How Jaime Diglio Helps Leaders Move From Burnout to Breakthrough

Jaime Diglio, founder and CEO of The WIN Room™, joins The Female Founder Show to discuss how leaders can redefine success, overcome burnout, and build confidence through authenticity rather than constant pressure. After a 15-year career as a top performer at Gartner and Microsoft, Diglio experienced a stress-related health scare that forced her to reevaluate the way she approached achievement. That turning point inspired the creation of her coaching framework designed to help leaders move from self-doubt and comparison toward clarity, confidence, and sustainable performance.

Diglio explores the difference between the “War Room” mindset—where fear, self-sabotage, and external expectations take over—and the “Win Room,” where leaders operate from their values and personal definition of success. She shares how role play, preparation, and intentional communication help professionals perform under pressure, while her Interaction Economy framework highlights trust and connection as critical leadership advantages. Through her Moneyball Leadership philosophy, Diglio challenges leaders to recognize their unique strengths and create impact by embracing what makes them different.

Join us as we discuss:

•  Moving from burnout and self-doubt to sustainable success 
•  The War Room vs. Win Room mindset shift 
•  Building confidence through preparation and role play 
•  The New ROI: Revenue, Retention, and Reputation on Interactions 
•  Why trust and connection are becoming key leadership differentiators 
•  Finding hidden strengths through Moneyball Leadership 
•  Creating authentic leadership without chasing perfection

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Transcript

Welcome And Guest Introduction

SPEAKER_00 0:07

This is the Female Founder Show with host and entrepreneur, Bridget Fitzpatrick, exclusively on ASBN.

SPEAKER_01 0:18

Today on the Female Founder Show, I'm joined by Jamie Diglio, founder and CEO of The Win Room, a performance coaching and training company that helps leaders, entrepreneurs, sales professionals, and customer-facing teams strengthen their confidence, communication, emotional intelligence, and ability to perform under pressure. Before launching the Win Room, Jamie spent 15 years as a top performer at Gartner and Microsoft. Like so many high achievers, she appeared successful on the outside, but behind the scenes, the pressure was taking a toll. A stress-related health scare landed her in the ER and forced her to rethink everything she thought she knew about success. That experience became the catalyst for creating the win room method, a system designed to help people move out of the war room where self-doubt, pressure, burnout, and outdated leadership habits hold them back, and into the win room where confidence, clarity, and performance can thrive. Today we talk about how leaders can improve what she calls the new ROI: revenue, retention, and reputation on interactions. Because every interaction with your team, your customers, and even yourself is either building trust and opportunity or costing you both. Jamie, thank you so much for joining us today.

The ER Wake-Up Call

SPEAKER_02 1:34

Thanks for having me.

SPEAKER_01 1:36

Now you've spent years working in high-pressure corporate sales before launching the Win Room, and you've shared that after 15 years as a top performer, you found yourself in the ER with two young children at the time. Talk to us about that moment and the impact that that had on you.

SPEAKER_02 1:54

Well, I think it's it's like we we operate, you know, slowly we start to take on more and more. Um, specifically if, you know, when you're someone who's highly ambitious and you take on and you do well in your career, you continue to take on more and more, but it it it slowly creeps up on you. So it's like the temperature rises, but you don't realize it. It's like you know, you wouldn't, you know, you wouldn't put your hand in scolding hot water, but you don't realize your that that it is because it's just risen a little bit every day. And so that for me was um a wake-up moment for me. Uh yeah, I ended up in after you know years of of performing um at a high at a high level and having two young children, I yeah, I I ended up like losing feeling in my legs and sent me to the ER thinking there was something you know dramatically wrong with me. And they checked me out and said, You're having a stress response in your body, which was really a representation of that I I'd kind of lost myself and I didn't know where I stood. I didn't have a foundation that you know, I I I didn't have that foundational footing, and it was this sort of wake-up call. I was the breadwinner, and my husband's a teacher and a coach. Uh, I had to figure it out. And this was 10 years, like 11 years ago now, and nobody talked about burnout back then. So it wasn't something I could like talk about. Yeah, I had to figure it out.

SPEAKER_01 3:17

Yeah, you probably had no idea what what was going on.

SPEAKER_02 3:21

No, nobody talks to us about this. Like, wait, like um, you know, that how stress impacts the body.

unknown 3:27

Yeah. Yeah.

SPEAKER_02 3:29

Yeah.

SPEAKER_01 3:30

So crazy. So then that led you to talk to us about um so going through all of that, what what did it make you like come to realize that you needed to do?

SPEAKER_02 3:43

Yeah, it made me realize that this was something like as a high performer, we're taught, um, we're taught how to like do all the the sort of one size fits all. This is how you manage, this is how you sell, this is how you do this, this is how you perform. And it's a very um one size fits all view of how what success looks like. And I realized that as even though I was like performing at a at a peak level, I was empty on the inside. And it was because I was so fixated on everything that I wasn't doing. We we operate in this um sort of society, um, specifically in corporate environments, but also in just as the founder as well. Um, we operate in this sort of what I what I call a war room where we were we work against results. It's where we doubt ourselves, we self-sabotage, we focus on everything we're doing wrong. And so I found myself, you know, trying to be like everybody else instead of figuring out who I who I was. And so that was actually the foundation of of the win room um company that I have today, which was how do you how do you help yourself find your own winning formula? And so I found that I was able to do that and then find help others to uncover their winning formula so they could stand in their strength instead of standing in their self-doubt.

SPEAKER_01 5:10

I love this story that I love the stories where something comes from such a need that you know you go from needing something and then realizing so many other people's so many other people need it as well. So you created it and now you're helping people go through what so many of us are are going through on a daily basis. So congratulations on your success. That's fantastic. And thanks for all that you're doing to help people. And so many of us are running on empty, like you said, but we're still showing up every day acting like we have it all together. Now, what is there one piece of advice that you would give to those watching um that you might be able to help right now that could help us navigate that a little bit?

SPEAKER_02 5:51

Sure.

War Room Thoughts And Self-Talk

SPEAKER_02 5:52

So, what most foundationally, like so much of the things that I talk about and teach and coach is like nobody teaches us this. Um, and that our brains are wired to um put us in fear and in doubt of ourselves. And so we tend to actually minimize the things that we're we are strong in uh because they're easy for us. So each of us have our own unique strengths, but we tend to go, oh, well, that's not a big deal. Yeah. Uh because it's easy for me, but you don't realize that it's not easy for other people. And so most of us are operating from what I call um bad data, like the war room. So they're operating from all these stories they make up about how they don't fit in, what they're not good at. And we actually have been living in this society where it's it really is, it's always about all the things you don't have versus what you do have. And so what we want to do is we want to be able to gather what I call win room data, right? The opposites out of the war room, right? That's self-doubt, comparison, head trash, all the stories you tell yourself about what you're not good in. What we want to do is we want to get people into this head space of when the win room, win stands for what I need. And so this is where you're clear on your goals, your values, the direction you're going in. And so the most to the point, your point, your question of of what's what's good advice is that the noticing when what you're with the conversation, the interaction you're having with yourself, just noticing that self-talk is one of the most important first things because you have to be able to notice it, to normalize it, to neutralize it. Okay. So how we talk to ourselves is one of the most foundational um keys to our performance in our in early in our career and in our life.

SPEAKER_01 7:42

Yeah, I know a lot of um your core beliefs and a lot of things that you talk about is mindset and um and as well as leadership. So

Mindset As Beliefs And Self-Leadership

SPEAKER_01 7:50

talk to us about how important that is, um, having a good mindset as a leader of a team or a company.

SPEAKER_02 8:00

Well, I mean, I think that mindset is like one of those words that's overused or misused, and it feels very big. And so what we want to do is we want to actually think of it more as like, what are your beliefs? What are the things that you're sort of that data you're telling yourself? Um, we are wired, like I said, we are wired to sort of focus on the negative data instead of the positive. That's why when we get 10 compliments and we get one one complaint, we focus on the complaint. So we have to be like tripling down on the positives in order to just neutralize that negative. Uh, but we get caught here, and this is where we get stuck. Yeah. And everyone, I I know whenever I do sessions for teams, um, um, you know, we're all leaders in in in any in a certain way. And this is all about self-leadership. So first step of leadership is self-leadership, building that, building that out. And it is super, super important to understand what is your philosophy, what do you stand for, what do you believe in? Um, what do you care about? You have something, a point of view. Um, and so we really are like trying to pull that out of someone because we each have it. It's just that it's usually buried in a sea of sameness because we all, you know, everybody wants to stand out, but everybody wants to fit in. And, you know, the key here is that you, you know, to be successful, you want to be um less predictable, more memorable in everything that you do. And the first way to do that is to be able to sort of have a stance, have an opinion. So we really think about like, well, how are we building up our self-leadership, building our leadership language so that we can be consistent and clear in what we do? And when we're consistent and clear in what we do, what we believe in, people start to trust us, right? Because we because it's consistent. And um, most people are out there just saying, you know, saying whatever they think is like, you know, the the the the thing of the month. And so when it comes back, when it comes back to mindset, it's like getting super clear and specific on what you want versus what you don't want. What do you believe? What where are you going? And um where I like break it down is like, okay, so your belief, you know, your beliefs, um, they're what drive your thoughts. And your thoughts are what drive your feelings, and your feelings drive your actions, and your actions drive your results. So we have to start with our beliefs and like our self-belief. Um, super, super critical.

SPEAKER_01 10:30

I mean it sounds super, it sounds simple, but but I mean, and it part it kind of is, but it's you just don't think about it that way. You think it seems like, oh my gosh, that's that's I'll never be able to do that. You know, I'll never be able to focus on what I'm believing when I've got all of these things going on. I don't even have time to think about what I'm going through. But it's kind of like that analogy where you have in the airplane and you've got the oxygen mask, you have to put yours on first and make sure you're okay before you can help your team or anybody else, right?

SPEAKER_02 10:59

Exactly. And I think that one of the things specifically for leaders, um, you know, people who are leaving teams, um, would or you know, just a few people, um, is this it's important to know that, you know, all of us have those war room thoughts. Like I typically share like some of the the when I've worked with tons of leaders, and you know, the sort of I'm not smart enough, you know, people are gonna, you know, people are think that there's somebody could be doing it better. I'm not like you know it's like the self-sabotage, like this whole list of things that consistently that people people believe that are in the top performing in their career, that this is what they're thinking of.

SPEAKER_01 11:38

Yeah.

SPEAKER_02 11:38

And so noticing how important our thoughts are about this, of what we know, what we believe is what we become. We have up to 60,000 thoughts a day, up to 80% of our thoughts are negative. And then up to 90 to 95% of our thoughts that we have today are the same ones we had yesterday.

unknown 11:59

Right.

SPEAKER_02 11:59

So we're in this repetitive pattern of loops of sort of how we behave, what we do, what we think. And so a big part of the win room is about up, like it's about rebooting that operating system, noticing your habits and your patterns so that you can sort of get out of that negative space and spend more time in that building that win room muscle of that's that's where you're operating from a place of performance, a place of where you want to be going, not where you're afraid of failing. So it's really the self-doubt to that self-leadership and like that shift in how we're teaching. That's the mindset every moment of the day.

SPEAKER_01 12:37

You really have to pay attention to what you're thinking about constantly.

SPEAKER_02 12:42

Right, exactly. So it's really thinking of like you're thinking about your thinking, um, and then listening for other people's listening. So that's a whole nother part of it. So at the foundation of what we teach, from a performance standpoint, it's emotional intelligence, which is understanding self, combined with social intelligence, was which is understanding others. And how do you read others and how people other people think because they think differently than you? But the first step in that ability to have more effective interactions and and show up more effectively with people is you have to understand yourself first.

unknown 13:20

Yeah.

Train Like An Athlete With Practice

SPEAKER_01 13:21

Now I've heard you compare business leadership to elite athletic training. Can you talk to us about what entrepreneurs and executives can learn from the way athletes prepare and perform and recover? Talk to us about that.

SPEAKER_02 13:35

Yeah, absolutely. Um, so much of what we do in our programs is really if you think about how you train like an athlete. And athletes, what do they do? They practice. But what do we do as professionals? We just expect uh to perform, but that we don't put any practice in place. That's right. So so much of what we do is when we're thinking about what are these practices of how you are having your conversations? Who are who do you want to be having a conversation with? What message do you want to get across? How are we practicing it? So much of it is role play and you know, uniquely coming across as yourself and getting those reps in. So everything is about, it's not about perfecting, it's about about practicing. And I say this to my kids too, you know, we're we're taught that everything has to be perfect, but it's not it's not about perfect, it's practice. Yeah, it's practice. We're constantly practicing. I'm practicing with you right now.

SPEAKER_01 14:34

And I'm practicing with you right now.

SPEAKER_02 14:37

And so when we and when we think of it though, if we think of a moment where because the idea too is how we practice then becomes how we perform. And so if we've already practiced it, then once we go to perform it, there's no like we can stay calm. And it's the same way with athletes. So this is what we do and instill within the mindsets of the clients that we work with, um, so that they can perform at that level under pressure, because we're all under pressure. Like, how are we managing this through practice?

SPEAKER_01 15:06

I love that. It makes so much sense. So you've also talked about, and I love this about um you have an interesting take on ROI and what you call interaction economy. Can you

The Interaction Economy And New ROI

SPEAKER_01 15:17

explain what that means? Because I thought that this was very interesting.

SPEAKER_02 15:20

Sure. So we believe that we are either making money or losing money in every conversation. And this is an area that most people are not paying attention to, they're not measuring. And so when we think about ROI in the win room, where we we think about it is return on interactions, which is revenue on interactions, retention on interactions, reputation on interactions. So every person you know is either trying to you know grow revenue, retain customers, or build a reputation. And how do you do that? We're now today, we've been in this information economy with AI. You know, you have access to everything. Everyone has access to this information. And what does AI do? Is it nor like it it it it um it's the average? So of all the information, so everybody has access to the same information. So you have AI, I have AI. Okay, you cross that out. What do we both have? Our ability to interact with people. And so I we can have so we have shifted to this interaction economy where your value and your ability to be successful is not the information, it is your ability to build trust and connect with others. So that's what we do, right? It's all about how you are showing up consistently. Um, in in because most people like who do you trust? Right. How do you know what to try, like how to trust people? So, this is this the idea around your interactions, how you show up more memorably, you build that compounded interest with people because you're showing up from a place of presence and and authenticity, you're being the real you. And it's so such a low bar today. Yeah. Because everybody else, yeah, it, you know, you don't know. You can't, it's hard to trust people. You don't know what to trust.

SPEAKER_01 17:22

Yeah. And in a world, you know, post-pandemic where so many people are still working from home and not interacting with people on the daily basis that that they used to, I know there's still a lot of people that don't have the ability to socialize intelligently, like you're talking about, because they are at home not socializing. So important.

SPEAKER_02 17:43

Well, absolutely. And you know, we found so many reasons. You know, we're like the most connected yet disconnected society ever. And people don't know how to have real authentic interactions, conversations. And we're how do you have a conversation? How do you interact? How do you connect with a person? Like it it it like it it starts from yourself. Yeah. And so when you can show up present, um, knowing what you stand more, what you believe in, and have consistency in that, that like puts you that puts you way above so many other people who are basically just following the same script and you know, uh what everybody else is saying.

SPEAKER_01 18:26

Yeah. And that's in everything you do, whether it's business, social, family, everything. So that is so important.

SPEAKER_02 18:33

What do you stand for? What do you believe in? Yeah, um, what do you care about? And that was that was the thing that I noticed over and over again. When I could pull that out of someone, their performance would increase because it was like, you know, it's like it took a weight off of them. Like that, no, you can actually be who you were meant to be. You don't have to keep trying to pretend to be like someone else. And the more you are you, this is the irony of it, of what it's the opposite of what we're taught. The more you are you, the more successful you will be.

SPEAKER_01 19:03

Makes sense. It makes sense. I'm gonna ask you one more question before I let you go, because we have to talk about your book. We

Moneyball Leadership And Winning Formula

SPEAKER_01 19:10

have to talk about money ball leadership. Now, talk to us about what are some of the takeaways that you want your readers to take away. Talk about that for a second.

SPEAKER_02 19:17

Sure. So, money ball leadership, if you're familiar with, um obviously have a sports theme here. Um, but money ball, money ball leadership is all about how to find your winning formula. So, similar to Moneyball, the movie, you know, with with Brad Pitt, where it was like, how do we, how do we, instead of looking at like the superstar person that has all these qualities, this traditional way of measuring success, figuring out how do we find the hidden value in players? How do we find the hidden value in ourself? And how do you then use that to amplify your success? So, from a leader, so many leaders, it's not their fault, but what how they've been trained is to be very one size fits all in how they are just following what everybody else looks like and does. And so, this is about how do we unlock um the leadership language of the individual so that they can stand out and perform at their best. Um, so really like that step, that method of really what I what I coach and teach is sort of how do we unlock that winning formula within the individual? Fantastic. And then then, and then once they unlock it within themselves, they then can practice it with their teams. And when they do that, that's where the performance rises, right? But it has starts with the leader first. Uh, and that's you know, that sort of personal responsibility for how you're showing up and interacting with your people every moment of the day.

SPEAKER_01 20:41

I love it. Jamie, thank you so much for all your great advice that you shared with us and everything that you're doing to help leaders figure this crazy world out. You're doing great work and we really appreciate it. Thank you so much. Thanks for having me. Yeah, thank you for joining us.

SPEAKER_00 20:57

This

Final Takeaways And Invitation

SPEAKER_00 20:58

is the female founder show with host and entrepreneur, Bridget Fitzpatrick, exclusively on ASBN. If you're a female founder and would like to help other female founders with your inspiring story, we would love to hear from you.