Episode 207: Success Is a Numbers Game: Kyle Austin Young on How to Change the Odds of Your Goals

Most advice says work harder and keep trying. We put that to the test and reveal why so many smart teams still miss: they average their confidence across steps instead of multiplying their true odds. With award-winning strategy consultant and author Kyle Austin Young, we break down a simple, rigorous way to change results by changing probability—without needing a PhD or a spreadsheet marathon.

We start by exposing the averaging trap and building a clean success diagram: a left-to-right map of every step that must go right to hit your goal. Then we estimate the likelihood of each step, multiply to reveal real odds, and hunt for the failure modes stealing your probability. Kyle calls it “think negative” thinking: not doom and gloom, but a disciplined scan for what could go wrong—glitches, delays, weak offers, misreads—so you can de-risk them in advance. You’ll hear how he used this method to land a leadership job at 21 by neutralizing age bias, shifting interviews to future-focused plans, and mirroring team language drawn from their favorite books.

Inside this episode, we cover:

➡️ The 34% Trap: Why most leaders mathematically overestimate their chance of success and how to fix it.

➡️ The "Beard & Book" Strategy: How Kyle probability-hacked his way into a Director role at age 21.

➡️ Think Negative: Why identifying "failure modes" is the ultimate creative tool for CEOs.

➡️ Tuition Costs: How to view high-stakes mistakes as the price of your leadership education.

➡️ The Revenge Tour: Lessons in humility and strategic adjustment from trout fishing.

We dig into a nonprofit case where donations fell off a cliff. Agencies tried fresh stories, but a success diagram pointed somewhere less glamorous: a deliverability glitch that blocked a major inbox provider. Fixing the pipe beat rewriting the message. From there, we explore Hail Mary diagrams for stalled goals, when to pause versus quit, and how to stack smaller wins—bylines, relationships, proof—so big moves become high-odds plays. Along the way, Kyle’s stories about resilience, iteration, and the math behind confidence will give you tools to raise your odds in hiring, product launches, fundraising, and personal goals like marathon training.

If you’re ready to stop guessing, map your steps, and steal probability back from failure, this conversation gives you the playbook. Subscribe, share with a friend who bets on big goals, and leave a quick review to help more uncommon leaders find the show.

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Transcript

The Math Behind False Confidence

SPEAKER_00 0:00

Some people would even tell you, I think I have a 70% chance of accomplishing this. And even if they don't know the math, they're still, they would feel pretty good about that. 70-70-70. You do the math, which is actually multiplying 0.7 times 0.7 times 0.7, and you find that you have a 34% chance of being ready on race day. We don't expect you to be successful at school. I have made a career out of people coming to me saying, we feel great about this. This is gonna go really well for us. Look at our, you know, kind of our plan, 70-70-70, and I say, oh, you have a 34% chance of success. Interesting.

SPEAKER_01 0:39

Hey, Uncommon Leaders, welcome back. This is the Uncommon Leader Podcast. I'm your host, John Gallagher. So you've probably heard the advice before. If at first you don't succeed, try, try again. Well, my guest today, Kyle Austin Young, is going to tell you why that's some of the worst advice you could ever receive. Uh he's got a book out a new book, Success is a Numbers Game, Achieve Bigger Goals by Changing the Odds. And he's not just an author, he's also an award-winning strategy consultant. And he's written uh articles for major publications like Harvard Business Review, Fast Company, and Forbes as well. So I'm excited about having Kyle on the podcast today to talk with you and add value to you. I we had uh before we hit the record button, had talked about some of the things that uh we have in common with our consulting and some of the methodology. So this should be a great conversation. So Kyle Austin Young, welcome to the Uncommon Leader Podcast. Great to have you on the show. Thank you for having me, John. Call me Kyle. I will call you Kyle. You just never know. When you see folks, you got all three names on the front of the book. That's what we got to do. So is there anything there for you?

Childhood Lesson: Tuition For Mistakes

SPEAKER_00 1:38

Gave me such a common name, Kyle Young, that I had to make that adjustment when we went to print because there were so many others on the internet. Even here in Nashville, where I live, the country music hall of fame, its director's name Kyle Young. And once in a while I'll get a call confirming a tea time that I didn't make because it's him. You know, he called in, made a tea time, and they just typed in, we need to check this Kyle Young's tea time. They find somebody in the database and call me. And so I've thought about stealing him a couple times, but I've I've never done it. Yeah, never done that. So many different things.

SPEAKER_01 2:04

I mean, I remember I'm a junior, and so growing up as a kid, and my voice started to change, I would answer the phone, and my dad's friends would think it was him, and my friends would think it was me. I mean, it created quite the challenge, even just in simple things like John Gallagher, which is our names can be so unique and so val and so uh precious. So I'm I'm glad to have you on, and we will go with just Kyle. But I'll start you off ultimately. This is what it sounds like too. I'll start you off with the first question. I always start off my first time guests, and that's uh tell me a story from your childhood that still impacts who you are today as a person or as a leader.

SPEAKER_00 2:35

Yeah, I'm gonna be a little bit liberal with my interpretation of the word childhood. I'm gonna say my very first job out of college, I think I was 21 years old. I was really fortunate early in my career. I tell the story in the book of how I got this job. It was a pretty remarkable accomplishment, but I ended up as the 21-year-old product development director at a health organization. And that was a pretty ambitious thing to accomplish. I'm leading people in their 50s, 60s, 70s. This was a long time ago for me, but still, it was a challenge and there was a lot of scrutiny. A lot of people saying, even after I got the job, I don't know if we should have hired somebody so young, so inexperienced to lead a department in this health organization. So I was under a lot of pressure and I was committed to doing everything I could to not make a mistake because I knew there were people who would be happy to see me gone just out of suspicion that I wasn't gonna be able to do the job well. And very early in that appointment, just in the first few months, I made a really significant mistake. We had a contractor who was working in graphic design, and my predecessor had communicated to me, or at least this is how I understood it, that we were working with this guy on a project basis. So his fee had been paid, and now he was gonna stick with us through the end of the project. Well, I would later find out that we were actually working with him on an hourly basis, not a project basis. And so we were making decisions about the work we allocated to him, thinking he had already been paid for this project, thinking everything was okay. I inherited all these agreements, and I should have taken the time to read every single one of them personally and confirm that. I didn't do it. That was a mistake. So I ended up getting an invoice for this guy, you know, this is about 15 years ago, six thousand dollars. It's not in the budget. And I've been on the job for about a month, and this was again all just because we thought he was project-based, he was hourly based, and so we we allocated some work to him that we probably shouldn't have. So I reported directly to the CFO of this organization, and I knew that I was gonna have to face the music. I didn't have the money to pay this bill. So I walked through the office down at the CFO's office, knock, knock, knock. He's sitting there looking at his computer, does kind of a slow turnaround, and he said, you know, what's going on? Didn't expect to meet with you today. And I said, Well, I I've just got to tell you the truth. We have an agreement with the contractor that I misunderstood. I should have confirmed it myself, but I I didn't. And I owe$6,000 that I don't have in the budget. And he sat there for a minute, got really quiet, and I thought, well, this is it. You know, this has been a good run. Uh, you know, I I got this job, it was pretty incredible, but now I'm already gonna be fired, it's already over. And he said, You know, Kyle, you just finished school, so you're used to the idea of tuition. And he said, What tuition basically means is when we learn something, there's usually a cost. And I want you to remember that as you do this job, that there's usually gonna be a cost to the things you learn. And I think it's important to understand that because when you realize what it costs, you're less likely to have to learn it again. So we're gonna call the$6,000 invoice tuition. Go read all the agreements, make sure you know what your predecessor actually agreed us to, because he said I I might not agree with some of the agreements that he made. So please go take a look at that, understand them better, and let us know if we need to make any changes. And that walk back from the CFO's office to my office was one of the most I mean, yeah, I thought I could fly at that point, you know, talk about a weight lifted. But that idea that learning comes with a cost, we can call that cost was exciting for me because a lot of times when I make a mistake or when I, you know, learn something the hard way, as I often do, there's maybe a shame that comes with whatever the cost was. And so I I still hear that voice in my head of a a leader who was in my life about 15 years ago saying, you know what, that's tuition, and we don't need to explain it away. We don't need to, you know, go eat some ice cream and try to numb the pain of it. Just feel it. There was a cost to what we learned today, and that's in some ways a picture of the value of what we've learned. So let's try to do what we can to make the most of it. I love that.

SPEAKER_01 5:58

Not all leaders be that empathetic right at the start, but for you to get that lesson early on, it's pretty powerful.

SPEAKER_00 6:02

I was very fortunate, and it put me in a position where I was able to continue in that organization for a while. There were there was a layoff later. This was uh an organization that went through some layoffs. I ended up at another job, went through some layoffs, but ultimately that early acceleration of my career is what allowed me to start consulting and you know, later go on to write some of these articles, write the book, and again, I'm very thankful for that.

Debunking Hard Work And Try Again

SPEAKER_01 6:20

Love that. And as we go into that, I think we might go into how you got that job to begin with as part of the story that was in there as well. Have you still had the beard? You did read the book carefully, my goodness. I did, absolutely. Hey, no, no doubt about it. So, and I go back to that kind of how we teed it up here a little bit, and you said some of the two things. Worst advice, if at first you don't succeed, try, try again. And the other is hard work is the key to success. Now, there are more inside of your book, but those were two that I wrote down that I'm sure that I had heard before uh that you keep going. So dispel that and tell me why that's the worst advice we could possibly receive.

SPEAKER_00 6:55

Well, I'll lean into the idea first of just that hard work is the key to success. I think that people have, especially in the last few years, it's been a common headline for different business publications. People suggesting that all these different things are the number one predictor of your success. Your emotional intelligence is the number one predictor of your success, your you know, your habits are the number one predictor of your success, your work ethic is the number one predictor of your success. Well, I think the number one predictor of your success is your odds of success. I'm trying to get a job like you just described. And so now I need to, you know, get an interview and then ultimately get an offer. And, you know, those different skills could be a part of that, but how is the hiring squad going to be able to identify and perceive my resilience? Like, are we really sure that that's the number one indicator of my success? Or do I have an opportunity to ask the question, what's in my power that could put me in a position to get an interview? What can I do to try to turn that interview into an offer? I think we can usually be a lot more focused than that. So when we tell people to work hard, I mean, my attitude is if you're working hard at the wrong things, what should we expect to come from that? If we have somebody who's working in a fast food restaurant currently, their goal is to be a millionaire and they're working really, really hard. Is there any way that hard work turns a minimum wage salary into a million dollars? Now, I still, you know, I still believe in integrity. I maybe, maybe that hard work earns favor with the person who owns the company. Maybe he writes them a great letter of recommendation or she writes them a great letter of recommendation and later they get the job that could actually make that dream a reality. But I see a lot of people working very hard who are frustrated by the results they're getting, and I'm looking at their model saying, I don't see how you thought hard work was ever going to turn this model into what you you're telling me you want. So I think that's part of it. You mentioned the idea that if at first you don't succeed, try, try again. I'm actually a pretty big fan of the power of multiple attempts, but I do think that we have an opportunity to optimize our odds of success, and in doing so, we can not have to try as many times. You know, in the book I tell the story of Thomas Edison, he's in a race to invent a practical filament for the incandescent lamp. If he can pull that off, he's gonna have some patents that are gonna change the trajectory of his career. But he needs to find a filament that can get hot enough to glow without catching on fire or burning out really quickly and not being worth the hassle. And the way that he outcompeted the other inventors of his day is he experimented with 6,000 different plant materials and he ultimately found one that worked better than the others, carbonized bamboo. So I think there are goals where trying more than once is a big part of it. But what I try to teach people how to do in the book is optimize their odds of success. Instead of approaching things with the idea of just kind of dumb luck, we'll try and we'll see what happens. We'll try a bunch of times and we'll see what happens. I want them to have a sense of whether this is a goal where multiple attempts might be enough to get them over the hump. You know, if the odds of success are one in a hundred thousand, are you gonna try a hundred thousand times? You know, that's not a good model. And at the same time, if we had an opportunity to optimize your odds where maybe you could get there quicker, you're gonna have more opportunity for that success to ultimately change your life afterwards. I could tell the story of compound interest and show that, you know, when you're even at the halfway point of maybe a month of compounding and kind of the common example of doubling a penny every day for 30 days, you have a pittance. Almost all of the money comes in like the last five days because that's how compounding works. So I want to help people succeed faster. I don't want them to just go out there, try some stuff and see what happens. I love that.

Why Write A Math-Lite Strategy Book

SPEAKER_01 10:01

I can't wait to talk and dive into some of the math of that as well and hear your personal story about how you used it, probably before you uh did before you even uh were aware of the framework that you were using. Sure. Let's kind of take it a step back though. So you so you brought the book out in November 2025. You've been writing articles for a long, long time, but to put this into ultimately print in terms of a book, who did you write the book for and why did you choose to write it now?

SPEAKER_00 10:23

I was really fortunate. I had a few offers for this. I ultimately chose Hay House Business. They were people who I just felt like understood the the message of the book. This is a a weird book, right? A lot of people don't want to talk about math, particularly in the United States and probability too. I think about the school system. So many of us took classes on like trigonometry, which is important, but it's pretty specific in terms of which careers you might actually use trigonometry. You know, maybe an architect, maybe an engineer. I'm not either of those things. But I think that our odds of success impact every single person every single day. And so I wanted somebody who shared, you know, an interest in that, a passion for that, and was willing to kind of empower me to write the book that I felt like would ultimately explain it. So I take some risks in this book, and and it's there's a lot of stories. There's uh there's some math, and which you know it's funny, I just had an opportunity to maybe be featured in a a book club for a museum of math, and it would have been a neat opportunity. I got the email back from them. They said, you know what, we decided no, your book doesn't have enough math. And I kind of chuckled at that because I've had other people say, you know, I was intimidated by the amount of math, so who knows? You can't please everybody. But that was part of how I chose that publishing partner. It felt like they understood the vision and wanted to help me bring it to life, and I'm very thankful for that.

Dedication, Resilience, And Iteration

SPEAKER_01 11:32

It's funny because I haven't I got another interview this afternoon, and I know in the appendix of this book that I'm talking about, they got integrals and they've got limits and they've got the sum. And I'm like, dude, I'm going back because I am an engineer, and I start to have some bad memories of going back into college and going through some of those numbers. So there's a simplicity that I love about what your math is, and sometimes we can overcomplicate it, no doubt about it. But hey, let's learn more about your personal side of writing this thing as well. So I I'm gonna start right off with a dedication. I think it's fun. You dedicate it to the people who inspire me. Chief among them, your wife, your children, and the red-hot chili peppers. Okay, I gotta know what's going on inside of that dedication.

SPEAKER_00 12:12

Well, there were a few things that always meant a lot to me, but I mean I'm gonna take for granted that you can understand why I would be grateful to my wife and children. But my my children in particular, really, that's not a throwaway line. I have a daughter who was born deaf, who got cochlear implants to give her access to sound. Thirteen days after those went in, they hadn't even turned them on yet. They were waiting for the inflammation to die down. We get a letter in the mail saying they've been recalled, saying that that those devices are known to more than likely be faulty, or that there's a high probability that they will become faulty over time. So she ends up going through that entire surgery again in the middle of a pandemic, it kept getting delayed. So those are people who inspire me. That there's been tremendous resilience, and uh I even yesterday just at the park with her, was reminded of just what an opportunity we have to experience joy and you know, live in the moment despite some of the challenges in our lives. So that's not a throwaway thing at all. The red-hot chili peppers, I tell a little bit of a story of them in the book, but there's some people who are well, a lot of people would maybe even consider them an overnight success, but they're one of many examples of people who had, you know, three albums that went largely unnoticed, and then they ultimately made some changes. They didn't just, it wasn't just like you said, it wasn't just try, try again. They made changes to try to optimize their odds of success. They switch up who they have on guitar, the next album hits platinum, they later sign with a larger record label, the next album hits seven times platinum, and I think that is a story that in some ways exemplifies it. There is going to be typically an iterative component to this. We are probably going to need to try more than once for really big goals, but when we're making adjustments as we go, we're improving our odds and we can put ourselves in a position to ultimately get what we want.

Building A Success Diagram

SPEAKER_01 13:47

Love that. And I appreciate you sharing about your daughter's story as well. I think those I often find as I read the books of the folks that uh I'm interviewing, the uh dedications, the introductions, and the conclusions or acknowledgments are some of the most fascinating stories that uh come along with the book uh and the content that's inside the book. But that's what we're here to talk about, really, is the content and how uncommon leaders can utilize some of the framework that you talked about. So inside of your book, you said your your odds of accomplishing a goal is the odds of each step multiplied together. So let's do a math class and help me understand kind of the framework of what you're saying there with regards to that.

SPEAKER_00 14:25

Yeah, I'd be happy to. I think this is one of the most important things I can teach you, at least about understanding your odds, maybe not about optimizing them. But let's just use the made-up example. Let's say that we're interested in running a marathon. It can be any amount of distance, maybe you want to do a 5K, whatever. But let's say you want to do a marathon, just that's a concept we're all pretty familiar with. So you hire a running coach and she says there's three things you're gonna have to do in order to be ready on race day. For this period of time, you're gonna have to eat, sleep, and train the way that I tell you to. So if I were working with somebody who wanted to run a marathon, that'd be kind of an odd project for me as a business strategy consultant, but we could do it. I would create what I call a success diagram, and I would list out the three things that have to go right for you to get what you want. You're gonna have to eat, sleep, and train according to these regimens that your running coach is gonna create if you want to be ready on race day. So there's three things that have to go right. What I would then encourage you to do is check in with yourself and ask the question, how likely do I think I am to be able to do each of these three things? And for our purposes, I want to keep it really simple. Let's just say that we think it's 70% across the board. 70% chance I'll eat the way I'm supposed to, 70% chance I'll sleep the way I'm supposed to, 70% chance I'll train the way I'm supposed to. Well, this is where most people fall into a really uh detrimental thinking trap. It's called averaging. How it works is as humans, if we set a goal, we instinctively try to get a sense of what's going to be expected of us, and we instinctively try to acknowledge whether or not we think we have what it takes to get each of those things. Where the mistake comes in is if we feel good about the individual steps, we feel good about the goal as a whole because we're averaging. 70, 70, 70. Okay, some people would even tell you, I think I have a 70% chance of accomplishing this. But even if they Yeah, yeah, sure. And even if they don't know the math, they're still they would feel pretty good about that. 70, 70, 70. You do the math, which is actually multiplying 0.7 times 0.7 times 0.7, and you find that you have a 34% chance of being ready on race day. We don't expect you to be successful at this goal. I have made a career out of people coming to me saying, We feel great about this. This is going to go really well for us. Look at our, you know, kind of our plan 70, 70, 70. And I say, Oh, you have a 34% chance of success. Interesting. And this is a pretty important project. So we're sure we want to, you know, bet the future of the company on those odds. Are we positive about that? So we put people in a position where we help them realize that uncertainty has the opportunity to derail even plans that intuitively feel pretty good to us. So I wrote a book where I teach a framework called probability hacking, which is once we get a sense of what our odds are, we try to change them, we try to improve them and hopefully put them in a position where we can turn a predicted failure into a predicted success and maybe get a better outcome. Love that.

SPEAKER_01 16:50

And I love that you're talking about and get a better outcome, that probability. Now, you've got a personal story that you talk about early on in your book. This hence the beard story that helped you get a job that you probably never should have gotten. Uh tell me how you use this uh probability thinking to get you there.

Probability Hacking In Job Hunting

SPEAKER_00 17:05

Yeah, great segue. So again, how do I help people change their odds of success? I call it probability hacking. And in many ways, the foundation of it is something a little bit counterintuitive. I find that when we're pursuing a big goal, the advice we typically get is we need to think positive. Don't worry about what can go wrong. You know, if it's meant to happen, it'll happen, whatever they might tell us. But but think positive. I actually encourage people to do the exact opposite. I literally tell people that we need to think negative. And the reason for that is we need to identify the potential bad outcomes that could happen instead of what we want. You know, if you flip a coin, let's say you need it to land on heads to win the game, there's a 50% chance you're gonna win the game, but there's a 50% chance you're not gonna win the game, and that's because it might land on tails. Tails is a potential bad outcome. Now, I don't know how to rig a coin toss, but in life, we have an outcome we want, we have some outcomes that we don't want. And a lot of times one of the most straightforward ways to change our odds is to de-risk the bad outcomes. If we can identify that, you know, the coin lands on tails, we ask the question, what can I do to make that less likely we can change our odds of success? So just like you said, when I was 21 years old, had graduated college, I was applying for jobs, and I wasn't very excited about the entry-level positions I was seeing. It just wasn't very inspiring to me. And so I wanted to see if I could skip a few rungs in the corporate ladder. So I applied to be the product development director at this health organization, which again would have put me in a position where I was managing people in their 50s, 60s, 70s. It was going to be pretty uh, you know, ambitious for a 21-year-old. Are you tired of being tired?

SPEAKER_01 18:28

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Sponsor Break

De-Risking Interviews: Beard And Plan

SPEAKER_00 18:57

Now, let's get back to the episode. They gave me an interview, which was great. Uh they gave me an interview, and so at that point there was only one more thing that needed to go right. I just needed a job offer. So I sat down even at that time and tried to identify what were the potential bad outcomes that could keep me from getting what I wanted, because that was where I was gonna have an opportunity to maybe change my odds. So the first one that I perceived was I might walk into the office and they might not hire me because I looked so young. They might take one look at me and say, this kid can't manage somebody 50 years older than he is. And so I thought, what can I do about that? What can I do about looking too young? And the creative solution I came up with was I was just gonna grow a beard and I've still got it. I need a haircut right now, like we mentioned, we've had some weather and now it's throwing some schedules around. But I just grew a beard to look a few years older and take the edge off of that concern. What what if the first thing they saw when they looked at me wasn't somebody who looked so young that it was a concern? So that was what I did about the first potential bad outcome. The second one that I identified was what if they were concerned about my lack of experience? You know, that would be a valid concern. I didn't have a deep resume. I just graduated college, and I wasn't gonna lie, and I certainly couldn't conjure up experience between the time I got the interview and the time the interview was gonna happen. So what I ultimately did was I just decided I was gonna try to redirect the conversation to be more future-oriented instead of past-oriented. So I went out and typed up a plan for everything I would do to turn this department around. I it was so thick I had to spiral bound it. It was a book, and I took it with me and I gave it to the people I interviewed with. And when they would ask questions about my past, questions like, you know, why or you know, to tell us about a time when you've had an experience that relates to this. Well, I didn't necessarily have an answer. So I'd say, well, as you can see in the plan, my vision for the department in this area is here's what we're gonna do. We're gonna do this, this, this, and this. And it was a way for us to have productive conversations that felt rich and meaningful, but ultimately were an opportunity to kind of de-amplify my lack of experience. The third and final potential bad outcome I envisioned was just they might be concerned I couldn't fit in with the team. He's younger than them, there's a generational gap. Are they gonna want to listen to him? So one of the things that I did was I asked an existing team member if they'd read any books lately as a group. And she told me the team, told me a few titles. I went out and read all of them. When I showed up for the interview, I could make inside jokes, I knew the company's jargon, I knew the frameworks that they were familiar with, and so I could have conversations that made it feel like I'd been reading their mail because I'd been reading their books, right? I we really were on the same page. I remember there was a book at that time, it was like 15 years ago, it was called The Wuffie Factor. And it was a book about how brands generate social capital. And not a lot of people are talking about that book today, as far as I'm aware, but I remember sitting in a group interview, and it was me and candidates who were just much more experienced than I was, quite a bit older than I was, and somebody suggested an idea, and I said, I think that's an idea that could get us a lot of Waffy. And I remember looking around the room and their eyes were bugging out their heads. What on earth did this did this kid just say? Is this some slang term? What on earth is is Waffee? And I look at the existing team members though, and they're just like slapping their knees. Like they love it, they know exactly what I'm talking about. They've just read that book, we're on the same page. So I end up getting that job. I beat out people who had so much more experience than I did. I became the product development director at a health organization. And again, some layoffs would derail my career years later, but ultimately the time that I did spend in that job allowed me to get an even more prestigious leadership position after that first layoff. And then the second layoff is where I finally got fed up and said. I need more diversification in my life and use the connections and experience from that job to start consulting. Love that. I appreciate you sharing that story.

SPEAKER_01 22:06

It makes me smile just as I read through it. Now, so you brought that framework, you bring that into consulting. When you go in and work, and look, uh, you talked about inside of your book that took a while, even and of itself, to get you going with consultants, because now you don't have consulting experience. And so you've got to take that out that they have and say, this guy hasn't done consulting work before. What are we going to do? So you're using your own framework there. But tell me a story about how you've had a client and you don't have to share in terms of name or anything else, but uh a big success story that you've had with a client that you're proud of that you've done.

Consulting Wins With Nonprofits

SPEAKER_00 22:36

You know, I had one recently that I think really speaks to the opportunity that companies have to create success diagrams and use it to identify problems and change their odds. I got brought in recently to work with a nonprofit that helps people dealing with homelessness, addiction, even victims of human trafficking. And they're in a part of the United States that has tremendous need. And so they're able to pay for about half of the operations of this organization through some thrift stores that they own. And we're talking tens of millions of dollars. That is a pretty big impact that they have. But that's not enough for them to keep up with just the amount of need in the area where they are. So they also, in addition to the thrift store revenue, they have donors, and the donors help supplement some of that income. And so they have a newsletter, and that's a big source of donations for them. And they'd seen growth for years, but over time that growth started to actually drop. It didn't even really plateau, it just turned the corner and started going the other direction. And they weren't really sure what to do with that. It felt very sudden. And so they made a guess, and their best guess was that maybe their content was getting kind of stale. Maybe people just had heard the same story over and over of transformation, and for whatever reason it wasn't inspiring them anymore. So they were bringing in different agencies to try to reinvent the content strategy. It wasn't working. Finally, they brought me in, and I was hired under those parameters. It was, you know, take a look at our content strategy, see if you can reinvent it. Maybe we can find a way to re-engage this audience that seems to have kind of lost interest in us. I did what I do, which is I created a success diagram of what's it gonna take for somebody to go from newsletter reader to donor. What's the actual list of things that has to happen in order for that to come true? And the first thing on the list was we had to make sure that people were receiving the emails. If for any reason they weren't actually seeing what we were saying, it wasn't gonna matter what we were saying, you know, in terms of the actual content. And so I looked into the technology and found that there was a glitch. There's a glitch that had been made about a year before I got there, year and a half maybe. And because of that, everybody who had a certain inbox provider, a very popular provider, wasn't even seeing these newsletters. And that unfortunately wasn't something that had been caught. They'd instead been trying to reinvent the content strategy. So I changed the technical issue. People started receiving the emails that had already been created, and we were able to start turning that around. And it didn't end up having anything to do with what they hired me to do per se, in the sense that it wasn't that we reinvented the content strategy, it was that we created a success diagram and asked the question what's everything that has to go right for us to get what we want? What are the things that could go wrong instead, the potential bad outcomes? And we just went through and systematically de-risked this goal, found what the issue really was, and were able to, you know, thankfully create some meaningful change. Love that.

SPEAKER_01 24:59

I love to hear that story. And I love using a framework for something that has that much uh value, not just in terms of the business side, but also in the impact that can have in the community and and the world, frankly, uh as you go through that. Because I do believe many times organizations uh truly have great intent as to what they want to do, whether it's in product design or whether it's in some service design or or something they want to provide to the community, uh, and they and they don't go through some of those potential, my word, uh that would use potential failure modes. Sure. And ultimately mitigate the risk of those failure modes to be successful. You use the term success diagram. While I don't obviously we don't have time to go through the entire, that's really the essence of the book is inside of that success diagram. Give us a quick synopsis synopsis of what a success diagram is uh and how folks use it.

How To Map And Steal Probability

SPEAKER_00 25:49

Yeah, identify what's gonna have to go right in order for you to get what you want. Just list them left to right as if they were, you know, steps on a map, draw a line connecting them, and then at the far right, write the goal. Write exactly what it is that you're after. If you want to then start trying to estimate your odds of success, you're gonna ask the question, how likely do I think I am to get each of these things? You can do some multiplication there. That's an estimate, but you can certainly use it to try to understand at a deeper level what your odds of success are. And then beneath everything that has to go right, start brainstorming what are the things that could go wrong and start trying to identify what are the bad outcomes that are currently hogging some of the probability that I want. We can understand probabilities similar to how we've traditionally understood matter. We've all heard the phrase that matter can't be created or destroyed, it can just be transferred and rearranged. And that's true here. I can't wish better odds for you. I can't conjure them into existence, but I can go to the bad outcomes and steal some of their probability and bring it over to our side.

SPEAKER_01 26:42

Love that. I love that. I think it again, it is that simple and it is that difficult to implement in terms of uh putting that through. Now, many times organizations get frustrated, individuals get frustrated as they use a tool like that and they'll quit. And you talk about this in the book as well, is that sometimes we quit too soon. You have a tool you also referred to as the Hail Mary diagram, which kind of flips this negative thinking uh on its head in just a little bit. Tell me about the Hail Mary diagram and how it works.

Quitting Versus Pausing: Hail Marys

SPEAKER_00 27:08

Well, one of the reasons I believe in diagrams to begin with is I think there's a value in taking things out of our head and putting them onto a sheet of paper. I think that creates opportunities for us to maybe be a little bit more objective. I think it creates opportunities for collaboration. We can now show our thinking to other people, you know, have a shared text for giving advice and receiving advice. So that's in some ways the motivation behind it. The Hail Mary diagram is kind of the reverse. It's what are the things that, if they happened, would turn this around? What are the things that if they went right would save the day? And I encourage people to make a list of those. And I encourage people to write down how likely they think each of those things are, and then you have an opportunity to actually look at them and say, do we really feel like this is something we should continue to pursue? Or is this a goal we should push pause on for the time being? I'm I'm not a big fan of quitting goals. I tell people that I think they should consider sometimes pausing goals. And I say that because it's entirely possible that a goal you're pursuing today is something that will be more attainable in the future. Your odds might change as time goes on. I give a few examples of that in the book, but a very you know simple, short one is just the creation of the book. I had the goal of doing this long before I actually did it. First, I went and accomplished smaller goals like writing for Harvard Business Review, like you know, getting some of the credentials that I have and refining my framework, working with doctors out of Harvard Medical Schools and big technology companies and all these different organizations, it helped kind of build my resume as a consultant. And one of the things that I also did was I took some contracts with literary agents who weren't necessarily the best paying opportunities I had at the time, but I knew what my goal was, and I knew that if I had those pre-existing relationships, this was going to be easier. So after years of doing that, when I decided to actively pursue the goal of getting a book deal for this, it really wasn't that challenging. I'm very thankful for it, and there were years of work that went into it. Don't miss that part. But when it was time to actually do it, it was pretty easy. I already had a relationship with literary agents, I already had a platform, I already had a lot of demonstrations of my expertise, and so the rest of it wasn't really all that complicated. So yeah, Hail Mary diagram, write down everything that, you know, could save the day, and let's see what we've got. Let's see if one of those are things that we could try to invest in, try to make it more likely to happen. I tell the story in the book of a restaurant that's going out of business, and really their only hope was just a breakthrough publicity moment. And there was a local food reviewer who would go to different restaurants, and if he reviewed your restaurant, it was going to be a breakthrough. And sure enough, he comes into this restaurant. The next day the owner shows up and there's a line around the block of people waiting to try this food. He said overnight they went from the problem of they didn't have any customers to they didn't have enough staff. They had to try to figure out how to serve all these orders. And what an incredible, you know, moment. How did this happen? Well, unbeknownst to him, he finds out later that a staff member who I think was maybe his daughter-in-law, she reached out to the guy and said, Would you come in and review the restaurant? Just hoping he would look at it. He never responded, but he did see it, he did do it, and it did change the fortunes of this restaurant. So sometimes it's worth considering what are the long shots that might be worth taking because a lot of times we've spent a lot of work just to get to that point. So I want people to be pretty confident that they're out of options or at least that they're ready to click pause before they actually do it. So cool.

SPEAKER_01 30:07

Love that story too. I read them reading that in the book in terms of saving the restaurant and some of the unique things that happen. Hey, I want to know this is the book test that I think about when I when I chat with authors. Somebody's gonna read your book, they're gonna set it up on a shelf just like one sitting behind me, and it's gonna kind of see they're gonna see the binding of it a year later. When they see that binding after they've read it, and maybe it's shortly after that, whatever that is, what do you want them to think and what do you want them to do ultimately after reading your book?

The Two Hidden Numbers Of Goals

SPEAKER_00 30:33

Well, I want people to understand that every goal that you're pursuing has two hidden numbers attached to it. There's your odds of success and your odds of failure. And I think that we have an opportunity that has not really been taught to us for the most part, to understand our odds at a deeper level. And I think we have an opportunity to change our odds. And so that's the number one thing I want people to realize is if you're pursuing a goal that's important to you. Maybe it's an initiative in your church, maybe it's a project in your business, maybe it's something, excuse me, within your own family. I want you to recognize that we don't have to let uncertainty have as much power as possible. We can take some of that back and we can do what we can to demonstrate how much we value this goal by trying to ultimately change our odds. And if we do that in the context of one goal, we might change our outcome. If we do that in the context of several goals, we almost certainly will change some outcomes, which can ultimately change the trajectory of our career. If we do that over the course of a lifetime of goals, I mean that's something that could really even change your legacy. It can it can result in a very different life if you're winning more and losing less because you're paying attention to your odds.

SPEAKER_01 31:32

Amen. Being intentional about that and addressing those uh and what they might do to bring you success. Absolutely. Thank you for sharing that. Kyle, I knew our time was going to go fast. I want to ask you kind of a one question again, back to uh some of the bio that I read about you at Nashville, Tennessee. So I have an assumption, but it also says you like to fish. I do like to fish. So what's fishing? Well, you bass fisherman, you trout, what is it? What is it that uh brings you joy?

Trout Fishing, Humility, And Iteration

SPEAKER_00 31:53

You know, I grew up in in Oklahoma where there's a farm pond every hundred feet. And so I grew up bass fishing, and largemouth bass fishing is the easiest thing in the world. You tie on a lure, these fish are just manic, and so the second they see it, they attack it. And it's a lot of fun, but it's also I learned later pretty easy. I thought I was really good at this. I thought I knew how to fish. Then I come to Tennessee, it's all rivers, it's not farm ponds. The fish are all hiding under a stick in the river, wants to get you hung up. It's a totally different experience. They had a winter trout stalking program, and I decided I was gonna try to figure this out, and it was kind of fun. I went out there and I got skunked my first seven attempts. I didn't catch anything in seven tries when I tried to transition to trout fishing. I'm getting hung up right and left. Terrible experience. But it was also just kind of a call to humility for me. One of the nice things about trout fishing is people were keeping what they caught. You don't keep the largemouths as much. And so you just look for somebody who had a good stringer of fish, and I just started going over to them and saying, What are you doing? What are you doing? And I asked question after question after question, and I changed my gear and I changed my approach and I changed where I was standing and I changed the time of day I was showing up. And when it was all said and done, I finally got my first one. That was pretty cool. And I decided I was gonna go on a revenge tour. And so there were five different locations in town where they stocked fish. I'd failed at every single one of them. I went back to every single one of them and I caught a fish. And I've actually got a video of when I caught the fish at the final place, and now I'm a great trout fisherman. So I do a little bit of everything, I had a lot of fun with it. You know, even if I don't catch anything, it's nice to just be out by the water, calms me down a little bit, and I'm always thankful for that.

SPEAKER_01 33:17

I hope you're that sounds like a great outcome as well. You're probably using success diagram for uh your trout fishing as well to get better at it. And you're right, sometimes the outcome is not just catching it, it's it's enjoying the experience that's absolutely there. So, Kyle, I've enjoyed this. Where can folks learn more about you, connect with you, and ultimately where do you want them to go to get the book?

SPEAKER_00 33:37

You can get the book anywhere, Amazon, Barnes Noble, Target, directly on the Penguin Random House website. If you want to connect with me, I I have a website, you can go to kyleustinyoung.com. But what I've really enjoyed out of these podcast interviews is I one time just kind of said, not really even thinking about it, find me on LinkedIn. Well, some people did, and I woke up the next morning to a bunch of people sending me messages saying, hi, I have a question about this, that, or the other. I wanted to connect about something. So I started saying it on every interview, and it's really become one of the hidden blessings of this experience has been how many people I've gotten to connect with because of that and actually have conversations with. So I'm Kyle Austin Young on LinkedIn. Would love for you to just find me there, send me a message, would be happy to connect with you. I think I've replied to everybody who's reached out, everybody that I'm aware of, and I intend to keep doing that.

SPEAKER_01 34:17

Kyle, I love it. I'm gonna give you the last word here as we finish up. Question I always ask my first-time guests as well. And I know you've got a message to share, but I'm gonna give you a billboard. You can put any message you want to on that billboard. What's the message you're gonna put on there and why do you put it? Why do you put it there?

Where To Find Kyle And Final Billboard

SPEAKER_00 34:32

Yeah, it's gonna be a confusing billboard if you just drove by, but I would tell you to think negative. I think that there's this fear that we need to run away from the things that could go wrong because if we identify them, it's just gonna make us sad, it's just gonna demotivate us, it's just gonna be something that causes a lot of anxiety. I find that there's a tremendous freedom on the other side of that fear. If we identify, you know, if I'm training to run a marathon and and I'm worried, what if there's some bad weather like I've dealt with that makes it hard to go run? I would say, great question. What if that happens? Well, let's sit with that for a minute. Do we need a gym membership so that you can train inside for the next few months in case something happens? What if my schedule gets derailed? Well, do you need an extra pair of running shoes to keep in the car in case, you know, there's a gap in your schedule and we need to make the most of it? Do we need to train first thing in the morning before the demands of the day catch up with us? So I think that what if thinking can be really appropriate if we sit with it long enough to find a creative solution, change our odds of success. And then there's a point where we say, all right, I've done what I can do. Now it's just time to take the journey and we'll see what happens. It might go well, it might go poorly, but we can be confident that over the course of our lives, because our odds are optimized, we're going to be experiencing some of the success that we want. Kyle, I've loved that. Think negative.

SPEAKER_01 35:38

An uncommon response, certainly from an uncommon leader. Kyle, I have truly enjoyed our time discussing that. I appreciate you adding value to the listeners of the Uncommon Leader podcast. I wish you the best in the future, okay? Thank you. Hey, Uncommon Leaders, thanks for listening all the way through. I'm sure you enjoyed that conversation. I know that I did. Think negative. Something you don't hear all the time on the Uncommon Leader podcast, but in context, it absolutely makes sense. How do we ensure that those negative things can be overcome, that we can mitigate those risks, and put change in to avoid those happening and help us to reach the positive outcome that we're looking for. Hey, if you'd like this episode and know someone who needs to hear it, please share it with them. That's how we get it into more hands of other listeners like you to hear the Uncommon Leader podcast. And certainly, if you're willing to, you can put a five star review out there on Apple Podcasts or Spotify or whatever platform you listen to the podcast on a regular basis. Until next time, go and grow champions.