespeople are afraid to ask. Yeah. Because they just asked the question, did you understand? You know, did you hear? And, and, and they stop right there because they have their agenda.
B
Right.
A
And they think their agenda precedes anything that you care about. How do we, how do we get that? Because I truly believe that follow up question, that's the one where you get the really good stuff.
B
Yeah.
A
How do you get that embedded into people to be doing that every time?
B
It's a practice. So it's, you know, it's get, putting it into practice. And you know, it's like I was just on a call with a leader this morning talking about, you know, how you're bookending your, your, your one on ones. Right. With your people. Like the number one thing when you get into the, into the meeting, you might have a bunch of things you want to talk to that person about, but you say, you know, what would be the most helpful thing we cover today? And then at the end, what was most helpful we covered today forcing them to tell you. So that, that works in for a leader, it works for a seller that's selling to a prospect. It's the same, it's the same method. But you're, it's that reciprocation, you're listening, you know people at the end of the day, why do people struggle? What do people not buy? Why do people not move forward? Why do people not achieve their potential on your team? It's because they don't feel seen, heard and valued. It's a fundamental need. So by breaking down the things that we do, I mean how many hours I was in a, I did a keynote earlier this week and I asked, you know, writing down how many, how many conversations are you in a week? I was teaching them the new ROI and like 30, 40 hours a week in conversations. Okay, how do you know your conversations are actually connecting? Statistically we know that like 50, it's like 50 to 70% of the time they miss the mark. How do we so any improvement there? That's money. So teaching people how to do this by doing something that seems so simple but yet very few do is be present and have a next level of listening and self awareness.
A
Oh wow. There's so much there to unpack because you know, you said, you know, key I do believe is, you know, why did you say that? You know, it's that follow up piece. But I got a theory. As sales leaders manage their people, it's in direct relationship to other people manage their customers. I mean it's, it's the parent child relationship. Isn't it scary? I mean it really is. And yet I see so few leaders really doing that well because they have their agenda and like said they. I had all these interactions this week, but I just go through my agenda. I, I met with them. Check, check, check, check, check. Right. Then we wonder why salespeople have bad behavior.
B
And I think, you know, I know you have a lot of leaders that listen to, to this. One of the things that's really important for leaders to understand is that people listen differently. And so I have a whole framework where I teach how to decode your buyer or in this situation, how do you decode your rep on your team? There's four kinds of people. I keep it simple. I always say people are effing predictable. And I usually get. So people are either fast, feel, focus or facts.
A
Okay, run through those four again.
B
Fast.
A
Right.
B
Feel, focused or facts, bottom line.
A
Oh, I love that. Okay, can you give us a little detail behind each of those four? Because that's, that's a mic drop moment. That's great. I love that. Yeah.
B
And you use this to code your buyer or your decode your rep or whoever you're talking to to know what kind of words to use. It's a completely different way to think about how your, you're connecting with someone. Have you ever heard of like love language?
A
Oh, yeah. Oh, yeah. Yep.
B
So it's a way to do this immediately in an, in an interaction. So fast people are like you and I, a lot of salespeople, entrepreneurs. How do you know people are fast? Is that they talk very fast. They're animated, they talk with their hands. They like, they like speed, they like new ideas, they like big, you know, big picture. Okay. And they're people people. They're very like engaging. They need to be connected with people people first, then process. The second kind of people are what I call facts people. So these are a lot of executives. They're the bottom liners. They don't want the details. They want you to just tell them what is the return they're going to get on this. How do you know it's a fax person is because they're like tell you what they want and then, you know, they want you to shut up.
A
Short brief to the.
B
Yeah, short, exactly. So those are your fast and your facts facts, types of people, Innovation, more bottom liners. Your third type of people are your feel people. A lot of times feel people are in hr, customer success. These are our customer success people. Marketing. These people will, will not listen until they feel like you're listening to them. They care about connection, teamwork. They want to make sure that we're on the same page. You know, it's a, it's a field person. If they're really, you know, making sure that in the conversation like teamwork is a big important value for them. Collaboration. And then the final quadrant is focus. A lot of technical people, a lot of operations people are what I call focus people. They need detail, they need to know the steps. They are also more reserved and they talk a little bit more. They'll wait to. The reason where you would know that either with a feel or a focus person you're going to know is because they're more reserved, they talk a little bit softer and they're going to wait for you to ask them a question. These are the ones that do not love to be called on. And so when you understand immediately, you can, when you get into an interaction, when it's a one to one, what do you like? How is this person showing up? You're really present in the interaction. And then what are the words? Do you need to talk? Hey, here are the steps. So if I'm talking to a focus person, I'm like, you know, these are the steps with the win room method. If I'm going to be working with you, we take everybody through this method. It's understanding yourself, understanding others, mastering and practicing the new roi. That's how people work with us. If I'm talking with a field person, I say in the win room, what we do is we give your people a completely different way to communicate and understand each other on a deeper level. Removing all these invisible barriers, bringing your team together, moving forward faster. Right. Feel people. I'm talking to someone like you. I say in the win room, what we do is we give you a completely different way to show up more memorably in every conversation so you make money faster. And if I'm talking to a fax person and executive, I'm saying in the win room, 98.4% of people who use our method and practice it hit their targets.
A
I love it. Now you got to understand who that, what category that person's in, right?
B
Yeah, but that's what teaching them how to read it immediately. You're either going to read it because of their communication before you first, like you can, I'm hypothesizing based off of their role. But then as soon as you get into the meeting, like bottom lining it, you know that they're going to be either fast or they're going to be facts. So I want to give them something quick. I don't want to go into all these details. So the biggest challenge you have is when, if you're trying to sell to someone, if you're a fax person, this, I had this earlier this week. I was working with a financial services company and a lot of them are like facts and they just want to bottom line and tell them what's the money. But they're selling, they're selling to benefits people and they want to feel like you care first. So it was like this. So teaching them how to shift the language and put in here where, you know, I, I really value collaboration, you know, putting those kinds of words into the conversation but tying it to their own personal value. As well. So how it ties together so that it, you know, we want. This only works if you understand yourself first. Yeah, right.
A
I love what you're saying there, because you do. You get you. First of all, you got to find out which one of the four you are correct. And correct the dog don't hunt.
B
It doesn't matter. But, you know, it's so funny because everybody goes, well, I just want to go, you know what? How we break this down is really. The first step in the win room is understanding self, which is emotional intelligence, right? That building that skill of eq. So the emotional intelligence, how do you stand in who you are, but this. And the second is what I call understanding others, which is social intelligence. How do you read the room? How do you, you know, how do you understand, like, who. Like what do they need and the different types of people? And so everybody wants to jump to the social intelligence. And what I try to explain to them is, like, if you skip the first step, it doesn't work because you show up fake. You have to stand. What is the connection? What is a sale? It's. It's making a. Making a transaction. You have to start with where you are and then go to meet the person where they are. And so the only way you could do that is if you know who you are.
A
Now, if I'm one way, you know, can I. Oh, but she's somebody else. Can I adapt to her style? I mean, is this okay?
B
Oh, absolutely. That's where, you know, it's. It's so you would, you know, and that's where we anchor everything in your values. So for me, like, my number one value is courage. And it's talking. It's not jumping out of airplanes. I don't know about airplanes. What I do when I. When I. What I mean by courage is speaking up and talking about things that other people don't talk about but need to know to win. Right? So that's my definition of courage. So if I'm talking to somebody I know that if I'm talking to somebody that I know is a focus person, they need details. I say to them one of the biggest things, because fast people like us, we can go and would you define. Would you say you're fast? I would think you are.
A
I think I'm fast.
B
Yeah, yeah, yeah.
A
No. Yeah, yeah, yeah, right.
B
So people, right now, if I say to somebody that's listening, and I'm like, all right, you know, if it's somebody who's a focused person, I'm going to say, I Move really, really fast because I get excited about the things that we could do. Permission to slow me down. I want to make sure that today I take you through the steps of what we would do and the details. And so I'm speaking to their language. What they want is details. And right. Immediately, their. Their emotional. They just go, oh, thank God.
A
Yeah.
B
And Jamie, can you slow down, please? Right. We want our self. Self awareness is a superpower. And so when we go back to what you asked in the beginning about in the age of AI, where is our competitive advantage? It is in how we show up and have a more memorable conversation. In a world where everybody else is rushing, being present is the present.
A
I totally. Because I think this is more important than ever because of AI.
B
Thousand percent.
A
Yeah. I mean, and unfortunately, this is a skill and a trait that we're just kind of glossing over. We think we don't need. No, we need it more now than ever. I mean, this is the Ying to AI being the Yang a thousand percent.
B
And when I'm working with companies that have all these AI tools, I'm like, that's great. What I'm here to show you is how to actually build trust and be more memorable. Because the more that you can show up as a real person in a world that we don't know what to believe. Trust is everything. And if you can show up knowing yourself deeply, people will trust you faster because you're not putting a facade on. It's not this. And the biggest. The reason why I started all of this was. Cause I saw, you know, my biggest struggle in sales and throughout my career was I saw that everybody was very much one size fits all. They wanted everybody to follow a script. And I, when I would try, I was really successful. But when I was forced into a script, it shut me down because I wasn't being myself. And so teaching. So what I do is in my programs, I'm able at a larger scale, able to give everybody a personalized experience so they all walk away with their winning formula. What we're trying to. What we're trying to uncover from people is their winning formula. And everybody has one. I call it your money ball. Right. That's what I wrote my book on, Moneyball leadership. So your Moneyball is when you're using your. Your words that are your power words that are yours uniquely, because you have different ones than I do. Right. And when we're in those words and we're owning it and we're practicing it, we show up more consistently. Consistently more with more Clarity. And, and it, It. It just changes the dynamic. So we want people to find their winning formula. And every person that. Every person that can then be in that. That's where they make more money.
A
Wow. And. And you unpack that in your book, right?
B
I unpack, yes. I unpack. Well, I unpack the challenges of, of trying to one size fits all.
A
It. Right.
B
And why this is so important. I want to make sure I mention this because you were mentioning about sales leaders. Oftentimes and this happens with leaders and companies as well as they have a specific way that they want the services pitched. Okay. So now we think about they want them pitched that way. But what happens is that's only like how 25% of people want to hear it. They're missing the mark because they want it to be like them versus thinking about what does the other person need? That's where we go back to the wind room. What do I need? What I need? And what do I need? What is that individual need? And when we can, when we can, we can connect that and tweak what. How we're communicating so that we give the person what they need. That's where the sale happens faster with more trust.
A
Man, I love what you're talking about. We got to wrap this show up here. Your book, Moneyball Leadership. Where can people get the book?
B
Amazon.
A
Amazon, of course. That's where you get everything. That's right. There it is. Moneyball Leadership. I love it.
B
Yeah. I gotta send you. I gotta send you one here.
A
Oh, yeah. Hey, send that to me. Yeah, yeah, great. I can throw it through a window. No, it's okay. No, I'll keep it up. Anyway, for those of you not watching the video, she just held up a Moneyball Money ball. Ball. So how's that sound?
B
Yes. Yes.
A
Hey, Jamie, thank you so much. Where can people get in touch with you besides getting the book? Moneyball Leadership.
B
They can come, they can connect with me on LinkedIn. They. My website, the win room dot com. I'd love to hear from people.
A
Great. The win room.com we've been talking with Jamie Diglio. Absolutely fantastic, fascinating conversation on roi. Return on interaction. I hope that's what you got here today, because each week we deliver you two episodes, one like this, where we do a deep dive with a subject matter expert. Jamie certainly hit the mark on that one. Second episode is just me, where I do a single topic. Hey, why do I do the show? It's to help you see and achieve what you didn't think was possible because that's my goal every week. I want to help you do just that. Hey, would you do me a favor? Leave me a review on your favorite podcast app. And, of course, make sure you subscribe to the show. Thanks so much. We'll see you on the next episode of the Sales Hunter podcast.
Host: Mark Hunter
Guest: Jamie Diglio (Founder, The Win Room)
Date: February 26, 2026
In this insightful episode, Mark Hunter welcomes Jamie Diglio to explore a fresh take on ROI—moving beyond "Return on Investment" to embrace the concept of "Return on Interactions." Jamie shares actionable advice for sales professionals on personalizing their pitch, mastering self-awareness, and adapting communication styles to connect and convert more quickly. Together, they discuss frameworks for understanding both yourself and your prospects, highlighting the essential human elements that drive sales success in an age dominated by AI.
Jamie introduces a practical framework to quickly adapt your messaging:
Memorable moment:
Mark: "Can you give us a little detail behind each of those four? Because that's a mic drop moment." (11:25)
This episode is essential listening for any sales professional or leader seeking to sharpen their edge by harnessing both self-awareness and social intelligence to personalize every sales conversation and drive faster conversions.