How to Apply the Lessons from Simon's Books | Full Conversation

Welcome. It's fantastic to be here. Simon, thank you so much for joining us here at DocuSign. We're really thrilled to have you here today.

Thanks for having me. I appreciate it.

So, hey, for the few, you know, 5% of DocuSigners who don't already know you because of the incredible success you've had with your books and your speaking, can you maybe just give a little bit of background to who you are and what you do and maybe give us some insight why you think you've become so influential?

Well, I have a vision of the world that does not yet exist. I imagine a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are, and end the day fulfilled by the work that they do. I believe that leaders are the best tool that we have to build that world. So I've built a career where I've found a way to support and celebrate those leaders that I believe are more likely to build that world. I do it all kinds of ways. I've written books about it, given talks about it and stuff like this.

Fantastic. It's easy to see why that worldview would be so inspiring, not to use your catchphrase, but let's start at the why. Let's talk about your early work and really what I think really captured the imagination of so many people. That was, again, so inspiring as you sort of really encapsulated such a core concept. Can you maybe just share with this group a little bit about what you mean by why and why that's so important?

Well, it was a bunch of years ago where I'd sort of lost my passion for my own work. And I discovered this naturally occurring pattern based on how the human brain makes decisions that every single one of us knows what we do. We know the jobs we do, we know the products we sell, the services we offer as companies. Some can articulate how we do those things. These are the things that you may say are your differentiating value propositions, the things that make you different or stand out from the crowd. But very, very few people and very, very few organizations can clearly articulate why they do what they do. And by why, I mean to make money. That's a result. By why I mean what's your purpose? What's your cause? What's your belief? Why does your company exist on a level beyond your product? Why should we get out of bed every morning? Why should anybody care? And what I learned is that the most inspiring, the most influential, the most innovative companies and organizations and individuals all Think, act, and communicate the exact same way. Everybody from Martin Luther King to Apple Computers, they start with why. And so when I first realized this, it not only profoundly changed my own view of my life and my organization, but I talked about it. And I guess it resonated with other people too.

Yeah, a lot of other people, for sure. And when people say to me, what is the docuSign why? I've talked a lot about a vision we have of trying to make the world more agreeable. And I think that sometimes captures imagination, but sometimes I also have people say, well, what does that really mean? What does it mean to make the world more agreeable? If you were sort of a expert in this field, which you are, and you thought a little bit about DocuSign in that construct, and what's your reaction to making the world more agreeable as a why, what's good? Where do you see gaps? And let's chat about that.

So for me, a good why has two pieces. There's a contribution and an impact to do something so that something happens. So, like my why, for example, is to inspire people to do the things that inspire them. So together, each of us can change our world for the better. So when I hear to make the world more agreeable, what I hear is the. So that I hear the outcome that the world is more agreeable. And the question that it raises for me is, what's your contribution? What's the specific thing that you're doing to help make the world more agreeable?

One of them is that we provide a technology solution which of course, allows people to come to agreement. And we make it much easier than it used to be to facilitate those sort of, if you will, sometimes contractual like agreements that people make and have a way for them to do it in more of a sort of a win win capacity because it takes a lot of the complexity out of the process, allows people to really focus on the core of that agreement. We also think there's another side, which is there's a broader, almost environmental impact. Right. We think about our piece of digital transformation as making the world a better place, not just because people come to agreement faster and more easily, but they do it in an environmentally more sensitive way. So that's kind of how I think about that. Why in making the world more agreeable? Give me critique.

Well, there's two parts. One is, you know, punny visions or punny whys, like a chemical company saying it's all about our chemistry. Get it? Get it? It's the same kind of thing, which is One of the problems is because the people who come to work every day, they're more familiar with one definition. And then so it becomes the product being in the hierarchy higher than the more human element of it, and you really want it in the other order. The product serves the cause, not the other way around. Which leads to the second point, which is your whole description of it was largely based in product. For me, a why is about the history of the company. It's the founding of the organization. A good why comes from the past and is disconnected from the product. The product is the primary means by which you're building upon your why or advancing your cause, but it's not a description of the product.

But one of the things that's happened with DocuSign is we don't sort of think about it as we're one of the players in a particular business. We actually sort of created an industry, if you will, around E Signature. And there was a famous report some years back that Forrester put out and. And they said DocuSign's become a verb. So people don't think about it as the product per se. They think about the act of creating an E signature or a DocuSign. So I think that gives us some benefit and allows us to transcend, as you said, the product. But it also can become a hurdle for us because then it embeds so much in that. The product aspect.

Yeah, I mean, it's sort of the innovator's dilemma, Right? Which is you're a pioneer and you become the generic. You become the Kleenex or the Q tip. But eventually, when there's a marketplace, others will do it, and those industries will mature. When JetBlue first showed up as an airline, they were the first airline to make all of the seats on their planes in leather and put TVs in every seat. And I remember that was their advertising for quite a while. It's like everyone gets a leather seat, everyone gets a tv. And then it turned out to be a thing. And before too long, every airline had all leather seats, and every airline had seats on every plane.

And.

And yet I remember the advertising. JetBlue was still talking about how they invented it. Nobody really cared anymore because it was now generic. You know, I think what makes innovative companies innovative is that they recognize that they create something. Everybody else is the follower. And now you have the opportunity to create it again.

How do you think about that mission or the why and how that translates into the strategy?

Great companies, especially the ones that continue to innovate year over year, they think of their companies less like companies, think of themselves more like social movements. And so that why becomes a filter? Are we doing this? Are we building upon this? And unfortunately, success becomes a great liability for a lot of organizations where all of a sudden the thing that inspired them and drove them in the early days, the thing that was the foundation for all their innovation, gets replaced by quarterly or annual goals.

Short term incentive structures. And unfortunately, that foundation, that very inspiring foundation, becomes forgotten. Dare I say. So it has to be a filter for decision making and a rallying cry for people to try and figure out how to advance.

But in Leaders Eat Last, it was something that spoke to me more about my own sort of role and who I wanted to be. Maybe synopsis a little bit some of your core thinking around that work.

I was going through a period in my own career where, where I was struggling to trust people and didn't know who to trust. And I know trust is important. Everybody keeps telling us trust is important, but they don't tell us what trust is or how it's built simultaneously. I just happened to be spending time with folks in uniform, with folks in the military, and I kept meeting these people who would willingly risk their lives to save the lives of people they didn't even like. Whereas in business, we don't even want to give up credit for things, let alone our lives. I started asking the question, how do I get people like that at work? And my original theory was that they're just better people. And better people are drawn to this life of service, which is why you find a disproportionately high number of these high trusting, high sacrificed people. And the more I started to learn, the more I started to investigate, the more I realized I was completely wrong. It's not actually about the person, it's about the environment. You can take a good person and put them in a bad environment and they will do bad things. Conversely, you can take someone who may have been perceived as untrustworthy. You can change their environment and they can change their lives and become valuable members of a team. And who's responsible for setting the environment? Leaders. Leaders set the environment. So if you can create environment biologically, trust will follow.

Super powerful. And I want it sort of segues for me into the values that we have. We have three core values. Trust is hugely important that our customers come to us and say, here's this incredibly powerful data we have and we're trusting you use it right, you prot it for us, but it's also the way we feel about our employees. Right? We want employees to feel that the company's looking out for them, you know, and they can feel that we have a trust based relationship around their career. But we also talk about responsibility as our second, you know, core value. And this is the sort of back to your decision making processes. Do you make decisions in a way that you treat people equally and fairly? And do people say yes, whether I agree or disagree with every single decision? And then the last one, love as a corporate value. And I always start off by saying, if you, you had said to me before I was at DocuSign, would I ever work at a company where love would be one of our three core values? I would have said no, I don't think that would happen. When you meet someone that you don't know and you tell them you work at DocuSign, the vast majority of people say, I love DocuSign, and then they tell you their story, how do you think about those values?

Well, if love is the one that everybody loves, then maybe that one should go first, especially if it guides others. I mean, trust for me is a tricky one. When we put it on the wall as value because. Because we can't instruct people to trust. And values have to be things we do. I like when values are written as verbs. It's not innovate. You can't walk into someone's office and say, please innovate. But you can say, think of the problem differently. Honesty. You can't put honesty on the wall. It's tell the truth. And trust is one of those weird ones because trust is a result. You can't tell people. Trust me, it doesn't really work that way. In fact, the least trustworthy people are the ones who tell you that they're the most trustworthy. What generates trust is, is when we actively work to make others feel safe, the result is trust. So trust is a value. Though not intellectually wrong, it's very hard to execute. Because you can't tell people to trust. It's not an instruction. And I'm a great believer that, as I said, the best values are often written as actions, as verbs, because you can tell people you can do them, you can hold people accountable to them, and you can even measure them and build incentive structures around them.

I like that. I think we have work to do on that. We've had this model for a few years now and all things need a look, you know, and they need to be reviewed and make sure we're there. When we talk about bringing people into the company we talk about culture fit for sure, and we want to think that they're going to have that value match to be successful here. But I also think we implicitly have a little bit of what you said. We sort of expect that that person gets here, they're going to get it. You know, they're within the range that they'll be able to flourish in a community like this. And sometimes we're mistaken. I think the vast majority of the time we make it work. How do you think about in sort of action mode, understanding whether people really are living to our values? And how do you act on it when you sort of sense that there might be a gap?

Well, I mean, and like you, I've been talking for years about cultural fit, but, you know, fit can be sometimes very passive. And I like to think now more about cultural contribution, which is if someone fits our values, if they believe what we believe, we want them to take our values and go and build upon them. We want them to go make things based on our values, help contribute to the culture, make it grow. Now, one of the ways you hold people accountable to values is recognition and reward. You get the behavior you reward. I did some work with the Navy seals. The director of training for that group drew a graph for me, performance and trust. And what they learned was that the high performer of low trust is a toxic team member. And they would rather have a medium performer, sometimes even a low performer of high trust, than the high performer of low trust. And if you think about business, we have a million metrics to measure someone's performance, and we have negligible to no metrics to measure someone's trustworthiness. And the irony is, trust is actually a very easy thing to measure. Go to any team, ask them who the is, and they'll all point to the same person. And by the way, likewise, if you go to any team and you ask them who has your back always, they'll also point to the same person, which is your best natural leader, that may not be your best individual performer. And so it raises the question, are we putting the right people in leadership positions because those people are more likely to engender trust and perpetuate the values.

And it's so funny, as you were just describing it, you say we don't have this way to get data on the people we trust. I said, we do. The answer is ask the colleagues. It's just that we don't normally build those processes. But I talk about this concept of the impact. The success of our employees is three factors. They have to have skills and smarts. And then you take that and you divide that by your ego. And the way I define ego is a person with a high ego. A positive ego is one that puts the team first. And someone who get a low score for ego is someone that's very self centered. And you take that ratio and you raise it to the power of how hard they work. No matter how hard you work, if you don't have a good ratio of your contributions from skills relative to the ego you bring, sometimes it's actually toxic. Your point? Right. So a person's working really hard, but pushing an agenda that's all about them. It, it demoralizes other people around them. Does that make sense to you conceptually?

I mean, in theory? Yes. I mean, I think we forget that we're human and the way we track metrics and the way we measure each other is. If we're machines now, those output is very important, but input is really important too, and it's just harder to measure. Like we talked about trustworthiness and cultural contribution and creativity, these are things that are in all of us, but we don't know how to measure them easily and objectively in the short term. And so yeah, philosophically, I think what you're talking about is right. It also reminds me of my favorite definition of humility. Bob Gaylor, who is the fifth chief master sergeant of the Air Force, said, don't confuse humility with meekness. Humility is being open to the ideas of others. And I've met some pretty remarkable powerful people in leadership positions who act absolutely have big egos, but they're still open to the ideas of others. A healthy ego is thinking you're good. An unhealthy healthy ego is thinking that you're better than everyone else. And I think that definitely taps into your formula.

So I want to get to your point. You just started talking a lot about the long term and I think that's super important. Do you want to talk a little about the infinite game and just try again? Quick little synopsis and then I got some very specific things I want to talk to you about.

Yeah, absolutely. In the mid-1980s, a philosopher and theologian by the name of Dr. James Karst articulated these two types of games. Finite games and infinite games. A finite game is defined as known players, fixed rules and an agreed upon objective. Football, baseball, there's always beginning, middle and an end. And if there's a winner, then necessarily there have to be losers. Then you have infinite games. Infinite games are defined as known and unknown. Players, the rules are changeable, which means every player can play however they want. And the objective is to stay in the game as long as possible to perpetuate the game. Turns out we're players in infinite games every day of our lives, whether we know it or not. There's no such thing as winning. Global politics, for example, no one wins education. Well, turns out nobody wins business either. You know, there's no such thing as winning business. But if you listen to the language of so many business leaders, it becomes abundantly clear that they don't know the game they're playing in. They talk about being number one or being the best or beating their competition. And this is a problem because when we play with a finite mindset in an infinite game, when we play to win in a game that has no finish line, there are some predictable and consistent outcomes. The big ones being the decline of trust, the decline of cooperation and the decline of innovation. We have to play for the game we are in. And most businesses play with a finite mindset.

One of the challenges for how the, the game gets defined is the, the state, if you're talking about, for a business, the state of the company. We are as you know, a public company. And so on the one hand we have aspiration to think, you know, infinite. I also have a, every quarter I report my earnings to Wall Street. And so now I've got a different game that has to your point, a very specific timeline with a very specific metric. You know, in order to kind of thrive in the long game, you got to put some wins up in the, in the shorter term game to have that flexibility and right to keep playing.

I mean, bluntly, the best companies ignore Wall Street. You know, why are you making decisions to help some 27 year old analysts meet their financial objectives so they can get their bonus? You know, fundamentally if you do well and they believe in your vision, they'll invest in you. But ultimately, like a good customer, the best customers are not the fair weather customers. They're the loyal ones that they stick with you through thick and thin. And the same goes for investors. The best investors are the ones who believe in the management, believe in the vision, and understand that you're making decisions for the long term and are willing to take some short term hits and stick with you because they believe in you. We also have to remember that the concept of shareholder supremacy as a sort of a standard in modern capitalism is relatively recent. And has it actually been good for innovation in business? And I think the consensus is it.

Hasn'T been well Keep in mind though, for us, every one of our employees is a shareholder, right? And so it's an important piece. So when we have short term fluctuations, just be really straightforward, it impacts them both positively and negatively. So we do have to factor in that reality. Last thing I want to talk to you about that is actually about our employees. So we got thousands of docusigners out there chatting with us. One of the things I think is interesting is some people get motivated by that short term game, right? There are a lot of people who are competitive here, and I'm one of them, and like that concept of a game and a win and a path to feel that success. At the same time, there's a lot of docusigners that say, you know, what's inspiring to me is about I want to be a part of something that's bigger than myself.

Those concepts are not mutually exclusive. Being a part of the infinite game is not the absence of finite games. It's the context within which those finite games exist. And when we, when we think only in short term, in an infinite game, like I said, you don't know what it's a part of. And at some point you start saying, is this worth it? Or what am I doing here? Is this, you know, this becomes exhausting, quite frankly. We have to change the analogies. We have to change the metaphors. We overuse sports and war analogies in business. Those are finite constructions. Think of it more like a lifestyle, right? Let's say you want to be healthy. And there's many things you have to do to be healthy. You have to eat right, you have to sleep. You can absolutely have arbitrary short term goals. And if I happen to hit my goal on the right day and the right time, I'm ecstatic. But here's the joke. I have to keep exercising and eating healthy for the rest of my life. The game hasn't ended just because I hit a goal. What's more interesting is what happens if you miss your goal, right? Do you know what happens if you miss your goal? Nothing. Nothing happens. Because when you have a vision, when you have a just cause that you're striving for, you're making constant improvement. And if you go back to our metaphor, I'm way healthier now than I was when I started, even if I missed my goal. So the two are not mutually exclusive. You can absolutely have arbitrary goals. It's very exciting. It drives people. Metrics are good, but to what end? Like, what is this all actually building towards? And that's the vision and the just cause.

How would you think about what sort of tools and approaches and what makes the people the best leaders for their colleagues in the organization?

Well, as you said, the primary responsibility of a leader is to build new leaders. You know, and one of the ways we do that is we teach leadership. You know, when somebody joins a company, we give them lots and lots of education on the product and how the company works and how the systems work, and we give them mentors and all of these things. But if we promote someone to a position of leadership, we usually give them little to nothing. And yet leadership is a skill like any other. We don't expect them to be good at their job unless we train them how to do their job. So how do we expect them to be good leaders? We don't train them how to be leaders. You know, are we teaching things like how to give and receive feedback, how to do active listening, how to have an effective confrontation, how to have a difficult conversation? Like these are leadership skills and the.

Motivation, do you think? Then you really have to figure out a way to go back to that kind of core values that's going to give people that direction. What are you seeing right now that people are doing to best motivate in this crazy time we have with COVID And let's face it, there is a malaise over the whole world.

Well, I think a big part of it is empathy, quite frankly, which is, do people feel seen and heard? When Covid first struck people in leadership positions, whether they were effective or ineffective leaders prior to Covid, they sort of leaned back on their own humanity. And they picked up the phone and they called their team members one by one and said, are you okay?

But I think this concept of the humanity that you hit on, I think it's what's special to me about DocuSign in the end of the day.

And one of the secrets to building trust, by the way, is not offering your help to others, but asking for help from others. When leaders say I don't know or I need your help, it's more likely to create the same kind of behavior from the people who work with them too.

It's interesting to think about that construct we're having where there is this sort of COVID driven malaise. But in some ways, I think it's even more than that. I think it's what you talk so much about, about a purpose and people sort of thirsting for that purpose. And when the whole world gets changed as it has been changed, we think differently and we've been Talking a lot about this idea of the great embrace and how do we create an environment and culture where people say, I want to be a part of that? What's your sense about where you see people who are doing a great job at that, Inspiring people to say, yeah, let me come be part of that family.

One of the things that we don't talk about with the great resignation is, you know, we talk about the fact that some people are leaving because they've got government checks. That's a very small percentage. You know, some people are leaving because they want to follow their dreams, and this is not what they want to do for the rest of their lives. That's true, too. That's also a relatively small percentage. I think the larger percentage, quite frankly, are people who. They've been taken advantage of as a population for decades, let's be honest. And companies have gotten away with it, you know, so many people for most of their lives. If you ask them, how's your job? They go, it's fine, you know, and yet they don't. Would you quit?

Yeah.

But, you know, they're more afraid of the unknown. And we went through Covid where some people were furloughed, some people were laid off, some people didn't lose their jobs, they kept their jobs, but they had fear. All of a sudden we realized we got through it. Like, we made it through it. And so when I'm faced with fine or the unknown, all of a sudden the unknown is much more appealing. I think people are willing to go on a search. And I think we've had massive imbalance in corporate culture for decades where we've largely taken advantage of people. And now this is a great correction. The indictment is that we haven't focused on culture enough in corporate America for too long. And I think the companies that really have focused on culture, they're suffering a lot less with the great resignation. Jobs are like children, right? You don't have to like your kids every day, but you can love your kids every day. You don't have to like your job every day, but you get to love your job every day, and that really is the responsibility of the company.

Thank you so much for joining us. It's been fantastic. And thank you for helping us kick this session off. It's. It's just awesome.

My pleasure. Thanks so much for having me. Take care of yourself. Take care of each other.