Asking The Right Question and Second Order Thinking: Smartcuts Miniseries Pt.4 with Shane Snow

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I’m extra excited about this one.

So a lot of you know that I have listened to Shane Snow’s audiobook Smartcuts many times and how much I was looking forward to having him on the show for the first time back in April. Well the only thing better was when he agreed to come back and do entire deep dive miniseries into the stories of those who have built these skills of avoiding unnecessary work and, instead of slowly climbing the “supposed to” ladder, building their own ladders to success faster, as well as how-tos of for how the rest of us can do the same thing.

A new episode of the miniseries will be out each Friday for the next 6 weeks.

If you missed the first time he was on the show you can listen to it here.

Thanks for Listening

Jess

P.S. If you like the episode please shoot me an email and let me know what you liked about it: Jess.Larsen@GraystokeMedia.com

Bio:

Shane Snow is an award-winning journalist, explorer, and entrepreneur, and the author. He speaks globally about innovation and teamwork, has performed comedy on Broadway, and been in the running for the Pulitzer Prize for investigative journalism.

Snow has helped expose gun traffickers, explored abandoned buildings around the world, eaten only ice cream for weeks in the name of science, and taught hundreds of thousands of people to work better through his books, including the business bestseller Smartcuts.

Snow's writing has appeared in GQ, Fast Company, Wired, The New Yorker, and more. He is also a board member of the media technology company Contently, and the journalism nonprofit The Hatch Institute. Make sure to check out ShaneSnow.com. Follow him on LinkedIn.

Here is the auto-generated transcription of this episode:

Jess: This is part four of our mini-series on Smartcuts with Shane Snow author of the book Smartcuts. Shane, what are we going to talk about today?

[00:00:08] Shane: So today we're talking about step two of the scientific method, which is the part where you find questions to be asking based on the observations that you've made and really what this is, is about exploring how to think about the right trees to bark up.

[00:00:23] When you're trying to engage in innovation, you're trying to solve problems, making sure you're solving the right problem that you're asking the right questions. So you don't spend all of this mental effort on the wrong things.

[00:00:36] Jess: Well, what's the first part of that.

[00:00:38] Shane: Okay. So if what I just said sounds too basic and too simplistic, it quickly gets, more than meets the eye, this topic and it starts with a concept called second order thinking.

[00:00:51] And what second order thinking is it's thinking about not just the consequences of what happens so the direct actions, right. You knock something over. It's thinking about the consequences of those consequences. So you're not something over, and that does something you knock over the vase and the water spills and it fries the electrical outlet or something.

[00:01:13]so the second order thinking is more than just short term thinking versus longterm thinking, it's about the ripple effects. And I think ripple effect is a good metaphor because a ripple, you know, you throw a stone and upon, and the ripple goes in all directions, at least two dimensionally. And, so what second order thinking is about is thinking through all the ways that the world could be affected by the things you do.

[00:01:38] And this will play into coming up with better questions to ask when we're trying to solve problems, but it's really this idea that a good chess player doesn't just have great strategies, they're constantly asking. And then what will happen if I make this move? So they're thinking several moves ahead, and it's not just outsmart people like you would in chess, but to not, it's this kind of thinking is to make sure that you don't end up with unintended consequences for what you do or

[00:02:07] You know, in legal terms, negative externalities. So, if you, you know, you've taken economics classes, you'll know that externalities are usually taught. Like we, the factory makes a thing, but it creates waste and that waste goes in the river. The factory doesn't own the river. So the waste in the river, the poison water is a negative externality.

[00:02:28]those can be fairly obvious, but what is the next thing that happens if the, you know, the waste goes in the river and this often comes about, I'll share a real quick story about this. it often happens in laws or in policies or plans or solutions to problems that are meant to help the not thinking through the second order, thinking makes basically good.

[00:02:50] Intentions go bad in ways that are often really hard to detangle. So recently this one's on my mind cause it affects, writers like me and then a lot of writers who I know. California recently designed a law to protect Uber drivers and other freelancers in the gig economy from getting screwed. But that law inadvertently screws over freelance writers and, you know, the details don't matter so much, but by not thinking about.

[00:03:18] All of the potential people that could be affected by something that, that was meant to protect someone suddenly you're throwing out a bunch of people on the street. So second order thinking is thinking in that way so that when you ask the questions that set you down your path of problem solving, you're not asking a question that certainly leads you to screw yourself or other people over in the process.

[00:03:39] Jess: You know, I immediately was thinking about sales teams and when we create incentive programs that create, you know, maybe a higher volume of sales right now, but then invite everybody in the rest of the company to hate the sales guys or, you know what I mean?

[00:03:56] Shane: Yeah. Or, Oh, sales is such a good example, right?

[00:03:59] You, you incentivize the salespeople. I mean the most basic this version is you incentivize the salespeople to close deals by March 31st, get good deals in by the end of the quarter. And so they close a bunch of deals that then are an enormous pain for the account management team to handle, or that cancel immediately.

[00:04:17] So then you say, well, let's incentivize them to close deals that renew and then the unintended consequences that it takes a long time to close those deals. And so suddenly you're like, well, we need to now close the deals by the end of the quarter. So it's like constantly only thinking through that first step

[00:04:33]and not, you know, it's hard to come up with commissions. I, you know, you probably know better than me coming up with incentives for salespeople that accomplish the short term needs without the long term, you know, damage or, you know, counter effects. That's really difficult.

[00:04:51] Jess: Well, and you want it. You know, very often it's you want to incentivize them to, to get out there and get after it. Right. And you want to incentivize their work, but when there's no incentive to cooperate or to treat their support people well, you often invite intense degrees of individualism, which is something that salespeople, you know, as a sales guy, I consider myself a sales guy for 20 something years, 25 years, even when I was CEO of an investment fund, I still feel like he has top sales guy.

[00:05:25] Right. And, you know, there's a temperament given to individualism and ambition and competition very often. And so when we then create systems to double down on that, like, you know what I mean? It's like asking me if I want three root beer floats. Like you didn't, you don't need to push that hard.

[00:05:44] Shane: All right. Well, I think I may have mentioned this before to you, either on air or off the air, but I've been watching The Wire lately and I'm like 20 years too late to it. but in The Wire, there's this constant thing that drives me crazy. Which is that all of these detective, not all of us, but so many of these detectives and their bosses and the majors and the colonels and the police department,

[00:06:06] they're so worried about their potential for promotion or how will this look for me that they don't want to take on the case? It's like 13 people have been murdered, Oh, no, I hope I don't get it. Cause then my, you know, clearance rate will go down and I'll never get the job. And it's like, yeah, but those 13 people have families and like, you know, the individualism thing.

[00:06:28] I do think it's both short term thinking and often inadvertently. you know, not good for second order thinking, cause say, say you do, you know, in that detective job, you end up advancing and getting promoted cause your rate is high, cause you haven't solved that many murders, so you don't take them on or whatever, but then more people are getting away with murder and more families are upset that the police don't solve the murders.

[00:06:51] That's gonna make your job harder. At some point, kids are throwing rocks at you because they hate the cops, right? Like in a, you know, there's, there's something there and there's something you said too about, that, that makes me think of, of just adding a moral filter to the incentives that we have.

[00:07:08] And I'll get to that later. If we have time, when I talk about chaos theory, there's something really interesting that when you're thinking in these terms of second order thinking, there's a little bit of a trick that you can use to sort of show or yourself up against the worst kinds of unintended consequences, but we'll get to that.

[00:07:25] Jess: Well, I'm going to use an example and you can tell me if you don't want to continue on this one, but I heard this story about you as a 16 year old, creating your own business with greeting cards that ended up becoming so successful. You ended up making more money than your dad. At which point the parents got really involved in whether this is a business Shane is allowed to do or not.

[00:07:45] Shane: Yeah. Yup. So that happened. I, you know, now, you know, decades later, it's a, I look on that story only as a lesson learned and as a motivation, but at the time it was really infuriating. And, you know, part of it was because I was like a crappy teenager, but, but the, the story was I started making this greeting card site.

[00:08:06] A couple of my friends were doing similar things and I started making a lot of money and my parents got nervous that their 16 year old kid was getting these huge checks from the internet and his early days of the internet. And so they wanted to know, are you doing something illegal? Is this a scam? Who are you involved with?

[00:08:20] And I, you know, I showed them, no, no, no, everything is fine. But they got worried that I would, basically learn the value of hard work. And so they made me shut down the website and that was furious and they made me get a job at the gas company, digging holes and spray painting gas meters, and

[00:08:39]you know, I don't know what you're getting at with this from you know, the second order thinking standpoint, but the unintended consequence of that for my parents was I vowed to become an entrepreneur and to never let anyone tell me what I can't do in terms of my career, which, you know, early on ended up being extremely good and sent me on a path that has led me to be a little bit contrarian and also to, you know, all this stuff that we're talking about, I think is to some degree, a consequence of

[00:09:07] me wanting to prove that you can find a better way to do things than just the traditional, you know, you learned to be a good worker by digging, literally digging holes with shovels. So, you know, I may have like the wrong lens on that, but it definitely backfired on my parents to some degree. And that that's exactly what I went out and ended up doing.

[00:09:28] Jess: That's funny, you know, I'm interested. You know, years later you ended up building a multimillion dollar tech company. Can you think of a time there where you thought, Oh, this is going to be the greatest and then it gets going and then it cause a different problem?

[00:09:42]Shane: yeah. Well, one that I've shared quite a bit over the years is a couple of years in mean it was like a year and a half and we almost ran out of money in the business for the dumbest reason.

[00:09:54] And basically what we did is we had freelance writers and editors, and we had clients, we facilitated them to work together. And then because freelancers, they really have a hard time with cashflow. They often get screwed by their clients. If you get paid, like you're an agency, which is like 90 days later, then that might, you know, you might not be able to make rent if you're a freelancer.

[00:10:15] So part of our value proposition, why we could take a cut in the middle is we said to freelancers, If when you file your assignment, the first draft of whatever is your client asks you for, we will pay you right then. So as long as you do the upfront work, we'll pay you understanding that if you need to make changes or edits, you will do that.

[00:10:34] Cause you want to keep the client and you want us to keep you as one of our freelancers and it went over extremely well, freelances love this because we solve their cashflow problem. You need money on Saturday. Then you do some work during the weekend. You cash out on Saturday and it's all through PayPal.

[00:10:49] It's super simple. And we got incredible loyalty from this. A lot of signups, a lot of freelancers really wanted to work with us, but the unintended consequence was the thing that happened next. So the consequences was freelancers were happier. Our clients were happier. But then we ended up having cashflow problems ourselves because our clients paid us 90 days later.

[00:11:10] And so the more successful we were, the more clients we got, the more freelances we had freelancers we had making money getting paid. The more we were acting like a bank and floating cash that our clients had not paid us yet. So the irony was, you know, we have a million dollar quarter and couldn't have been more broke.

[00:11:29] You know, we got to the point where we had like two weeks of cash left and had to panic and rethink our strategy. So we had to add, you know, how do we to the questions, you know, that we're trying to accomplish? How do we make freelancers, happy and provide value to their cashflow situation so that it's worth it for them to give us a cut without

[00:11:50] Causing us to go bankrupt ended up being a key thing, but it's, you know, that sort of thing, you know, you can only get fooled once by that thing, but you can get fooled a million times by that thinking, that, you know, where you don't think enough through these second order consequences of things.

[00:12:07] Jess: So what did you guys end up doing?

[00:12:09] Shane: The thing that ended up working there is a, actually a really simple solution. We told our clients that, we asked them, can we build you up front for the work that you estimate you're going to do? And a large percentage of them said yes, because it turns out that for our clients were marketers and every time they needed to pay a bill that did go to their finance team, their accounting team, you know, whoever, and basically be a pain for someone to get a check written for us.

[00:12:37] And so if we could reduce the number of times that they did that, that was good for them. So we said pay for a year upfront. And, you know, maybe we'll give you a little discount or, you know, just pay for your up front. What do you think? And a lot of people didn't even, we didn't even need to get to the discount part before they said, Oh yeah, I got a deal with my finance team once, great.

[00:12:54] So we ended up having a positive cash flows from our clients. So we're essentially holding money in escrow before our freelancers made it. Every client can do that, but enough of them did that it ended being in our favor, which was surprising. A nice surprise for sure.

[00:13:11] Jess: Wow. That's awesome. So, any other stories come to mind on this or any other examples come to mind for you?

[00:13:20] Shane: So the thing that I like to think about it, like if you're trying to wrap your head around this second order thinking idea and trying to separate it from just like long term thinking, like to really dig in, an analogy I like to use is, not an analogy, like a thought experiment, I suppose, is think about

[00:13:39] Evil genies. So, you know, not every genie is nice, like the genie and Aladdin, like trying to look out for you most genies and, you know, mythology, they're trying to screw you over. Cause they hate being a genie they're trapped. And so, you know, there's that Brendan Frazier movie, Bedazzled, I think, where he meets the devil and she kind of grants wishes, but sort of like a genie.

[00:14:01] And, and he says, I want to be rich. And so she makes them a drug lord and he has all the problems associated with being a drug lord. but you could say even like a less mean genie, that's trying to wriggle out of, I want to be rich, could just rename you to Richard. And, so that's, that's not necessarily second order thinking.

[00:14:17] That's unintended consequences, but the genies scenario that I like to ask, maybe I'll, I'll actually ask if we can talk through this, I'll ask you this. If the Beach boys got their wish that all of them could be California girls, I wish all the girls were California girls. What would happen then? So let's say that all females on planet earth suddenly are in California.

[00:14:41] They get teleported there, Beach boys get their wish. What are the kinds of things that would happen? What do you think.

[00:14:48] Jess: Man. Well, I mean, my, my initial thought here is you go from a population of 30 million, something to 3 billion. You got some infrastructure problems is day one. I mean, there's so many things that would happen.

[00:15:02] Shane: Yeah. So California. So there's, you know, it's interesting as I didn't even think about California, when I kind of started thinking about this hypothetical, I think a lot of people would jump to like California is gonna be in big trouble. You're going to have supply chain problems to get food there.

[00:15:17] Where are they all gonna live? You know, what's going to happen in California, but where I immediately jumped to, and this speaks to, I think the power of having cognitive diversity, you know, in your brain trust when you're thinking about these kinds of the second order of consequences, you're going to think of things and I'm not going to think of, but I think of, you know, all the mothers in India are now gone and there are a lot, lot of children, I think India and Africa has more youth under 21 than they have people over 21.

[00:15:47] I think that's right. Either way there's places in the world where that's going to happen something. So there's going to be kids with no moms. A lot of those kids don't have dads either. So there's going to be like an enormous set of problems there. But even the ones with dads, like third order consequences, might not just be the dad has more work, but that's my, it's actually lose jobs because they have to spend time dropping off kids and then there's going to be an unemployment problem in these places.

[00:16:10] And then if there's unemployment problems in these places, then what happens. So, yeah, there's all sorts of things that would happen. I mean, I think it's a juicy question because once you start thinking about that, like if all the women are in California, you know, who's picking coffee beans, and there's places in the world where the women are the ones that can pick the coffee beans, you're going to have to restructure that economy, or there's gonna be no coffee for a while, which means a bunch of people are going to be grouchy, which means they're going to make bad stock trades and so on.

[00:16:39] Jess: Yeah. It's interesting to think of, you know, Because so many things like virgin virtues take into access, become problems, right. You know, you think like how great it would be if everybody was buying our stuff, which. You know, if you're a cool skateboard brand, you and I both grew up being skateboarders, right?

[00:17:00] Yeah. I mean, I remember being like offended when you could get Etnies at the mall. I was like, hold on. What are you, what are you doing with those skate shoes? You don't skate. Do you know what I mean? And like, look at, look at how classically, you know, youth fashion is notoriously unforgiving right?

[00:17:18] Right. As soon as the exclusive brand, isn't the exclusive brand. You know what I mean? All of a sudden the profits are gone. Like you look at with the exception of maybe Volcom, hardly any of those brands that went big and that you could start buying it, pack somewhere, you know, real skaters weren't getting tattoos of those logos anymore.

[00:17:36] Shane: Right. You know what I mean? Yeah. It reminds me of Krispy Kreme. So when I grow up Krispy Kreme donuts, where this like prestigious greatest donut ever, you drive four hours ago, get Krispy Kreme. And then when they started putting them in gas stations, You know, now they can sell more Krispy Kreme allegedly, but they actually sold weight less.

[00:17:54] Cause people were like, Oh, these are not quality donuts anymore. I think the donuts were still the same, but people lost faith in them that, you know, that I think that falls in the category of unintended consequences, rather than necessarily like the second order thing. But the second order thing of that is they had to lay people off.

[00:18:12] Like they had to restructure, they, they created a whole set of problems because of that. but I think even, even if you're just thinking about it in terms of unintended consequences, not even like the step two unintended consequences, just thinking this way is a useful exercise. Cause it helps us to figure out the right questions to ask.

[00:18:29] You want to add those parameters. So the genie doesn't screw you over basically. And you want to start from, you know, from the right point, you know, Krispy Kreme, or, you know, these brands Etnies that, they want to increase their distribution. Right? The question they probably asked when they, before they made these moves, that ruined their brands was how do we sell?

[00:18:47] How do we increase our distribution? It probably wasn't how do we increase our company's profits? Right. It probably was something a little bit further down the chain. They weren't, zooming out enough to a question that wouldn't have these other consequences. So, you know, a better question than even how do we increase our company's profits might actually be how do we increase our distribution without decreasing our brands cache.

[00:19:16] Without it it's like adding those parameters without losing our most loyal customers without having to lower our, you know, our costs or our prices, that sort of thing. So this really gets into the second main idea that I want to talk about here, which is how do you drill down to the right questions to ask?

[00:19:36] How do you ask awesome questions and there's a couple of things here, but the starting point in general, whether we're talking about these kinds of business problems or just in general, good questions. I think the principle is that you want to ask questions that open up the most possibilities you're trying to explore.

[00:19:58] You're trying to set yourself up, with the most potential to succeed. And you want to ask questions that give you the most possibilities. So that means the worst kinds of questions are multiple choice questions. And this is actually the worst kind of question for an interviewer to ask.

[00:20:14] So if, if I'm interviewing you say I have a podcast I'm in, are you interviewing you? And, I say, Jess, how is it that you became so successful in, you know, the eight enterprises that you're involved in? Is it because you're going to time management or is it because, you know, you're just a, like a smarter thinker than other people, or is it because like something that your parents taught you?

[00:20:37] That's not a good question because either, Hey, I'm going to, it reminds you of something that you should talk about and get you off track of something that's interesting, or I'm also, I'm taking way too much time on that question when you could be taking more time helping me to understand you.

[00:20:55] So if, instead I say, how is it that you know, you're so successful with the eight enterprises that you have, and I cut the question off of the question mark, that you could go in a bunch of directions that I'm not even thinking about. And so this idea of multiple choice questions, you know, in business, how do we increase our profits for Etnies shoes?

[00:21:17] Should we go to the malls or should we open a website or should we do something else? That's the wrong question. You don't even get to the should ways until you explore what is the underlying best question so that the, should we sort of cut off possibilities? the other thing I'll say is you don't want questions that are

[00:21:39] sort of fishing for an answer. And this often happens. This is the way that, that this whole scientific method approach to, innovation can be hijacked by people is if and you kind of want a certain outcome, you're hoping you have the idea. And you're like, okay, we're going to go through this to try and be buttoned up about it.

[00:21:58] But I'm really hoping we arrive at, put the donuts in the growth in the gas stations. Then you'll be inclined to ask questions that are fishing for that answer. Like. What kinds of places where motorists stopped to refuel might be good places for us to increase our market share that it's not going to be that dumb, but we're often guilty of that sort of thing.

[00:22:20] So leading ourselves or leading people to an answer. And then along that line, I would say in general, yes or no questions should be very deliberate. You should only use yes or no questions when you really only want to confirm something as a yes or no. So you want to confirm that something's a fact, great.

[00:22:42] You want to find an idea you don't want to use yes or no questions unless those yes or no questions are helping you to boil something down to a principle, but should we go, I'm going to really just sort of, these are bad, hypothetical. Should we put our donuts in gas stations? Yes or no? Maybe that's a good question, but if you're asking that question before

[00:23:04] you ask the, the better, more underlying question of how can we increase our profits without ruining our brand reputation. Then, you know, you don't even need to ask the yes or no, if you've done that kind of a proper foundation, does that kind of make sense? Here's the, do you have any rebuttal to that actually?

[00:23:25] Jess: Yeah, well, it makes me think of a few examples and a couple of questions. One, it makes me, the example was, Stephen Colbert on the Colbert report when he's got, you know, very left wing, movie star on him, he asks the question says, you know, George Bush, your favorite president, or the best president of all time, which one?

[00:23:45] Jess: But it's interesting how often. when we throw out suggestions too early, we unintentionally bias them. Right? And it's like, to me, I think to me, I guess, suggestions or what could be considered multiple choice could be a form of prompting lateral thinking. You know, like let's say that they get out everything that they can, they come up with as many things options that they can before we bias them.

[00:24:14] Or they're just like deer in the headlights. They're like, I have no idea, right. Going like,  well, how about A or B or C or D just to like, get them on the train of getting their brain to, to go wider with it makes sense to me. And I guess my question is, in your mind, how do you walk that balance beam of helping them to think laterally versus biasing them?

[00:24:35] Shane: Yeah. I, awesome question. it gets at actually a key thing with this scientific method is, don't jump to the next step before you're ready, because those kinds of questions. What if questions are awesome for exploring ideas? They're awesome for exploring new territory and for combining ideas.

[00:24:58]and we'll get to this actually in the next episode, when we talk about brainstorming and hypothesis. So when you're in the hypothesis stage and you were trying to find an answer to the right question, then what if we did this like a ballet dancer would, even if that's a crazy question, that's a useful question.

[00:25:15] That's exactly what you want for sparking lateral thinking. And same thing with why not questions. These are the kinds of questions that open, hidden doors. So we'll talk about those. We'll dig in deep into those next time. Those kinds of questions are fantastic for exploring possible answers.

[00:25:33] And so I think what you might be getting at, which is interesting and sort of meta is when you're trying to win. The question is what's the right question, then, you know, the answers to that question could be helped by what if and why not. Exploring the different kinds of questions is itself its own

[00:25:53]you know, this whole thing can, can kind of splinter out into little mini scientific methods. So you absolutely can do that. But you said it itself, the key is you don't want to and one of the reasons why multiple choices bad is a or even yes or no. Is that right? You don't want to fixate

[00:26:14] On the wrong things or get stuck, sort of thinking about a given particular direction before you've explored enough to find, the best direction. So, yeah. So if you the good news is once you know all this stuff in you, you're being cognizant of it, then you can catch yourself when you're employing that bias.

[00:26:35] Well, we've been talking about, you know, gas stations this whole time let's stop. And, you know, and say, is this actually coloring the way that we're even going along this line of inquiry? Okay. Let's, let's take that off the table and explore elsewhere for a while. You know, once you're cognizant of that, then you can, and in general, I would say that the, the best questions for exploring answers are those hypothetical type questions.

[00:27:01] So what ifs and the why nots the best questions for drilling down really are how and why questions. So why is it that we aren't increasing our market share? Why isn't that our customer, why is it that our customers aren't out renewing? and those kinds of questions can help us to sort of broaden the aperture and then while you're exploring, well, what if then those can help us with the ideation for those right questions. Does that make sense?

[00:27:29] Jess: Yeah, it does. I think maybe the takeaway I'm getting from this and I want to have you weigh in on it, but I guess I feel like it's becoming even more clear to me this idea of separating out. Am I asking this question because I'm in persuasion mode, and I'm trying to get people to come to my conclusion?

[00:27:46] Or am I asking this question out of curiosity and exploration and discovery? Like, am I currently pursuing truth or have I decided I have all the truth I need and now I need the troops on board so we can get everybody rowing in the right direction.

[00:28:03] Shane: I love that. I love that. It's just a, like a stop and ask yourself question, right?

[00:28:08] Like check in with yourself. What modem I’m in. Similar to a question that I like to ask when people are talking about problem solving with teams and they say, how much of a diverse pool of thinkers do I need for this question or for this thing, do we really need to go through this whole exercise of recruiting a team for this?

[00:28:27] Can we just use the same people as last time? And you know, the stop and check yourself question is for that kind of thing, is it's really relevant to what we're talking about is are we trying to solve this problem in a novel way? If the answer is no. Then who cares? Just gather up as many bodies as you can to do the thing that you've always done.

[00:28:45] But if the answer is yes, then you want to be thoughtful about who you gather up to solve the problem. And I think to your point with this, am I in exploration mode or am I in persuasion mode? And if you're in persuasion mode, then sure use all the analogies you want, lead people, you know, using questions.

[00:29:02]you know, I, I think there's some value in not relying on rhetorical smarts to outsmart people into believing you and, and actually, you know, allowing people to argue with your logic, so that you can make sure that you're right about things. But, you know, if you're in that persuasion mode, there's no time for dilly dallying, then use all the tools at your disposal.

[00:29:24]but if you're not, then that's when checking in and saying, you know, are we operating from a place of bias? Is there a better way to zoom out and ask the question here? Do we need to answer an underlying question first before we can get to this question that we think we're asking that sort of thing?

[00:29:43] Jess: Well you know, for me, I think the reason that I bring that up is, so often when I'm trying to give myself pass of looking at open-minded, I am and look at, look at how well I'm taking everyone else's ideas into consideration. I'm not sure bulldozer. Right. And it's kind of like that self deception thing of like, Oh really?

[00:30:03] Then why are you asking the questions? You know, Jess, you're so proud of yourself for being open minded and asking questions instead of making declarations. Should you really be so proud of yourself or are you just disguising your persuader mode and giving yourself a pass when you shouldn't be?

[00:30:20] Shane: Interesting. Yeah. Oh, you know, the Socratic method using questions to get people to come to the conclusion you want them to come to ideally the correct conclusion that is an incredibly effective form of persuasion. But also you can outsmart people that way and get, and outsmart yourself. Like you're saying that like, Oh, I'm actually allowing my team actually leaders do this.

[00:30:42] Yeah. I got participation from my team. I have buy in because I let them be part of the process for exploring this thing. That really was the answer that I wanted all along smart people see through that in a lot of cases and say, no, we're not allowed to participate. The boss has led us through this exercise so that we could be tricked into thinking that it was our idea.

[00:31:01] So, yeah, it's, there's so many pitfalls to be falling into. It's like once you unwind this stuff, you realize, just how easy it is for you to deceive yourself too. And, and then when you get to that level, you being more smart actually gives your subconscious. Ego more intelligence to deceive you in other ways, too, which is like the brutal irony of getting smarter is our ego gets smarter too.

[00:31:32] Jess: Yeah. You know, I think my next question then is. We’ve pat ourselves on the back so much for coming up with good answers. Right. And I think that's one of the reasons when I am less collaborative is I want to be seen as the guy with the answer. And I feel good to be the smart guy who came up with a good answer or the whatever.

[00:31:51] Right. Why do you think so few of us spend as much time questioning if I'm asking the right question and we jumped straight to the answer and then we don't collaborate on the answer.

[00:32:02] Shane: Interesting. I don't know that I know I can be confident in this answer, but I'd say I suspect it's a couple of things.

[00:32:09] One is our brains work really fast. And our brains are good at coming to conclusions because they work very fast and because naturally that's helpful and effective. If you're surviving, you know, in the wilderness with the saber tooth tigers, being able to come to conclusions and make good, quick educated guesses is

[00:32:30] you know, is good for survival. So I suspect that some of that's a foot that we just jumped there and yeah, once you see a potential solution, we, you know, we get attached to it. And so then, you know, we don't want to go back and ask the questions. We don't want to rethink that because we think it's extra work and we've already gotten there or, you know we're or we like our idea,

[00:32:50] And so it's hard to go and rethink it. The other hypothesis I'd have is that we don't like being a pain. So the person who asks the question or says, you know, I think actually we might not be asking the right question often is hated, you know, cause they're creating this will back up and do more work thing for everyone else, whether it's to yourself or the team.

[00:33:16] And I don't think we like to be that person. I think we like to be cooperative. We like to get on board with ideas and jump to the point where we're trying them out so I could be wrong, but that's where I go.

[00:33:28] Jess: Well, it brings up a couple of things for me right off the bat. You know, it, it's interesting to think about this survival mechanism of efficiency, right?

[00:33:36] Energy conservation, efficiency, it's like a built in survival trait that we pursue and we hold on a pedestal and I mean, look, this, this whole program is about more with less in so many ways. Right. And yet that survival mechanism can sometimes self-sabotage when we, you know, it's like when somebody successfully builds a product and overcomes all the obstacles to then find out nobody wants to buy it.

[00:34:00] Right. you know, I think about, you know, it's impossible for me to get through one of these episodes without a special ops example.

[00:34:07] Shane: I love it though,

[00:34:08] Jess: but, I remember a Navy seal guy talking to me about good friend. we were talking about different things. We were talking about this concept of when our natural impulses have the opportunity to do as harm, right?

[00:34:24] And he says, you know, in a firefight, when people are shooting at you, it actually takes training and conditioning to hunker down and stick behind this rock and to not run. And he said, what happens is that when the lizard brain takes over, if we haven't conditioned that panic out of ourselves, that you'll unfortunately see people pop up to start running away, not from a place of conscious thought, but from, you know, natural survival reaction

[00:34:55] and that gets them shot. And so thinking about this idea of like, you know, boldly quickly solving the problem without like taking the tactical pause to consider the second order effects, including going back and asking, you know, we can solve this problem, but is, you know, does solving this problem, encapsulate the full thing we're up against, or I don't know the right way to ask that, but it's some sort of conditioning and it must be some sort of like reward loop of the times that I have slowed down.

[00:35:34] It's like slow down to speed up. And there's some sort of reward loop of the times I have slowed down where we came up with an even better question that negated unnecessary work. Is my reward to remember to do it next time. I don't know. What, how did you react to that?

[00:35:47] Shane: Well, you're making me think of it.

[00:35:50] There's a, in psychology there, it's a pretty well established that humans have a bias for action. And I think that's, you know, it explains what you're talking about with the soldiers jumping up, you know, like we want to, if there's a problem to be solved, we want to take action. And so, you know, the pause is unnatural.

[00:36:10] I'm actually really curious. So everything you're saying resonates with me, I'm really curious. How do special forces soldiers conditioned out that, you know, that sort of panic, I need to do something. How do they, I mean, part of it is like being able to, you know, you almost could call it courage. It's like being able to be comfortable in this incredibly uncomfortable situation while you think things through, how do they condition themselves for that?

[00:36:35] Jess: Yeah. You know, the stories that they tell me, in some ways, it’s similar to how astronauts are trained, not to panic by running through the same scenario over and over and having simulations of the problems thrown at them, right. and there's that conditioning factor. but in their case, I mean, A, they actually shoot live rounds and there are real bombs going off in the middle of army bases in America.

[00:36:58] Right. So there's, yeah, there's some aspects of that, but, there are other things like simunitions. Have you heard of that before?

[00:37:04] Shane: Simunitions, no.

[00:37:05] Jess: Yeah. It's basically like a super paint ball. Okay. It looks similar to a regular bullet. It's got gum powder, right? All these things, right. But it shooting like a wax looking paintball kind of a thing. And it hurts really bad.

[00:37:21] Shane: I was going to ask is it worst,

[00:37:24] Jess: it's not like a paintball or an airsoft gun. Like sometimes they break skin. you know, they're one of the best special ops books of all time is called Fearless about Adam Brown, a seal team, six guy. It's just the most incredible story, but you know, he lost an eye because of it.

[00:37:39] Yeah, cause it got in on the side, he was wearing eye protection, but he had turned his head at the last minute and it got in through the side of the glass and he lost an eye over it. Like, this is no joke. Right. That they're survivable. You just get a big welts and you, but I mean, it hurts like a mother, like you would really like to get through a whole training class with no getting, getting hit zero times, like a real gunfight.

[00:38:01] Right.

[00:38:02] Shane: Yeah.

[00:38:02] Jess: Yeah. And so it has a much higher correlation to the actual event they're going to need to participate in the, like the emotions and the adrenaline and cortisol. That's getting dumped in the bloodstream, and except it happens to be survivable. You know what I mean, super painful, but happens to be survivable.

[00:38:22]you know, you can see this, I'm not sharing any secrets here you can see in, in buds and SQT SEAL qualification training, you can see, they do things like, they'll put guys in a room. They put a big hood over their head, that's got a rope coming off the top, almost like a small hula hoop around their neck and a pole in the ceiling.

[00:38:43] And they'll put three people in front of them and he has to quickly, and I don't know if they have air soft guns. I can't remember what they used for this part, but you can watch videos of it online. Somebody will yank the rope. So the hood comes off their head and they have to quickly decide.

[00:38:58] Who is the enemy combatant, who is the hostage. And they have to shoot the enemy combatant before they can get shot without shooting any of the hostages, and it's it's just, you know, stretching the brain, right? It's like lifting weights that are too heavy for us to handle and doing it repeatedly

[00:39:17] so the brain says, send some protein down there, right there. They're doing meaningful repetitions outside the comfort zone to create you know, myelin around those neural connections so that their brain is literally able to process those things faster and, you know, maintain it in their sub in their neocortex.

[00:39:37] Right. It doesn't just have the thalamus I'm going to get all sciency on you, but, but it doesn't have the thalamus kick the neocortex offline and have the, amygdala dump adrenaline to the bloodstream. Like we all learned from Billy Madison, right.

[00:39:50] Shane: Medulla oblongata. No. Is that a yeah, that's a different one.

[00:39:58] Jess: Okay. Yeah. so it, that's probably more of an answer than you were looking for.

[00:40:00] Shane: I mean, I, I love the neuroscience, part of these kinds of, you know, human behavior, things, I mean, that is that cause with games, like what I, from what I know about the psychology of plays, you know, in my explanations is that playing games simulates the situation of anxiety, but where, you know, what's safe.

[00:40:23] And so, you know, what I've studied is how people that you play with end up becoming more safe and trustworthy to you simply by the act of play. It's a really fascinating, you start to see them as part of your team because you went through this anxious situation and got out of it. But the problem with plays, you know, that it's not real, so you don't get

[00:40:45] the kind of life or death stress response that, that you get when you know that it's real. So this, the super paint ball thing is, is particularly fascinating. So did they do have they done like neuroscience, kind of a look at that specifically, what's going on in their brains, in that.

[00:41:04] Jess: I don't know. I just have talked to a lot of guys who've been shot with simunitions and they say it really hurts and that you don't want to get shot.

[00:41:11] Shane: Wow. That's fascinating. Maybe

[00:41:15] Jess: one last thing on that is have you heard of SERE school before SCR E?

[00:41:20] Shane: I have not

[00:41:21] Jess: survival escape. Oh, now I'm going to quote it wrong.

[00:41:25] Shane: I would argue

[00:41:26] Jess: survival, escape. Man. That's hilarious that I can't remember it right now. Anyways, the last one's evasion, but they, they live take you to a swamp and you get hunted by other special ops guys until they catch you. And depending on which level of SERE school you go to there, they get to torture you a little bit and let certain levels of sear.

[00:41:47] Like they were allowed to break a bone, but not the sternum or a femur.

[00:41:51] Shane: Okay.

[00:41:52] Jess: Yeah. And like they don't give you food and they, and they're trying to simulate being captured by the enemy and having the mental head game to be able to survive it. And you know, one of the guys on our consulting team was, Counter intelligence officer for the FBI

[00:42:06] And he went over and deployed with one of the special mission units for interrogations. And, you know, he says, when they're prepping you for this stuff, they teach you things like how to get the enemy to humanize you, like trying to get your characters, to use your name instead of calling you a number, things like that to humanize you.

[00:42:23] We've got to have your head on straight to do that. If you're in panic mode, that's not going to happen. Right. I guess my question for you is I'm thinking about this and I think how many times I successfully solved the wrong question and I'm going to kind of re ask the same question again, if any tips of how I could program my brain, how I could get more neural connections, myelinated of, you know, just

[00:42:49] Don't just think don't just act like, think harder. Don't work harder.

[00:42:52] Shane: when I do think a big part of it is practicing it, you know, it's the repetitions that, that make you remember. You want to have, I think with anything, the more that you can have a trigger that you recognize that when this trigger happens, I will do this.

[00:43:12] It's part of, it's almost like the, you know the whole sort of habits theory, right? A habit is something triggers you and then you take an action and you get a reward. That's the three steps of the habit cycle. And so if you have a bad habit, then what you're supposed to do is, when you recognize the trigger

[00:43:31] you do something differently that gets you that same reward. So, or a similar reward. So instead of, you know, you're a lot of where a lot of habits turned to addiction is when you're, the reward is avoiding pain, like you're, you get to run away from or escape from something. So, you know, the addiction it's the substance itself, like most substances, even, you know, there were

[00:43:56] Vietnam soldiers that were on heroin that came home and were not, did the heroin just like doing it, doesn't make you addicted, but the ones who remained addicted were the ones to use it, to run away from the horrors that they were, you know, had in their heads or their other problems that they already had.

[00:44:12] So the idea with addiction or habit is, you know, same trigger. Like I started thinking about the war, whatever, and I want to avoid that awful, horrible, traumatic feeling. Do something else that helps me to avoid that. And this is one of the key principles that like AA operates on. You would get the, you know, you want to have a drink and you feel that panic, you feeling, you call your sponsor or you call a friend and you get that social connection to that social reward.

[00:44:41] Instead of you drink the alcohol and you get that, you know, you're that fuzzy feeling that helps you to, you know, to suit the pain or whatever. So, I use that to say that it's, you know, you can apply the same kind of trigger thing to the habit of not of action rather than thinking. So then the question is, you know, what are the kinds of scenarios that over and over and over again, you tend to do this, I think in business, like it could be easier to sort of figure out what are the triggers for me to have this bias towards action.

[00:45:14]And then just when you recognizethat then stopped stop yourself. I think with this, like just a real simplistic way to think about it would be when you find yourself proposing doing something. Stop and ask what's the question that this is answering and is that the right question? And, you know, it can be hard to remember just like any, any habit, but it's really focusing on what is the trigger that I will remember.

[00:45:45] So it's, you know, an example, another one for something different is, someone once told me that if, like I have always every year forever made, have good posture. My new year's resolution, like since I was 20 and what really helped rather than just making that resolution every year and then not having good posture is when someone told me every time you walked through a door, check your posture.

[00:46:11] And so now walking through a door is my trigger to ask myself, Oh, how am I standing? Stand up straighter. And so it's like, without that trigger, it's like, I just have to rely on myself to, to have good posture that has not worked for 15 years. So that, that would be my, my sort of main recommendation is figure out what the trigger is, before you tend to do this and then use that as an excuse to backup.

[00:46:37] Jess: You know, as you were saying that I was thinking how often this is me and my business partners, we're up, something's happened or we're trying to, you know, either something happened or somebody asks the question, how do we do this? Right. And you know, maybe this is like too elementary or something, but I think like why couldn't we start business meetings with like, get up on the whiteboard and say, whatever happens

[00:47:02] we are going to ask ourselves, are we asking the right questions and just like, literally write it on the whiteboard in that room? Or could we start business meetings, like verbally acknowledging that, you know, and repeatedly doing that and make it part of our internal culture of like this is how meetings are started at our company.

[00:47:19] Shane: Yeah. I love that. It also becomes a ritual, which is great. That's good for culture itself. Yeah. You know, someone, one of my mentors told me a long time ago that if you care about something, put it on the wall. You know, the photos that you hang on the wall are often things that you care about, at your company, if you actually do care about, you know, whatever your mission is and write it on the wall, make it permanent, we did that at Contently.

[00:47:44] You walk in and there's this huge mural that says those who tell the stories, rule the world. And, you know, that was our kind of like little mantra of storytelling is powerful and we believe in that and use it. And so we put it on the wall, I think, same kind of thing. Like write it on the whiteboard, if it's important, even make it into a poster or make it into a ritual.

[00:48:04]I think that's fantastic. Even just modeling the behavior as a leader of, you know, you're in the meeting and say, and just saying to the point that everyone knows you're going to say it well, let's step back and make sure we're asking the right question. Once people know that this is the question that you're going to ask every time that will help to create the habit too.

[00:48:24] And it also creates, I mean, all of those things, like either making it, the ritual or putting it on the wall, or, you know, recognizing that this is your habit creates a little bit of social pressure. Sure too for you to keep it up, which is great.

[00:48:36] Jess: You know, it actually makes me think of about a principal you've talked about in the past.

[00:48:40] I remember watching one of your keynotes or interviews or something from five or six years ago. And they, I believe the interviewer is asking you kind of about like, why did you write this book? Or why did you write it this way? Talking about Smartcuts. And you mentioned something about by intentionally pursuing stories of people you admire, and I'm going to quote you wrong here, but by intentionally pursuing stories and finding stories and recording stories of people you really admire who have done stuff like this, it helps you.

[00:49:08]like it helped you compound it within yourself and you were able to make it more of a permanent part of your vision and it became more aspirational internally. Am I misquoting you there?

[00:49:18] Shane: I mean, I don't think I could properly quote myself from that video, but I know exactly what you're talking about and you're right.

[00:49:26] It's whatever you can put, just because of the way that stories work. Whenever you can put something into a narrative, you will be more likely to remember it. And, you know, this is, there's actually great neuro science around this too. You know, the more of your brain that's active when you receive information, the more hooks you have to potentially remember it later.

[00:49:46] And stories are one of the best things to sort of light up multiple parts of your brain. And so there's a lot of applications to that. But if this is why having lots of examples to reinforce a principle ends up being useful, because you may forget the principle, but if you have enough stories and enough examples that will help you to conjure it up when you need to, which is maybe it's also my excuse for telling so many stories during interviews like these, but it does, it does actually help from a brain and memory recall standpoint.

[00:50:23] Jess: Well, and I can even see, you know, the author, Shawn Achor that wrote the Happiness Advantage and Big Potential. And you know, where he talks about, we have too much information coming into the brain, normally needs to pick out what we've told that is important and spam filter the rest, you know, by intentionally pursuing the stories of others that you admire, who have accomplished things, using the vehicle.

[00:50:43] You want to pursue yourself, train the brain, to get even better at finding those stories. And like, you know, I think about somebody we had on the podcast recently, Tyler Tringas, when I was a client of his back, when he worked at Bloomberg before starting his fund, I remember asking him, how do you, how do you learn?

[00:51:01] What do you think are ways to learn an industry the fastest? And he said, Oh, you should start a blog about it. Because if you have to write about it, you don't, you're not going to want to look dumb and you're going to research so hard that it's going to stick in your brain better than other ways. Anyways it's just kind of what came to mind as you were talking.

[00:51:20] Shane: Yeah. It's so skateboarding, you will know this when you started skateboarding, suddenly everything starts to look like something you might skateboard on. And so once you know the principle, then, suddenly it's easier to see that principle and action.

[00:51:34] And if you make a habit of collecting stories of that principle, especially if you have an excuse, like a blog, or, you know, you're deliberately trying to come up with, this is why teaching, if you're assigned to teach something, it's easier for you to learn it because you will look for those things that make it easier for you to teach, which then reinforces your memory.

[00:51:53] So all of that plays together.

[00:51:56] Jess: Well, maybe before we move on to the third principle here, maybe you can I'll steal some of your questions and you can explain them like the idea of the difference between, how do we kill the rats versus why are there so many rats versus how do we end up with zero rats? Can you talk about that?

[00:52:11] Shane: Yeah. And this, actually, this question comes from, I would say it's maybe a little bit too strong to say that this is the question that led me to meet my wife, but it's not far off. Because this is the conversation I had with the guy I met at the bar who inadvertently introduced me to his ex girlfriend, who I ended up marrying. So,

[00:52:36] Jess: this is already a great story.

[00:52:38] Shane: Yeah. And I think he actually introduced me to her mistakenly thinking that I had been hitting on him while having this conversation. And thinking that I wouldn't be interested in her, but jokes on him. so. How do we kill the rats is a question that anyone who's lived in a big city, or certainly that's run a big city has had, and never been able to answer in a way that's worth repeating in history.

[00:53:05] Otherwise we'd have no rats. How do we kill the rats  is such a tack. Tack is the wrong word, distressing question. And I actually think it's the wrong question, which is part of why we haven't gotten rid of the rats. So, If you haven't been rat problem in a city like New York, and you ask the question, how do we kill the rats?

[00:53:24] Then all you will do is come up with ways to try to kill the rats. The problem is the rats always come back. You can't kill them all. They all come back. And this is because it turns out that rap like pop, rap communities are aware of the size of their population. And if their population goes down significantly in a short amount of time, they will breed faster to make up that population.

[00:53:49] They're always trying to basically fill the, whatever the container of their population is. So anything you do, you can wipe out, you know, tents of the rats and they will immediately come back by breeding nine times as fast or whatever the math isn't exactly like that. But that's what rats do.

[00:54:06] So, how do we kill the rats ends up being this really feudal question to be asking. And so better question, if you want to get rid of the rats is not, how do we kill them, but why are there so many rats? So this gets at something that I think is important is, the why questions are often the questions that we should ask before the how questions, why are there so many rats can help us understand the principle.

[00:54:30] Behind a situation I get to those first principles. This is actually where the scientific method kind of goes backwards to what we were talking about last time. But why are there so many rats? It turns out that one of the answers is because rat populations will expand to fill their container, no matter what you do to them, they will vary the rate at which they breed.

[00:54:47] And also, you know, there's a, once you ask, why are there so many rats, it gets at some of the things that can help with getting rid of the rats. You know, like there's a lot of rats because there's a lot of garbage. Actually, why there are domestic cats is because there used to be a lot of rats and there used to be a lot of garbage.

[00:55:04] We domesticated cats do get rid of the rats. So, but when you dig into that, it can help you to understand the first principles that then allow you to ask a better question. So to me, what's interesting about this is, if you were to ask, why are there so many rats and spins a lot of time on that train of thought.

[00:55:21] Then that can help you to ask a better question. When you decide you do need to get rid of the rats, the better question than how do we kill the rats is how do we end up with zero rats? How do we kill the rats presumes a methodology for accomplishing the goal? The goal is zero rats. So how do we do that is the better question.

[00:55:41] And I like this as an example, because so often we think that we are asking a really good question. But we're presuming something in that question again, there's an assumption killing the rats is the way to get to zero rats. We want the end goal of zero. Right? So how do we get that and how this comes into play with the story of me meeting Sylvia is a, I just read this article about these two ladies in Arizona who invented rat birth control.

[00:56:08] And I, that was the thing that I talked to this guy at the bar when I showed up to this birthday party and, you know, and I was waiting for someone and he was at the bar waiting for his ex girlfriend. And I got to talking to him and he brought up like, the rats are awful. And here in Alphabet city, in New York.

[00:56:24] And I said, have you heard about rat birth control? And then we talked about that for like an hour. And, and then later in the night he came by with Sylvia and he's like, Oh man, you gotta meet this guy, Shane. We he's like such a great guy lives in the neighborhood. Yeah, you should meet him. Shane here's Sylvia.

[00:56:40] Like pretty much like sure that I was gay. And, and then I got her number and we went out and we eventually got married. So the rat birth control thing is basically these ladies in Arizona actually a gay couple. So it all connected, I suppose. And these ladies in Arizona, they were working on the rap problem from this.

[00:57:01] Like what if we didn't kill the rats? We just, we could somehow get them to die without making more rats because then ask the question why there's so many rats well, cause they breed faster when they need to. And so what this rat birth control thing isit's actually taking cities a long time to roll it out because they're worried about the second order effects of this.

[00:57:21] But basically instead of poisoning the rats, you feed them this spread rat birth control, everywhere that, and then they just can't make new rat babies. And so rats live like five years or whatever. And then when they all die, there's just no more rats. So that's a much more elegant solution to the problem and they get to live their little rat lives or whatever.

[00:57:41] But, so they had just come up with this idea and they were rolling it out in Seattle or something like a pilot in a limited way. Cause they, they want to make sure that this doesn't cause other, you know, effects are the rats doing something positive? It seems likely not, but could this rat birth control actually lead the rats to like poop something that actually is really harmful to cats or whatever.

[00:58:03] So they were working on that, but also it could be that, you know, I wouldn't know it's, you know, we, she and I met three years ago, so maybe they have rolled it out and they're just waiting for the rest of die. But that whole story is to say, be careful even of your questions that you think are good because, they may not be.

[00:58:22] And so how do we kill the rats versus how do we end up with zero rats is the thing to remember?

[00:58:28] Jess: No, it's interesting. You know, I think about it for us at Graystoke it's like maybe instead of asking, how do we get more investors? Right. That's not really the question is how can we get the large amount of assets under management?

[00:58:47] And, you know, maybe that's maybe that's one investor or a lot of times we think in the investment world, we are thinking that way, we're thinking, how can I get the biggest investor? Right. But sometimes you have to jump through so many hoops, like to get one guy to put in the first million is sometimes a lot longer of a process than, getting 20 guys to put in 50 grand.

[00:59:10] Even though that sounds like so much effort because you can just buy a guy $50 steak, show him what's going on. And it's like, it's just below the number where he has to ask his wife.

[00:59:22] Shane: yeah,

[00:59:23] Jess: yeah. And there's a whole different social dynamic when you show up and you need a million dollars in this one, person's going to grant you future.

[00:59:31] They, it tempts them to act like a king, you know, and to make you jump through all these hoops and stuff, when they find out they're one of 20 and that you're talking to 50 people to try and get 20 yeses, and they're just one of them. In my experience, they treat you much more like a peer. They don't make you jump through all these hoops and, you know, it's just been my experience.

[00:59:52] Shane: Yeah. That's a fantastic example. And it also, I mean, even just framing the question, how do we get the most assets under management when you get to the hypothesis stage? You know, that right there, you know, flipping. You know, the paradigm on who your investors are and how much they put in is one.

[01:00:11] And that's maybe even one of the more obvious things that you could end up coming up with, you know, once you start asking those, what if questions? And, you know, I suspect that, that you could come up with five other ways besides just that if you ask that question rather than just the question that you default to.

[01:00:28] Jess: But back to what I feel like I've learned from you so much both through the books and watching interviews and actually interviewing you is you're constantly asking or inviting me to ask, it's always been done that way. Does that mean it always has to be done that way? Yeah. And like it's prestigious in my space to have the biggest fund put cash into your deal or to have the richest billionaire in your deal.

[01:00:51] That's prestigious. It's cool. It's magnetic. It's attractive. Yet, it may not be efficient. You know what I mean? It may not be that shortest route. And so, getting to that place of like deeper intellectual humility, deeper intellectual honesty, where, you know, it is a legitimate, we were having this question yesterday.

[01:01:11]If we hired tons and tons of sales reps everywhere, and it started to feel like multilevel marketing, and we got that reputation, would that disqualify us from having more serious players want to talk to us because they wouldn't want to be associated with us?

[01:01:27] Shane: Yeah. Oh, it's interesting. It actually, it gets at the downside of the, the thing that I was about to say is, you know, going back to sometimes asking these questions makes you look bad, you know, sometimes proposing the strategy of, you know, not going after these

[01:01:44] big whales that make your fund look good, actually, you know, people will poopoo you. If you, you know, you get little guys to write $50,000 checks. However, there's also the downside of that too, which is the, you know, you could get to the point where that actually does hurt your brand and does have the negative consequence of you can't even get those guys because we look like an MLM and the last quick

[01:02:08] example of this, that I I'll share is it's like the guy, the world champion food eater who eats the hot dogs and wins the Coney Island hot dog thing. Every year. The game used to be, it was like 10 minutes, who can eat the most hot dogs. And the game used to be shoved hot dogs down your mouth, like eating a hot dog.

[01:02:27] And the world record was like 25 hot dogs. And when this guy Kobiashi, did it, he did like 50 hotdogs, like literally doubled the world record. It's like Usain Bolt runs a four second, a hundred meter dash, is like so insane. And what he did was by eating the hot dogs in like kind of an embarrassing way.

[01:02:47] He took the hot dog out of the bun, broke down hot dog in half, shove that in his mouth. Cause it's just like, he's chewing with his hands essentially. And he dipped the buns in and he'd eat a bunch of those. And then he'd catch up with the buns, dip the buns and water and show those in his mouth. It turns out that after, you know, a lot of trial and error, that was twice as fast, even though he looked ridiculous doing it.

[01:03:09] And it was like, these macho guys will look, that's not the way it's done, but it's asking the question not how do you eat hot dogs faster, but how do you make hot dogs easier to eat? That was the source of, you know, that breakthrough. And anyway, that's a,

[01:03:26] Jess: I'm really interested because I know that you have thought about, and, this idea of how second order thinking relates to chaos theory. Can you, can you jump into that?

[01:03:37] Shane: Yeah. So this is a kind of the nerdy wrap up to this principle is. Chaos theory is super interesting. But one of the things in chaos theory is this idea of a fractal or like a repeating pattern, a thing that you look at, and, it's like a micro version of itself in it.

[01:03:56] So like you look at a fern and, and the leaf of a fern, if you zoom in on it as like a bunch of mini leaps of ferns, you zoom in on that, it's a bunch of mini, mini, mini leaps, the ferns. So, what chaos theory deals with is a things that, in life in the universe end up being patterns that you don't see.

[01:04:16] And, and one of those patterns is these things that just repeat themselves over and over again. And so there's two angles of the chaos theory thing that I say, keep it in mind when you're thinking of the second order, thinking of better questions than the first, is that okay? Questions and the scientific method quickly turn into a billion versions of themselves.

[01:04:36] So that was one question can lead you to have 10 new questions or 10 new observations that then lead you to 10 new scientific methods. And each of those can turn into 10, so can quickly get out of hand. And on the one hand, that's okay for these things to multiply. If you're really trying to find the truth, trying to find the best possible way to do something,

[01:05:00] don't resist that don't try and shut down the process. If it, it starts to get more, you know, sort of more of a runaway process. And actually, if you want to guide that fractal thing in a more productive way, you want to start with the why questions before you go to the how questions. So the why questions are the ones that are more like the trunk of that fern tree.

[01:05:26] That then you can build the how questions off of, but if you start with the how question, it's like, you're working on the leaves that you don't know the trunk. So, I'm using analogies, which I know the last time I warned against. So caveat is it's not the perfect analogy, but if you want. Do not have chaos.

[01:05:43] If you want the chaos to actually turn into something that's useful, like a pattern, then start with why questions before you go to how question. So that's why the, why are there so many rats is the question that proceeds the how do we end up with zero rats? The question without why are there so many rats you move, you won't necessarily get to the right health question.

[01:06:02] So that's the first thing with chaos theory is just think of that repeating Fern fractal thing, and think about how am I going to not get sucked into that forever, starting with the why questions. And then the second thing with chaos theory is really this idea that even in randomness, all what chaos theory really is about is even in randomness patterns emerge.

[01:06:23] And, there's all sorts of really cool. If you want to like an hour long diversion, on the internet later today, anyone who's listening to this, look up the Wikipedia page for chaos theory, or look up chaos theory gifts on the internet. And see what you find and what they you'll find is a lot of stuff where it's like random generators, like drop like a pixel in a random spot based on some math.

[01:06:47] And if you run the random generator long enough, it will eventually turn into a pattern that the math ends up unfolding in a, you know, these random pixels turn into what looks like a Christmas tree or whatever. And this is kind of what happens with complex systems with the world, that everything in life is connected to other things in the universe.

[01:07:10] It's all connected. So everything does have second order consequences that eventually come around. Like nothing that you do, no decision you make is going to be truly random. It's all gonna end up being part of something and being part of a pattern. So thinking about this, you know, second order of consequences.

[01:07:28] You just can't ignore it because there will always be a second order consequences. It will always come back to the pattern even if you can't see how this has to do with anything. And, and within that, I guess with that knowledge, what part of our goal is, is to make sure that what we do doesn't

[01:07:48] cause the system to go into whack that like, we're really trying to, so this is where it's not exactly chaos theory, but I like chaos theory is the way to think about it. You're trying to not cause chaos with whatever you do. And so the best advice for a hack, for how to cut off that endless question, cycle is to

[01:08:09] come up with guiding principles or moral virtues that you can use as filters on your questions. So we don't have enough time to explore every question. So we've come up with the best question we can. Now let's run it through some filters and the filters basically are, should be, how do we not do bad things?

[01:08:28] It's like the, to use the genie thing. Alright, so I'm going to ask the genie for a wish and I'm going to add as many caveats as I can so that it maybe doesn't go wrong. Because I don't have, I don't have time to think of the perfect wish. So I'm going to do my best here. So this is where, you know, what kind of was brought up before having guiding principles around, you know, how do we do this while minimizing harm, the guiding principle, or how do we do this while preserving our reputation?

[01:08:58] Or how do we do this while not screwing over our customers or whatever it is. So it's, how do we stop the cancer without killing the person? Cause if you ask a genie to stop the cancer, they might just kill you. or how do we, you know, to use a real life example instead of how do we get rid of the drugs?

[01:09:17] How do we prevent drug-related health crisis in a way that leads to the least amount of harm to communities and families? So, you know, if we'd asked that question at the start of the war on drugs, then we would have made a lot of different policies. That wouldn't have led to second order effects, like, you know, drug lords show up when you make something illegal.

[01:09:35]so how do we stop people? Really the problem with drugs that, that we were worried about stopping, if you strip away kind of the racist politics that were involved in the creation of all of it. If we, you know, the genuine concern was certain substances cause health problems and people who become addicted to those that have those health problems or will have mental health problems or have behaviors that then are a public health crisis.

[01:10:04] So how do we prevent that in a way that causes the least amount of harm to communities so that in the way that causes the least amount of harm to the communities is the filter. So the thing that I would say is, as you're trying to come up with the right questions and you want to not cause chaos, you know, that everything is going into the system.

[01:10:24] Eventually it comes back around, come up with your filters. And this is, you know, I think a lot of people will call these values. I like to not call them values because values get conflated with ways of doing things or with best practices. I do like to think of them as principles or moral virtues.

[01:10:41] Like for me, I'm always going to run everything through the filter of wisdom and kindness. Before I do anything. So this thing, how do I do this thing while also being kind while also maximizing, you know, the chances that I'm not hurting people? So that's sort of the capstone to my thinking on second order thinking is that because it can get out of hand,

[01:11:07] having some principles that you then tag onto your genie query, can often help you to ask a much better question than you would before.

[01:11:17] Jess: You know, I love it. It reminds me so much of the law constraints. Other people have called it where it's like, you know, the Dr. Seuss story, where he brings his publisher a book and says, Hey, this book only has 250 words in it

[01:11:29] cause I rhymed so much. And the editor said to him, I bet you couldn't write one with just 50 words. And he comes back with green eggs and ham. That ends up being one of the bestselling children's book of all time. Right.

[01:11:39] Shane: I've never heard that. That's awesome.

[01:11:41] Jess: Yeah. And it's interesting, cause it feels like such a limit on creativity, but yet

[01:11:45] those walls, give us something to push against, you know, like, I think about when I was running my fond, I was this young CEO and I ended up needing a CEO coach, right. And, and then I loved it so much. I actually took classes to do it for other CEOs, right. And over the years they have been able to do a lot of this.

[01:12:04] And one of the questions I ask when I'm starting off with folks is like, we get there, like, do want lists, don't want list as a starting place. And when they say things like, I want to make more money. I say, well, like how much, they're like, I would like to double, I would like to double my take home and then we start adding constraints.

[01:12:21] And I say, would you like to double your take home as long as you work less then 16 hours a day, less than 14 hours? Yeah. Today? Like how much? Oh, no, no, no. I don't want to work extra. I just want to double my income with a maximum of 10 hours or, you know, and it's like, and is that 10 hours, no vacations, or how many?

[01:12:39] Oh, no. I want to be able to go on a trip at least one cool trip a month, you know, and we start adding all these constraints and it's like that destination clarity actually helps them in their vehicle selection. You know, it's like, Hey, if your spouse says, if you live out by Park City in Utah and your wife says, Hey, I want to go East for our anniversary.

[01:13:01] Like, how far are you telling me? Like, are we biking? Do we, do we need to like rent an RV? How far are you? And she's like, I want to have lunch at the Eiffel tower. You're like, Oh, okay. Basically no vehicles except an airplane, you're going to be okay. So no matter what, good a deal I get on an RV or another mode of transportation.

[01:13:18] If we can't get back and forth to Paris, it's really easy to say no to those, right?

[01:13:22] Shane: Yeah. I, you know, you're making me think of like, actually something that could be a good exercise for people is to think of your questions like Google search queries, or even better, like querying your inbox. If you want to find something

[01:13:36] and if you put in just the key word. Or, or the basic question you might end up with a lot of stuff. I think email is especially good. Like if I type in, Jess in my email, I'm not necessarily going to get the specific email I want. I might do Jess minus. You know, whatever, I could get, you know, Jess at GQ might send me an email every day from GQ, right.

[01:13:57] For their new center. So Jess minus GQ, or, and plus Graystoke or plus attachment, thinking of those things, like the question doesn't have to be small. Right. In fact, the question that gets you exactly what you want, may end up being a really long query and that's okay. And I think maybe that's actually a misconception, you know, assumption that it has to be an easy question, to say that it can't actually be a formula.

[01:14:24] Actually, you know, formulas often get us the thing that we, that we want, they often help clarify. So I liked it. The Paris analogy or scenario for that too, is it's like, East is not enough if you want a really ball or honeymoon, you know, if you want it to turn out the way that she wants. So yeah.

[01:14:42] So add, add those constraints or those queries so that you can narrow down between Paris and Prague or whatever, rather than you know, between, you know, Sandy, Utah, and Prague.

[01:14:54] Jess: I love it. Well, I know that you have talked at times or at least have thought about this idea that kind of eventually everything is connected.

[01:15:03] Can you, can you talk about this second order thinking, chaos theory, everything's connected and like systems thinking and how that could help us.

[01:15:11] Shane: Yeah. So systems thinking is a really interesting, and it's an interesting thing to explore in general and it's kind of I think this is something that I've been thinking about writing about actually, because it's, when you read about systems thinking it's really complicated to figure out it's hard.

[01:15:28] It's not easy, but the basic idea of systems thinking is this everything's connected, idea, or really that things that are connected are a system. So, and it, especially if the things that are connected, create something new because of them. So, you know, the simplest version of this is that a family is a system because the parents create something new in the family together actually create new things, traditions, and memories, and, you know, all of that.

[01:15:58] So that's what a system is. And Complex systems are the ones where things are not so straightforward and figuring out A plus B equals C and you know, the world is a complex system and the economics are complex systems. Companies often are more complex systems than we think. And so, you know, when you're trying to solve problems in companies that the danger that happens, especially for, I would say people who are founders or people who are coming in from, you know, say management school or from a certain paradigm.

[01:16:32] You think that things are simpler than they are because they used to be simple when it was early on or because it's simple in your textbooks. But you know, questions like how do we make the morale not bad at this company? You know, how do we improve the morale? You know, can have unintended surprising, you know, consequences in the context of a complex system, you know, a system of a company where people talk and there are ripple effects that happen.

[01:17:02] If you, you know, you say, how do we make the morale here? Not bad. Even posing that question might create a feedback loop that causes the morale to be bad. You know, if you say, if the CEO says, how do we make the morale here not bad then, people hear that they get scared. The CEO thinks the morale is bad.

[01:17:19] Maybe, you know, maybe the, the writing's on the wall. Maybe I should look for it's time to move on. And so someone who's like a linchpin in the company starts putting their resume out there and maybe they do get a great job. And then them leaving causes other people to panic, which causes the morale to be bad.

[01:17:35] Not saying that that's, that is what's going to happen if you pose that question. But because the system is more complex than morale, good people doing good in morale, bad people doing bad. It's like even the question of morale could change the system. And it's like, Oh, sorry. You're about to say something.

[01:17:53] Jess: Well, I'm just thinking, you know, this idea of that systems are complex, right. And the cause and effect are not always so simple. Because we often can do decent at cause and effect on the one part we're working on, but have not thought about the second order effects of what this is going to do the whole system.

[01:18:12]I guess I'm kind of fascinated by your life of going to journalism school and end up with multimillion dollar tech company, right. So, and, and you've got this great Rolodex and you get to meet all these cool people I wish I knew and all this kind of stuff. Right. So my goal in life is to hopefully end up being Shane if everyone could just acknowledge that. Yeah. So

[01:18:33] Shane: with that goal, I'm flattered by,

[01:18:38] Jess: so my question here, thinking about, thinking about your business or your life, this idea of, specifically when cause and effect wasn't so simple and how you eventually figured it out. And then how the next time you made a decision, you did have it in systems thinking, which I'm putting you on the spot.

[01:18:59] So maybe you don't have a story like that, but

[01:19:01] Shane: yeah. The first, there's two things that come to mind the first is that anytime you solve a problem, because you screwed up and you have to save things, you know, like a casual thing, it helps you to be more aware of the systems that you're operating in.

[01:19:20] Which helps you to make, hopefully if you learn the lesson and you know, you think through things, it helps you to be more smart about the second order effects of decisions you make in the future. And I think it, it gets up for me why postmortems are such a good idea, even postmortems on things that go well, being able to, to ask the question, why did this go well and actually take the time.

[01:19:47] You know, especially with victories, we don't actually go back and say, let's spend a day deconstructing all of the things that happened as a result of the actions we took that led us to be right. We just say, let's do that again. You know, and too often with, with failures, even like even the well-meaning approach of get up and dust yourself off and try again, or it's okay.

[01:20:10] You know, failure makes us stronger. So let's push forward. Without the interstitial step of the post-mortem. Why did that happen? We don't necessarily learn enough. And in thinking of that in the context of systems, the more you can do those postmortems, the more you can understand the why things happen and understand the principles that are operating on.

[01:20:34] And, you know, understanding of the principles helps you to ask better questions in the future. That's why first principles and observations come before questions in second order thinking. So that's where I go with that is, that the being able to see more of the system helps you to, to ask the better questions.

[01:20:51] And for me with my career, I guess if I were to connect those things, I do think that one of my natural things has been systems thinking why I'm so drawn to explore different areas and, you know, and as we'll get to, in future conversations about this, one of the ways to employ lateral thinking is to reach across, you know, to different industries or different systems and import ideas and principles from those systems.

[01:21:19]That’s like a fundamental approach to innovation. And, and so I think knowing that I am, I've sort of reinforced that it has become a little bit of a feedback loop. I tend to pursue that and so I tend to do more of that and it helps me to then look at things from a systems point of view. But if I'm going to move from journalism to, you know, starting a tech company, I tend to ask myself what from journalism can I bring to do better than other tech entrepreneurs in tech companies?

[01:21:52] What are the unique things from journalism that I can bring? And that necessitates an analysis of the system of the way that I operate in journalism and the way that the best people operate in journalism and why the things work and don't work in journalism in order for me to import those ideas. So, and actually it literally comes back to what you were saying before.

[01:22:13] I've deliberately written about these things so that I could explore them. I've written various articles, especially when I first was starting Contently about what entrepreneurs can learn from journalism so that I could do that analysis. Like that was the excuse. I don't think I thought of it as systems thinking necessarily.

[01:22:32] But now I do. So that's where I go. When you ask that question, I don't know, is that kinda what you're getting at?

[01:22:38] Jess: Yeah, that's great. Well, we covered a lot of ground and I know there's like 50 other stories that I didn't let you tell. What, how do you want to wrap this up? What do you feel like would help kind of encapsulate the last 90 minutes we’ve covered here.

[01:22:53]Shane: encapsulating it all. I mean, I, I think

[01:22:57] Jess: We're just ending on a high note either way.

[01:22:59] Shane: Oh, sure. Well maybe, maybe we can do the, all of this as an entree to the fun part, which is the coming up with ideas. So yeah, I mean, can I go ahead and do that?

Jess: Okay. Go for it.

Shane: So all of this is an entree to the fun part, which I think a lot of people who are familiar with lateral thinking a little bit, or at least listened to the first episode that we had in this mini series, what people are hoping for, and hoping we get to faster, which is the, how do you come up with awesome ideas?

[01:23:31] How do you use lateral thinking to be more creative? How do you do brainstorming better? How do you do thought experiments? That's all the hypothesis stage. Which if you've done these first two things, the observations first principles, and you've done the question stage, right. then it just sets you up to make it even

[01:23:50] easier on yourself when you get to the creative part, some creative ideas right. Themselves when you set them up in the right way. So that's what we have to look forward to next. And you'll notice Jess and anyone who's listening that when we, the dig in, into that part, all sorts of things from these last four episodes will tie together and it will itself start to look like a system that wasn't there.

[01:24:17] And the benefit of systems by definition is that they they're supposed to add up to more than the sum of their parts. So hopefully by the time we get through the next one, you will have quite the toolkit to think dramatically differently and dramatically better. And then of course, we'll dig into some more things to make sure that we bullet proof your hypothesis, that you come to conclusions in smart ways and that you can then, you know, I'm really excited for the end of this series.

[01:24:45] We're going to dig into multidisciplinary and cognitive diversity and setting yourself up for the maximum, leverage, I guess you could say, for employing these kinds of things. But basically what I'm trying to say is we've, we've had some fun stories and some good principles, but now we're getting to the fun part.

[01:25:04] Jess: I love it. Well, everybody please tune in for the next part of the miniseries series. Thanks again Shane.

[01:25:09] Shane: Yeah. Thank you.