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Leadership Lessons through Chess with Elliott Neff, Founder and CEO, Chess4Life


Elliott Neff S2F Podcast Image

It might seem like chess has nothing to do with business. But Elliott Neff, Founder and CEO of Chess4Life, blows that misconception out of the water.

He’s built a business that teaches kids how to play chess, yes, but it equips them with the skills of life. And in this, there are lessons for us as leaders and entrepreneurs.

Plus, Elliott is a national master in chess, so we definitely wanted him on the Stride to Freedom podcast! Check out his full interview on episode 58 and read the main takeaways here.

Elliott’s Journey: Chess Master to Business Owner

Elliott learned to play chess with his dad. At just eight years old, he fell in love with the game and dedicated himself to improvement. Between the ages of 12-16 years old, he committed to practicing chess four hours a day! Talk about commitment.

This dedication and passion for the game earned him the position of High School State Champion. He wanted to support his team, so also began coaching and mentoring other chess players. This organically grew into many opportunities to coach players of all ages.

At this point, Elliott never expected to make a career from chess. But he received so much positive feedback from parents—chess helped their kids focus on their studies, make better decisions, and become more resilient.

At that point, Elliott knew chess can make a difference in people’s lives. Chess4Life was born out of that goal to positively impact others through the power of chess.

Life and Business Lessons from Chess

Chess is a game of strategy and decision making. You start by coming up with a plan based on the rules, your skill, and chess strategy. But you’re playing against someone—things change and there are endless possibilities. So, you need to pivot and be open to a new goal.

And this is the same for business—you have a plan, a strategy, but are continually adapting it and improving things to make it better.

There are many other parallels between business and chess that Elliott made throughout the interview. Here are two big ones:

  • FAIL is an acronym for “First Attempt In Learning.” In chess, life, and business, use your “failures” as learning opportunities to improve.
  • We’re better together. Each chess piece has its role—the Queen might be the most powerful, but they all work together and bring something unique. This is the same for business—embracing difference and learning to collaborate is so important.

Pivoting During a Pandemic: How to Scale a Business

Pre-pandemic, Chess4Life held in-person chess clubs and classes, primarily in the Greater Seattle area, where Elliott lived at the time. But in those first weeks of the COVID19 pandemic, all in-person meetings shut down.

Elliott and his team had to pivot—fast. In just three weeks they were able to make a massive pivot to online meetings and virtual classes. This has continued to grow over the last years, helping Chess4Life scale and grow to reach more people all over the US.

The pandemic was a catalyst for change. But how can companies pivot or scale without such a catalyst? Here are some of Elliot’s ideas: 

  • Cut the fluff. Organizations tend towards inertia—we’ve always done it this way, so let’s keep doing it. Instead, fix problems by simplifying and eliminating red tape.
  • Have an extremely clear vision. Be singularly focused on what you want to achieve and ensure it aligns with your company’s big goals and values.
  • Empower everyone to make changes. Change is not the responsibility of just one person—everyone needs to be part of it to make it work. So, empower employees to be creative and autonomous in their decision making.

Elliott had so much more to share with us during our interview. It made us want to go out and start playing some chess! The lessons learned in chess, life, and business are invaluable to all business leaders and entrepreneurs.

Catch Elliott’s complete interview on episode 58 of the Stride to Freedom podcast. You can also connect directly with Elliott on LinkedIn or see what he’s up to with Chess4Life.

If you want to know more about us at Stride Services, contact us today.

The Stride for Freedom podcast is hosted by Stride Services. Contact us today to learn more about our back-office accounting and CFO services, including stable and efficient bookkeeping, cash flow management, and actionable analytics for growth.

You’ll enjoy this Podcast episode with Elliott

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We are fortunate to have Larry available to spend time with us on this edition of Stride 2 Freedom. If there is a speaker you’d like us to interview, click here and let us know. Stay well. Stay safe. Stay healthy.

Show Notes and Links From Episode:

Elliott Neff: LinkedIn

Chess4Life: Website/LinkedIn

Elliott Neff: Top 10 Takeaways

Elliott Neff: elliott.neff@chess4life.com

A Pawn’s Journey:  Amazon Link

And if you want to know more about us at Stride Services, contact us today. We offer back-office accounting and CFO services, including stable and efficient bookkeeping, cash flow management, and actionable analytics for growth.

Episode Transcript:

Russell Benaroya: Hello, everyone. Welcome back to another episode of the Stride 2 Freedom podcast. I am your host, Russell Benaroya. What is the Stride 2 Freedom podcast? It is an opportunity for us to bring on guests that help business leaders get and stay in their genius zone. What is your genius zone? Your genius zone is that thing that you do that feels effortless for you, where you are in that state of flow, where people say to you, “Oh my gosh, how do you do that thing?” And you’re like, “I don’t know. It’s just what I do that gives me energy, where I feel complete, where I feel I can make the greatest impact.”

We want to help business leaders stay in their zone as much as possible to create the value that they set out to when they started the business. The Stride 2 Freedom podcast is brought to you by Stride Services. We are an outsourced back office, bookkeeping, accounting, and fractional CFO services firm for high-growth professional service companies. What is our genius zone? Our genius zone is helping our clients use data to make better business decisions. That is where we get energy. That is where we thrive.

Today, our guest is my good friend, Elliot Neff, founder and CEO of Chess4Life. How are you, Elliot?

Elliot Neff: Thank you, Russell. I’m doing great today.  It’s always good to connect with you.

Russell Benaroya: Such a pleasure. Now, why would I have a company on the podcast that teaches kids chess? Well, because chess might be the game that Elliott teaches, but what he really teaches and what his company is uniquely equipped to guide on is the skills of life. There is so much for us to learn as leaders about how we lead ourselves. Elliott has chosen the vessel of chess to teach kids and youth how to better manage and lead themselves so that they can become great leaders in whatever they choose to do.

Elliott is also a national master in chess. He’s going to tell us more about that. Second, he is an extraordinary entrepreneur who made a major pivot during COVID, which we’ll get to hear about. Third, he is the author of a book called A Pawn’s Journey, and fourth, he is just a great guy. Is that enough accolading?

Elliot Neff: I was trying to see who you were talking to here, Russell.

Russell Benaroya: It’s such a pleasure, Elliot. Let me fire off a few quick questions, and then we’ll get into the business of business. You live in South Dakota now, right?

Elliot Neff: I do. I used to live in the greater Seattle area, and just in the last two years during the COVID pivot, I realized we could live anywhere to accomplish our mission. We hit the center of the country. For the chess players out there, we teach a principle called “control the center of the board”. So I was living in the corner of the US and decided to move to the middle to follow my own chess advice.

Russell Benaroya: I love it. You’re already teaching us through chess. Of course, there’s probably good entrepreneurial energy in South Dakota. For those of us that haven’t been there, what’s it like living there?

Elliot Neff: South Dakota is a little bit of that best-kept secret that they want to keep kept secret. Most people don’t know but Sioux Falls is the largest city in South Dakota. I live right on the edge of it and there are over 100,000 people in this metropolis. It’s actually state-of-the-art when it comes to medical services. A lot of people are actually retiring here.

Why did I pick it? Well, it’s a nice regional airport; easy in and out. Not quite like Seattle, sorry. I had my days in Seattle, but I can literally hit anywhere in the country through this regional airport in at least one to two flights. I love that fact. I have accessibility. We live on 10-plus acres and my kids are now experiencing a country-style life that I had as a kid and value. My wife did also, so it’s a bit of a personal move here, really. We could move anywhere and we picked this beautiful place.

Russell Benaroya: I’m so happy and you’re building chicken coops.

Elliot Neff: You picked up on a little hobby. My 10-year-old daughter is actually raising chickens and selling farm-fresh eggs. It’s a little bit of an entrepreneurial journey for her that she’s loving with a younger brother helping out, who she pays. There’s almost anything in life. If you look at it through a certain lens, you can learn from it. You can have fun with it, and just find what you love doing and press into it.

Russell Benaroya: A good segue into chess; tell me a little bit about your chest journey and how you translated that into chess entrepreneurship.

Elliot Neff: Going way back, I learned how to play chess with my dad. He put me in a tournament when I was eight years old and that was the hook that led to me loving the game of chess. I enjoyed it before then, but the competition, I was like, “I can do this.” And I set out to try to do it.

One of the stories I like to share is that I studied so hard for that whole year, I came back to that same tournament, did my best, and guess what happened after a year of study? I did not win it. But I still didn’t give up. I repeated the process and kept on. It took me over four years before I won my first chess tournament. But that perseverance that I learned was a huge part of my life.

I heard someone once say there’s just one rule about succeeding in business: just never quit. Never give up. So, I competed as a kid. I became a high school State champion. I had a big dream to achieve that. I put in 1000s of hours because I was not born with this ability. I just worked hard. I self-taught and read 100-plus chess books to achieve that. We didn’t have the resources to pay professional coaches so it was really self-teaching, and learning from all my opponents as I played. That was the start of my chess journey.

Russell Benaroya: What was it about chess that unlocked this kind of perseverance and commitment and desire? Because that’s quite unique.  Some people spend so much of their life trying to find that thing they want to go all in on.

Elliot Neff: I appreciate you asking that question. I don’t often talk about this piece, but as I reflect upon it, I think this had a huge part to do with it. My dad was a high achiever. He was a black belt in Judo, he was the first French horn for San Jose State Symphony. He won a gold medal in pistol shooting when he was in the police Olympics and things like this. He was always saying, “If you’re going to do anything at all, do it to the best you can be.”

But with that mindset, it was really hard to get his approval. I think there was an aspect in me that said, “I want my dad’s approval. I see I compete in chess and I’m getting better than my dad. He’s encouraged me in this.” I think there was a little bit of that going on, even though the majority was that I wanted to win. I had this desire to win and I was willing to go through whatever it took.

In fact, something I learned in my own process, which I’ve translated into lessons we teach the 1000s of kids now, is the importance of having a dream, setting a goal, but much more important than the goal is committing to the process. So I set a goal of being the high school champion and a national master. And I said I’m willing to commit four hours a day on chess study to get there. I literally wrote down the hours to fulfill my commitment. And if I messed up on a day, I didn’t beat myself up but I kept on at it.

After several years of that level of commitment from age 12 to 16, I was indeed Washington State High School champion, national master strength, and represented our state nationally. The key there that I would translate to everything that we do is actually talked about in our first life principle: you can win, you can draw, or what else can happen, Russell?

Russell Benaroya: You can lose.

Elliot Neff: Well, almost. You can learn. We’ve done this play on the words and we call it the “Win, draw, learn mindset”. Because where in life do you go where you don’t experience loss of some kind? Are you willing to embrace it? Are you willing to develop that growth mindset, that grit that no matter what happens, I’m not going to give up? It feels bad and there’s pain, but what did I learn from it?

Without pain, we don’t often learn something. So let’s learn to embrace that process and use it to propel our progress; hence my focus is on inputs, not just outputs. Have the dream, have the goal, create a plan to get there, and then commit to the effort.

Russell Benaroya: Now, can everybody see why Elliot Neff is on this podcast? This is so core to building a business, being able to articulate a goal. And by the way, that goal may or may not be the right goal.  What matters is, is it clear? Is the outcome understood? And is there a plan to get there?

Elliot Neff: Absolutely. You’re talking about chess in business because, in chess, you create a plan or a goal, but there are so many possibilities. You would blow your mind with the number of possibilities in a chess game. It’s critical to make good decisions and judgment calls every move.

With every move, the position shifts a little bit. And with the new information, you may find that the original goal you had needs to adjust. And how true is that in business? What you don’t want to do is every move just willy-nilly switch, you want to have that long-term goal and process. But sometimes there’s enough shifting in the position that you need to be willing to say, “It’s time for me to shift the goal.”

Russell Benaroya: Okay, keep going. So you achieved in high school, and you moved on from there.

Elliot Neff: Continuing this path towards how chess turned into an entrepreneurial business, I was just loving the game and representing our state. I ran a few small businesses even when I was a teenager, selling chess products, which today has become chesshouse.com, run by my younger brother. He’s done an amazing job taking it online. That was just part of my learning and entrepreneurial experience, but never once in all those years did I ever once dream that I would spend my life in the chess business. I was just doing it because I loved it. I enjoyed it, I pursued it. However, I did start coaching at a young age, and the reason was that I was on a high school team and I wanted to win.

I was the strongest player on the team and I wanted to help my teammates get better. It’s like we talk about Better Together. We work together. There’s teamwork. There’s collaboration.

So I would coach my team members, and we never won state as a team but we got top five. We worked super hard at that and I was coaching the others. Then people would ask me, “Could you coach this team?” And I started coaching multiple high schools shortly after I was out of high school.

Then parents asked me, “Hey, our kids are over at this middle school. Could you coach their middle school club?” So I started coaching the middle school club. Again, I never once dreamt that this was going to be my full-time job. I was doing a career in other businesses in cellular phones and construction and a number of blue-collar type fields. I ran an internet business for a time. I ran the Chess House. I have a good variety of businesses in my background.

Then after I was doing this for a while, I reflected on my mid-20s and thought, “I’ve got all this experience, but I have not found my passion. I really want to make a difference. I should probably go back to education, complete a degree or two, and see what I could do to make a difference.”

I was about to quit teaching all my part-time students to free up my time to go back to university. Instead, the light bulb went on that I was already making that difference in the lives of my students. The catalyst for me recognizing this was the parents of youth coming to me and going, “Hey, thanks for coaching chess. The kids are doing well. They’re improving in chess, they did well in the state tournament.” Then they said a couple of profound outcomes.

They said, “Here’s what we’ve noticed. While you’ve been coaching them, their ability to focus on their homework has dramatically increased. Before we did chess and chess coaching, they would come home from school and they would spend 10 minutes on their homework and it was like pulling teeth to try to focus and finish their homework.” They said, “After a year of training and working with you and going to events, they can come home and focus for an hour, no problem. The outcome of what you’ve been doing is they’re taking their time, they’re thinking ahead, they’re being slower in their decisions versus reacting. They’re thinking ahead and their grades have gone way up.”

They said, “Beyond that, they don’t give up quickly. When they lose, they’re learning. And even they’ve learned to be nicer to each other.” They said, “You’ve been a mentor as well as teaching these skills. Thanks for that. That’s what we appreciate.”

Those conversations were the lightbulb that triggered my switching to chess as a career. Literally, within a month of those conversations, I quit everything else I was doing. I went, “This is it. I can make a difference.” Little did I know it would turn into an actual business beyond me being a solopreneur. Over time, that vision has grown to where we’ve had dozens and dozens of employees and team members until we quantified it into a goal. Seven years ago, we said, “We’ve been making a difference. We’ve been growing and serving the greater Seattle area. What if we could impact a million youth a week with these life benefits through the game of chess to help them succeed in any field they go into? And for the last seven years, it’s been my joy to work with different team members to create what would be necessary to accomplish that vision.

And just like in chess, we can pivot, we can move, we get new information. But I’m really happy to say we’ve made significant progress. Our tools have been in front of hundreds of 1000s of students continuing to grow all the way from preschool, where at-risk preschools, such as the Headstart Association in Washington State now have access to chess benefits for their youth to prepare them for kindergarten, to the elementary schools, to the middle schools, to the high schools, to even in college to career.

We’re partnering with groups like people from Amazon. We’re seeing the connection between chess thinking and problem solving and the STEM careers, and how the thinking in chess directly translates into the problem-solving of computer programmers. Hence they start sponsoring events that support chess. Anyway, I’ve touched on a lot there, Russell. But that was the transition from a kid’s passion into entrepreneurship with a big dream.

Russell Benaroya: Let’s talk about the business model transition because you went from having centers to navigating through COVID and doing a pretty major shift. Can you talk about that because now in many ways, Chess4Life is a technology company?

Elliot Neff: I appreciate that question too because the last couple of years, like most people, have been a paradigm shift. Our world has gone from a place where technology was rapidly advancing to where technology is the baseline must-have everywhere. The reason I say that is because many people were already in technology, especially in the greater Seattle area. However, if you work with schools and districts around the world and around the country, there were still a significant number that while they brought technology in, didn’t see technology at the level that it really could be.

I mentioned that just to say this paradigm-shifting, many teachers who may have been a little bit intimidated by technology, today are confident with it. It took this COVID disruption for that leap forward in capability, which is fascinating.

Now, how that affected Chess4Life: in our mission to impact a million youth over the last seven years, we had started building out some technology because we knew that to scale, we would need to have the tools to empower educators around the world to bring the benefits to their youth. I’m not going to hire coaches in every State, city, town, or country. But we can empower others who already are good with kids to do so. So we were building some of these tools out, but like you mentioned, we had physical centers. We had 1000s of kids coming to our physical centers every week and learning the game, learning life lessons with camps and programs.

In March of 2020, all of that shut down in basically two weeks. We had to pivot fast, and a huge hats-off to my team. We had a roadmap and some things that we were planning to do in the digital space to enhance what we were doing and move some things online. Well, much of the dream was clarified and put in place in about three weeks.

We were shut down for only one week during that time and then we did all this work. We pivoted all of those in-person programs to virtual programs so that we now have students in the majority of the states in the United States. Our core programs where our coaches are live-coaching students have become something that’s nationwide. Of course, we still have a large base of students in the greater Seattle region.

For the last two years, we’ve been able to expand those services and expand the experience of learning the game of chess. As much as I still greatly value in-person experience for chess, virtual technology has allowed us to scale, but life lessons to the game of chess can be greatly enhanced with that in-person social connection. I think we’re seeing more and more that the challenge of shutting down so much of the country for two years, was extremely negative for many youths when it comes to their social development.

Russell Benaroya: What is the lesson learned around the reflection around being able to make such a fast pivot? I think this is something that all entrepreneurs and leaders will face sometime in the development of their businesses. It is not just the ability to execute in a moment, but it’s also the ability to see that it is, in fact, a moment.

Elliot Neff: I appreciate that question. I’ve actually done some reflecting on this. One of the things I said to a mentor of mine as we were talking about some elements is, the fact that we made so much advancement in terms of our ability to deliver services, to scale, we did so much within a month or two — three weeks was the primary push that allowed us to accomplish it — and the ability to make so much change that we originally thought would have taken three years, why is it that it took COVID shutdowns to cause that level of progress? And what would it take to make that kind of progress without a COVID catalyst?

Russell Benaroya: Exactly.

Elliot Neff: I’ve been asking myself that question and here are just a couple of things that have come to my mind in terms of what it is. I think there’s a tendency in organizations towards inertia. You start moving in a direction, and you literally create drag and things slow down. What I mean is, when there’s a problem, you fix it, but how often is your fix to the issue a creation of more red tape versus a solution that is oriented towards speeding up? Is the right solution more red tape? Or is the right solution cutting away some more fluff?

There were some changes that I probably should have made a couple of years ago that took the COVID timeline for me to make those shifts. How much of our thinking is based upon the sunk cost bias? I put so much time and energy into this, therefore, I continue pursuing it. Rather than going, how has this position shifted? And going, “Is this the right time for me to literally shift my tangent? Instead of attacking and putting pressure and all my resources towards this sector of the board, maybe they should be over here.

How has the world shifted? How is my new information now influencing that? Or am I so focused on the little things that I lose sight of the opportunity?

Now, I’m not a fan of the shiny coin syndrome. I’m at fault so many times for pursuing those, which also slows down a team. Because then the team doesn’t know which direction you’re headed. But there are times when you have to go, “No, that’s the goal.”

So that’s part of the thinking on it. The other piece is when a team has an extremely clear vision and a singular focus on accomplishing it. And a team where you’ve literally removed the restrictions and red tape and opened it up.

I believe there’s an aspect of what I think it was Stephen Covey who wrote the book called Business at The Speed of Trust. I believe we experienced a lot of that in that segment. We opened it up. Here’s the vision: now, let’s get there. Use your talents. Don’t ask permission. Do. And applied the principles that we now have clarified since the start of COVID into our core operating principles of going, “You know what, we fail fast.”

You see, fail is just an acronym for “First Attempt In Learning.” Let’s do it fast. Let’s learn fast. Let’s move quickly. Let’s not be afraid to make mistakes. Of course, we strive for excellence, but let’s not be afraid of mistakes because those mistakes are going to be some of the best learning we can do.

So fail fast and work better together. Who’s got the unique ability in this area? Okay, do your skill here. Toss the project to this person. We get ego out of the way. It’s a “we” approach, not a “me” approach.

Those are just some of the reflection points I’ve had, and I’ve not finished yet in terms of learning. But as you pointed out, I was asking myself that question because I thought: imagine the progress we could make in our businesses if it did not take a COVID situation to be the catalyst for such positive change.

Russell Benaroya: 100%. Peter Thiel, who’s a challenger of people that are like, “Oh, this is a five-year vision,” is like, “Get it done in six months.” And it’s amazing what’s possible with that pressure and the impetus for action, or the bias for action.

What I’m curious about is when you said a really clear vision that everybody gets around. For this particular shift that you were making during COVID, was this a clear vision for the next three months or the next six months? When you say vision, was it just the distance enough that people can be like, “Yeah, that mountaintop, that’s pretty clear,” or was it grander than that?

Elliot Neff: I’m so glad you asked that because it was a short-term vision that aligned with the long-term vision. It was like, “Here we are. We’ve served these 1000s of students in person. They’re going to be shut in. We need to continue serving them. We’ve got to figure out how to do it remotely. How do we effectively do that, and at the same time, not denigrate ourselves, and lose sight of our core mission of teaching life through the game and just become a digital chess company? That was the guardrails.

How do we do it virtually and how do we continue to incorporate our purpose of bringing life skills through the game? By the way, you mentioned Peter Thiel. Did you know that he was a very strong chess master as well?

Russell Benaroya: I did not.

Elliot Neff: He did. He’s the founder of PayPal, right? Yes, as a kid, he competed in chess, and look at what he’s done to apply that kind of strategic thinking in business.

Russell Benaroya: Glad you drew the link. You’ve given me a lot to think about. I hope people that are listening to this are also cycling in their minds: what is that clear articulation of a goal that would rally a group of people to execute it with an understanding of what it looks like to get to the top of that mountain? Not knowing exactly how to do it yet, but at least consensus around that’s the top of Mount Everest. I see where we’re going on top of Mount Everest.

Elliot Neff: If I can, let me throw out something that I’ve learned through the game of chess that I think is critically important in business. To achieve that mission and vision, in a chess game, you have six different types of pieces, in case anybody’s listening who hasn’t played chess. Those six types, even though there are eight pawns and there are two each of some, and then there’s one king and one queen, they each move in their own unique way.

The King is the goal; you’re trying to get the King. The Queen is the most powerful. But the knight is the only one that gets to jump other pieces. The pawn is the only one that captures differently than it moves. And it’s the only one that can be promoted when it reaches the other side into one of the other pieces and becomes a stronger piece.

These differences in the pieces, a beginning player might say, “My Queen’s the most powerful. I’m starting out with my queen and I’m going to take everything with her.” Against a team that plays together, they always lose.

In business, I think it’s essential in the leadership team, in your management team, in your front-line customer team, and in any team, that you have differences.  Actually, seek out differences. Don’t surround yourself with people like you. Surround yourself with others who have those unique abilities. I believe every person has been created and gifted with something unique in them. Every employee, every team member, and every chess person I meet who I can beat is better than me in some way, in their unique gifting.

As an entrepreneur and a vision leader, I believe it’s one of our primary jobs and a means to accomplish the vision of identifying unique abilities and bringing them together to then accomplish that mission. So never fear differences. Instead, celebrate them.

Russell Benaroya: How do you evaluate that when you’re hiring?

Elliot Neff: I’ll just use some business pieces here. I’m always applying our own life principles of always improving and always getting better. I’m always looking for better ways to do this. I have, by no means, mastered this, and I never believe I will. I just believe I will always get better.

Some of the tools I’ve used over time: there are, of course, disc profiles to understand people. There’s the Enneagram, which has a different view. Kolbe has been a really amazing tool that we’ve used significantly in our organization. Whatever the tool is, if you can understand people better, and then look at how they pair up together, you can identify what the gaps are and then be aware of that. Or identify the strengths and then go, “Hey, this kind of position needs a person who’s high in detail, thinks deeply, looks through all these pieces. Great, that’s who that is on our team.”

Or, “Hey, we need someone here who can come up with ideas in the moment. We’ve got to pivot. COVID just hit, what do we do?” You don’t want that high detail right now. Now you want somebody who can think quickly with ideas right out of the gate, out-of-the-box ideas?

There are tools out there that can do that. Pat Lencioni, from The Five Dysfunctions of a Team, recently started a new segment called The Working Genius. This is another way to understand how people operate. And if you use tools like this, it can greatly help you.

Now, you might be able to, just in your interview process, ask the questions that will let you know how people operate, and then you can do it yourself. But there are tools that streamline this if you leverage them.

Russell Benaroya: We have every one of our prospective candidates take the Enneagram. The Enneagram has become core to the fabric of our organization. And it’s not so much an opportunity to help that individual learn a little bit more about themselves, which is obviously interesting, but it’s an opportunity for us to understand how we can best help them unlock their genius zone and how we can help them achieve their highest and best use.

Because if somebody is a six versus a three, as an example, this is a person that needs a lot of information before they feel confident to make a decision. So that when they show their fear, like moving forward with something, well, that’s understandable because they are a six. Because they don’t have the information they need.

So it’s not personal, it’s personality. What can I do as a leader to better meet you where you are, and also celebrate all that is amazing about a six, who are highly loyal individuals, and really embrace that and be a guide and mentor for those areas that they want to develop?

Elliot Neff: And if I may add one other thing I found useful, and for any entrepreneur or business leader, something to consider is I did quite a bit with unique ability, the concept from Strategic Coach by Dan Sullivan, along with Kolbe. And one of the questions I love asking people I work with pretty much every quarter is, “As you reflect upon the last 90 days, what are the one or two things you would love to do more of? And what are the one or two things that you would love to do less of?”

Because most of the time you’re going to find, in their answers, the activities that align with their unique skill sets and abilities, and the things that are irritating and not good. And guess what? If they’re spending their time in their irritating activities, they’re probably not great at them. And you probably have a team member who is good at them. So why not just ask the question?

Russell Benaroya: I couldn’t agree with you more. We call it energy gains and drains.

Elliot Neff: Nice. I love that.

Russell Benaroya: What are some other key learnings that you communicate/guide your students to learn over the course of their experience with you?

Elliot Neff: In terms of the life skill benefit through the game of chess, let me just mention we work a lot with elementary-age kids. In that space, they’re not going to sit there philosophizing about life, or a small percent will be happy doing it. The other ones are like, “What are we doing next? Let’s move. Let’s go. Let’s play.”

So the experience kids see is primarily loving the game of chess because of how we teach it. Because we teach it in a way that every experience is a positive, energy-building, fun activity, not a boring lecture. It’s like one key concept for a couple of minutes. Now, let’s go practice this and play this mini-game while doing it, then we’re going to have fun in this competition. We’re going to win, draw, learn.

But what are we teaching throughout? Here are the healthy habits we’re teaching. One, we’re teaching them: You’re thinking about a move, pause. Let’s think about an alternative choice. Okay, impulse control, slow down. Think about other choices. What could be better?

Two, when you lose a chess game, what a perfect opportunity to learn! That’s why we call it the win-draw-learn. We’re going to look through that. In fact, we’ll build that skill by giving them activities where they are going to lose with their partner, but then they switch sides, and now they’re going to win. The whole point of the exercise was to practice certain things like how long can you survive and try to avoid checkmate.

They’re learning that it’s okay to be checkmated. It’s a healthy thing. That’s the goal. Did you survive 10 moves? 20 moves? 15 moves? 2 moves? Hey, what did you discover? It’s discovery. It’s a collaboration. It’s collaborative problem-solving.

Then we build these healthy habits. Did you go through the habit of, before the game, getting ready for it? Now you are building good etiquette and good collaborations as part of the rules of chess. Are you shaking hands before and after every chess game? After COVID, some virtual handshakes are allowed now. And you say, “Good game,” and be a good sport.

There are all these elements built into the experience. Talk about goal-setting. In a chess game, what’s your goal? If you play the move in front of you, you’ve got like 200 choices. But if you know what you’re trying to accomplish and think backwards, now there are probably three that support your goal.

So we teach analysis, goal-setting, planning, strategic thinking, and that all in the context of these social and emotional abilities. So it’s pretty amazing that kids experience learning chess, but they’re developing these other abilities.

And then you have opportunities to really bring magic to it by drawing the occasional parallel. Like, “Wait a sec, you just lost that game. You just figured out something from that. Where in life are you afraid to fail right now? What is it that you’ve been afraid of trying because you think you might fail? Well, what do you think will happen if you actually try and don’t succeed? What do you think you’ll learn from it? And what if you win?” Build grit, build growth mindsets.

So being able to draw those connections is one of the things we strive to have our team do at appropriate moments. They enjoy their time, they’re learning chess, and having fun celebrating their progress because we’ve built a visible progress chart so you know that you’re progressing from this level to this level. You’ve got all the achievements you’re getting along the way. It’s energizing for any kid to see their progress. And for a parent who might not even play chess, they can see the progress on the chess skill. As you can tell, I kind of enjoy what I do.

Russell Benaroya: I can absolutely tell. Key takeaways from that: think about your move, and then pause. What’s an alternative? I like that. When you lose, look through that and build that skill. Evaluate what you learned. I heard discovery, collaboration, and problem-solving. I heard preparation, habit-building, and collaboration. I heard goal-setting. So many tools, so many skills. All I’m thinking to myself is, is it too late for me? Is Chess4Life available to adults?

Elliot Neff: Our mission and our focus is impacting a million youth a week. However, much of what we teach — we’ve got YouTube channels, we have videos — a lot of adults value these kinds of things.

I remember speaking at an event in a business setting and using chess as an analogy for this. One of the ones that I love to share is, think about it this way, when, as a leader in an organization, have you had a need to fill a seat? You’ve got this open seat, you’re growing or someone left and you need to fill it. And you’re looking around because you want to hire from within because you know the people already.

You look around you and go, “Oh, they would be really good. Look at how well they’re excelling here. Let’s just move them over there.” Pause a sec. What if the abilities of that person are like a bishop, which moves on diagonals when you really need a knight who can jump over things? Well, if you try to make a bishop move like a knight, it’s not going to go well.

If you move that person to that seat, it’s not going to go well. So learning to think very carefully about the decisions you make in a business, thinking about how these pieces move, not denigrating people in any way, but talking about their strengths, makes sure it’s the right fit. One of the biggest mistakes I’ve ever made is along those lines and it took me forever to figure it out even though I teach this.

Russell Benaroya: You’re human. Oh my gosh, finally you reveal yourself. Thank you for sharing that. There’s a “great” book out there called Topgrading. One of the biggest risks is you turn an A player into a C player because you put a bishop into a knight’s role. So I get it.

I really love the analogy that you consistently draw between chess and business decisions. I have a guy on my team right now who is a lacrosse coach, and he loves the game of lacrosse. I played lacrosse. So much of our dialogue and training is about talking about our business decisions in the context of being a coach on the lacrosse team, running for the ground balls, and being aware of the play on the field.

And it’s so helpful to abstract from the actual business that you do to the thing that you love as a metaphor for helping to catalyze smarter decision-making. Obviously, you live in that world all day, every day. That must be great for the culture at Chess4Life.

Elliot Neff: I think it really does affect it. That being said, I am human. I make tons of mistakes. I make lots of them and I learn from them. And there are many times I need to ask other team members to do things and to help me with things where if I try to do it, I’m going to be that bishop trying to jump like a knight.

So recognizing, valuing, and utilizing them. I love the fact that these analogies are just truths. I’m using chess as a metaphor for them to illustrate them to make them understandable. But in reality, we’re talking about life. I believe that everybody plays chess in life, even if they don’t know how the chess pieces move. The question is, how well are you playing it? Do you play it forward? Do you play it reactively? Do you play it without thinking and just let it happen? Or do you play it intentionally?

Russell Benaroya: Do you play it scared?

Elliot Neff: Are you afraid of what’s going to happen so all you do is play defense? There are so many analogies. And to your question about whether it’s too late; no, it’s never too late. In fact, chess is a great game, and here’s why I say that. Some people say, “Well, it’s hard for me to learn new things. I’m at an age where it doesn’t come easily. My time is limited…”

Well, the greatest benefits that we’re talking about from the game of chess come from early learning through the few levels. There’s a point of diminishing return where becoming a really strong chess player may not be a great life choice. I enjoy the game and if it’s your hobby, fine. But you look at Peter Thiel; he was a master as a kid. But did you pursue it as a Grandmaster? I think he could have, but he probably made a better choice in not.

Russell Benaroya: What is a scary situation that you’ve been in a chess match, where you recall having to make a bold move, but you are scared or nervous?

Elliot Neff: Thank you for the question. That brings back some amazing memories. The one that I’ll share goes back to the US Open Chess Championships in 1990-something. I forget exactly which one it was.

I was a teenager competing in this event and it was a long tournament, 12 matches. I had played a hard game in rounds eight and nine, and I did not do well. And I came out of these going, “Ah, I missed my opportunities. I need to finish this tournament with three solid wins if I’m going to land anywhere in the top prizes, which I’m trying to do.” I’m a bit competitive.

And I look at the pairings when they come out. And in chess tournaments, what happens is you play according to the point scores. Well, what occurs is, if there’s an uneven number of players, the bottom person in that group plays the top-ranked person in the next lower score.

I had the misfortune to be the lowest of an uneven group of players, which meant I got paired with the highest possible opponent in the next point group, who happened to be an international master in chess and one of the very few people who had defeated Bobby Fischer in his day, who I checked a database of games before the match and I could only find two losses in hundreds and hundreds of games of his where he was playing the light pieces.

I was going to play the dark pieces against him, which is a bit of a disadvantage because light pieces move first in a match. Here I am as a kid going, “What?” So I look at those games, and the only two losses are against US champions, who are so far beyond where I was. I looked closely, and I discovered one thing, and that one thing that I discovered as I looked through this gentleman’s games, was the only games he ever lost were when his opponent went all out attacking in a wild, hard-to-understand position.

If you played anything positional, slow, or strategic, he was just a master at it. I went, “If I have any chance of winning, I have to do this.” But that’s not me. I don’t like being aggressive. But sometimes you have to rise to the occasion, and sometimes you have to play a little bit outside of your natural style.

In business, you don’t always do only the things that you’re great at. Sometimes you have to put your energy into other areas.

So I went into that match with a mindset that I’m going to go all-out attack no matter what. I sacrificed material, and I attacked him and I attacked him. And he was thinking so hard. This match lasted about five hours. He was sweating. I was working hard. And guess what, I sacrificed material and he took it. And then he just gives all the material back to me to equalize the position. And as hard as I tried, we ended up with a tie game.

I went out of that game disappointed because I hadn’t won when I knew I needed three wins; when most people would have gone, “What? You just drew this guy and he’s so much higher rank than you.” But I went into the game with high stakes.

Long story short, I won my last two games and ended half a point out of the position I was really trying to be in. Yet, what an experience! I was normally terrified of this and now I’m going to have to even fight harder and I’m on the dark side. But I embraced it and did my absolute best, and ended up with a memorable match.

Russell Benaroya: So memorable. You definitely developed some muscles in that game.

Elliot Neff: Yes. And from the win-draw-learn, so what I didn’t win the prize in that tournament, look at what I developed from doing that.

Russell Benaroya: I love it. Fortunately for all of us, you have chronicled these stories in a fictionalized format in a punch journey. I do want to put a plugin for the book because it’s a great book, and provides a lot of these key takeaways that you’re expressing today.

Elliot Neff: Thank you. And let me just say it’s A Pawn’s Journey: Transforming Lives One Move at a Time. It’s a novel like you said, but it’s truly inspired by many true life stories with little bits changed.

Russell Benaroya: Thank you, Elliot. As you know, I gave you some questions to think about in advance today of which I have asked you none of those because I can’t help myself and follow your lead and stand on the shoulders of your energy to ask questions that spark good conversation and learning, which this totally has. Thank you so much.

Elliott Neff: Well, thank you, Russell. It’s been awesome dialoging here with you because I also get inspired by meeting other entrepreneurs, who like yourself are playing chess in business.

Russell Benaroya: You’ve given me so much to think about and I’m hopeful that everybody that listens to this feels the same. I’m excited that applying chess to helping business leaders achieve their highest and best use by giving them other ways to think about the problems before them is such a gift, and it’s a privilege to be able to do it. You being on the show is fantastic.

Elliot Neff: Thank you, Russell. It’s been a pleasure. And I would just say this as we wrap up. Can you imagine a world where the majority of youth are growing up and are making decisions with careful thought for what consequences come down the road, not just the next move? Imagine that happening in our world, where kids naturally think about the consequences of their choices and are not just living in a reactionary place. Imagine what that would do for politics, for business, for life as a whole.

Russell Benaroya: Thank you for giving us the opportunity to play the long game on that and look out a generation or two generations. Because you don’t snap your fingers and this happens tomorrow. We have to plant the seeds and you’re helping plant the seeds to ultimately a million kids a week.

Elliot Neff: I hope to see that come true, where it’s no longer unusual to think that chess is an educational tool that every single person on this planet has at their fingertips.

Russell Benaroya: Awesome. I will put in the show notes, links and resources that people can access. Elliot, thank you again. Thank you, everybody, for listening to this episode of the Stride 2 Freedom podcast. We will see you on the next show. Have a great day.

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