ep. 106 - Diana Kander:

NYT Best-selling Author, Entrepreneur, Forbes Contributor, & Sr. Fellow at the Kauffman Foundation


Diana Kander's family escaped from the Soviet Union when she was 8-years-old. By the time she was an American citizen, she had perfected her skills as a capitalist – selling flea market goods to grade school classmates at a markup.

Today, Diana is a successful entrepreneur, having founded and sold a number of ventures, a Professor of Entrepreneurship at the University of Missouri and a Senior Fellow at the Ewing Marion Kauffman Foundation, the largest non-profit in the world dedicated to entrepreneurship and education. A Georgetown-educated attorney who left a successful practice to launch her first company, Diana draws on her experience as a founder, investor, and academic to train companies and non-profits how to be more innovative and how to get their employees to think like entrepreneurs.

Diana is the author of All In Startup, a New York Times Best-selling novel outlining lessons for launching successful products through a story of a struggling entrepreneur making his way through the World Series of Poker.


Kyle Davis: Okay so with us today on GDA Podcast we have Diana Kander. She is a serial entrepreneur focusing on culture and innovation and normally when people listen to these podcasts they know that I don't do the whole [00:01:00] readout introduction because I'd rather have our guest do that. So with that being said, Diana please introduce yourself to everybody.

Diana Kander: Hello everybody. I am Diana Kander. I help organizations with innovation of strategy and creating a culture of innovation. My background is as a serial entrepreneur. I've owned equity in nine different companies. I've done all kinds of things, and my favorite thing to do is to make people question their own assumptions about their [00:01:30] business.

Kyle Davis: I think that's a good place for us to start. When you're talking about questioning people's assumptions, and I kind of know where you're getting at coming from the startup space myself. What is it you're finding when people haven't challenged what their assumptions are, and what's that big "Ah-huh" moment where they know there's so much out there?

Diana Kander: The more familiar we become with what we're working on, the more confident we become in what we're doing. [00:02:00] Often times that confidence becomes over confidence, and we start getting disconnected from reality, what's actually going on, but we feel like we can predict what our customers are going to do, what they're going to want because we've been at this so long. We expect everything that's worked before to work again, but people are delightfully irrational and unpredictable, and interacting with them is the only way to figure out if you're on the right path.

Kyle Davis: So [00:02:30] basically just to break that down, you're saying that the old way of doing business of it's kind of my way or the highway, if I'm selling you a Model T and I'm Henry Ford, the only color you can get it in is black. That way of doing business is out, and now the new way of doing business is legitimately listen to the concerns, wants, and needs of your customers, and then providing an experience tailored towards that?

Diana Kander: Yeah it's not just the my way or the highway. The old way of [00:03:00] doing business is also the "Mad Men" scenario where there's a bunch of smart people in a room coming up with brilliant ideas that customers are just going to love. Well, there are hundreds of brilliant people in the same business coming up with ideas, and so people have more choices and options than ever before. They don't have just one car in one color, right? They can choose whatever mode of transportation that they want. They don't even need to buy a car. They can just Uber the rest of their life.

So [00:03:30] you need to understand what it is that's actually driving your customers and create products and services that actually create value for them.

Kyle Davis: So one of the things, I want to get into your background but I'm fascinated because I think you mentioned something pretty cool and we can probably scratch on the surface on this, but what questions are you asking to find out what's driving your customer? I know that a lot of people when they think about startups or this kind of agile philosophy or whatnot, [00:04:00] they don't think it's applicable to maybe their business or their industry or something like that.

But in reality the fundamentals are kind of the same, so I'm curious as to what, if there's a checklist or something, like what are you looking at when you're trying to find out what's driving your customers and their buying habits and whatnot?

Diana Kander: So, one of the places that keeps having me back is the National Association of Electrical Distributors, and you would think that that's one of the least techy businesses [00:04:30] ever, right? Like, they supply electrical parts to construction companies that are building large scale businesses, and yet, this is just as relevant in their business as it is for a tech company like Square.

And that is that people are constantly unsatisfied with what they have. Like, whatever it is that you want in life, once you get it, you're immediately unsatisfied with it and you want the next thing. There are tension points in your business that are constantly developing between you and your customers, [00:05:00] so the important thing for companies to do is to identify those points of tension, those things that the company is doing that is making their customers unhappy, but also other things in their business that are creating tension for them, that they might have an opportunity to solve and maybe create a new revenue line doing so.

Kyle Davis: Can you give some examples of just general tension points that people maybe overlook?

Diana Kander: Sure. So, one [00:05:30] of my favorite companies is Domino's Pizza, and they're really good at identifying customer tensions. Most companies, they spend every day going off a checklist. Like, "What do we need to do to get ready for the next quarter and executing our plan?" But at some point, none of that stuff was working at the Domino's executives decided to stop and start looking for these points of tension, and they found out that people thought their pizza tasted bad.

And not just that the actual pizza tasted bad, that the idea of their pizza tasted bad, that their [00:06:00] brand had negative taste value. They would like put pizza in a Domino's box, and the exact same pizza in a Pizza Hut box and found that their pizza was ranked lower when it was in a Domino's box. Like, that's a huge point of tension, and they went to fix it but they didn't just stop there. They continued to come up with points of tension.

So, they found that people had trouble ordering pizza on Friday and Saturday nights, because those are the busiest times. They created a way for people to order online, so that they could avoid [00:06:30] being on a loud phone call where people could barely hear them, or waiting on hold forever until a person was ready. One after the other, they keep trying to find these points of tension with their customers in order to be able to solve for them.

Kyle Davis: I like how they dissect it and they really look at every touchpoint, every point of interaction that they could cleanup or simplify. Maybe it's even just down to packaging, something as simple [00:07:00] as that can just change the way your customers perceive you.

Diana Kander: Yeah. If you think about Domino's commercials, very few of them actually involve pizza. If you look at them, like right now they're airing a bunch of commercials about how they're redoing all their stores, because they found that is a point of tension. People didn't feel like the stores reflected the kind of quality that they wanted them to think about when they think of Domino's, so that's actually one of my favorite things about this company, that focuses so much on their customer's perspective, is that [00:07:30] very few of their pizza commercials actually have any food products in them whatsoever.

Kyle Davis: So, to backtrack though, and to help our audience for those who aren't necessarily aware here, let's talk or do a little deep dive on your history as a serial entrepreneur and what you've done, and what lessons learned came of that.

Diana Kander: Sure. I have bootstrapped companies, I have raised angel investment, nearly half a million dollars [00:08:00] for one company, and have businesses in all kinds of areas. Software, services industry, and I mean, they were incredibly valuable experience about how to give customers what they want, and also how to spend money and [inaudible 00:08:17] things that nobody ever wanted.

I've probably, of my own money, spent over a quarter of a million dollars creating products that nobody cared about. That was very painful for me, and so I [00:08:30] try to figure out ways to stop doing that, to not waste as much time and money, because it was my own money, and I want it to stop.

Kyle Davis: When you look back on the quarter million dollars that you spent making products that people didn't care about, what was like, of all the products, was there some commonalities? Was it you thinking that it was something the customer wanted, but in reality it-

Diana Kander: That's exactly right, yeah.

Kyle Davis: Yeah, the customer needed something.

Diana Kander: Yeah. [00:09:00] Think about the world as a giant Venn diagram. In one circle, that's my worldview, my reality, and in the next circle it's like a little bit of overlap, it's the customer's reality and their worldview. We often think that we understand what it's like from their perspective, but we don't really know until we really get in there, right?

So, I'll give you an example. I created a software product that helped organizations manage all of their legal projects. Like, inside [00:09:30] of a legal department, inside of a company. Nobody really knows what projects are going on, where they are, and the legal bills from the law firm don't really help because they just say what they did this month, but not where the project is as a whole.

So, I created a software that took legal invoices and turned them around to where they showed you where the project was and whether it was going to go over budget for what they were going to do. It was really exciting and when we were manually doing this for customers, we were saving them 20 or 50%, 20 to [00:10:00] 50% on their legal fees, just by overseeing the projects in a unique way.

And when I started going out and marketing this to other legal departments, like I got laughed out the door because the general counsel who was in charge of all the legal invoices, they're the only ones who know what's going on in every project. They thought I was going to create a piece of software that would make them much easier to replace, right? And, they thought [00:10:30] I was creating software that would give them more work to do because if projects were going to go over budget, they would now be expected to go back to the law firm and try to negotiate or try to reduce things, and they were just fine. Like, nobody complained about the legal budget. That was not one of their problems.

So, I was actually, I was thinking I was trying to solve a problem, but in reality I was creating all kinds of new problems that they didn't need to deal with.

Kyle Davis: Yeah, it's interesting. [00:11:00] Especially when you think about software. I mean like, so many people play in the software space. I mean, I've been in it for years and I'm now out of it, but it's interesting when people spend all of this time, effort, capital to build something and then just it's the user uptake isn't there, people aren't using it, or they're not using it the right away, as it's been envisioned. Or, if it's just a bad experience or something like what you mentioned where you're just making [00:11:30] more work or at least perceived more work, it complicates things unnecessarily.

Diana Kander: That's right, and it's not just for software. Like, it applies to everything. Anybody who's in a sales role is trying to guess what it is that their customer wants, right? They're trying to push something on the customer and what they really need to be doing is getting out of their little circle in the Venn diagram and really trying to get curious and understand their customer in a very different way than trying to guess what [00:12:00] it is that they want.

Kyle Davis: So, to that point, what is it that you do when you're working with these companies and brands, taking your experience and lessons learned? When you're interacting with the customers, how is it that you're able to then pull on the right strings versus again, creating a product and trying to force it down the customer's throat?

Diana Kander: I did this really fun demonstration on stage [00:12:30] to show people that no matter how good of a sales person they think they are, they're not genuinely curious about their customers. It's a great way to demonstrate it, so I have two people come up and I'll ask for somebody who has $40 in cash, and then ask for anybody in the room who wants to earn $40 in cash.

I'll have them come up and then I have the person who wants the money try to create $40 worth of value. Like, they're going to try to create [00:13:00] a cash transaction on stage. They have to come up with something that they can physically do or something that they have on their person that they think is worth $41 to the other person. I've done this with like the million dollar sales folks, like the best of the best sales people, and it pretty much goes that exact same way every single time.

So, the person who's trying to make offers, they'll first [00:13:30] go with their gut and instinctually offer something funny or just something silly to break the tension in the room, and then the person in the room will say, "No, that's okay. Thank you." Then, they'll go back and start to outsmart them. So, they'll come up with creative things. They'll be like, "If I was you, I would want to give me $40 for this."

Again, they'll fail, and they'll try one more time, and they'll again try to guess. They're like, "You look the kind [00:14:00] of person that wants this." Again, they'll fail. So, they have three attempts, and usually they fail to make any kind of a cash transaction. Then, I explain to the room that the way that we come up with questions, they originate in three places in our body. Our gut, our brain, and our heart.

So, our gut is like this visceral reaction like, "I'm hungry, I need to put something in my mouth that's going to satiate this need." So, I just try to come up with anything crazy. Our brain is [00:14:30] that place of logic that's still trying to satiate the hunger. It's like, "Okay, if I was the other person, what would I want to get their $40?" Then your heart is a place of like true caring, where you actually care about giving the other person $41 worth of value for their money, okay?

So, I explain how all of that works and how ... We go through each one of the transactions and everybody in the audience tells me whether they think they came from the heart, the gut, or [00:15:00] the brain. Usually almost every time it's gut and brain, right? Interchangeably. They never use their heart. We never use our actual empathy or caring about people in business transactions.

So, I have the two people come back on stage and I say to the person who wants the money, I say, "We're going to try this one more time, but this time I want you to try to channel your heart. I want you to actually care about the other person, I want you to actually care more about creating value in their life than getting the $40." [00:15:30] What do you think they do?

Kyle Davis: I don't know. I'm assuming that they're trying to sell a product, but my guess is that they probably just start asking a bunch of questions to learn more about what the needs are of the potential customer.

Diana Kander: It is the first time in the entire exercise that they start asking real questions, caring questions, right? They ask them questions like, "Where are you from? How's your business? [00:16:00] What are your biggest struggles?" You actually start getting responses from the person and the things that actually end up working are crazy. Like, one time somebody got the money because the person with the $40 was really into karaoke singing, and so the person who wanted the money was turns out like a really good singer, and had their own CD album and so they sang the song together, and they got the $41. It was amazing, it was beautiful, but [00:16:30] they never would have guessed that, right?

It's a very powerful example of how we try to give people what we think they want and what they need, but we never try to stop and really listen. Like, we hear what they're saying, but we're just thinking about the next thing we're going to say, or what we came there to sell, but we're not actually listening to what it is that they care about. Thinking about where your questions come from can have a powerful effect on [00:17:00] your interactions with other people.

Kyle Davis: You know, at least from my time in startups and everything else, the real push has been towards this consultative selling model that you just described, where it's far more questions than it is pushing. I mean, maybe even in the first two or three meetings, I mean we say certain things that we can do, but the reality is I'm trying to see if there's still a fit and what the needs are for the customer. So, we may go back and forth [00:17:30] two or three rounds just trying to figure out what the needs are before we ever put together a demonstration or a pitch deck.

Whereas the old school method is trying to fit a square peg in a round hole, and so I'm just curious as to when you're working with companies and you're trying to put in this consultative selling model where you're actually asking questions versus pushing something, what are some changes that you've seen when [00:18:00] adoption has occurred?

Diana Kander: I mean, so there's one series of questions you can ask of the customers, right? To really understand, but there's another series of questions you can ask your internal employees, and I feel like my claim to fame is I had this consulting project for a large company, and I made them $8 million in my first day there. Then, they just let me stay as long as I wanted, all because [00:18:30] I asked, "Why?"

So, this company had a software product and they had this checkout screen and they wanted to increase how much money they were making in the checkout process, how they could get people to select more [inaudible 00:18:49]. So, I asked about a simple [inaudible 00:18:54] which seemed very obvious to me and they said, "No, no, no, no, no. We've already tried that. We've talked about [00:19:00] hundreds of times. It's a non-starter. We can't even bring that topic up. We can't even mention it."

I said, "Well, why?" They said, "They're afraid it'll drive a significant amount of customers away, that doing this is going to scare off a lot of customers." I was like, "Oh, well I totally understand that. I don't want to scare off your" ... I mean, they were thinking like 400,000 customers would leave if they did this one thing, and [00:19:30] I said, "Well, can we just run an experiment of some kind where we try it on 1% of the customers going through? Or maybe like 1000 customers going through the checkout process to see what kind of impact it would make? Then if it doesn't have the impact that you're afraid of, then we'll try it on a little bit more."

At this company they were thinking like, "Should we or shouldn't we do this thing?" Instead of, "How do we test whether this is a good [00:20:00] idea?" Right?

Kyle Davis: Right.

Diana Kander: When they tested it with 1% of the customers, nothing happened. Like, nothing bad happened. When they tested it with 5% nothing bad happened. In the course of a year, the company ended up making $8 million more just by making a teeny tiny change that they refused to even talk about until I started harassing them about why that was.

Kyle Davis: Yeah, it's funny. People [00:20:30] get weirded out with questions and like, "Can we ask that?" The answer is, "Yes, you can" but it's all about how you ask it, and how you approach it versus it's not what you say but how you say it, so to speak.

Diana Kander: Yeah, absolutely. So again, I try to make sure that all of my questions come from a caring place, and that I'm not questioning what it is that they're doing but I'm trying to help everybody create more value. [00:21:00] Often times that involves experimenting and trying things that they thought could never work in new ways. Because the [competition 00:21:12], the companies that are just clammering to be your competition in the future, they don't have like, "That's never going to work."

A lot of them, they're just trying stuff and they have this appetite for experimentation and trying things, [00:21:30] and if you're the kind of company that's experienced success and you think you know how it works, and you're just resting on your laurels, then you're in big, big trouble.

Kyle Davis: Right, yeah. I mean, I like it. I like what you're saying here, is you have to ask the question because, and I learned this lesson, I don't want to say the hard way, because there was nothing lost on my end, but I realized that once I handed over an account, being the account executive, over to the account manager, the account manager was then going [00:22:00] in and asking all of these additional follow-up questions to add onto the purchase, if you will. I was like, "Man, I could have asked for all of those things and it would have made a better experience for the customer on the frontend, because they would have had everything that they wanted to begin with." Versus slow rolling things out over a three or four month period.

Diana Kander: Yeah. I think companies are so scared of their customers, and that's a crazy thing to say, [00:22:30] but they're so scared to ask about how things are going. Because they're worried about what people will think. Actually, like I understand it. I'm married and the scariest thing to do is to ask your spouse what they don't like. Like, what you could be doing better, and I feel like that's how a lot of companies think about their customers. As long as they're not complaining, everything must be going great, so I'm just going to keep doing what I'm doing, expecting the same results will occur over and over again.

Kyle Davis: [00:23:00] Right. Yeah, I mean the importance of asking specific questions is just huge. I mean, I remember one company, we were getting to the budget question of like how much money do you want to spend on this? But we did this very early on, just to make sure that it was a right fit. Ultimately it wasn't the best fit for either of us to work together, but it made for a much easier parting of ways versus slapping them with something huge [00:23:30] in the tail end, and just having them go silent. I think ultimately-

Diana Kander: And wasting a lot of your time.

Kyle Davis: Correct, yeah. I mean like, it saved me so much time and hassle and it was better for everybody.

Diana Kander: Right. I think companies will have a lot more respect for you if you have respect for [inaudible 00:23:49] product, it's not for everybody.

Kyle Davis: So let's talk about your book. You mentioned that you're the author ... Maybe I mentioned it, but you're the author of "All In Startup." It was a New York Times Best Seller. [00:24:00] Can you talk about the book and what came of it, and everything else?

Diana Kander: Sure. So, the book is a business fiction. It is a narrative about all the wrong assumptions people make about their business and their business ideas, and the right way to test your assumptions and talk to customers. It's all about launching new initiatives inside your organization, or as an entrepreneur. [00:24:30] It's got some sexual tension in it. Probably why a lot of people like reading it and using it. It's been used in over 70 universities to teach entrepreneurship and innovation courses, and launched my speaking career, because a lot of organizations got a copy of the book and wanted me to come in and help their employees be more entrepreneurial in their everyday work.

Kyle Davis: [00:25:00] Let's talk about the importance of empowering employees and making them much more entrepreneurial versus cogs in the machine so to speak. Giving people ownership of project or allowing them the free time to work on something seems I think for many people very foreign and very like, "Oh, that's what they're doing in Silicon Valley but it's not going to work here in [00:25:30] so and so city in the middle of America." But talk about why it's important to empower employees and to give them the ability to be their own entrepreneurs inside of your organization.

Diana Kander: Well, this might be a controversial statement, but I actually think there's too much emphasis on asking employees to come up with big innovative ideas. Like, just starting from scratch, it's really hard to come up with the big hundred million dollar idea that's going to save the company, but organizations keep having these contests in [00:26:00] order to have the next big idea. But what they should be doing instead is encouraging their employees to be more curious, instead of more innovative.

You see, curiosity is the foundation for innovation, right? The more curious you are, the more you understand what's working and what's not working and what problem areas exist, the better ideas you're going to come up with. But I feel like we're skipping the curiosity step and just telling people to brainstorm big ideas. The reason it's important to have a curious workforce [00:26:30] is they're going to start thinking about what it is that they're doing that they could be doing better, how they can get more engagement from other employees.

It can have unlimited benefits to an organization to have a workforce that's more engaged and empowered to create big differences. Because not everybody's going to have a hundred million dollar idea. In fact, it's hard for one person in a company to have a big idea, [00:27:00] but everybody needs to be more curious about their work. Everybody could question how they could improve their own skillsets. We get to a place where we're pretty good at what we do and then we just stop trying. We just stop growing.

But what if we didn't plateau? What if we stopped settling for what's been working and we started asking more questions about how we could be doing it better? If you had everybody inside of an organization questioning the [inaudible 00:27:26] position and their own skillset, that would be [00:27:30] a pretty lean, mean, innovative machine.

Kyle Davis: I like the fact that you said question everything, like it's an episode of "The X Files."

Diana Kander: Yes, but not like lifeforms on other planets, but like question what you think you're doing well that you could be doing so much better. Like, I like to do this in my speaking where I have, I'll pick a product that works the best, that gets the most audience interaction, reaction, and people seem to love the most, and then I'll say, " [00:28:00] Okay, I'm not allowed to use it next time. I have to try something else." Like, forcing yourself to experiment and to try to find new ways to do what you already do well, even better, that's how you go to the next level. What companies need in a fast changing, hyper competitive world, is to continue to evolve and disrupt themselves.

Kyle Davis: Yeah. I think it's really important, like you said, to disrupt yourself. By empowering each employee to be able [00:28:30] to make small changes or to be their own mini entrepreneur, to improve operational efficiency in one area, or to rethink how we do something in another, the accumulation of all those little changes will far outweigh trying to find that one hundred million dollar idea.

Diana Kander: Oh yeah. Having a big competition of the next big thing. I mean, that is the riskiest thing [00:29:00] you can do, right? It's like putting all your eggs in one basket. That's probably not going to work out. That's not how innovation works. Innovation is, Steve Jobs famously said he found 10,000 good ideas that weren't good enough before he found the ones that worked.

Kyle Davis: Yeah. Back to your point, I think it's such a huge thing that is really overlooked. I mean, I think a lot of people, and this is something that you've talked about a moment ago, but a [00:29:30] lot of people rest on their laurels and they think, "Hey, this is how we've been doing it and this is how we should continue to do it" but by empowering your people and encouraging them to be more curious and to look outside and bring knowledge in from other industries, or to bring in new software solutions or new ways of doing something, each little thing that improves something by 5% or saves an hour here, 20 minutes there, at the end it's so much better for everybody.

Diana Kander: [00:30:00] That's right. That's absolutely right.

Kyle Davis: Cool. Well, I'm glad that we could agree on that. So, with this book and now that you have this book being used in over 70 universities, colleges and universities, what are some of the questions and things when you're going to universities or to these companies that use your book as an outside resource? What are some things that the companies are asking of you that you think [00:30:30] have applicability outside of not just those organizations, but everywhere?

Diana Kander: I think my most helpful role has been that of a provocateur inside of organizations, and it's a new kind of title that most people aren't familiar with. So, I'll give you a distinction between like a coach, a mentor, and a provocateur. A coach is you set your own goal and then a coach will come up and make sure you're doing all of [00:31:00] the things that you're supposed to be doing. You're making all the phone calls you're supposed to be making, to get to your eventual goal.

A mentor is a person when you have a specific question, you go to your mentor and they use their own expertise and experience to help answer the problems that stand in your way. A provocateur is a person who asks you questions that you didn't even know you needed asked, right?

Kyle Davis: Mm-hmm (affirmative).

Diana Kander: It's those questions that [00:31:30] challenge you and push you, that help you grow in exponential ways. So, I had a provocateur in my life when I was an entrepreneur. I had this business that I started and it was going really well, and I made $70,000 in my first year, and I wanted to join this entrepreneurship mentoring program, and I got a meeting with the guy in charge. I was like, "I've got this business, it's done 70,000 this year. I think I can do 150,000 next year, [00:32:00] so I want to be in your program."

He looked at me and he said, "Yeah, I don't really care about 150,000." He said, "You can be in the program if you do a million dollars in business next year." I was like, "Okay, sure. Yeah I can do that. It's not problem." We shook hands and I walked out and when I walked out I was like, "What did I just agree to?" I wrote down on a piece of appear like everything [00:32:30] that I had done to make the $70,000, all the time that I'd spent, and my full capacity, working 20 hours a day, 7 days a week, like barely sleeping and eating, I could do 150, $180,000. Like, it's nowhere close.

So, I turned the piece of paper over and I put a million dollars at the top and I started working backwards. I said, "Okay, if I'm going to make a million dollars, what kind of customers do I need?" Then, let me figure out what kind of problems [00:33:00] those people have. I spent the next year reverse engineering, going to a very different goal than the one I had, and I did not hit a million, but I did over $800,000 in revenue which is like 1000% growth from the first year, and it's all because somebody asked me a very simple question.

One question was the reason that my business grew 1000%, and ever since that happened to me, I've been trying to do it for other people, and ask them questions [00:33:30] and to think about things in ways that they never thought possible, and to help them grow in very innovative ways. So, that's probably my most useful role. That, and telling people that they're not actually listening to their customers the way that they think that they are.

Kyle Davis: Right, well, because they aren't.

Diana Kander: But a lot of people interact with their customers. So, I had a client, they had three focus groups before [00:34:00] they launched a product and they're trying. So, they had three focus groups, each one of the focus groups said that they were interested in the product, and when the product launched, like nobody bought it, including none of the participants of the focus group, right?

They were like, "What happened?" It was all about how they led the focus group. They were like, "Wouldn't it be amazing if a product like this existed?" People were like, "I mean, sure yeah. I guess so." [00:34:30] They were like, "Would you rather have it in red or blue?" So, the way that they were asking the questions didn't allow their potential customers to actually be honest with them.

Kyle Davis: Yeah, and I think it's also important when you're talking about the provocateur, the person who really in all honesty asks the tough questions that you've never really thought about, because when someone's passionate about something, the blinders go on, so to speak.

Diana Kander: That's right, that's right.

Kyle Davis: [00:35:00] They don't have the opportunity to look outside, but when someone's a provocateur and they're just simply not passionate about something, they can ask the real questions of, "Why are you doing this?" It's not like a negative thing. I mean, so many people want to shoot the messenger when it comes to this provocateur that you're talking about, in reality they're just trying to help.

Diana Kander: Right, and they care. They care enough to be there, but they don't care enough in the [00:35:30] outcome of what's happening to be emotionally invested in it. That's a key to finding a good provocateur, is to find somebody who's a proven value creator that cares enough about you to help, but is not actually a team member. That's why I don't feel like picking one your employees to be your devil's advocate, like they're scared to death of you. I can't imagine that that ever works. But picking somebody who just doesn't care that much, but cares [00:36:00] enough to help.

Kyle Davis: Yeah. I don't think an employee will ever give you the right feedback or what you really need to hear. They're always going to be in agreeance.

Diana Kander: Yeah, because they have too much to lose, you know?

Kyle Davis: Yeah. So go find an outside provocateur.

Diana Kander: That's right.

Kyle Davis: Cool. Now, since this book came out and you've gone on the speaking circuit and you've spoken to all these companies, large events, small events and everything else, what have you learned [00:36:30] along the way, and how is that now impacting the new book that you're working on?

Diana Kander: Well, I have things I've learned about speaking and I have things I've learned about content. So, which one of those would you like for me to-

Kyle Davis: Let's do speaking, then we'll do content, because I'm a firm believer in content, content, content.

Diana Kander: Yeah, so I've learned that there's nothing you can say to someone to change them. There's virtually nothing [00:37:00] you can say that will change another person, but people are capable of immense change if they tell themselves. So, I try to make everything around my speaking not me telling people, but me trying to show them things on stage to get them to say to themselves what it is that I'm [inaudible 00:37:20].

The first book that I wrote was very much this way. Instead of writing out all the nonfiction lessons that I wanted them to learn, I showed them the story [00:37:30] of somebody who did it the wrong way and then fumbling and having a lot of pain with that. Then, how they worked to do it the right way, so that the reader can actually cheer the person on and know the right answer because they're being objective and they can see it in front of themselves.

I find those lessons to be a lot more powerful. As a speaker, my principle concern is that people not only understand the material but that it actually changes their behavior. [00:38:00] So, a lot of what it is that I do on stage is interactive. Not me asking the audience questions, but actually people coming up on stage and doing these kinds of activities where if I say, "Confirmation bias affects all of us and it makes us only look for evidence that we're right," people are like, "Oh yeah, yeah. That's a big deal. I don't do that, though."

Then I bring somebody up on stage and I tell them exactly what's going [00:38:30] to happen and they prove the point over and over again. People think about it in a completely different way. That's been my biggest takeaway in speaking.

Kyle Davis: I know that I said, "Hey, let's talk about content" but I love the fact that you brought up confirmation bias. Like, it is just one of my giant pet peeves. I'm one of these people where honestly, I joke about the fact that I'm always right, but the reality is I know when I'm wrong, and when I'm wrong, I'm very scientific about something. I'll take in that new evidence and I'll adjust [00:39:00] my opinion. I'm not married to anything, and I just move on, but it just kind of, when people invest so much time, effort, and energy, or money, something into that, the lies that we tell ourselves, the confirmation bias if you will is just one of the worst things that we could possibly do as entrepreneurs or anything else.

Diana Kander: One of the most interesting things about confirmation bias is not even that you're like necessarily lying to yourself, or not listening to negative evidence. It's that you only ask [00:39:30] questions to confirm your belief. So, it's very difficult to seek out, so I have this fun game that I play. You want to play a fun game?

Kyle Davis: I'll play a fun game with you.

Diana Kander: All right. Here's the fun game. I have a series of three numbers, and there's a rule that they have in common, okay? You're going to try to guess the rule. You ever play this game before?

Kyle Davis: No, I have not.

Diana Kander: Okay, well this should be super fun. Okay, so the numbers [00:40:00] are two, four, and eight. Now, you can either guess the rule or you can give me another three numbers and I'll tell you whether or not they fit the rule.

Kyle Davis: Well, I think the easy thing for people to do is say, three, six, nine, but my guess is that you choose numbers that double. So, if it's two times two is four, and then two times four is eight. [00:40:30] So, then the next number would be 16.

Diana Kander: Okay, so the three numbers you're guessing are?

Kyle Davis: Well, I went both routes.

Diana Kander: Or you're guessing what the rule is?

Kyle Davis: I was guessing what the rule is, is that everything doubles.

Diana Kander: That is not the rule. So, would you like to guess another three numbers and then I'll tell you, yeah, whether or not they fit the rule?

Kyle Davis: Then three, six, nine.

Diana Kander: That fits the rule.

Kyle Davis: [00:41:00] That fits the rule?

Diana Kander: Mm-hmm (affirmative).

Kyle Davis: Interesting. So, I kind of know what it is but I don't know what the words are to explain to it, so if you could explain.

Diana Kander: Sure.

Kyle Davis: Yeah, go ahead.

Diana Kander: No, you go ahead and explain it.

Kyle Davis: Like I said, I'm at a loss for words right now, but if it's two, four, eight, I mean, why am I forgetting what the word? It's [00:41:30] like triple, it's like everything's doubled, I don't know.

Diana Kander: You're saying it's like a multiple of the original number?

Kyle Davis: Yeah.

Diana Kander: That's not the rule.

Kyle Davis: That's not the rule? Okay, sorry. See, I was a history-

Diana Kander: That's okay.

Kyle Davis: ... major, not a math major.

Diana Kander: No, no, no, that's all right. I went to law school, so that we could avoid all math questions. Actually, I have a calculator in front of me, just in case you give me some big numbers.

Kyle Davis: What's the rule?

Diana Kander: No, no, no. I'm going to make you guess one [00:42:00] more time.

Kyle Davis: Well, if it's two, four, eight, everything can be divided evenly in half. That's not going to be a rule.

Diana Kander: Give me three numbers, give me three numbers.

Kyle Davis: I said three, six, nine. So then, I don't know what would be another one. Like, [00:42:30] I don't know.

Diana Kander: Give me three numbers.

Kyle Davis: Just give you just general three numbers?

Diana Kander: No, no, no, but ones that you think might work.

Kyle Davis: Ones that I think might work?

Diana Kander: Ones that will help you answer the question.

Kyle Davis: 12, 15, 18.

Diana Kander: Interesting. That fits the rule.

Kyle Davis: So, then everything's a multiple of three if we go that route?

Diana Kander: That is not the rule [00:43:00] and I will let you off the hook, and I will tell you. I don't want to give away what the rule actually is, because I don't want people listening, there's so many people listening, I don't want the magic to get out but ... All right, I'll tell you. It's very [crosstalk 00:43:19]. Each number has to bigger than the previous number.

Kyle Davis: That's it?

Diana Kander: Oh, my God, that's so simple, right?

Kyle Davis: So I could have done one, two, three?

Diana Kander: Here's the most powerful thing about the exercise, [00:43:30] right? We started it by talking about confirmation bias. You were like, "I hate confirmation bias. I look for it" and then I say, "The magic thing about confirmation bias is that we only look for evidence to support what we believe," right?

Kyle Davis: Right.

Diana Kander: And then you only guessed things that supported what you believed. Like, at no point were you like, "Well, I think it's double, so let me guess the opposite," right?

Kyle Davis: Mm-hmm (affirmative).

Diana Kander: "Let me guess 10, 5, 2," right?

Kyle Davis: Mm- [00:44:00] hmm (affirmative).

Diana Kander: It just feels you need to think about guessing like that, it just feels so awkward. Like, "Why would I ever try to disprove what it is that I'm" ... And it's coming up with ways to actually be [inaudible 00:44:17] about whether or not that you're right, and maybe even trying to disprove yourself. That's how we figure out whether an idea is a good idea, or worth pursuing, or whether we're on the right track. It's just the most [00:44:30] unnatural thing to do. That's how we fight confirmation bias, is that we look for negative evidence. Nobody ever looks for negative evidence.

Kyle Davis: I like it. It's also hard to prove a negative, but it's not. It's not. I like it, that's good. We talked about confirmation bias, but one of the things that you mentioned before was the differences between things you learned why you were speaking, and also when it comes to content. What were your thoughts on that, on content?

Diana Kander: [00:45:00] Sure. So, a lot of people were interviewing customers and they thought that they were interviewing customers to test their assumptions, but they were leading them. Like, I gave you the example of the three focus groups where they asked some questions, but they asked them leading questions. So, the second book that I'm working on is what it means to be genuinely curious about your customers, about your work, and how to continuously work to [00:45:30] improve it. How to never settle even when things are going well, so that you never peak, so that you never start going downhill in your workplace.

Kyle Davis: So, when you're talking about how to never settle, my phrase is, "Choose growth, because if you're not growing, you're dying." What is it like to embrace that philosophy and not just in personal development, in [00:46:00] one's guiding philosophy and how they run their business, but also how they help their customers grow as well? What are some takeaways that you're seeing now to tease the book, so to speak?

Diana Kander: Yeah, so like I told you, I believe that our curiosity is the centerpiece to innovation, and that most people overlook it. It's also the secret to continuous growth, so most people, once they experience ... Like, nothing kills [00:46:30] curiosity like success. Nothing. Because once you find something that's working, you're just like, "Good, I'll just keep doing this over and over again." How do you push yourself to stay curious and to continue experimenting and pushing the boundaries? Because that's the only way that you're going to grow and get better.

You have to create things in your life to outsmart yourself basically, because your natural place is to get comfortable, [00:47:00] and you're certainly not going to innovate from a place of comfort.

Kyle Davis: Nope. I think that's a good place for us to wrap up. Look, yeah. Don't be comfortable, people. Just don't do it. Cool. Well hey, if the listeners, if y'all want to have Diana Kander come and speak at your next event, you can do so by contacting GDA Speakers. The number is 214-20 ... Oh, that's my cellphone number. We're not going [00:47:30] to give that one out. 214-420-1999. The website's GDASpeakers.com. For the transcript and the ability to buy Diana's previous book, "All In Startup," you can go to GDAPodcast.com. With that being said, Diana, thank you so much for your time.

Diana Kander: Yeah, thank you so much for the opportunity and for letting me put you on the stop in front of all the people that you know so well.

Kyle Davis: Well, I can deal with it.

Diana Kander: You were fun, so thank you.

Kyle Davis: Thank you.