Because you can't be successful in any organization unless you're selling to others, and particularly early on in your career where you don't have any authority. Here it comes from your persuasive ability. It's the one role everybody has. And whether you lead a team or aspire to, you can't afford to ignore it. And we're going to dive into that and so much more in today's episode of How Leaders Lead. I'm David Novak, and every week I have conversations with the very best leaders in the world to help you become the best leader that you can be. My guest today is Alan Teagasen, the CEO of DocuSign. Before that, he led Google's $100 billion advertising business in North and South America. So I think it's safe to say Alan's got his finger on the pulse of technology, and today he's going to share some insights into artificial intelligence that every leader needs to hear. But he's got some old-school wisdom too, especially when it comes to sales. Now look, you may not have the word sales in your title, but you're still a salesperson. As Bob Dylan used to say, "Everybody sells somebody." And everyone is a salesperson when you think about it. And if that makes you a little uncomfortable, don't worry. Today, you're going to see how to embrace that role and why you can't overlook it if you want other people to follow you. So here's my conversation with my good friend, and soon to be yours, Alan Teag asen. I got to start out at the top. I was just thinking about this, but what would be the most important DocuSign document that you've ever signed? Wow, I've signed a lot of DocuSigns in my time. I suppose signing my awful letter with DocuSign, which of course came on Docu Sign. I love it. That is a great answer. Something that I learned in my research is that you and I, we both have fathers who are in their 90s. My dad is 95, he'll be 96 on May 25th. What would you say is the biggest lesson you picked up from your dad? Yes, my dad just turned 90 here about a month ago, and still going very strong and staying very active. And my lesson is really that. I grew up in Denmark and my parents both had big jobs, but at 70, big organizations, whether government or private sector, make you retire. And so my mom really didn't have another outlet for her intellectual energy, but my dad had this connection to international organizations, and he was able to stay engaged and work literally until a month ago. And I think that has a lot to do with just how intellectually and physically, Bible, he still is. And so kudos to him and I think we're like sharks, but don't keep moving, we sink to the bottom. So I told my wife, don't expect me to retire anytime soon. I like it. I like to stay busy. I think that's a lesson. I don't know how old you are, but I know you're older than you look. You look great, so I think you're going to go a long time. And we're going to get into DocuSign and now you're leading the great company. But first I want to take you back a bit and you just talked about your dad. What would be a story from your childhood that shaped the kind of leader you are today? Look, as I mentioned, I grew up in Copenhagen. I lived there until I was 24 and then came to the US. But those were very formative years. And I think, you know, my parents and Danish society in general, it's really built on these concepts of fairness and equal opportunity. And those are very foundational values for me. And so I try to bring that to every organization that I lead. I want to evaluate people on merit. I want to give them every opportunity. And I recognize that people have different ways of expressing their talents and different ways that they get to be successful. And I try to look for what that is and then help them tap into that. I think people have generally regarded me as a very fair leader and manager. They know they're going to, I'm going to look at things, you know, fairly clearly. And I'm going to be clear and direct to my communication. And I'm not going to have any biases or preferences. And I think that comes from wanting to give an equal opportunity to everybody. That's a great learning from your upbringing. And, you know, I also understand that both of your parents were economists. They were. Give me a taste of what a dinner conversation would be like at the Teagas and household. You know, they were both, yeah, they were both economists. My dad was a professor his whole life. My mom started out that way and then worked in the government. And so there was just a lot of discussion about politics and policy, both in Denmark and at the European level. You know, one thing that really came up a lot was Europe and integration of Europe. Most of my dad's sort of life work was working on that. And so Denmark joined the EU. I think from an American audience, maybe a little hard to imagine, but imagine that vote to decide to give up a lot of your sovereignty to this transnational, or authority. And why that was a good trade to make. I think the Danes voted in favor of that. And then later when they introduced the euro, decided not to join that, right? Those are big decisions for society that the US made a very long time ago, but there were big decisions then. And those are the kinds of topics that came up all the time. And so I had a very keen interest in politics and policy that I still have. So it was sort of my side hustle, I get involved in some things that Stanford on that end. But my day job is business and in business, I think it's best to stay out of politics. Yeah, I think you're right about that. I think my dinner conversation was more like "pass the potatoes." You know, there was a lot of that. So when did you first believe that you had it in you to be a leader? You know, it feels sort of self-aggrandizing. When you feel like you're ready to be a leader, I think that that's earned over time. Look, I was always a natural initiative taker and organizer of things. And so I suppose it was sort of the earliest indications that I just naturally was somebody who wanted to organize things, who wanted to take initiative, who wanted to get others to follow, and you know , early on, I don't know what I was at it, but I think I've hopefully developed over the years. You've had an interesting life and you grew up in Denmark and you make your way to the U.S. What was the biggest lesson you had as you worked your way into the United States of America? I know you have many lessons. So I came here to go to graduate school. Met my wife. We decided to settle in the Bay Area and I worked in the Bay Area and in tech ever since. I think some early lessons. I determined that I wanted to lead people. So I sought a management job coming out of business school, which is not necessarily typical. A lot of people were banking and consulting, but I really wanted to run something and lead people. And I found this to be incredibly rewarding and so I looked for that opportunity over time. I think the second thing I learned about myself early on was that it was good if there was an element of sales involved in the job. I had a natural affinity for that. Most people don't like that. And I like it. I think people who are uncomfortable with that tend to think it means being sort of greasy or in some way duplicitous or not representing things accurately. And I think that couldn't be more wrong. I think the more deeply you understand that and the more honest and forthright you are, the more believable and trustworthy you are, the more effective you are. That is so right. You think that you not ultimately don't have to learn that selling skill to move up the ladder. You're kind of crazy. How do you learn it? I actually got my... I mean, you learn it internally in companies because you can't be successful in any organization unless you're selling to others. And particularly early on in your career where you don't have any authority, it comes from your persuasive ability. And then a few years after grad school, I'd been running various parts of the customer service organization and a job opened up to run the Fortune 500 sales organization, which of course I was utterly unqualified to run. But I'd gotten involved in the process and it was in the early... in the still in the early days of the PC revolution. And I'd seen, you know, I think I could do this and the company of course, Anum ia as a leader and a manager and they gave me that opportunity. And that was my beginning of sales. And a guy I've since run almost every part of the company. I mean, one of my key messages I always tell people is, look, you want to own and really master your craft in whatever you... where you start your career and you don't want to move on until you've done that. But then it becomes very important to move on and take the risk to move sideways and learn other functions of the company. And so over time I've run a practical network function of the company and I enjoy all of them. And I think that really helps me be effective because I can empathize with the perspective of all the leaders in the world. Absolutely. And I've heard you say that for 12 years, you wrote what you called the Silicon Valley roller coaster. I mean, tell me what that was like. You know, I really had a full range of outcome. It's a bit of a cliché, right? That in Silicon Valley is this boom and bust thing. But I experienced that very directly. I joined a company out of business school that was sort of mid-size and just gone public. And we kept growing. And so that was a mid-size opportunity. And then they ran into a lot of competition. I left to join my first startup. I was employing number 10. And so that had a very different feel, right? We got bought within a year. And then the acquire 18 months later went bankrupt. So within a span of five years, I had sort of been part of, you know, post IPO, mid-size growth phase, the very early company formation and a bankruptcy. And then I, you know, I had some good success and company I joined in '96. We ended up being able to take public. I was a big success and a huge home run. And so that, you know, you obviously want to have one or more of those. And so that was that. Oh, he sells a little bit. He sells a little bit. There's always so many of those at bat you get. So I had a mix of, I'd say, strikeouts and singles and a home run. And so that put a put me on the map a little bit more and gave me the credibility to have access to other opportunities. You've had a lot of experience building things from the ground up. What should be a part of every company's foundation if they really want to be successful? I think the two most important things, you have to have a clear idea for a differentiator product in a market that's large enough to be exciting. On second, you have to attract a team that is capable of executing. Those are the two things. I think everything else is noise. My experience is that a lot of people who try to look around the coven, okay, what title they're going to give me, how much money they're going to give me or other sort of more superficial attributes. But ultimately what matters for your ability to grow in an organization is the organization itself well poised for growth because that is what unlocks opportunity. And are you working with people you can trust in your spectrum and so that's what I've sought. And whenever I've not done that, which I have, that has happened a few times, I 've come to regret it. Hey everyone, it's Kula. We'll get back to the interview in just a second. Before we do though, I have a question for you. Have you downloaded the How Leaders Lead app on your iPhone? If you haven't, take 20 seconds right now, go to the App Store, search for How Leaders Lead and download the How Leaders Lead app. In the app every day, you'll get a two minute video that'll give you a leadership insight from one of our amazing guests for our podcast to inspire you and to really get your mind in the right place before you start your work day. So go to the App Store, search how leaders lead, download the How Leaders Lead app and start your day every day with two minutes of leadership wisdom. It'll take 20 seconds. Go to the App Store, download the app, and you'll be able to watch every day, just like me, the leadership insight from How Leaders Lead. Now I understand you spend a lot of time in venture capital, where you really leaned in to be in a coach, which I found to be very unique from that perspective. You always think of these venture capitalies, these muddy, hungry grubs that are going after it. But you really leaned in to be in a coach. What did that experience in that world with that kind of desire to be a coach? What did that teach you? I think that, look, that's the aspiration. I think if you're a VC, what you should want to be is to get into a coaching relationship with your founders. You're not supposed to be running the company. You're supposed to be helping them maybe see around the corners, anticipate things and maybe identify their blind spots, be a source of support. I think a lot of VCs are either too passive or try to get overly involved. There's very much a Goldilocks balance there, where you want to be involved enough that you're helpful, but not think that you're on the management team. The other thing I think I learned from being a VC is, look, you see so many companies. I probably looked at a few hundred a year. Once you do that, you start to develop a lot more pattern recognition, both for what constitutes good team to constitute the opportunities and how to differentiate between things that are really super early, very formative to that are in the growth phase, to things that are more in the scale up phase. You look for different things, depending on what size company it is and what trajectory it's on. That turns out to be, I mean, it's obviously essential in the venture business, but it turns out to be super helpful in most companies because at a place like DocuSign, for example, we have a scaled mature business in our well-known signature business. That requires a certain skill set model to run that well. But then we have some new initiatives that are much more growthy, much more like a venture operation than you need to understand what are the signals you should be looking for in those businesses that are very different. Then you might see in an existing more cash-calm or cash-calm or in a business. I think the venture skillset turned out to be super useful in my many years at Google afterwards and now at DocuSign. If you're intellectually curious, how can you not love that? You get to work with some of the most motivated, exciting people. I love my time in the venture business. Speaking of people and speaking of coaching, when you look back, what's one of your favorite stories where you know you really brought out the best in one of your venture capital partners or one of your teammates? Quite a bit of that on the teammate side. Let me use the teammate side. So I'll use one example. So I was at Google for 12 years after being a VC. When I joined I inherited four senior leaders and their organizations reporting up to me. Several of those leaders were incredibly talented but very monochromatic. I'm sure you've had people who are working for you. They were really good at one thing, but they needed to develop a broader skill set to really become senior executives and be able to run something more broadly. I had a guy who was super creative and fun but lacked some of the discipline and process. Another person who was very much an engineer, very analytical, but wouldn't let people in. He had a lot of EQ but he didn't show it. So trying to bring that out in them so they could become well rounded and be successful and then seeing that they've both of those folks have been incredibly successful and are very, very senior roles now. It's just incredibly gratifying. There's nothing better. So you feel the same when you get a note from somebody or you ping somebody, you see a big progression for them and they kind of come back and say, you know , that was really formative and really helped me develop and big reason why I am where I am. So that's really my favorite thing in management. How did you help them gain the self-awareness that they needed to develop some of those skills where they might derail or not achieve what they had in them? You can't do it for people in particular when they're pretty senior. You kind of have to throw them into the pond and give them some coaching, but a lot of that I think is about opportunities to force them to tap into those sides of themselves. So as a take the person who was more of an engineering type and very analytical , brilliant, we gave him a sales leadership role. How did I know that? The flip side is a game strategy role for a creative person that he needed more structure. And I think for both of them that turned out to be really great. Maybe another one that comes to mind is another senior leader who was maybe reluctant to toot her own horn as much and wouldn't maybe insert herself as much in the very senior discussions. Absolutely brilliant. And I really sort of pushed her in a couple of occasions to take that seat at the table. And of course, you know, she's phenomenal, phenomenal, successful now. But they all need different things. That's exciting. You know, you were a rock star at Google as well. I mean, you run the America's business, which $100 billion in advertising, you know, in North and South America. What was one of the, what would you say would be the most significant leadership challenge you had, you know, in that role? Google, Google since its early days, is a very engineering center company. That's well known. And so Google had built the best digital advertising engine on the ecosystem and had the most reach. And of course, search was an incredibly important platform for people to discover information. And so there was this idea that, well, if we just built this, everybody will come. And literally all the small customers, Google at that time, not only could you not, would they never call them, you couldn't call Google. You could go to the help center. It was totally self-service. Well, I mean, when people are spending 50, 100, 100, 1000s of dollars with the company, and it's life or death for them, you know, because it drives their business. Chances are they probably need a little bit more than that, particularly as the system got super complicated. And so that was the business I ran initially at Google. And there was just so much opportunity to bring both a human factor and intelligence to that, to run that better. And of course, it turned out that every business in the world wants to advertise and reach more customers. It's just historically that most media could only really sell to large companies. If you're a television station, you only have a small number of ad slots. You can only afford to, if you sell, send a salesperson to every company. And so you're only selling to the large advertisers. But there are millions of small businesses that, if they could be really targeted, they would really like to do that. And so we had a good opportunity to do that. And that was a huge driver, remains a huge driver of Google's. I'm going to get to DocuSign in a minute, but just one more question on Google. It is one of the most respected companies in the world. You know, what's one of your favorite Google stories that highlights what makes it a special environment to work in? Or did you see it that way? Yes, I did. And I still do. It's a very important company, right, where it's shaped how people consume information and media. And that was true everywhere in the world. And so I love that opportunity to have impact at that scale and the responsibility, frankly, that came with that. So that was fantastic. What's the story from Google? Well, I'll share one that I think is perhaps less obvious. I think Google, when I joined Google, I was a little surprised at how somewhat chaotic it felt internally. You know, there would be multiple projects that were pretty overlapping and competing in different organizations. And it just was sort of happening organically, bottoms up. And at first, it sort of offended me. If you're sort of a manager person, you'd be like, well, you know, we should be top down. We should be structuring this and put all of our work behind this one arrow. And the reality is I think the insight the founders had is if you want to have the best talent and you want to drive innovation, that comes from the bottom up . And the way you do that is by giving people time and opportunity to develop their ideas. At some point, sure, you're going to win or them down and you're going to put more resource behind one or the other. But you're going to be pretty disciplined about that because the way you attract the best people, which is what's going to drive your innovation pace and agenda, is by giving them those opportunities. And so I just came to realize that that was a small tax to pay for the amazing innovation and caliber of people that the model enabled. That is a very counterintuitive lesson, right? And runs counter to how most of corporate America runs the innovation agenda. And so people come to Google all the time. Tell us how you become more innovative. And I'm like, well, you actually kind of have to undo a lot of the cultural things because that's really what's blocking you from attracting or keeping the people who are the innovators. That's great. You know, so you had this fantastic job at one of the top companies in the world. And why leave a trillion dollar business to run a much smaller one, like, like DocuSign? My wife asked that question too. That's a good question. You need somebody to ask for those questions. I love my time at Google. And I have so many friends there in respect to the company. But I was very keen to, instead of having this super large violin section, to have the whole orchestra. And that wasn't really going to be possible at Google. And the reality is, Google is a very functionally organized company. And the only thing that is, with the exception of Google Cloud, which is sort of an operating division within the company that's somewhat autonomous, everything else is functionally organized. You're working in sales or you're working in marketing, you're working in product or you're working in finance. But you don't have that cross functional responsibility that you have as a GM or CEO. And I really wanted that. And I've been wanting it for a while. And look, I had an amazing job and I loved it. I was eager to try my hand at conducting the whole orchestra. So you were licking your chops to get the company like DocuSign? Exactly. And then you're like, "Well, but it has to be something good." At that point in my career, even though I had obviously a lot of startup DNA and experience and appetite for that, it didn't really make sense for me to go run a 10 or 100 person company. So I was looking for something a little bit more sizable, but where there was still a big growth and transformation opportunity. And where I felt like you were starting with enough quality that you could build something great, because it's hard to fix something the company once it's broken. And so DocuSign came along. I mean, I was literally sitting at my desk one day. And I see the news in my browser that DocuSign has hired their CEO and that the chair has stepped in as interim CEO. And I knew DocuSign really well. I've been using DocuSign for years. Google was a bit customer. I'd been in to meet with the management team, he was CEO. And to top it all off, because I mean, obviously, we can come back. We'll come back to DocuSign. But to top it all off, the incoming interim CEO, the chair, was my old boss from over 20 years ago. And so I was like, okay, this is kind of a sign. I'm just going to send her an email right now and say, "Hey, it looks like you're going to be looking for a full-time CEO at some point. I might be interested." And she wrote back right away and said, "Let me put you in touch for it." I think it was a high-grade running process. And obviously, there was a lot more to it. And they did a very rigorous process. I was very fortunate to be selected. And that's how it happened. Here we are today. Give me a snapshot of the DocuSign that you joined and the business that you lead today. Yeah. So, look, everybody already knows DocuSign. So just to frame it a little bit, so DocuSign was started about 20 years ago and had pioneered this idea of signing contracts in electronic aid, and it was an almost heretical concept when they first started. Nobody thought either on the sender or the signer side or in government that this was something one could or should do. And to the amazing credit of the founders and the early team, DocuSign really pioneered that, built that category, and up going public and so on. And then COVID happened, where it took a business that was already public, was growing nicely at 30%, and took growth to 60%. I mean, orders were coming in from everywhere. New use cases where the government needed to start lending money, but they had no way of powering executing the agreements. And so there were a lot of one-time use cases also that pioneered that. DocuSign went through this incredible cycle, externally imposed, if you will, very, very rapid growth. And then as COVID waned, the deceleration then came from unwinding some of that external stuff. That can be a near-death experience for a company, right? Because when that happens, everybody sort of forgets how to do their day job. And they're just looking at the stock, it's at 300. And if we can't even process all the orders we have. And so I think what I saw, looking at DocuSign from the outside, was an amazing franchise with the trust and affinity that people have for the brand. A company that could be run more efficiently and needed to get through that trough and address some of the new competition that had emerged over the last five years. But if that was all there was, I don't think I would have done it, right? Because that sounds kind of like a low growth, not interesting business, but maybe highly profitable. And I'm a growth person. When I think about contracts or agreements, they remain an unsolved problem. They're one of the last frontiers of digital transformation. We've taken contracts and we've digitized them, right? Maybe we have them in word now and we send them around email. And hopefully we signed them electronically. And other than that, nothing has changed. The contracts that you and I would sign, whether they were sales agreements, purchase agreements, employment agreements, are still, those processes are just as brittle and broken and inefficient as they've always been. And so I knew that. And I thought that is an unsolved problem. That is a very large market opportunity. And DocuSign is incredibly well positioned, the best positioned to try to deliver against that. Because DocuSign is already in the contract flow for so many of these companies . And so I didn't have a specific roadmap. I mean, I said I have a general idea, but that was the leap. And so that was status quo in October, 2022. And we've made, I think, really good progress in all three of those fronts. So we've stabilized the existing signature business. It's now continuing to make progress. And we have an amazing franchise. It's still, I think, significant headroom there. We've made the company a lot more efficient. So there's a lot of unnecessary expense. And we've, I think, trimmed that and refocused and invested more in product. And then most importantly, I think we've gotten our innovation mojo back. And so we've articulated and developed this suite for what I call intelligent agreement management. We launched it earlier in April of last year and started shipping at the end of May. And you know the early, the early progress is really, really good. What do you mean by that? Tell us what that business is exactly. Yeah. So if you think about agreements, agreements go through a journey, right? Somebody has to draft them. If it's a negotiated agreement, then, you know, there's a negotiation process and editing that goes back and forth. Then it has to get executed and then they can always be in a series of steps of approvals and execution associated with that. And then once you have a signed agreement, you need to manage that agreement. You know, if you're in a sales agreement, you may have made certain commitments to your customers and vice versa if you're in vista procurement agreement. There are no tools today that help companies do this. And so we took our existing signature franchise, some early efforts we had made in work for sort of lawyers and other contract specialists and said we can deliver a holistic end to end platform for managing the workflows associated with that agreement journey and layering intelligence on top. And sometimes it's good to be lucky. I joined DocuSign in October 22. That was literally a month before GPT 3.5 came out. I knew, obviously, that there was a lot happening in AI from my time at Google and had an innate sense that we were going to have some transformation opportunity. But I think I couldn't even have foreseen just how much capability is unlocked. If you think about agreements today, they're in essence unstructured flat files . There might as well be documents in an old style hanging folder file cabinet, right? There is no visibility into what's actually in them. But with AI, we can just extract the metadata, the central data from those agreements with very high reliability and give you access to all of your agreements. That is incredibly valuable, something we can do nearly instantly upon execution of a licensed deal. We can deploy this. We're deploying that capability faster than we deployed in Sine, which historically has been very easy to adopt horizontal software solutions. So I think we are onto something. It's very exciting. And one thing that you might say, well, isn't that just a problem that very big companies have? No, we started out with the small and midsize companies, companies with maybe 52,000 employees. The average number of agreements that those companies upload to us is over 4, 000. That's amazing. It's interesting. I have a friend who's a regional vice president of a spinal device company. It's not a huge company, but she has over 50 salespeople reporting into her. And I said, I'm talking to the CEO of DocuSign today. And she goes, wow, that is such a great company. And I said, do you use DocuSign? She goes, all the time, I said, well, can you give me a hardball question that I ask you? What's wrong with their customer service? Or what can we do? I don't see anything. I think they just do a great job. We love that company. And so it's very interesting, though. Here you have the signature business. Now you're moving into this intelligent agreement management, which, you know, it's got to be a much smaller business. It's off to the side to a certain extent. It's smaller today, but I think the total opportunity is much larger. Yeah. Okay. I got that. But it's small and you've got today, but you've got this other business that kind of brings home the bacon. How do you, as a leader, really go after that small opportunity that can be the big idea and still, you know, get the focus you need on the real big revenue opportunity? Yeah. I know. Look, I mean, that is obviously the big tension and worry that you have when you do something new like this. The good news is we're not asking our sellers or our customers to buy something auxiliary and standalone and separate from our core. We're really sort of reinventing the plumbing on which the signature sits on top of and extending. It's a very seamless add-on. So we're, I mean, my pitch to you would be, let's say you run a small business and you have all your sales agreements done with DocuSign, like your friend. I would say to you, keep doing what you're doing and send the agreements out with DocuSign and get them executed that way. And now I can seamlessly give you insight to all the agreements you've ever signed with DocuSign and everyone, everyone ever going, you signed in the future and compare them and give you, you know, how do these deviate from what you might offer as a standard term? What should you be looking at? We negotiating next time your company that that opportunity comes around, which agreements are coming up for renewal. Those are things that nobody knows today and we can give it to you out of the box. So it's a very nice upgrade story, if you will, as opposed to, oh, I'm asking you to buy something completely separate and distinct. So it's not like you're going after light users or non-users. You're basically got a way to take your heavy user and get them to buy one more time, you know, which is always, that's paid for any time I've ever looked at. Do you think that's right? I mean, we have 1.6 million businesses that pay us monthly for our signature product. That's an astounding number, right? I mean, most software companies have thousands of tens of thousands of clients. Very rare company, you know, might have more than that. And so the breadth of opportunity that we have to then go and pitch this expanded story to is good. So as we, I don't think we could take this on if we didn't have that because the cost of sales and marketing would just be too high. We'll be back with the rest of my conversations with Alan Teagasen in just a moment. Well, it's Valentine's Day tomorrow and because love is in the air, I've got to talk about this fantastic insight from Jesse Cole, the owner of the wacky and wonderful Savannah Bananas baseball team. Love your customers more than you love your product. We all love our product. We talk about what we sell, but how often you talk about who you serve. And so we started loving our customers and I'll tell you the name of our company is Fans First Entertainment. Our mission's fans first entertain always. Every decision we make is, is it fans first? So like for instance, when someone buys a ticket from us, they get a video of us celebrating. So they congrats, you just made the best decision of your day. Right now as you bought tickets, we all celebrated. We grabbed your tickets, a banana, banana, put your ticket on a silk pillow. We put it up in the air. We had a seance around your tickets and then we now put them in maximum security in our vault. They're ready for you to go bananas. That's the first touch point. And then every single person that buys a ticket gets a thank you call from us. Now, most of the times they think, was it my credit card not work? We said, no, no, no, we're just calling to thank you. You have to map the experience and love them. And how do you want your customers to feel? Now go back and listen to my entire conversation with Jesse, episode 32 here on How Leaders Leave. So, you know, AI, you know, it's such a buzzword today. You're into it. You know, how do you, what advice would you give a leader today on, on how to really understand AI and more importantly use it to grow your business? And how do you get up to speed on this as a leader? Look, it's hard, right? We're all incredibly strapped for time. It's not like I suddenly have four hours of my day to go, you know, take some class on it. I think what I would push on teams is really look for credible opportunities to get started in ways that are tangible and real, not sort of super exotic or futuristic. So as an example, I think one of the things we're looking at and that a lot of companies looking at it, how can I augment my customer service with AI, right, by providing, take all the existing answer base that I have and make that available in a self-serve way. And that's relatively straightforward to do and gives, of course, immediate return in terms of customers being able to get a better experience. Maybe you can shift some of your labor resources to higher quality, higher opportunity tasks. And I think that that's an easy and easy and easy win. Another place is you can make your engineers a lot more productive. There are very mature proven tools where your software developers can become more efficient. Those are not pie in the sky things. There's not things that require you to completely reimagine how your company operates. That's not to say that they're not that, as always, you know, with any type of changes to how people work. The human factors are always the most important. So that's why I say rather than say, Oh, I'm just going to offer this new broad AI capability to everybody. I'm going to buy a GPT license or whatever it might be for everybody. You know, chances are, you know, five or 10 percent of your employers take advantage of the rest of them are going to ignore it. So picking something that is a high value use case where you can put a lot of wood behind the arrow and you can, there's very credible and near term ways to get value, I think is the place I would start. And obviously I'm biased, but contracts would be another area. And then want to start with that. One of the guys I know that I learned a great deal from was Warren Buffett and he taught me the importance of sober selling to investors, you know, because I didn't, I was more on sales and operations and, you know, so I went to him and he said, you know, David, how often do you talk about what goes wrong in your business? And I said, well, not very often I'm always, you know, talking about what's what's right. And he says, well, you know, why don't you talk about the things that could go wrong, and you might even gain more credibility with with investors and you know I think it was like a great example of like sober selling, you know, when you look at when you look at the DocuSign, you know, do you ever talk to investors about the thing, the, the risk that. Oh, yeah. Oh, how would you describe it? Look, I, I mean, hopefully you've gotten a taste of this, but I try to be a very balanced assessment of anything I think or one case and investor relations wishes. More optimistic, but I think long term, I think long term, kind of abilities built by giving people a balanced perspective and recognizing it I think as a leader, you want people to come in and point out to you what's not going well. And I want to hear the happy talk about what's already going well I probably know that already. So what are the warning sites with DocuSign? Well, I think in my first two years, the big ones were, well, what about the health of the core? I look, I hear you about the innovation agenda, but you've got more competition , you've got decelerating revenue growth. Why should we believe that that is that those trends aren't just going to continue and that you have a business as well as we're going to shrink. And I think the good news is that, you know, that's the kind of thing you can talk about, but at the end of the day, you just got to prove it through actions . And we have shown that our net retention rate or our churn rate has now stabilized and we're now starting to pick up a little bit. And, you know, that's a very positive story, because that takes away the sort of the downside scenario that people are worried about. I think the next one is, okay, okay, so I hear you on all this opportunity, but are the customers going to eat this dog food and, you know, how likely are they to adopt this and are they going to want to let you run their AI on their agreements and so on. And again, I don't, I think you can articulate reasons why they should believe, but at the end of the day, there's nothing that speaks like the dogs actually eating the dog food. My biggest, the biggest development area of a DocuSign now is to become a real enterprise company. If we sell to enterprises day, over 85% of the Fortune 500 use Docs on today and it's the same in other big markets around the world. But, you know, we're a little bit more of a departmental level by, it's not like we're a CIO level priority or a visibility in that way. But this broader story that we're now articulating, that's very much an enterprise wide C-suite story. And there's a lot of maturing that we have to do as a company to be able to fully service that. And so I'd say to me, that's my biggest risk going forward is how well can we execute on that. And, you know, early signs are really good, but I, I, I'm in years of building to do that. I could tell you're a salesman. It's like, you know, one of the biggest risks we have is being able to execute up against the huge opportunity that we have. There you go. Your version of silver salad. There we go. I love it. You know, you do identify the issues. It's obvious. And you don't shy away from them. And you tell it the way how it is. You know, when you think of yourself as a leader, Alan, you know, how are you, what are you pushing yourself to do? I mean, what do you, how are you sharpening your axe? And, and what process do you use to, to get it, what you need to get better at? Well, you know, that's a, a, it's a tough question. Like everyone would like to be more introspective. I like to think of myself as a lifelong learner. And I do think I push myself on that. It tends to be on the easy stuff. Like, you know, I'm good at assimilating your content. So I'm not, but like, how do I hover less, get, get less involved in the details? I think if you were to ask my team, you know, I, I go pretty deep. If I don't have something better to do. And, and I think, look, there's a balance there. You want to use your time effectively. Now, I don't think just flying super high at 50,000 feet is an effective leadership style. I think you have to have the ability to dive down deep to, to really address the problem and recourse when that's necessary. But learning to pull back and, and, and not, not stay there or not rely on or over, overuse that mode is, that's not, not still working on. I think we all do. It is the art of management. It is the toughest thing of all , you know, but I think it's great. You know, I'll tell you Alan, this has been so much fun. And I want to have some more with my lightning round of questions. Are you ready for this? Okay. All right. What three words best describe you? Optimistic, energetic, easy laugh. If you could be one person for a day beside yourself, who would it be? I think one of my idols, Todd B. Winston Churchill. Your biggest pet peeve. Obfuscation. Who would play you in a movie? Well, I, you know, if you get it, be aspirational. I, you know, wouldn't we all like to be, um, Ryan Reynolds? What's something most people don't know about Denmark? Well, I think more people know it now, but Greenland is, is Danish territory. What's a traditional Danish food that everyone should try? The Danish pork roast is unbelievable. I mean, Danes do an amazing job at pork. And the Danish pork roast, they literally leave the, the crackling on top and, and they cook it in the oven and it gets all crinkly and, and, and, it's amazing. I love it. What's the one thing you do just for you? Look, I, I, I swim, but that's more to stay healthy than for enjoyment. Um, probably my favorite leisure activities, play golf. I don't get to do it very often, but I love it. So that bad, bad, but enthusiastic golf. I look forward to playing golf with you. Okay. What's your most prized possession? I don't know that I, that there are material possessions that I care much about right now. Um, probably the most important thing to me would be my grandson. If I turned on the radio in the car, what would I hear? Uh, you might hear, um, some, uh, 70 and 70s and 80s rhythm and blues soul. Like I'm a huge Stevie Wonder fan. All right. What's something about you? Few people would know. I sound very American, but I actually grew up in Denmark. But the part that's interesting is I originally learned to speak British English. So we lived in Malaysia for a year when I was seven. So that's where I first looked to speak English. But my experience with the American accent is that, it's like a virus. I came here when I was 12 for three and a half weeks, stayed with some friends of my parents. And when I left that American accent and it's never left me. You definitely have an American accent, which is basically not understrip or random strip. Okay. What's one of your daily rituals, something that you never miss? You mean besides checking emails, stuff? Um, let's see. Um, I'm a big news consumer. I am compulsively checking, um, the news, whether I'm on vacation or working with a friend. Or working, I try to be engaged in the world. That's fantastic. Now we're out of the lightning round. Ryan Reynolds, you did a hell of a good job there. I've got to hear about that from my family. They're going to be like, you are such a different. Yeah. You know, now you and your wife, speaking to your family, I believe you have four kids, right? You have four kids and, uh, what's the best practice you'd share about leading at home? Well, first of all, I'm not sure I am leaving at home, but, but to the extent that I do, I am the family, uh, sort of organizer and the initiative taker and, you know, those kinds of things, vacations and so on. Um, I try to, I do try to lean in hard to create memorable moments. Fantastic. And, and, and, Alan, I mean, you're, you're, you're big time in the docu-sign. Now you have so many things that you're working on. So then I'll ask you this anyway. When you look at your life, what do you see as your, your, your most significant unfinished business? I mean, look, I've taken on a big project here. I'm very happy with the progress, but I, it's definitely not a finished project . So, um, I look, my kids are grown now. Um, you know, you never see as being a parent, but, um, my ability to influence their trajectory is greatly reduced. Probably no longer desired. So, um, I would have said that earlier in my life. Um, look, I, I think, uh, probably figuring out how my wife and I are going to spend the next 20, 25 years, hopefully good quality years in a meaningful way. That's probably the most important. Fantastic. And last question here. What's one piece of advice you'd give to anyone who wants to be a better leader ? I think, um, people who, uh, sit in the ivory tower and don't get out and people don't see you putting yourself out there, um, in ways where you're taking risk and, and, um, experiencing those ups and downs, you can't expect them to do it for you. Um, so I, I, I really try to, uh, um, be available and present and, and engaged , um, and risk taking so as to give permission. I covered to others. You know, I've done well over 200 podcasts. I've heard a lot of answers, but that's the first time I've ever heard that one . And I, you know, I've heard maybe articulated in different ways, like stay in touch with the front line. But being a leader that, that basically projects and emulates what you want to have with everybody else taking the risk and, and being visible in how you do it. You know, how do you stay visible? What do you do to, what do you do to lead from the front? It gets hard. That's the team gets larger, right? More dispersed. Um, I don't think there's, you know, one thing. So we're doing this over video, right? Virtual. And, um, there's a lot you can do that way, but I don't think there's any substitute for engaging in person. And so I've put a lot of time and energy into traveling, seeing the teams. I've been five continents this year, or this last year here. Several of them many times. Um, and, um, and I do that, um, not just because I want to be out meeting with customers and partners, but because I feel it's important to engage with the teams. In person that they see you and feel you. Um, so that would be my. That's fantastic. And, you know, I, I've always believed that, you know, people always say, "Who do you invest in?" And, you know, I've always believed that you invest in people. You invest in the people that you, you think are that you can build a business and grow it. And this is my first time I've ever had a chance to talk to you. And I, I have to tell you, you know, I mean, I would, I would invest in a leader like you. And, and I, I thank you very much for taking the time to, to be on this podcast . It was a lot of fun. There was a lot of fun. And, and David, I think you have an amazing format and just engaging. And the fact that you're a former CEO yourself, and I can just, uh, tell, um, just that it just informs your perspective and super fun, a great conversation. Now, like I said, you may not think of yourself as a salesperson, but you better put your sales cap on. Because let me tell you something. Everybody needs to learn how to sell, especially leaders. If you want to build internal consensus or create a partnership or secure funding, then you need those persuasive skills. And like Alan points out, that doesn't have to mean being inauthentic. In fact, it's the opposite. Nobody's going to buy anything from a phony. Sales follows trust, which is why the most effective salespeople are the ones who are honest and upfront and absolutely genuine and stay true to who they are . If you want to level up your sales skills, here's an idea. Grab coffee or lunch with someone you trust who sells for a living. Ask them to share their advice with you. Or better yet, watch them in action and see what you can learn. And I got another idea for you. You got to read Dale Carnegie's book, How to Win Friends and Influence People. It's one of the best selling books of all time because believe me, Dale Carnegie knows how to sell. So do you want to know how leaders lead? What we learned today is that great leaders know that everyone's a salesperson. Coming up next on How to Lead us Lead is Ken Bacon, co-founder and managing partner at Railfield Partners, a multifamily investment and asset management firm. I always say that trading relationships are then their real partner relationships. A trading relationship is just very transactional. You really don't know that the person's just a trading. But a real relationship, a partnership is that we know each other. Yeah, we've got contracts. We have agreements. But we trust each other. So be sure to come back again next week to hear our entire conversation. Thanks again for tuning in to another episode of How leaders lead where every Thursday you get to listen in while I interview some of the very best leaders in the world. I make it a point to give you something simple on each episode that you can apply to your business so that you will become the best leader that you can be. [MUSIC]