David Sobeski

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Chris Williams: To say that David Sobeski has led an interesting life is a vast understatement. From small town Pennsylvania, he rose through a remarkable selection of world-famous companies, and now alternates his life between Seattle and Prague. His eclectic career has taken him from Microsoft and Yahoo to Disney and Nordstrom. Today, he’s leading Salesforce’s efforts to make managing a nonprofit less harrowing. His journey alone makes a chat with him fascinating. 

But perhaps David’s most interesting quality is what Bill Gates once called his ability to see at both the 100,000-foot view and the one-foot view at the same time. Following David on social media is to be greeted several times a day with astute observations about the future of the tech world, the business world, and life. His ability to distill complexity into a clear view of the horizon is often surprising, even jarring. Perhaps that’s why even Steve Jobs listened to him.

We talked from his home in Prague about his journey, the culture of the various companies, and working really remotely. And that’s what this is all about.


This is Leading Smart, the show about managing in the brainpower age. It’s a field guide to the joys and challenges of leading and working in the modern workplace. I’m Chris Williams, your guide to the stories and ideas that I hope will inspire you to be a better leader in the world of knowledge work.

This episode’s conversation is with a leader who has seen an array of organizations and not only live to tell the tale, but thrive. This is Episode 234. my conversation with David Sobeski.


CW: David Sobeski grew up in small town Pennsylvania to parents who encouraged, if not understood, his passion for technology. They indulged him by buying the machines he coveted.

David Sobeski: I grew up in small town, Pennsylvania. West Pittston, Pennsylvania. So it’s between Philadelphia and New York to a middle class family. My dad and my mom were kind of givers and they tried to make sure that you had things. So when the very first version of Pong came out. Can I get a Pong?! Yeah, right. And like hook it up to the TV and my dad’s looking at it. And my mom’s like, why would anyone be interested in this, and I’m looking at the two little paddles. And that’s cool. That’s cool.

And then the TI94A came out. And then the, you know, the Apple one and the Apple II, the IIE, the Mac, IBM PC, PC, Jr… I don’t know how I convinced my dad to buy me all of these things. But he did. And I was fascinated by what the machine can do it. And that kind of drove some passion in me. And it wasn’t that I was the person who was like, Oh, I got a machine. Let me rip it apart and figure out how it works. That wasn’t me. That was kind of more my brother. But for me it was okay. What can I do with this?

CW: In high school, David was fortunate to find a computer class and the teacher suggested he enter a computer programming competition. He struggled to find a project to work on.

DS: And my brother used to play a game called Stratamatic baseball. And I don’t know if you remember Stratamatic or not, but Stratamatic was cards right? And you roll dice and you’d play a baseball game and and you would look up look it up. So I wrote a UCSD Pascal version of Stratamatic.

And I wrote this thing and I did it in, I think, three and a half months. And we went to the local computer saw the computer competition. And I was I was like, oh, and Mr. Coleman goes, Hey, that’s not bad. And he had no idea what I had, because everybody else was just kind of like, you know, writing for loops, the counting numbers and doing like, oh, type of math problem into something. And I won.

And he’s like, why don’t we do the state competition? Okay, I remember optimizing a thing or, or something in my head, went into the state competition, and I won. And so high school, 10th grade or 11th grade. That’s where I actually learned to program.

CW: David followed this passion and got a bachelor’s degree in computer science and got within three credits of a master’s degree. He joined the hometown company, IBM, but it was clear quite quickly that the wear-a-tie every day work environment wasn’t working for him. He got a call from a Microsoft recruiter who had seen a paper he had written. And he soon was working on Visual Basic in Redmond.

There he in a couple of colleagues invented a feature called IntelliSense. It was a programmers version of the autocomplete you have on your phone. But 20 years earlier.

DS: I did not know the Visual Basic programming language. I didn’t want to learn the visual basic programming language. So two engineers Matt Schulman and Martin Sibolcom, the three of us got together. And I said, their has to be a better way. Like we have the symbol table in memory. So we know what comes after the object we have. So why don’t we just prompt the user for what it is? Like, why is it so complicated? So they looked at me and they’re like, okay, let’s write that up as a prototype.

And we prototyped it. It’s the classic Microsoft, let’s prototype it in a weekend. We, I think we took two days, we did it on a we did started on a Thursday, Saturday morning, we had the prototype up and running. And that was that moment, I realized that at the end of the day, what I really care about is being a user, I just use stuff. And I know it drives me crazy when I use stuff. And there was this weird aha moment that that that happened there.

Then I remember we went into a BillG review. And people like drew Fletcher, and Craig Simmons and Scott Wiltimuth, were showing bill kind of, you know, the stuff coming in VB kind of some of the future stuff. And I don’t know really why I was in the meeting.

But I ended up at the end of the meeting, you know, showing Bill some of the work we did on on statement completion. And that turned into a hallway conversation. And he looks at me, and he says, you know, in that Bill, looking down at you, so not really looking at you, but looking down and talking to you. And he said, “you get the 100,000-foot view in the one-foot view at the same time. That’s unique. I like this”, and then you walked away.

But that was kind of that moment where team members kind of recognize that I recognize that. And it was that moment where I said, Okay, I kind of have this weird uncanny ability to think about what people are going to want, or what they should want to do. Now I was doing it within a developer context.

But that taught me something that people don’t always do. First off, be a user, just use things. And you’ll figure out if you like it or not, and you’ll figure out what what doesn’t work for you. Be a listener. And that’s kind of the new thing like every management book, today’s that’s all you got to be a listener. But what they don’t tell you is that’s only half of the problem. Because you have to be both a listener and an observer. If you’re not observing. At the same time someone is talking and someone is showing or doing whatever, you’re going to miss a lot. And that was something I loved to do. I love to this is kind of weird, strangeness of me, but even today, like I love to go to a Starbucks. And even if I’m on my iPad, I’m listening to all the conversations I am observing everything around me. And by doing that and putting yourself in situations, you will you will figure out kind of what works and doesn’t work and what people are frustrated with.

And that got me from this caring about how it works. The details of you know, bit shift this by, by, by X or Y To, to really caring about? Why are we doing it? You know, what is it we’re doing so the kind of the other side, but not losing sight of the implementation. So one of the things that I do even today, no matter what job I have, I still write code. Like a lot of people I know who’ve been doing this for this long, and who are now SVPs or VPs. They don’t write code anymore. I still do. And I love and it keeps you grounded. And it keeps you to understand how things work. So when you are having conversations, and tried to figure out things, you kind of know how things work today, and you know, where things are, just drive you crazy.

So that’s me so, so it was VB that kind of that taught me that. And then I was lucky enough to maneuver the the Microsoft political system and all of that to get to know some pretty interesting people that let me be me. You know, Ben Slivka on the Internet Explorer team, Brad Silverberg, Jim Alchin, Bill Gates, David Vaskevitch, all of these people, you know, saw something in me that that was, oh, wait a minute, this person kind of sees where things are going. And that’s valuable, and can articulate it.

One of the compliments I got once, and I never really thought about it until much later on in my career. You know, someone called me strange, they said, you know, you’re this weird person who can write code and actually stand up in front of 1,000 people and give a talk. Right? Like you, you can tell the story, and I was like, oh, storytelling, that is an interesting concept. And then, of course, I learned kind of some of the fine art of storytelling much later on in my career.

But But yeah, it was early it was it was kind of during my first year and a half at Microsoft, where I realized that, you know, you could sit there and just do as you’re told and write something, or you can have some kind of vision, some kind of strategy, you can see where things are going. And you can influence others, right? You can, you can, you can help change your products or better. And that was the little nugget that got me going.

CW: This ability to see both the details. And the result is not easy for most people. David seems to see it intuitively.

DS: Let me give you an example. So one of your guests talked about Tesla, and how easy the Tesla vision is, or something like that. But when you really think about it, it’s not using the Tesla that gets you a Tesla. It’s using the petrol car, it’s using a bike, it’s using a Segway. It’s getting into a plane. I mean, we’ve been in planes now for well over a decade where they are landing themselves, and we don’t know it. It’s understanding that and looking at all of these things. And once you look at all of these things, you ask yourself, okay, what, what, what doesn’t work? Like, what why is it annoying?

Or like, why do I like, one of my biggest frustrations of my iPhone, and the car that I drive, is that every time I get in that car, the music just starts playing. And a lot of us will say no, no, no, the simple case is… or the or the 90% case is you just want to start playing where you left off in your music when you got in the car. And the question is, well, not always. And if it really annoys you, how do you go fix that? Or how do you think about that?

So, you know, people, especially in the tech industry, which is kind of sometimes weird to me, they’re okay with the bugs, they’re okay with the thing not working. And they don’t necessarily always think about how to fix it, because it’s not their primary job. Like, your primary job isn’t using Zoom, but you know, 90 things that you don’t like about Zoom today, you know, 90 things that you know, prior to Zoom, you use Skype. And you know what, what noise you have so much from Skype that you’ve switched from Skype to Zoom. Right? Like, okay, so you did it, subconsciously You did it. But you don’t necessarily do that in your everyday life and in your everyday way of building products or engineering teams or whatever.

So, yeah, I don’t think a lot of people have it, and you kind of have to force it because I don’t think a lot of people are storytellers, I don’t think a lot of people… A lot of people want to say they’re their customer first or they they they put the customer first. But they don’t necessarily really do that. They put other factors first, what makes it appear that the customer is coming first.

And that’s why I say be a user, be a listener, be an observer. If you can don’t do those three things. You will start to understand if it frustrates you, it’s frustrating somebody else. So I think we we blindly take things for granted over time to say, Oh, that’s just just how it works. And we, we let the bugs and the flaws, just we work around them rather than the software being fixed or the the thing being fixed to do. What’s probably the right thing to do.

I want all of my engineers who work for me if I’m, if I’m running an engineering team, I want my engineers to be, you know, have empathy to customers, I want them to talk to customers, I want them to think about it. I’ll have meetings where I’ll say, Have you used this or that, and people sometimes look at me, like, what?

You know, a good example, is at Disney, you know, you you go to a park, and you stand in a long line, and you just assume that that is what you should do. And so I would have a meeting when we were talking about parks, I believe, what you do at the park, and I would get, oh, we rode this ride this ride, and this ride… Like, no, no, no, that’s not what you did. What did you do? Talk to me about, you know, that very first experience to buy your ticket, how did you buy it? Oh, I walked up to a ticket window, I stood in line, I gave them my credit card, I had to make a decision if I wanted Park Hopper or this or that, like, yeah, how do you make that simple? Why did you stand in the line? Why did you have to go make a decision about you know, do I want to, of course, you want to hop parks, maybe the right, that’s the default. And then in the smaller print is Oh, you can buy a single entry, one-park only like, talk about how you see it. And that, you know, is always this light going on for people, especially engineers who code all the time and kind of, you know, get their specs from from PMs or somebody else.


CW: David’s first leadership experience came at Microsoft,

DS: My very first experience was leading a very small team of five people. And that’s interesting, because it’s almost like you’re not leading anybody, because you’re all peers, and someone just kind of has to make decisions. And the decisions –while you’re stressed out and think they’re hard or whatever — they’re not that hard, right? But but it’s pretty simple. And you still are, if you’re an engineer, you’re still probably writing code. If you’re a programmer, Product Manager, you’re probably still writing a spec. So that’s kind of a funny one. When you get that first level of bump.

It’s the next one, where you need to learn to let go. And that is, I’ve never, I haven’t seen anybody, you know, successfully do that in their first three to six months. There’s that magic 90 to 120 days of getting that next level job where you need to let go. And of course, what does everybody think, Oh, I’m being micromanaged. It’s like, No, no, no, I just haven’t learned how to let go yet. Right? I mean, learning to figure out who do you trust learning to figure out, it’s okay. But deep diving in things that are important, so they don’t, they don’t fall off the rail. So it’s a fine art that you end up having to learn.

So there’s people management, there’s Process Management, there’s influence, there’s trust. And that was, that was a unique one for me, because I would say, I think I was probably terrible at it, at first, like really terrible. Yet, people wanted to work for me because they’re like, well, he’s really technical. He knows what he knows what he’s talking about. So we’ll ignore some of these things. So a little bit of that bad habit gets to continue for a while until you realize Wait a minute, this isn’t this isn’t the right the way it should work. So yeah, but Microsoft, I lead various teams anything from like four people to maybe 100 people at one point 100 and some managing all different kinds of pieces.

CW: But you bounced between doing sort of leadership jobs to being sort of technology strategist, right, you were a strategist for for Vaskevitch and you did some sort of strategy work for Alchin and that kind of stuff. Right? So So did you like one more than the other? Was one more… felt better to you? Or was it just where you could have the most influence or…

DS: At Microsoft, you know, the higher the title you had, the more influence you had? You know, it’s a little bit different today, under Satya but but you know, walking up that ladder was definitely a very important thing you had to do.

Lucky for me, you know people again, as I said trusted kind of my my vision of where things were going in the next three or four years or two years. And every job I had, where you look where you think I’m a strategist, I’ve also had a team like I like, under Alchin, I had a team that, you know, created sidebar was really doing the, the the apps on the, the inbox apps. Under Vaskevitch, we had something called Digital memory project that we that we built and ran. So I still ran organizations.

People tend to like my vision for things. So they put me kind of in these vision and strategy roles, and trying to influence others to get things done. I want to simply say, I’m, that’s always my favorite, but I am, I am pretty good at it. And it is something that comes easy to me and exciting to me to go talk about. And it’s about having a great team, either that reports directly to you, or to the side of you, that executes on those things. But I like being accountable and responsible for that in thing, what do we what are we delivering? So at no point do I ever want to just be or I ever thought of, Oh, I’m just kind of Jim’s, you know, strategy person? Like No, no, I, I want to be accountable. Just like Brian Valentine is accountable for shipping Vista. I want to be in that room accountable for how does the How does user experience work? or What did we actually get done here? Like, I want that accountability. So I can’t just ever be one of these pure strategy vision people, I still have to have roll up my sleeves, get into it, have those arguments of why are we building this? What are we doing? How are we going to get there? Who’s going to do it?

What I don’t like is I’m a terrible Scrum person, terrible, like having a daily stand up where you ask people like what did you do today? off? Right? Like, I’m glad people do it. I don’t. And I hire people to do it. But for me, it’s about, you know, here’s the product we’re building. This is when we said we’re going to deliver how we’re going to deliver it. This is what we believe is the right set of features. So what what is that thing we’re building? And I focus on that and I focus on user experience, I focus on interaction models I focus on, you know, in the cloud, should we be using rest API’s or Graph QL? So I’ll dive deeper I need to.

So do I like one over the other? I would say I like running organizations to go build products, I just happen to be good at the part of saying, what should the product do? And how should it How should it look and work for what we’re what we’re trying to accomplish. And I’m good at that. So in my day job, when I when I like look at my week, besides recruiting and a bunch of the management stuff that you have to do around P&Ls and stuff like that. You know, I spend a good chunk of my time in product reviews, you know, reviewing what does it look like? How does it work? why we’re doing what we’re doing? Who was the decision maker and not not micromanaging people? Right? They’re there every once in a while there’s something you have to dive really deep on because it’s driving you crazy that it’s not working. But you know, making sure you have that right team for all marching towards what we believe is the right product to build.

CW: So you made … a couple of interesting career choices. And I am trying not to say that with the snark that it just came out with like, for example, you chose to go to Yahoo at a really interesting time. I’m interested, like, what was it about Yahoo that was interesting and fascinating for you. I mean, you were there. Sort of, I mean, it was it was not going swimmingly when you went to Yahoo, right?

DS: Correct. Correct. When I got to Yahoo. Terry Semel was the CEO. And I think within a month after I got there, Microsoft made a made a bid to acquire Yahoo.

But I went to Yahoo for a very weird reason. So, Vista was finished. You know, Jim was leaving Bill was gone. I think Valentine went to Amazon and people were just leaving. It was one of those times where it’s like, Okay, what am I doing? And it was one of those times to reassess. And Yahoo gave me one of those jobs, which was: we’re gonna bring you on as a group Vice President of Engineering or something like that. We don’t know what your job is, figure it out. That was very compelling to me. And when I interviewed there, there was some just really, there were diamonds in the rough who were all over the place.

And I thought, okay, I can make a difference here. Yahoo is a very peanut butter company, as the famous memo said, and they’re doing a million different things. And Terry, and a couple others, Ash and David Filo. And Jerry Yang gave me the ability to just come in, look at it, pick a slice that I thought was super interesting. and run with it. So that’s, that is why I went to Yahoo.

CW: Was there something also about getting to the Valley?

DS: Yeah, so look, Microsoft is this amazing thing. It’s this amazing living being where you can spend a 25 or 30 year career at Microsoft. And the reason you can do it is because it’s Silicon Valley, all in Redmond. I can go work on databases, I can go work on AR, I can go work on entertainment, I can go work on on cloud, I can work on IoT, you can do anything. Any company that exists in Silicon Valley, there’s some group somewhere at Microsoft in 40-some buildings running around doing.

And I thought to myself, it’s like, wait a minute. I know, a lot of people in the valley, I know, it’s a different vibe. I just kind of want to do something different. So when I had that opportunity, yeah, I took it.

Look, it was part about different cultures. And, you know, I think once again, as I talked to you about observing and listening, you know, Microsoft created… I love Microsoft people. I mean, even when I dis it on Facebook or Twitter, I’m actually doing it because I love it. Like you just want it to work and be fixed. It’s a bunch of really great people. But if you grew up under the Bill and Steve management system, I would say if you took that to your next company, you were not liked very much. It was a mean way to manage.

And, you know, when I got to Yahoo, I first two weeks, man, was I a jerk. Like I was like, everybody was like a BillG review, right? People like, what is this? We’re, we’re passive aggressive people. Why are you being aggressive? So? Yeah. So you had to take a stop being like, Oh, I actually need to go unlearn a bunch of things. And it actually made me a better listener, a better manager a better, you know, hopefully a better person but but it made you understand that companies are just different. And they all have their strengths and weaknesses. And you need to understand the system you’re in if you want to be successful in the system you’re in. You may not like it and if you don’t like it, maybe you need to ask it did Why did you take the job to begin with, but but there are different systems in play and you need to try to understand them, and you need to try to be able to adapt to it, maybe change or educate the new system, you’re in to some of the benefits that you got out of the older system.

CW: Being in Silicon Valley also garnered some invaluable friendships. He managed to strike up a relationship with Steve Jobs, and they regularly spent time together, walking and talking over coffee, as David puts it. he befriended Marc Benioff, the founder of Salesforce, who would come back later to recruit David to run part of the company. After Yahoo. David ended up at Disney, but not directly. He followed an early passion for games to join a startup.

DS: I ended up going to a startup called Playdom. Playdom is a social gaming startup that competed with Zynga. We made highly scalable games. We sold that startup to Disney. So I didn’t necessarily make the choice to go to Disney.

However, the very first in my interview, NEA was one of our founders. It was one of the the funding, founding funding companies of platinum. And our CEO, I said on the My very first day, I said, we’re gonna get acquired by Disney. It’s like, we’re just in this entertainment content business with data. That’s what Disney does. And we got acquired, we got acquired by Disney.

So it worked out. I probably would have went to Disney anyway, right? I have to, I probably would have went shortly after to Disney, because it’s a fascinating company to me. But I got in through our acquisition, and then I became the one of the chief technology officers at the company.

Disney is a is a very different beast like it is. It is not a technology company. It is a, it’s lawyers who make decisions on how Mickey can be presented, its marketing, who makes decisions, you know, technology kind of comes a little lower in the stack. So while you’re very much appreciated, and everybody at Disney wants to be a technology company, it’s not one, and it thinks differently because of that. And it works differently. Because of that, it pays differently because of that. So here you are trying to hire some great engineers out of Google or Microsoft and you want to pay stock to them. Well, guess what? Anything above or below a certain level level doesn’t get any equity in the company, you just kind of have your normal salary and try to hire a Silicon Valley person on just normal salary, it doesn’t, it doesn’t work. So it was definitely one of the more fun times most fun times that I’ve had in my career. It was also pretty frustrating at times, which, which is also oddly fun, maybe sadistically fun, and how frustrating it can be. And I thought Microsoft would always be the pinnacle of where I had the most fun.

But but but Disney was pretty interesting. As you said, it’s it’s, it is a creative company. You know, it’s about the movies, the television shows the park experience, it looks at it that way. And how do you build brands? How do you sometimes milk the brand a little too much, because it will generate free money pretty…

But it managed very differently. It was it definitely was strange at first, for example, I come to Disney and I have a I had an assistant Her name was Ellen is Ellen. And I wanted to like do my own calendar. And she looked at me with a look like no executive at Disney does their own calendar. Like what? Like I can use Outlook? Like it’s not hard, right? No, no. Like, you’re not allowed to do that. Oh, and I have access to all of your email and all of everything, so I can see everything. Oh, okay, can I not do that?

Then I had my office and I didn’t like how the furniture was arranged. And if you’re at Microsoft, what do you do when you have your office, you move stuff because we weren’t, you know, open space, you just move your desk. So I repositioned my office to the way I thought it should be. And the next morning this, this man is standing at my office door before I get to work. And he asked me if I moved my furniture. And I said yes, I did. And he told me that I was taking away the wages from a union worker. I’m like, what they’re like, yes. Like, we have people to move a desk. Don’t do that. It’s like, okay, sorry. Okay, so like, you learn some, you just learned some new unique things that like that. That’s what that business is.

CW: A whole bunch of that comes from the fact that it’s a very old company. Yes, it’s all it’s less than 100 years old. But but in in its world, it’s an incredibly old company. And so it’s grown up around it means it’s it’s a) it’s very mature and b) all the things around lawyers and, and processes and those kinds of things are sort of what happens as companies get older, right?

DS: Well, don’t forget it. Disney is a movie company. So it’s lawyers and creatives dealing with agents and dealing with people who build sets. Right? And and so if you really look at Disney, the funny thing is most of the employees are hourly. Right? Like how many real movie people actually work for Disney? Not that many. Because when they do a movie, they say, okay, you’re going to be in Burbank, you’re gonna be in this lot. We’re gonna build sets, they hire all those people, they build the sets and then those people are gone. Actors come in, they act it for three months, and then they’re gone. Right? So there’s actually not a lot of people who work on a movie. So it’s a lot of lawyers and marketing people etc.

CW: It is an interesting company though because it has had for 50 years or 100 years or not quite but a had this ability to execute from, from a vision to an actual thing awfully well, I mean it you know, there were there were thoughts in Walt’s head that made it into celluloid. There were concepts about a ride at Disneyland that executed really, really well, that had to be kind for. That’s what I meant what I said, I sort of knew why you would be attracted to it. Because that seems to me to be right up your alley.

DS: There’s some interesting examples in the world that that, you know, if Steve had the vision, the vision for the iPod, right, you know, yeah, 1000 songs in your pocket. That wasn’t the vision. If that’s all that it stopped. Apple would kind of be dead, right? Steve cared about how the click will work. He cared about how the LED line scrolled up and down.

If Tesla’s vision was, were an electric car, it would go nowhere, it would go like it like it took Elon to actually care about, you know, how the wind noise went across the windows and that some people will say, Oh, no, that’s implementation. No, that’s part of your vision. That is part of instilling that in all the people that work around you.

And that’s what Disney does really, really well. So if you want to go build a movie, and you want to go do The Incredibles, you know, Lasseter was see that you have passion, you have the vision for The Incredibles. That’s your movie, and you care about all of it, all the time. And yes, you have people working for you, who will do the minutiae of the details, and make sure it gets over the finish line. But it’s your vision every single day, tweaking it. And that’s what Disney does really, really well. And I love that.

And we got to go do that across games, we got to do that across movies, got to do that across parks. And it was truly fascinating. Painful at times. But that is, you know, the one thing about Disney is if you are empowered to do one of those things to go have the vision to go do something the company backs you, they might backstab you later on or talk poorly of you later on for something, but not not in public. And they will ensure that you have the backing of everybody. And they will let they will let you let you go. And it’s very empowering. And and they let you be very creative to go do that. And that was fun. That was terribly fun.


CW: After Disney, David moved to another customer focused company, Nordstrom.

DS: So Nordstrom has this interesting problem. They have lots of stores. And they’re really, really good at brick and mortar. They’re really, really good at that store. But each store is an island. So the Seattle downtown store the way they merchandise and think of that it’s not just selling the same exact way they think of the Bellevue store or the store in San Francisco. So they’re kind of unique and these little islands.

Part of the problem is, is the model, right? But you asked that question is the model right in a different context. So they have this big competitor. It’s called Amazon. Now, the lucky part that Nordstrom has is that the high end designers don’t really want to put their goods on Amazon. They just don’t. Prada doesn’t want to go to Amazon, but they’ll go to Nordstrom. So while they’re competitors, and they see this big thing, they’re not really competitors. But Amazon has a great online business. Nordstrom has a great in mall business. Well, what if Nordstrom started online first and then bought stores? What if you flipped the model? What would that look like? And that was the challenge that I was given was okay. If you’re going to innovate, and you’re going to think of, of the stores as an asset to your online business, what would you do? How would you do things?

Nordstrom gave me this weird opportunity to actually be super customer focused, like the product was the store. People don’t necessarily ask the question, why do you go to a Nordstrom? Like, why do you go Why do you go to a store? Like why would you choose to go versus, you know, going to nordstrom.com or amazon.com? Well, as things evolve and change, why do you go? I need something today. Well, that that creates a very interesting problem. So stores have a problem of inventory. When you’re looking at Nordstrom store, if you take shoes out of the way, there’s no back room. So everything they have is on the floor. That is the inventory.

So you now have this problem of breadth versus depth. Do I know that David comes in and people like him come in and buy medium black t shirts? Well, if that’s true, I probably want 100 medium blacks. But if I don’t know that, well, then I’m going to carry extra small, medium, large, I might only carry two. But you’re not going to carry some big difference, because then you have an inventory problem, because clothing — which I learned — is like food, the second you put it out, it’s aging. And then you only have 60 days to sell that. And if you don’t sell that, then it gets discounted. And every time you’re discounting it, you’re losing more and more on margin. So you have these kind of fun computer science problems. And you have these fun customer problems. So when they were looking for, for creating this kind of innovation team to think differently to think design lead to take think product lead, it was like yeah, where do I sign? This is This will be fun.

CW: Yeah, right. Um, you are you. And it’s the first thing you said to me when we talked the other day, the first thing you said to me was I’m an observer. And and a lot of what you’re doing with I mean, a lot of everything that you’ve talked about in in, in the stuff that you’ve written and everything is really related to that. It’s it’s about your looking at stuff and and seeing things differently. Do you think that is? Is that something that was innate in you? Do you think that’s something that developed over time because of experiences you’ve had? And more to the point? Can that be taught?

DS: Good question. Very good question.

For me, I’ve always been I’ve been rather lucky, I guess I never thought it was a skill or I had something unique to be able to do that. But it’s something I’ve always done from from a kid through all of my, my journey is look at everything through first user eyes, first user mentality, be a kid be a child. And it’s it’s it’s, you know, I I’m always questioning and I don’t know if it’s because maybe I’m not trusting. And I said I can I say trust, but like I’m always questioning something. And I’m always trying to figure out, you know why that is or where something’s going. And I just kind of have this innate way of doing it. So, I’ve been, I’ve been lucky that that I’ve, I think that I’ve always been that way through through most of my life.

The interesting question you asked to me is Can it be taught? And I think the answer is yes, with a caveat. So I do believe we can teach people how to have better observation skills, better listening skills, better user skills. It’s almost like being a profiler in some way, like how do you how do you look at things? And how do you profile it. People don’t come out of university and magically become a profile and go work for the FBI or anything like that? I like it is definitely a taught behavior. So I think we can teach product people, engineers, all types to be users again, and to understand it, so I do believe we can get there.

The caveat is knowing… connecting the dots about where some technology might be going, isn’t necessarily easy. And it might just be gut instinct. It might be intuition. It might be experience. It’s unknown to me. And, and the reason it’s unknown is because I read a lot I’m naturally curious. So, you know, today before before this conversation, I listened to several of your podcasts, your early ones to see how you started and how you changed as you went from, you know, your beginning to now I looked at I listened to some some other famous kind of podcasters on what they do.

And then that after doing that, that took me into reading a little bit about the differences in in in cryptocurrency today. So I was playing with cryptocurrency, then that led me to looking at camera sensors to understand, I saw as I was reading the web, and maybe it’s my great ADD, but I was reading something on the web. And then I saw this, this this article where somebody was, you know, taking a photo, and then they wanted to manipulate the raw data on how camera sensor works.

So I have this natural curiosity, and I have this natural thing where I read a lot, I learn a lot. And and that I think helps me try to understand where things are going. So do I believe we can create people and people can learn, we can create education classes on how to be better observers and listeners, and help you to go build better products? I do. I think we can do that. Can I can I teach that? Yes, we’re going to use an ARM chip in the iPhone in 10 years and 10 years from now that same chip is going to power a Mac and going to power, you know, something else that I don’t think I can teach. I think that’s just kind of innate in some people to have that longer term strategy to see where things are going. So So, yes, with Yes, with a caveat.


CW: David now leads salesforce.org, the part of the company that focuses on the nonprofit world. And he leads one of the most remote work lives of anyone I know. He lives alternately in Seattle and Prague, where his wife is from. Yet Salesforce is headquartered in San Francisco. He’s managed to make that work for several years.

When we scheduled our chat, he was in Prague and I was concerned about the time difference. He told me not to worry, as he lives primarily on US West Coast time. When we spoke, it was the dead of night, at least on his clock. I asked David, if he thought this remote work thing was going to stick for the rest of the world.

DS: I do believe if COVID lasted three months, we’d be having a very different conversation. But the fact that it lasted a year the fact that people have changed behavior. I think that behavior change is, is going to cause changes. But we also need to look at the other side of that behavior, which is people being frustrated by staying at home by by not being able to go to an office.

I, I was just telling someone the other day, I said Look, I said, I am so happy for Microsoft. And they’re like why I’m like, because at the beginning of my career, I got to go to an office, I got to socialize, I got to be part of that group. And it felt good. And I think there was value in that. Then I said, we did something very interesting where we devalued the office and nobody realized we devalued the office. Open space is awful. Awful. And the reason it’s awful is because it is created High School cliques. So if you’re standing at a desk, and all of a sudden you see two people go off to a conference room or three people go off to a conference room, who you thought were in your team and you’re not invited. You’re kind of a little pissed. I wonder what they’re talking about? How come I don’t get to be in that conversation?

So once COVID happened and we got people out of this awful open space. People started saying, huh, I like working again. I’m not like cuz now to to have conversations, you get everyone on a Zoom or or or Teams meeting or make Google Meet or whatever. And you have the conversation with the right people in the room. So the clicks are going away. So so there is value in that.

So as all of these kind of different combinations are happening, do I think we’re fundamentally going to change? I do. The technology is there. I think we are more apt to work at home. I think it’s going to be a hybrid model. I think some companies will have offices, you’ll determine if you want to go in a couple days a week or not. I think Google’s gonna go do that when they finally reopen. But I do think I do think we’ve changed. I think society and the way people think have changed.

Look, I think the hardest problem is for managers, because people managers in particular, people, managers, whole job is figuring out how to walk around to people. What are you doing? How are you feeling? How can I help you? What can I do? How do I remove this roadblock? So I think people managers in this world are going to have a difficult time. And I think the number of managers you have goes down.

So at salesforce.org, we were remote from the beginning. And, you know, in, in an organization of 150 people, there’s four managers. When you’re a new employee, your machine, your phone is shipped to your house, NEO happens, new employee orientation happens right from your machine, you never have to go to San Francisco for anything. Your slack channels are done, your your, you know, everything is kind of ready for you. And we have you know, we record every Google Meet, we use Google Meet at Salesforce, every every meeting is recorded and stored. So you can go back and look at it. I don’t think many people do. But like, we have a new way of doing documentation, which is different. Managers, you know, a lot of my managers in particular, have 15 minute scheduled chunks, like just to go talk to people just to say, how’s it going? We’ve figured out, definitely a way to work remote. So.org is remote, but the rest of salesforce.com wasn’t that way. So when COVID happened, we’re like, no change for us. Right? It was.

And, you know, of of .org. I think, you know, there’s there’s a couple pillar officers are San Francisco, Bellevue, and Denver. But that’s still probably less than 30% of the employees that go to any of those three places. So 70% is truly remote. And we build software, we ship it, we deliver it with quality on time, usually on time, right.


CW: David has had the privilege to work with some of the most customer focused companies in the world. And it’s been fun to hear him talk about it. I want to thank David for his time, especially in the wee hours of the morning.


Leading Smart is from me, Chris Williams. You can find out more about the show and discover other resources for leaders at my website: CLWill.com. I’m sure you know someone else who’d like the show, please share it with them, or spread the word on social media. I’d also love your feedback. I’m “theCLWill” on Twitter, LinkedIn and Facebook, or send an email to pod@clwill.com.

That’s it for this episode. The next episode continues the series on organizational culture. We’ll look at how a great culture can drive success. It’s called “Harmonics”. I hope you’ll listen. Until then please remember that each of the several dozen decisions you make today are a part of Leading Smart.