in: Behavior, Character, Podcast

• Last updated: September 28, 2021

Podcast #121: Strategic and Critical Thinking With Tom Ruby

Few subjects are as important for men to master than strategic and critical thinking, and my guest on the podcast today has spent his career helping both military brass and business owners become better at both. His name is Tom Ruby and he’s the owner of Bluegrass Critical Thinking Solutions, a consulting company that helps companies develop strategies and doctrines so they can better manage the ever-changing marketplace. Before Tom did private consulting, he served 26 years active duty in the U.S. Air Force, serving in such positions as Squadron Intelligence Officer, Associate Dean and senior faculty member at the Air Command and Staff College, and Chief of Doctrine for the AF Intelligence, Surveillance and Reconnaissance Enterprise. He also served on General Petraeus’ Joint Strategic Assessment Team during the Iraq and Afghanistan Wars.

Today on the podcast Tom and I discuss what it means to “think strategically” and why and how average Joes need to become better strategists.

Show Highlights

  • How the U.S. military is anti-intellectual
  • The topics you should study to become a better strategist
  • Why it’s so hard for organizations to try new ideas
  • How to balance going against the grain to make an important change and going with the flow in order to advance your career
  • Books you should read to become a better strategist
  • What Ender from Ender’s Game can teach us about strategy and leadership
  • Tom’s maxims for leadership
  • And much more!

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Special thanks to Keelan O’Hara for editing the podcast!

Read the Transcript

Brett: Brett McKay here and welcome to another edition of The Art of Manliness Podcast. A common theme we write about on the website is big picture, strategic thinking. How we can become better, more critical thinkers. We’ve done content about the OODA Loop, psychological biases that get in the way of us making good decisions that help us live a good life.

Anyways, today on the show, I have a man who has dedicated his career, his life, to improving strategic thinking and critical thinking in life and death situations. His name is Tom Ruby. He served 26 years in active duty positions in the United States Air Force, from squadron, intelligence officer, to chief of doctrine for the air force intelligence surveillance reconnaissance enterprise. Also, the chief of special programs for Air Force material.

He was also on General Petraeus’s joint strategic assessment team during the Afghanistan and Iraq wars. This is a man who’s dedicated himself to writing documents that have been used in the military, developing strategy on how not only officers but soldiers on the ground can think more critically in life and death situations. Anyways, a fascinating, fascinating character.

Today on the show, Tom and I discuss thinking strategically. How we can do it better. We discuss how we can think critically. Whether you are a guy working for a corporation or you own your own business, knowing how to strategize is something that will get you far in life. We discuss the topics, the subtopics you should focus on in order to become a better strategizer. Among other things, we discuss Ender’s Game, and what Ender from Ender’s Game can teach us about leadership and strategic thinking.

Anyway, fascinating discussion. I think you’ll like it. You’ll get a lot of takeaways, really good nuggets there that you can sort of apply in your life today. Without further ado, Tom Ruby on strategic thinking.

Tom Ruby, welcome to the show.

Tom: Hey thanks, Brett. It’s really good to be here. I’m a huge fan from your early days.

Brett: I really appreciate that. Let’s start with your story, because it’s really interesting. You are, right now, an expert and consultant on strategic planning and critical thinking. How do you get to this point? You actually have a pretty interesting background story. Can you get us up to date on how you got to where you are now?

Tom: Sure. In some ways, I’ve lived almost a Forest Gump like life. I mean I’ve been in the right place at the right time, not of my own doing necessarily, but providence puts you there, and I think a lot of times, you make the most of your opportunity.

I was born in Belgrade, Serbia, which was then Yugoslavia, behind the iron curtain. My mother’s family were royalists who supported the crown and the pre-war government against the Germans and Tito’s communists during World War II. That set us up as enemies of the state when Tito came into power.

When I was a year old, my mom and dad took me and did a, no kidding, overnight escape out of the country. They made their way to Paris, and then on to Los Angeles. I grew up in a working class home, where my mom and dad both. My dad worked two jobs. I played football in high school and decided to go to the Air Force Academy after a recruiting visit there.

I played football and that was fun, but I had a really, really tough time with the military side of the experience at first. That was my first real taste of the need to turn you know, for what you espouse as the Art of Manliness.

I realize that I was constantly making excuses and I needed to be more disciplined in my life and in my skill and my studies. Like you discussed with Dr. Jay in the episode on why your 20’s are important, you become manly by doing manly things. Taking responsibility was a big one for me.

After I graduated, got married, we went off to our first duty assignment in South Carolina. I was an intelligence officer in the F16 wing.

I noticed really early on that we were training for combat missions with a methodology that can potentially prove disastrous. Everybody at that time, it was about how low can you go? How fast and how low can you fly? It was almost without regard to what threat was going to be from the other side. Trying to explain that to my leadership was difficult, because when you’ve done something for so long, it always seems right. If that makes sense.

When we deployed to desert shield in 1990, I really slowly and methodically showed my leadership why I thought that we needed to make a change from low level tactics to higher altitude to give us a better chance of survivability. We did make that change and a bunch of the other wings that were deployed also did the same thing, but it took several months, the training to fly the new way.

On the very first night of the war, back in 1991, those guys that flew in low were the first ones that got hit by any air craft fire and surface to air missiles. Really, by the next day, everybody had changed to our tactic.

When I returned from the war, the air force sent me to graduate school for the first time. Between a whole series of going back to school and going to operational deployments and back to school and operational deployments, I got to apply some of the concepts I learned about school, or read about from other people. I also got a chance to learn how to really patiently build momentum behind ideas. That’s focusing your peer group and with your leadership, to implement new ideas.

By 1997, I found myself deployed in Saudi Arabia, at the headquarters, enforcing the no fly zone in Iraq. Our American, British, and French pilots were coming back everyday saying that they were targeted by Iraqi surface air missiles south of the no fly zone line, but nobody in DC would believe anything they said.

They were like, “Oh these are just cowboy pilots, you know? They’re making it all up.” I get on the phone and say, “Why would anybody make that stuff up?” They’d say, “Because there’s nothing there.” I say, “Well could you look? Could you actually look and move some of our intel assets over there to look?” They’d say, “Why would we want to waste an asset to look for something that’s not there?” I mean it was just really circular reasoning.

Again, trying to build up some momentum among peers, I found some really good young people who were able to help and re-convince the intel people one day to move some sensors to look where we were telling them to look. Suddenly, all these threats are there that weren’t there to them the day before. In their logic, “Oh my gosh. They just moved this stuff down. The only reason they could be doing this is if they were getting ready to invade.” We’re telling them this stuff has been there for months. Okay.

That was a really powerful lesson for me. You don’t have to know everything in the world, but for the things that you’re responsible for, you can’t assume anything alike.

After that, I was a selected to go get a PhD. A light bulb really went off from me when I started taking methodology and critical thinking courses. That gave me a template for the first time to think about how to apply the things that I was learning to actual real world situations of life and death.

When I came back from getting my PhD, I was sent to Baghdad to conduct the Iraqi campaign progress review. I worked with an awesome British colonel and we were just astounded by the lack of preparation from everybody’s standpoint for this huge, international undertaking.

Strategic planning is not a secret formula, Brett. I mean you can find any number of checklists on the web that will take any family, any business or any government entity through a process to get you where you want to achieve. The US military and our allies had gotten really lazy in the prospects about thinking about war, we show over and over again that when we could get into a fight, we win the fight, and we can win every fight, but lose the entire war, because we don’t think through the long term.

When I came home from Baghdad for the last eight years of my career through three different assignments, really I spent a lot of time on the road. I mean, countless weeks on the road, giving seminars on critical thinking, strategic planning, and leadership development.

I was asked to be on General Petraeus’ joint strategic assessment team, which assessed the US and allies strengths, weaknesses, for the entire Middle East and the Central Asia region. That resulted in a report that General Petraeus put on President Obama’s desk right after his inauguration.

It got me thinking about what I wanted to do afterwards, when I retired, I mean, because I couldn’t stay in uniform forever. I knew that I’d have lots of opportunities to get in with one of the big beltway firms after I retired, but my wife and I had really, for a long time, wanted to get out of the city and move to our farm.

There was something that a friend told me years before that resonated with me. He was a small town newspaper editor. He’d been courted by the New York Times for years. He said, “People in small towns deserve good journalism too.” That really made an impact with me.

I thought, you know, people in small towns, and small and medium businesses deserve good consulting that’s affordable as well. That’s when I started thinking about how to do this and settle down into building up a small consultancy, that network of other good thinkers. That’s what I do today.

Brett: All right so you basically take the things you learned, the skills and expertise you developed during your military career, and help organizations think strategically. Let’s talk about that. Maybe we’re going on a rabbit hole, but what is strategy, right?

Tom: Okay.

Brett: What’s the difference between strategy, tactics, doctrine? How would you define that?

Tom: That’s a brilliant question. Before you can start, strategy is what links the ends that you want to achieve with the means that you have to do it. Okay? If you thinking from priority, or from time priority, what comes first? You should always have a policy, i.e., what is it that we want to do. Okay? I want to go do this. The what is your policy or your desired end. Strategy is the how. Strategy is the how you can do it.

If you live in Oklahoma and you want to go to New York City, your goal is to get to New York City. There’s multiple, different ways of how you can do that, right. You can get on an airplane, you can drive a car. You can take a train. You can hitchhike. There’s lots of different ways to do it, and combinations to those things too.

Strategy links the means by which you have it. If you don’t have the kind of money, well, you can still there, right? It might take you a little bit longer if you hitchhike, right? If you have a lot of money, well you can charter an airplane, or build yourself a hot air balloon. Strategy is the idea of connecting the what you want to do with the means that you have at your disposal to best figure out the way to do it.

Brett: So I’m always thinking trying to become a better strategist. Are there particular subtopics that individuals should study or research and read about so that they become better strategists?

Tom: Yeah, I mean I think the best thing that you can do to be a strategists is to make yourself a critical thinker. Really to do that, you have to think really, really broadly. Not just one subject, not just being expert in one thing, but try to learn as much as you can about as many different things.

I mean you do this on your site. If you look at the manly skills, right? On Art of Manliness, you’ve got pages and pages and pages of these things. Once you get good at one of these things, it’s going to help you get good at others. Okay?

First of all, to be a good strategist, you have to be able to think broadly beyond just one little thing at one time, okay? I recommend to people pick up all kinds of books, not just history books. You get a lot of guys that will say, the only really manly books are biographies and histories. I think that those are very manly, okay?

Biographies and histories can tell you what happened to a person or at an event in a given time, given a certain context, but if the context today is different, then the variables today are going to be different than they were back then. If you follow the same step that somebody did in another case that was different from yours, you’re going to come up with a different result.

I really recommend people to read fiction, to read novels, to read histories, to read biographies, to read books outside of your comfort zone. I recommend to my own clients to spend an hour a day, during your job, during duty day to read and go look at something outside of what you do. Okay?

There’s a grate Harvard Business Review article from 2009 on the innovator’s DNA. It’s called the Innovator’s DNA. It talks about the top CEO’s are those guys that go around and look at not just their businesses and their segment of industry, but other segments of industry, or other industries altogether.

I have a client now that was just saying that he goes out and he looks at how fruits are arranged at hotels and wonders about how he can make his business, how he can take that lesson and apply it to his own business.

That’s what makes a good strategist is continue in pushing the boundaries of the possible, not just when you see people in tests, right? That are given like a rope and a nail. What can you do with this? It’s the children that always come up with the most outrageous ideas that are really cool, right? They haven’t grown up enough for people to tell them that’s dumb, or you shouldn’t do that, right? I think that if you constantly challenge yourself to see the world in new ways, that’s going to help you be best strategist around.

Brett: So this sounds very somewhat similar to John Boyd’s thinking with the OODA Loop.

Tom: Amen.

Brett: Where you the idea … In order to become a better strategist and in order to succeed at the OODA Loop, you need to develop as many mental models as possible, from a wide variety of fields. What’s amazing with his OODA Loop, just to develop that, he brought in several different mental models. From thermodynamics to cybernetics to quantum physics, just to develop that idea, but by cross pollinating all those different theorems and ideas from science, he’s able to come up with this very simple mental model for success in the battlefield and success I any type of conflict.

Tom: You know, Brett, you’re absolutely right. To piggy back on what you’re just talking about, John Boyd, Scott Page, P-A-G-E, from the University of Michigan published a book in, I think it was 2010, it might’ve been 2009, called The Difference. It was a look at how expertise is almost in every case trumped by diversity. James Surowiecki, in his book, The Wisdon of Crowds, kind of wrote about that.

A lot of people poo-pooed that, but what Page does is he goes and says, “You can find any expert in any field and ask them a question. Almost invariably, if you ask a random group of people who know nothing about or are not experts in that field, the same question and take the mean answer, it’s always going to be more accurate than the experts.”

That’s what made Boyd so brilliant, but that’s also what made Boyd so threatening to his own leadership. Leadership in almost any business, and especially in military, are threatened by guys, people, that try to bring in ideas that are outside of the experience of the organization.

Brett: You were saying you’ve written an article how the military is anti intellectual. Is this what you mean by being anti intellectual? They’re not open to new ideas?

Tom: In a sense, yes. I mean the article was … The original title of the article was the impact of anti-intellectualism in the US Military, but it got changed when it was published in the American interest. The real point there is that anti-intellectuals are not dumb. They’re actually really intelligent people that they value experience and doing over thinking. Okay?

Richard Hofstadter wrote a Pulitzer Prize winning book called Anti Influential-ism in American Life in 1969. You know one of the Art of Manliness’ favorites Teddy Roosevelt played a significant role, albeit not purposefully, in the anti intellectual movement. Teddy Roosevelt was a fierce intellectual, right? But he was also a doer. When e wrote his famous poem, The Man in the Arena, right, that still resonates today.

What you’ll get is you’ll get people that are just doers and they can’t take anybody asking them, “How do you know that’s going to work?” They’ll say, “Hey, man. I’m the guy in the arena. I’ve been there.” I’ll give you an example.

When I was in Baghdad, we were going to go “do Falusha” for the fourth time… If we do this again tomorrow, is it going to necessarily and deliberately lead us to the attainment of our objectives? He says, “That’s the problem with you pointy headed ivory tower academic types. You know nothing about war.” I mean, first, it’s really condescending. Second, it also shows a lack of willingness to consider that even the possibility that there might be a better way, or that you might be wrong.

Mike Warden wrote a book called Rise of the Fighter Generals. He makes a brilliant case that when the strategic air commands looks at its ascendancy, not only within the air force, but within the department of defense. I mean Curtis LeMay was the chairman and joint chief of staff. We had STAC generals that were in all the key positions. They became ossified in Mike Warden’s words, like petrified wood, because they were so fixated on training and sitting alert that they didn’t think and they didn’t think outside their own day to day activities.

While they were just sitting alert and training, the fighter guys were sending their best officers to schools, and sending them to career broadening assignments, and sending them overseas to exchanges. Almost overnight, without even realizing it, the bomber generals found themselves on the out and out, and then the fighter generals were in the ascendancy. Yet today, those same fighter generals have ossified at least as much if not more so than the bomber guys did from that time. Boyd is a great example. John Body isn’t even discussed or mentioned among air force leadership today.

When I wrote that article on anti intellectualism, it was published back in 2009, a couple of colonels at the Pentagon said, “Dude, this is going to end your career.” I said, “If I’m right in what I wrote, then the senior leadership either won’t even know that the article exists, or if they do stumble upon it, they won’t do anything.” I ended up getting a lot of feedback from people in other branches of government and industry, but not a single word from anybody in senior leadership.

As far as outside the military, I think Hofstadter’s still right. Anti intellectualism is still strong. Again, he doesn’t say that anti intellectuals aren’t smart, but they just value doing over thinking. What you see today is the best company, the most successful companies out there are the ones that meld the two together, that find the practitioner scholar, that finds the person that can think and do at the same time. They can constantly say, “How can I do this better that’s an outstanding practitioner, but is also aware of what’s the latest thing out there that I can use?”

Brett: I think there is a tendency for any individual’s organizations to … You get comfortable, right? Something’s worked before.

Tom: Yup.

Brett: And you say, “Keep doing it.” Then you run into a problem and the typical response for organizations or for people, even, is that the problem is I just need to do more of what I have been doing. That will fix things.

Tom: Yeah, harder, better, longer.

Brett: Harder, better, longer, right.

Tom: If you work harder, work longer, and we need to be better, but at some point, you have to ask yourself, “How will I know … What are my criteria going to be to know that this doesn’t work?” When people say to me, “We just need to work harder. We need to work better. We need to work longer.” I say, “Okay, at one point are you going to know whether or not that works?” It’s not a challenge. It’s a serious question. When will you know if that worked or not?

I think one of the things that you should always think about in critical thinking, this comes from Alec Fisher’s book, The Logic of Real Argument, a really, really good book that … You know, there’s a few books that I always gave my direct subordinates that worked for me. This is one of them, The Logic of Real Argument.

He starts off by saying it’s amazing what you can figure out about a subject just by thinking about it. You think to yourself, “Well, duh.” Really, there’s some profoundness there when he says, “Ask yourself some basic questions. If that’s true, what should I expect to see?” That’s one of the questions that I always challenge my mentorees and my clients with. They say, “Well, this is going to happen.” I’ll say, “Okay. If that’s true, what should we expect to see? How long are you going to give it to see that?”

Another question is, “What would I have to know or accept in order to believe that could be true?” Right? “What would I have to know or accept in order to believe that to be true?” Another simple question is, “How do I know?”

A very, very critical part of planning, strategic planning and critical thinking is listing all of your assumptions. When we go through life, Brett, we really do, right? We go through life assuming that certain things are going to happen. At some level, to get anywhere, you have to …

Like for example, if you’re going to make your trip from Oklahoma to New York City and you’re going to drive, it’s a reasonable assumption that you’re going to have to find open gas stations along the way, right? There may be lots of other assumptions that you make without even thinking about it. One of them would be, that lots of people make is, they get in a car. They don’t realize that they’ve made an assumption that they’re not going to get a flat tire the whole way there, right?

Brett: Yeah.

Tom: When they get a flight, they open up their trunk and they got a spare, and then got the jack, but they don’t have that little mechanism that hooks into the jack to spin it around, right? You say, “Well I didn’t know that.” That’s because you made an assumption that you wouldn’t need it, all right?

It’s a very difficult step in the strategic planning process and it may be the most critical of all the steps in the strategic planning process to sit yourself down or your leadership team, whoever it is that’s going to be doing your planning with you, and to, no kidding, list out all the assumptions that you’re making for whatever the foreseeable time frame is that you’re working. Then you aggressively challenge those assumptions and then try to validate them.

If somebody wants to open a restaurant, right? I was helping somebody that opened a restaurant and they couldn’t understand why their restaurant was empty on a Wednesday night. Well, he said, “In the South, people go to church on Wednesday nights.” I said, “Well who goes to church on a Wednesday night?” I said, “Well you see, here you are. You’re opening a business with a fundamental assumption that hasn’t been validated.”

Those are just simple ones. Here’s another one if you’re going to open your restaurant. If you’re going to have a specialty packed restaurant that serves a certain type of specialty food, you need to know that your supplier’s going to be able to deliver to you all the days that you need it, right?

Brett: Yeah.

Tom: We go through life, whether it’s in a family, or whether it’s in a small business, or whether it’s in county government, or whether it’s in a large military, starting operations, without having actually listed and challenged and validating your assumptions.

Brett: I really love that idea. I can see that being very helpful just like on an individual level. I think a lot of people have their goals frustrated because they don’t stop to think about those assumptions and question those assumptions that they have. They don’t think about, well, I got this goal to, I don’t know, get this job at X place. Then they don’t think about, well, there’s going to be lots of other people competing for it. Maybe there’s something that will happen with the business that they won’t allow me to get that job. They have to take back on, or roll back on hiring, for example. So yeah, I like that idea.

Tom: Even something as simple as if you want to build a tree house, right? You can save yourself 10 trips to Lowe’s by sitting down and writing out the things that you need.

Brett: Yeah.

Tom: You know? Or, “Yeah, I know. I got plenty of that in the garage. I got plenty of those nails.”

Brett: I do that all the time.

Tom: You know, “I got plenty of those screws.” Think about this. It’s not unmanly. It’s not unmanly to go check to see if you actually have the screws that you think you do. In fact, I would say that it’s far manlier to go check yourself and to make one trip instead of having to make a whole bunch of trips because you say, “Crap. I really thought I had what I needed.”

Brett: Yeah, I do that all the time. Whenever I have a project around the house, I end up making five trips to Home Depot. One thing that I held too, so besides checking first is also, when you’re at Home Depot, whenever you’re there, buy more than you think you’re going to need.

Tom: Amen. That’s right, because you’re going to need them next time.

Brett: Exactly, or even if there’s not a next time. Assume that you’re going to mess up the first time. You’re going to need that extra material. That’s my bit of life advice there for you guys if you’re going to do something in your house. Buy extra.

Tom: I completely agree with you. I did my tree house with my kids a couple of years ago. It was great to have a whole pouch of extra screws with me 16 feet up in the trees, because you can’t get mad at the kids when they drop a screw.

Brett: Yeah.

Tom: You know?

Brett: They’re just trying to help.

Tom: You just need more.

Brett: Here’s a question I have. We were talking about John Boyd. You gave me that feedback saying that your career’s going to be over for this article that you wrote. John Boyd had that same sort of problem. Like he didn’t advance pass lieutenant colonel, I believe, in his career. He should’ve been a general, I think, but that didn’t happen for him.

Tom: He should’ve been a general but he was a colonel.

Brett: Colonel. Right. Here’s a question I had. How do you balance? Boyd said that you can either be someone or do something in life.

Tom: That’s brilliant.

Brett: To be someone in the military or any organization, you sort of have to be a yes man, sort of go with the flow. Don’t rock the boat. If you want to do something, you have to piss people off, for lack of a better word. You’re going to hurt your career.

Tom: It’s so funny that you say that. You were going to say buck the system, weren’t you?

Brett: Yeah, I was going to say buck the system, but it seems like you just piss people off. You irritate them. How do you balance that? There’s a part of you wherein like, “Yeah. I’m going to stick it to the man. I’m going to do something.” At the same time, you’re like, “Well, I got a family, right? If I lose my job or if my career doesn’t advance, that’s not just going to hurt me, it’s going to hurt my kids, who have nothing to do with this.” What’s your insight? How do you balance that well I got to support my family, so I kind of have to go along, but at the same time will actually want to do something.

Tom: I think that’s a brilliant, brilliant question. It’s a genuine and legitimate concern that people have. It’s really a legitimate concern. I will tell you that it starts with a mindset, okay? That mindset is not that you either buck the system or go along. Okay?

On the day of my promotion to colonel, my absolutely loving wife, who’s really quiet and normally shy, told somebody, “See, he bucked the system and still got promoted.” I really, gently asked her not to say that again, because I didn’t buck the system. I looked for an alternative path within the system. That’s the mindset that I took is instead of fighting the system, look to see if there’s an alternative path within it.

There’s a respectful way that we can say to our bosses and to our peers that we can do better instead of saying, “Hey, we stink.” Right? You can advance in your career by going along as time honored, right? The Japanese culture, the Japanese corporate culture in which the salaryman says, “Man, when I’m going to be a manager, I’m going to change things.” To get there, he has to be so completely co-opted by the system that he can’t make the changes that he wanted to make. How do you make that change?

First, you have to understand that any meaningful change is going to be slow change, okay? I know that you read countless articles about disruptive change, right?

Brett: Yeah.

Tom: People always say, “Yeah, we need disruptive change.” Actually, disruptive change is not really helpful. Disruption really disrupts people’s lives. It disrupts your operations, okay? That disruption often fails because people can’t cope with the pace of the change. If it’s really important, if it’s worth doing, then it’s worth doing slowly, and by building up a snow ball.

That’s what I always found the best way to do things. I’d start by making sure that my ideas are going to work. I try to patiently pitch my ideas to colleagues that I would really trust to tell me, you know, to wave the BS flag if they needed to, or to say, “Hey, man. I think that can really work. You listen to their input. Then you go to your boss.

One of my maxims is that they can’t say no if you don’t ask. I tell all my clients, and I tell all my mentorees that you’d be amazed at what your bosses will let you do if you just ask them. If you think about this from a sociology standpoint, it makes sense because the boss will get the credit if it works. He won’t take the blame if it doesn’t, right?

Brett: Yeah.

Tom: Always look to make things better wherever you are. Be ready to show your supportive reasoning. I’ve had guys say, “I think we should do this.” I say, “Why do you think that’s going to work?” They say, “Why do I have to give you evidence, man? Why can’t I just tell you what I think?” The answer is, really, because nobody gives a crap what you think if you can’t show them the evidence, right?

Your gut feel is never going to be sufficient reasoning, but when you can come to your boss with a good idea and then some evidence, you’ll be really surprised at how often that one change will lead to a cascade of changes that will make the company a new place. It will give you opportunity to rise.

Brett: So play the long game?

Tom: Absolutely. Now listen. You can’t play the long game, and there’s nothing wrong with this, if you’re hopping to job to job to job. You can’t play the long game for any of the companies. You can play the long game for yourself, but you’re never going to make meaningful change in those companies.

Brett: Got you. You wrote an interesting article I thought was fascinating. It was about Ender’s Game. Like you, I was late to the game on this book. I always thought it was a book … I didn’t read it when I was a kid. It’s sort of a book geared towards young adults. Yeah, I just never read it, but I finally got around to it. It’s an awesome book. If you haven’t read Ender’s Game yet, read it.

You wrote an article that Ender can actually teach us a lot about strategic planning, leadership, and within large organizations. What can Ender teach us about being better strategists and better leaders?

Tom: Yeah, listen. Like you, I was a really late comer to Ender’s Game. From the time I was in my early 20’s, I had people recommending to me to read Ender’s Game. Then when I was in grad school, getting my PhD, a professor says to me, “You’ve never read Ender’s Game?” At that point, I said, “All right. This is dumb.” I went and bought the paperback. It was like a gut punch. I mean it was a total gut punch. What an idiot I was for not having read this book.

Then I had an opportunity to meet Orson Scott Card when he came to Lexington on a book tour. I stood in line with everybody else and I just thanked him for what he said, and he looks up and he says, “Yeah, you don’t look like everybody else in this line.” I said, “No.” He asked me what I did and I told him what I was doing. That led to a long correspondence and a really close friendship.

I brought him to the STAC college. I was vice dean of the air command at STAC college, speak a couple of times. He asked me to write a chapter on Ender on leadership for is book, Ender’s World.

I really think that you know, people lose sight of a really important fact in this book is that Scott Card didn’t set out to write a book about science fiction as a future. He set out to write a book about sociology and moral situations and dilemmas and how to face those. That’s where I think the real leadership and manhood skills come in.

The first lesson from Ender’s Game is that skill and excellence are a muse to advancement and a threat to your peers and your bosses. If you’re really good at what you do, let your work speak for itself. Be humble.

Second, if what you’re doing doesn’t work well, at some point, you have to consider that doing it again and again and again also won’t work well. Find another way. Think through alternatives. Look for those people around you that have good ideas and then lift them up by empowering them to try their own ideas and tactics.

This is exactly how Ender built his team. He was given the dregs that nobody else wanted, right? What did he do with them? He found what each one of those kids was best at and used them for that at the right time. All right? He realized that everyone had to have some capabilities that he made the most of every person’s best and put them where they were needed most when they were needed most.

Then Ender does something else that’s really hard for all of us. I mean, I think this is one of the most important things that we can get out of strategic planning and critical thinking. Ender accepts the world as it is, not how he’d like it to be, right?

So many people get hung up on obstacles and they [inaudible 00:44:01] anything about. They start banging on their steering wheel, right? What’s the only thing that’s going to fix the flat? You getting out and fixing the flat, right?

Then again, I mentioned about being humble. Ender was never too proud to ask for help, and to make others better. The best leaders in any field of industry aren’t measured by what they do. They’re measured by, I think, how many of their former subordinates are promoted or hired away to other leadership jobs. That was Ender. They took every one of his kids and made them commander.

Brett: That’s awesome.

Tom: It is. I think that … I try to tell my clients, I try to tell my mentorees you’ve really made it if your people get hired away from you.

Brett: That’s a good thought. Actually, before i did the Art of Manliness full time, I had a boss who was like that. I told him, “I’m going to do this thing full time. I have to quit.” I felt really bad leaving because he’s a good guy and he’s like, “No, that’s awesome. Do it. I think that’s fantastic.” Yeah, there’s like no grudges. He was happy for me. To me, that was like a sign of a good manager.

Tom: Amen.

Brett: Here’s a question I have. You know , you talk about critical thinking, but are there biases that you see over and over again that cause the most problems for leaders and organizations?

Tom: Yeah, there sure are. I think Steven Levitt – the guys behind Freakonomics — they’ll tell you that have you ever heard them say what the three hardest words in the English language are? It’s I don’t know.

Brett: I don’t know. Yeah.

Tom: Yeah. I found this to be spot on. The greatest mistake that senior leaders can make is lacking the humility to consider that there’s something that they’re not doing right or to admit that there’s something that they don’t know. You were talking a little while ago about organizations that have been doing things the same way for a long time? They expect that tomorrow’s going to look just like today, right? Well the sun’s risen the last eight days. It’s going to rise again tomorrow. That’s pretty good. Not invented here is a huge bias that hurts organizations. On the other hand, the most successful organizations and leaders are those who make it part of their culture for people to interact outside of their own specialty.

It doesn’t really matter if you’re a lawyer and you can talk about the Heisenberg uncertainty principle. Somehow or another that’s going to make you a better lawyer. If you can talk about the sociology of power indices, who’s going to talk to you and give you bad news and who won’t when you really need to hear it? Just stepping outside of your bounds, and being willing to say, “I don’t know. Help me.” I think that’s the most important bias that any leader needs to get over.

Brett: I think it’s an important one because one thing I notice too with people who succeed in one area and they become a leader, they have a tendency, and I think other people have this tendency too, to see them as experts in a wide variety of topics, right? A lot of people do this. Okay, well you’re successful in X business, so I’m going to ask you for advice about my business that’s completely different. The guy, he’s flattered, because oh, this guy asked me. He’ll give an answer, but he doesn’t know anything about that business, so he can’t really give good advice.

Tom: Amen. You know, I’ve had people ask me well, “How come you don’t do finance and marketing and IT consulting? You’re a consultant. Shouldn’t you be doing that?” I said, “Well, I got to limit myself to something that I’m really confident at, okay? What I would really, really hate to do is to tell you, yeah, I’ll help you with your finance stuff and not succeed and then have you tell your peers don’t go to that guy. I would rather undersell and over deliver.”

Brett: Yeah.

Tom: Or under promise and over deliver. On the other hand, I’m going to continue to try to get wiser and wiser on those things that I don’t know about. If somebody asks me, “Hey, can you help me with this and I can’t do it, well, I’ll get somebody within my own network who can help.”

Brett: You have this great list of maxims you have on your website. I love maxims. Big fan of Baltasar Gracian and other guys who just wrote aphorisms. I love the idea of just packing as much wisdom as you can into a short amount of words. How did you develop this list of maxims and can you share a few with us?

Tom: Sure. Well, I was a professor at the college which is the air force’s graduate school that they send the top majors to every year per year, sit in seminar. While I was there teaching, I was also going off and giving seminars at other universities, at the NATO school, at foreign defense colleges as well. Everywhere I went, people would start asking me, “Hey, you mentioned these books and you mentioned these sayings on the board. Can we have a list of them?” I realize I really need to put these on paper.

I came up with a list of maxims. Some of them are goodness breeds goodness. Seek balance in life. Truth doesn’t change based on the rank of the recipient. If you have to eat a frog, staring at it won’t make it go down any easier. Iron sharpens iron. Bloom where you’re planted. Almost every one of these comes from real life experiences or multiple real life experiences.

Brett: I love the one, bloom where you’re planted, especially for young people, because I think a lot of young people have this idea that in order to succeed in life or to really get something out of life, they have to go somewhere else, right? They got to go to the big city. They got to leave their state. I really think there’s a virtue in deciding, “You know, I’m going to stick where I’m at and see what I can do here.”

That’s what I’d done. I live in Tulsa, Oklahoma still. A lot of people ask me why don’t you move to San Francisco, New York City, where there’s sort of like more connections. It’s like, “You know, I like doing what I’m doing while I’m here.”

Tom: You know, Brett, I think that’s brilliant. Those words came from a really good friend of mine, Scott Bethel. He used to be a general. Now he’s a consultant himself. We used to speak together quite a bit. We would go do the tag team on leadership and leadership development occasionally.

We would get the young kids that really had stars in their eyes. “Okay, I really want to get ahead fast. What is my quickest route to senior leadership?” We would tell them to bloom where you’re planted. That you get promoted in any business, in any segment of industry by doing what your boss tells you to do. Not by fighting. Like I said, you don’t have to always be the yes man. You could do what your boss wants you to do by telling him that there’s a better way to do it. That’s how you bloom where you’re planted. A lot of people say, “Well I don’t like that job. That’s a crap job. That’s beneath me.” You know what? Sometimes bosses just want to see if you have the humility to do that job. They know that you’re capable.

There’s a great movie, a 1964 movie called The Cardinal, produced by Otto Preminger, with John Houston was an Academy Award nominee. Tom Tryon was a young priest who rose to be a cardinal. He was really good. He knew that he was smart. Early on he asked his bishop for a really good assignment. The bishop sent him out to the hinterlands to work in a small community that wasn’t even a village. It was essentially to say, “Could you be humble?” He did. He bloomed where he was planted. He rose. It’s a great story and it’s a great analogy for getting ahead today in the world.

Brett: Fantastic. Well, Tom. This has been a fantastic, really fascinating discussion. You’ve referenced a lot of books, your maxims, of course. Where can people find more about your work and the books you recommend for becoming better strategists?

Tom: Thanks, Brett. They can go to my website. They can go to or That stands for Blue Grass Critical Thinking Solutions. They can look me up on Facebook. They can Google my name, Tom Ruby and critical thinking, and it will come up with the website. On the website, you can read my maxims. You can look at my reading list. It’s available for everybody. Articles that I’ve written and ones that I recommend other people read. I hope everybody can be intrigued enough to find one book off that reading list that they haven’t seen and go read it.

Brett: Awesome. Well it’s a good list. I’ve checked it. I love a good reading list. Got a few in my queue now because of it.

Tom: Thanks, Brett.

Brett: Well, Tom Ruby. Thanks so much for your time. It’s been a pleasure.

Tom: It’s been a pleasure talking to you too, Brett. Thanks.

Brett: Our guest today was Tom Ruby. He’s the owner of Blue Grass Critical Thinking Solutions. You can find out more information about Tom and his work at Again that’s Check it out. Lots of great free content out there you can read and peruse and add to your strategic repertoire.

Well that wraps up another edition of the Art of Manliness Podcast. For more manly tips and advice, make sure to check out the Art of Manliness website at If you like this podcast and you’re getting something out of it, I’d really appreciate it if you go to iTunes or Stitcher or whatever it is you use to listen to the podcast and give us a review. That would really help us out. Your feedback will help us out as well. Until next time, this is Brett McKay telling you to stay manly.

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