“Am I operating in a way that reflects my ideal self—or not?”
That’s the kind of question Kyle Sale, coach, operator, and fractional leader at think2perform, uses to guide both his leadership and personal life. On the Making the Ideal Real podcast, Kyle joined host Ryan Goulart for a candid conversation about personal transformation, leadership growth, and the courage required to face reality.
Drawing on his experience as a former owner-operator and a veteran of both Silicon Valley and private equity, Kyle shared how emotional honesty and self-awareness aren’t just leadership virtues—they’re strategic imperatives.
Authenticity Over Performance
In the early days of his leadership journey, Kyle found himself projecting a version of leadership he thought others expected—confident, commanding, in control. The reality? He felt uncertain, even overwhelmed.
“Behind the curtain,” Kyle admits, “I was dripping sweat. I was nervous. I was like, what am I doing?”
That moment of tension—between projecting strength and acknowledging fear—marked the beginning of his journey into authentic leadership. He discovered that it wasn’t about pretending to bench press 325 pounds when you’re only capable of 125. It was about being grounded in what’s true—and building from there.
The Soft Skills That Are Anything But Soft
In many organizations, the focus is on performance metrics: revenue, productivity, growth. But Kyle argues that the real leadership work happens elsewhere.
“We call them soft skills,” he says, “but they’re the hardest ones to master.”
He’s talking about empathy, humility, emotional regulation, and the ability to lead through—and with—others. Leaders, Kyle suggests, are culture setters. And culture, he notes, isn’t about ping pong tables or happy hours. It’s about how people behave, interact, and grow together—especially in the face of challenges.
Building the Muscle of Self-Awareness
Self-awareness wasn’t something Kyle naturally leaned into. He had to train for it.
“I started carrying a little pocket journal,” he says. “Every three hours, a timer would go off. I’d write down what I was feeling and why.”
That practice helped Kyle build a habit of emotional honesty, which now enables him to recognize and respond to stress in real time. It’s also given him the ability to coach himself—and others—through tough moments.
Personal Transformation Comes First
Whether you’re leading a corporation or a team of five, Kyle believes meaningful change starts on the inside.
“Before you can change a team or a business,” he says, “you have to be willing to change yourself. And that starts with asking for help.”
It’s a message he’s lived. From seeking out mentors to embracing tools like journaling and reflection, Kyle has learned that transformation isn’t a one-time event. It’s a practice.
Scaling Change, Without Losing Connection
In large companies, change requires buy-in across many teams. In small businesses, leaders often wear every hat—visionary, strategist, operator. Kyle’s advice for navigating both?
Be intentional. Share the vision early. And don’t try to do it alone.
“When leaders hoard responsibilities,” he warns, “they rob others of the opportunity to grow.”
Instead, he encourages founders and executives to involve others in the process, cast vision frequently, and embrace the discomfort of letting go.
Transcript
Ryan Goulart:
I have with me today, Kyle Sale from think2perform one of our newest fractional employees. Kyle, welcome to Making the Ideal. Real.
Kyle Sale:
Glad to be here.
Ryan Goulart:
Yes, I’ve prepped you hopefully for this conversation and particularly this next question. The next question that we’re going to ask, and our audience knows this, whenever we have someone new, we ask this question to frame our conversation. What does making the ideal real mean to you, Kyle?
Kyle Sale:
Yeah, I was thinking about it in your extensive and hardcore prepping. Try not to get too overwhelmed by it. I was thinking as I started to think about it, I kind of took a holistic approach to what it means. So I think initially you think about it through the lens of business and particularly working with having operated businesses and then working with owner operator founders. You associate the ideal with vision. What could we be, where could we go? What do I want my business to look like? Sort of set that as your north star, and now we work backwards to figure out how do we get to the ideal. But then I think maybe we can unpack this a little bit in our further conversation. Thinking about leadership. You’re like, well, am I the ideal leader? What does my ideal look like? Who am I as an ideal version of myself so that I can show up and drive the organization in the ideal direction?
And then getting more personal with it. It’s like, well, what’s the ideal version of me at home with my spouse, with my kids and my community? So all of a sudden, I think making the ideal real to me becomes an anchor point for a North Star that’s driving everything that’s important in your life, depending on how you break it down. It’s like faith, family, career, friends, community, and then almost having a core ideal self that’s got these orbits around it that you’re now using that to drive everything that you’re doing and to come back to a self check of, am I operating in a way that is my ideal self? Or at least making progress towards that or not.
Ryan Goulart:
That’s Kyle Sale, a coach, operator and one of the newest fractional leaders here at Think to perform. We’re talking about personal transformation and how real change starts with the courage to face reality, ask for help and lead with humility. Because in leadership, the hardest transformation is often the one we make within ourselves. I’m Ryan Goulart, and you are making the ideal real.
Ryan Goulart:
I love that answer. And you’re also speaking another language of mine, which is audience knows this, that I’m a huge nerd and I love space. So you’re saying orbit in solar system kind of metaphors plays right into my space passion.
But I won’t take it down there. I won’t do it to you.
Kyle Sale:
I won’t do it to you. I didn’t know I was going to trigger you in a positive way.
Ryan Goulart:
So let’s unpack those different levels. I think it’s a really good observation because it does ring true to everything that we do here at think2perform, whether it’s business, career, personal, there’s different layers that this question does tee up. So let’s start with business first.
You mentioned you’ve been an owner operator, you’ve done things across different industries, and one of the things that really stands out to just kind of as a foundation for our conversation, just because of that exposure to various things, what have you noticed in yourself in business as you have kind of climbed the ranks and operated the business? I know there was a time in your life that you were in Austin, Texas running a 30 to 60 employee business.
What have those moments in time taught you about leadership?
Kyle Sale:
Yeah, I think there’s kind of two sides to the coin or maybe two lanes that you swim in as you grow in your career and have those experiences. The easier one is looking at other leaders, right? When you’re younger in your career, I learned a lot both from the positive aspects of other leaders and oh man, this CEO is authentic and they show up and ask authentic questions trying to get the best out of their people. They’re willing to engage in hard conversations in a kind and caring way, not a berating type of way. Or oh, this CEO is putting on an act and trying to be kind of a CEO that you would see on Silicon Valley. I dunno if you’ve ever watched that show on HBO.
You see sort of the pros and cons of other people’s leadership style and how it is productive and healthy can actually be very productive and unhealthy and start to sort of pick and choose, oh, I want to be more like this or less like that.
On the personal side, I think it’s a journey of self-discovery in a lot of ways, and we’ve talked about prior to the podcast. I think when you get put in a leadership position, I mean I can only speak for myself and my own experience, but you get put in a high level leadership position at a younger age, there is a bit of a imposter syndrome because you’re like, I’ve never actually done this. I think I’m capable of doing this. So the pitfall is you sort of start to project a leadership style, but you haven’t really developed a leadership style.
And so I think that’s where it’s important to go find older, wiser, seasoned mentors. And or thing appealing to me about joining Think to perform is in some ways we can be that older, wiser, seasoned mentor where it’s like, Hey, I just don’t know what I don’t know, and I’ve got angst about what I’m doing, and you might be doing a great job, but it’s just like, okay, let’s have someone come alongside you and ask the hard questions, provide a different perspective. So yeah, I think learning from other people and then being self-aware in your own journey and willing to learn from other people is a key thing that I’ve experienced in my leadership process.
Ryan Goulart:
One of the things that’s really interesting about what you just said is the words you’re using authentic wise guide, if you will. I had the experience this past week of just, I know you’re a Seahawks guy, so what I’m about to say isn’t going to be all that exciting for you, but it might be for some of our, where we people here listening, Kevin, I had a conversation or I didn’t have a conversation. I listened to a conversation live with him talking about leadership, and it was really insightful. And this is the second time in a second year in a row that I’ve been able to have the opportunity to do this. And one of the things that he said, which connects to something you just said too, is that he always strives for two things. One is to be his authentic self, and he truly, truly means that. And it shows especially in a lot of the interviews that you see and even in how he talks about the camaraderie that he builds in his team. The second thing is that his career, his learning journey is all about failing forward. And he mentioned that he had five seasons in the NFL as a quarterback in those five seasons, he was cut seven times and you’ve worked out the math on that. Yeah, it’s,
Kyle Sale:
Wait a minute.
Ryan Goulart:
Yeah, you were fired twice in one year. So he makes a joke out of it, but it’s something that provides some good stable insight into how he provides leadership and coaching and player empowerment within the Minnesota Vikings. So it’s just taking some of those concepts and just kind of overlaying them on our conversation today. What have you noticed in that same light of just being authentic, failing forward? How would would you coach your younger self on some of the things that you’ve experienced in business and in life?
Kyle Sale:
Yeah, I mean, I think when people here, I mean, we referenced Silicon Valley. I spent time in tech organizations working in San Francisco in that kind of Silicon Valley environment. And fail fast is another, let’s fail fast, fail fast, and like, okay, I get it. Let’s try something, see if it worked, learn what we can and keep going. I think failing forward in leadership, when you pair it with authenticity, the way I would actually describe it is being firmly grounded in reality. So that goes back to that self-awareness piece. Like, okay, in my case, when I ran that organization in Austin, I was fresh out of business school. I’m 28 years old, I go to work for family office private equity group that just bought this company out of bankruptcy. I moved to Austin, Texas, they have an office in Austin and office in Dallas.
No one’s managing the Dallas office. It’s a nightmare. I’m like, okay, I got to go shut that office down, move everything to Austin. I’ve got to lay some people off. I’ve got to start building a team. And so the council to myself back then is I think what I did, I think I made hindsight’s always 20/20, but by and large the right strategic decisions and right business decisions. But I walk into those rooms and I’m projecting an aura of leadership or a presence that I’m behind the curtain. I’m dripping sweat, I’m nervous. I’m like, what am I doing? And I think it’s actually the counsel to my old self would be like, okay, stay grounded in reality. You’ve never done this before.
And I was bouncing the strategic decisions off of people, but I didn’t have the self awareness to manage my own emotions, my own fears, my own anxieties. And then that comes out in hard conversations with employees or in many ways, lack of conversation. As a leader, a lot of your time is spent casting vision, making sure people know this is the destination, this is why we’re going here, this is how we’re getting here. And when you’re racked with self-doubt and anxiety, it ends up becoming, I didn’t exactly say this, but it’s like just shut up and do what I’m telling you to do. Right? There’s no empathy, compassion, there’s no greater purpose. So I think staying grounded in being okay with the present reality of, I guess the analogy I would make is if you want to become a bodybuilder, I was projecting as if I was already a bodybuilder. You’re like, no, man, you can only bench press 125 pounds. If you go in the gym and put 325 pounds on the barbell, you’re going to crush yourself. And so projecting an image that wasn’t true is actually emotionally crushing and not healthy. And if you’re a leader, that’s not healthy. You’re not going to lead a healthy organization.
Ryan Goulart:
Super, super insightful, and I’m glad to hear that you could do more than just the bar. So that’s just kidding. Hey listeners, Ryan here. You can’t lead others well, until you’re honest with yourself. This week’s tip, build a self-awareness habit, set a reminder to pause, check in and write down what you’re feeling and why self-reflection is the first step to personal transformation and better leadership. One of the things too, and I think that’s a really strong point that you’re making there of particularly at that high level, and this is true up and down in organization, but you notice it a lot more in organizations of that have the decisions, the leadership, people that they’re making, the vision they’re casting, how the team is managing itself is a function of how well the organization’s doing. Again, back to some of the things that you’ve seen across business, what have you noticed that makes that statement ring true? That statement of trying to pretend that you can lift a 300 pounds on the bar barbell, but not being able to do it.
Kyle Sale:
I mean, it’s funny when you think about business, you think about profit and loss statements. You think about go-to-market strategies, you think about strategic decisions, all of which are important. But this conversation, I think keeps coming back more to the softer skills. People call it soft skills, but the soft skills are the hardest ones to master. And so I think what ends up happening, whether it’s in a business CEO, driving a business, large business owner, founder driving a smaller business, or even general managers over a business unit, the way that you show up and the way that you lead, and again, you could be highly productive and highly successful by the p and l metrics and the go-to-market metrics, but what we’re really talking about is culture. You’re establishing a culture and a way of working and a way of interacting because everyone’s looking to you and everyone’s seeing like, well, this is your tacitly setting. The expectation for how we behave and behavior is both what we get done and how we get it done. So a powerful thing that I’ve seen in organizations that, particularly with the leaders, are very self-aware and take culture seriously. I mean, culture is more than ping pong tables and Happy hours.
They will actually A, have their teams hold them accountable for how they’re behaving, and B, hold the organization accountable for how they’re behaving. And it’s not in a sort of strict authoritarian way. The simplest way I’ve seen it is in whatever your cadence is, monthly, quarterly, semi annually in reviews, everyone wants to go to, we call ’em performance reviews. How did you perform? Oh, you hit your sales target, you get your bonus. The leaders that are really emotionally healthy and are building a healthy culture say, Hey, Ryan, you killed it. Sales target was this. You got 112%, but here’s our core values, integrity, teamwork. You actually were a terrible teammate. You stepped all over your teammate’s toes. You’re gossiping integrity. Yeah, you hit your sales target, but you did some sketchy things to get there. So actually you don’t fit in our organization, even though the performance is fantastic, the way that you’re getting those results isn’t aligned with who we want to be. But again, it comes back to you’ve got to be in a place where you are holding yourself accountable. So now you’re not hypocritical in the way that you’re leading that organization.
Ryan Goulart:
Yeah, it’s such the culture. Word is such an important word, and I think to your point, it’s more than just ping pong tables and happy hours. And I think it’s such one of the best definitions, and I’m curious to see your thoughts on this too, that I’ve heard about defining culture, and this comes from, he was the CEO of Basecamp. They have a new company, I forget his name, really
Kyle Sale:
Insightful
Ryan Goulart:
Guy named Jason Fried, I believe.
Kyle Sale:
Yes,
Ryan Goulart:
Yes, yes, yes. That’s it. Thank you. But what he says is that culture is a 50 day moving average, and that is everything that is in those 50 days. It’s all the emotions, it’s all the behaviors, it’s all the decisions. It’s all the words that were said, and it’s a 50 day moving average. And we are also on day one and day 50 at the same time. So what’s really insightful about that though is it just makes it in how I’ve learned about culture. To your point, this is more than these things. It is all those soft, hard skills to learn, and it’s also the things that you would perceive culture to be really, what are your thoughts on that? What’s your read on that little quote?
Kyle Sale:
No, I’d agree a hundred percent. And I think it goes back to the first question of what does making the ideal real look like? And if you step back, it’s more than making the business ideal. We’re hitting this revenue or hitting this profit, we’re expanding our market share. It’s like, okay, but what’s the ideal version of me as a leader, as a husband, father, friend? And then you realize, oh, all the people showing up to work here, they’re spending 40 hours a week in our organization. What’s the ideal version of themselves? And then we all know that life is at work, certainly, but in general, life is filled with all kinds of ups and downs. And so in those 50 days, people are showing up to work with a death in the family, or I’m the parent of multiple teenage children. So I’m showing up at work with whatever’s going on in the house that’s driven by hormones.
And an argument happened, and now my daughter, my wife got into an argument, so they’re spun up and I got pulled into, so I’m showing up. That’s the state that I show up in. And so I think as a leader, it’s easy to look at performance only and be like, well, why was Kyle late today? He must not be committed. What’s the matter with him? You’re like, alls it takes is a couple of questions to realize like, oh, Kyle was late today. His family had a blow up, and his wife was crying and his daughter was this. And so he showed up late and he wasn’t engaged in this meeting because his head’s still spinning. So I think thinking about it in terms of what happened in those 50 days, and it’s an accumulation of life events, not just showing up to a project management meeting and saying, yep, my tasks are on time.
Ryan Goulart:
Right, right. It’s like honoring the human. It’s kind of connecting to that person when it comes to the personal side too. So as you’ve developed your own skillset over time, what have been some things that you’ve grounded yourself in to help manage? Because that self-discovery, self-awareness, the personal transformation, the ability to adapt to what the environment, business and otherwise, what are ways in which you’ve been able to navigate those peaks and valleys?
Kyle Sale:
For me, navigating those? I mean, I think for some people are more self-aware, some people are less self-aware. Naturally, my natural sort of bent is I’m a push through it. I can get it done kind of guy naturally. So for me, it was realizing humility and self-awareness, kind of back to the prior conversation, what is the actual reality? And then developing tools where I can take a break, take a breath, and the simple tool for me was I started carrying a little pocket journal, the little field notes, pocket journal, and early days, it was so unnatural to me. I would set a timer on my phone, and so every three hours, the timer would go off and I’d pull out the pocket journal and I would just be like, what am I feeling? Actually feeling in my body, in my emotions. You like, oh, I’m feeling overwhelmed.
I’m feeling stressed. Okay, why? What stresses me out this project at work or this thing at home? And then over time, I was able to, that became more of a natural, I developed that muscle back to the bodybuilding. Like, okay, I just need to pick up the lightest dumbbell, which was a field journal and a pen and call. Time out check in was where I’m at. And now, that was five years ago, six years ago. Now it’s like, okay, I can do this in real time. I can feel my shoulders tense up. I can feel my voice go up, maybe an octave, okay, something’s off. Why am I stressed? Oh, I’m nervous. I got to have this hard conversation with this person. I don’t like having those hard conversations, but if I avoid that hard conversation, what happens? Well, they don’t get the feedback. Nothing changes. So it’s actually loving to have this hard conversation with this person, and now your perspective changes, your temperature goes down, and you can enter in into those kind of conversations.
Ryan Goulart:
So you’ve been able to sort of coach yourself in a way through your documentation of your experiences?
Kyle Sale:
I should say in the humility side, I didn’t come to even that exercise alone. I sought out other leaders, other mentors, other people that, and it’s funny, you think, do you feel a little bit stupid? It’s probably the most blunt asking someone, how do I do this? The people I sought out, you’re like, this guy’s a fantastic leader. He’s got it all together. Turns out he only has it all together because he’s been practicing these things and using these tools for 20 more years than you have. And it was like he started at a same place. So being willing to ask for help made all the difference.
Ryan Goulart:
Yeah, that’s such a good point too. I mean, no one gets anywhere without help, which is always so counter to what you see. So I think that’s always such a good reminder. When it comes to just with that information, with the information from your field notes, how do you put those into practice? Usually what we’ve seen too is that you notice some things about yourself, you start to understand it more, and then finally you get to implementation. So have you been able to decrease the time to implementation because you’ve been practicing this for so long?
Kyle Sale:
Yeah, I think, well, I know the time to implementation is almost real time at this point. I can feel it, kind of process it and then make a decision to do something based on that synthesis. But I think the key trigger again, is the willingness to ask for help, which is an act of humility and an act of humility. You become willing to change. You reach a point where you’re like, there’s a difference between wanting to change and wanting to grow and being willing to do what it takes to make that change and to grow. So whether it’s growing as a leader, whether it’s physical fitness, whether it’s learning a new skill, picking up an instrument, you can want to do that for a long time and you can read about what it would be like to do that, watch YouTube videos. But until you pick up the instrument or pick up the barbell or pick up the field journal and be like, you know what, I’m going to do it. Just choosing to do it takes a willingness. Sometimes it’s born out of desperation. I’ll call it the gift of desperation to make a change.
Ryan Goulart:
Love that point. Love that. It connects to your personal transformation too, whether it’s skills, talent, decision making, which are things that we often talk about on these podcasts.
Want to roll that up because I think it connects directly back to where we started our conversation in that change, wanting to change, being willing to do what it takes, and to do that for oneself is hard. It becomes exponentially harder at scale. A business level, what have you seen work well and what have you seen work less well when it comes to implementing change initiatives? When the team believes it or when they don’t?
Kyle Sale:
Right. I mean, I think the key word in that question is believe. So change management is, in my experience by far, the hardest thing in business is getting a group of people with, they’ve got, when you announce we’re making a change, you’re on day, whatever of this 50 day window that we just talked about. So God only knows where everyone is at in life, in work, in family, and now you’re saying, we’re going to disrupt the status quo. And if there’s anything that we as humans dislike with a ferocity is disrupting the status quo. We just like to get into a rhythm and keep doing what we’re doing. So I think when it comes to the question that you asked, the way I’ve seen it done really well is getting people bought in and by getting people bought in, I mean, if you are trying to make a big change in your organization and you go off, come up with a plan and a silo, come back and say, alright, we’re going this direction now, everyone get on board and just go do it. It’s usually not going to go well. Bringing people along for the journey and getting them to feel like they’ve been a part of it doesn’t mean everyone in the organization is a part of every meeting, but figuring out how to, I think you think about it like a cruise ship actually. What’s the itinerary? What’s the port? What ports are we stopping in? Where are we ultimately getting to and getting people to get on board with the vision. Well, before you announce we’re changing this, let’s go.
Ryan Goulart:
So it’s a thoughtful, intentional, methodical process, even though it oftentimes for those that are hearing it for the first time, that’s not what they’re hearing. They’re not hearing about all the prep that went into it, but you have to manage that as you kind of cascade through the organization. Really cool. One other last question. So you talk about it from a kind of more corporate sense. What have you seen work well in small business? So where the doers and the strategic thinkers are the same person, how does one balance this need for innovation change, but also maintaining, got to bring cash in. We still got to be able to make payroll. It’s just this wobble. How do you manage the wobble? I like that, Ryan. I’m going to keep going with
Kyle Sale:
That. Yeah, I like that. Yeah. I think in a smaller organization, on the one hand it’s a little bit easier because you just have less people involved and you’re working as a tighter unit. So you’re not in the corporate world, you’re sort of managing an operation at scale, and you’ve got forces spread out all over your city, your country, even the world, depending on how big you are in a small organization, you’re like, well, I’m in a platoon. I got my group of people and we’re working together, elbow to elbow every single day. So the opportunities for conversation and alignment don’t have to be planned. It’s just we’re in this together. So as a leader, you can be casting, you don’t have to have a specific vision cast. I mean you should, but you can daily cast vision. The challenge though, in the smaller organization, particularly owner, founder led, is oftentimes they live in their own head.
They’re entrepreneurial, they’ve got a million ideas, they move at a fast pace, and so they become the visionary, but maybe aren’t sharing the vision and then the doer of the key activities to achieve that vision. And everyone else is just sort of on the back of the boat holding on being drug in a certain direction. So I think the challenge for the smaller organization is, as a leader, how am I casting vision? And then how am I actually, when we come back to the humility piece and the self-awareness piece, how am I empowering my team to be a part of what we’re trying to do and elevating their level of impact and delegating responsibility because my plate’s only so big, but we just keep trying to stack more stuff on our plate and we do it. Actually, a lot of leaders do it thinking they’re being helpful. Well, I don’t want to overburden this person, or maybe they’re not quite ready to take this on. I’ll just hold onto it. Well, all the times you make that choice, you look back over 50 days, over 50 weeks, every time you said, well, I’ll just hold onto it, you just stacked another thing on your plate, which means you’re probably not doing it as well as you could be. And there’s someone else out there that’s actually dying to be a part of contributing to where we’re going, but they’re not having the opportunity to do that.
Ryan Goulart:
Super insightful. Thank you so much, Kyle, for coming on. This has been very thought provoking. Thanks again. Well,
Kyle Sale:
Yeah, I appreciate being on. It was fun.
Ryan Goulart:
That’s it for today’s conversation with Kyle Sale. Personal transformation isn’t about a breakthrough moment. It’s a daily practice. It takes humility to admit what you don’t know, encourage to do something about it, whether you’re running a company or leading a team, change starts with how you show up. I’m Ryan Goulart, and as always, you are making the ideal real.
