Brad Silverberg – Part II

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Chris Williams: In Episode One of this podcast, I related one of my first leadership experiences. I was hired as a car stereo installer. But through a twist of fate, I became a professional hitman — sent around the company to fire people. That first experience in the world of management taught me a lot. It was a baptism by fire, if you’ll forgive the pun. If you haven’t listened to that episode, I suggest you do, if only for the story.

As I have grown into being a true student of leadership, I find that there are a handful of key moments like that in the lives of most leaders. As we talked about the last time there’s the moment when they discover their life’s passion. They find they really enjoy some field and become fascinated by the challenges and rewards it offers. It’s almost always by serendipity, simply pure chance that some of the most distinguished leaders even discovered their field in the first place.

Those stories always make me smile. And in the last episode, Brad Silverberg related his chance encounter with computer science as a freshman waiting in the course registration line. And one of the pivotal leaders in the development of the personal computer was off and running.

There are a few other interesting moments in the life of a leader that are fascinating to me. As we continue our conversation with Brad Silverberg about his fascinating career. We discuss a couple of them in detail. We talked about our shared passion for vision as a leadership tool, about how Brad’s clarity of vision played a role in both his biggest success at Microsoft and ultimately how it led to his leaving the company. 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 is the second of three episodes with Brad Silverberg. In this episode, we talk about leadership vision, and Windows 95. This is Episode 204, part two of my conversation with Brad Silverberg.

Chris Williams: Aside from the realization of their life’s passion, the first time someone manages people is another inflection point. Some people find their knack for leadership almost as vividly as they discover their love for their field. The transition from individual contributor to manager is fraught with complexity and results in immense personal growth. Most leaders I’ve encountered remember it clearly. And Brad Silverberg was no different.

Do you remember your first experience going from being an individual contributor to being a manager and, and do you remember what that transition was like? Was that something you looked forward to?

Brad Silverberg: I do remember it. I remember quite vividly. It was at Analytica, I was an individual contributor. The development of Reflex was not going that well. We had a lot of great ideas, but the development was pretty rocky. We weren’t meeting our schedules. The product wasn’t converging. There was a lot of conflict within a development team. We had a lot of very talented people with … not that easy to manage. And I felt I could do it better.

So I thought I could lead the development team better than what was being done. I learned a lot of lessons on the Lisa project. Mostly lessons. things not to do. I saw a lot of things being done, that as an individual contributor, that doesn’t really make sense. And that doesn’t really make sense. At it turned out, it didn’t make sense. And so I developed my own philosophy of how to do development.

So I kind of agitated to become the developer manager at Borland. I did. I’d say, it was a mixed success. As with many individual contributors who transition into managerial role, there’s a lot you need to learn. And I was I was a micromanager. I was hard on people. No harder on anybody than I was on myself, but I could have been a lot more empathetic. I should have been a lot more empathetic. Should have let go a little bit more. Pretty driven to see that product come to fruition which it did. That was a great product but a lot of great ideas but a little too early in the market technology wise. There were a lot of lessons I took away from that.

CW: A key transition many people are fortunate to make is becoming a parent. Many leaders I’ve talked to have told me how having a family impacted the way they lead their teams. I saw it myself to be sure. And I observed it firsthand as I watched Bill Gates change with the birth of his children. He went from an often short tempered leader to someone with much more tolerance for differences of opinion, and with far more understanding of the feelings of others. So it was no surprise when Brad’s cited of this as well.

Did you miss doing Did you miss being a coder? Or were you both both being a coder and a manager or …

BS: initially I was just I was doing both. I was coding and managing. But I would say the thing that really helped me become a better manager. And this was right around the same time that I became manager was being a parent. I wasn’t a parent at Analytica, but I was at Borland with so my first son was born 85, and we were acquired By Borland in 85. And learning to be a parent teaches you a lot about being a manager. And vice versa. Being a manager teaches you a lot about being a parent. And a parent teaches a lot about being a manager and being more patient, more nurturing, more empathetic, while still trying to provide some direction. And

CW: it’s very difficult to micromanage children, right?

You can’t, but you do have to lay out some principles and let them give them some structure. And you have to let them fail, learn to let them fail and learn on their own. And so I’d say, combination of being a manager at Analytica and being a parent really accelerated my growth as manager. And so when I went to Borland and became VP of Engineering, then we had a lot of different projects, not just one project, and so that also helped me, I have to do a lot of context switching. You have to manage much different groups and you have have to learn to be a lot more hands off and trust the teams.

CW: Leading is about building teams. And it’s only really effective if the team you’ve built has good people who get the vision. For Brad, that meant carrying the vision of the famous product Turbo Pascal, into the world of the C computer language.

BS: We were lucky at Borland to have really great developers really strong, passionate, creative developers. And that helped attract even more great developers. That’s another key lesson you learn as you create a great culture with a lot of high talent that attracts more great talent. That’s where the best people want to work. And so we were successful at really building an amazing development team and making very smart acquisitions to continue to grow.

Our product categories at Borland… really the only coding I did was on Turbo C. Turbo C was my baby. I saw the success of Turbo Pascal, but I saw that C was really the language that most people at least in the states were using and wanted to use for development of their applications. Anders had zero interest in developing a Turbo C he didn’t care for the C language at all. He was totally committed to Pascal and then of development environments like Delphi and so on.

Turbo C was, was my idea, went out and acquired a company called Wizard C, Bob Jarvis and Bob and Peter Kuckol on the most of the development on the turn Wizard C into a Turbo product. When you call something Turbo. it stands for something. It has to be faithful to the name Turbo. It’s not Wizard C anymore. It’s got to be turbo Pascal, but for C. It’s got to have that same speed. ease of use, nice development environment gotta have the whole gotta be Turbo from Borland.

And so I wrote the developer, I wrote the some some of the runtime libraries for Turbo C, and that was really the last code. For most part it was then managing, managing the other teams learned over time. That’s what I enjoyed more than writing code than sitting and doing I found I was, I was just better at coming up with product ideas, learning to communicate that product idea in a compelling, exciting way both to customers as well as to the developers in the development team, getting everybody excited and orchestrating the assembling the team and putting all the pieces together on beyond the team and leading the development efforts.

I found I was just a lot better at it. I was an OK coder, I was never going to be the type of coder of the people I was working with. They were way better than I was. And initially, that stung a little bit. I learned really at Apple that I was going to be an okay, you know, a B plus coder, but I was never going to be an A coder. But I learned I could be a much better product manager, program manager, project leader, manager than and it gave me a lot more pleasure to see working with teams of people see the teams of people come together and build a product that everybody is excited about, would win these awards and huge sales and happy customers. That feedback loop in and knowing that I was good at it. That was very rewarding.

CW: In early 1990, Brad made the jump from Borland to run the Windows and MS-DOS teams at Microsoft. This was a pivotal role for him. And it seems for Microsoft.

BS: So when I saw that opportunity at Microsoft to go on to a much bigger stage, really lead graphical computing for everyday people around the world. I mean, everything in my career up to that had trained me for that job. I had the right set of skills with the right background, the right the understanding of the technology in the market, and love, just deep love of personal computing and how it could be empowering and the desire to have it be democratized around the world on affordable computers, just seemed like this was the right time right place, I had the right skills and was really lucky to have that opportunity.

CW: But the scale was dramatically different, right. You went from Borland with a few hundred people to the Windows team which was, you know, thousands, right?

BS: Well, the Windows team at that time was very small. Windows 95, which was a lot bigger than Windows 3 and 3.1. Windows 95 was about 350 people. Windows, Windows 3 was probably 150 people. Things were still small, we fit all all of the Win 3 team fit in building 3, which was a small build.

CW: right.

CW: The next key transition period for managers is the time when they first get promoted as a leader, from a frontline supervisor, to the manager of managers. This is a moment of great transition. No longer can you reach down and just say, “Here, let me do that.” You have to lead by remote control. You have to trust in your ability to convince others. And this is where management turns into leadership.

You ended up having to lead managers of teams, how do you go about hiring or performance evaluating a manager? As opposed to a coder? What are the kinds of things that you find are more valuable to evaluate leaders for, rather than, I mean, there’s certainly an aspect of managing what they get accomplished. But there’s also … you have to judge them on their ability to do what you were just talking about, about sharing the vision, about building a team about how do you how do you evaluate people for that, how do you hire people for that?

BS: I found a had a good talent for that. I found I had a really good talent for identifying young talent early on their career, identifying their potential, and helping them reach that potential. Probably one of the things I did the best was being able to identify talent early on in their career before they really had accomplished much.

I could see that spark, I could see that they would be passionate about building software, that they were not just talented and capable, but they had that something extra that allows them to build and do extraordinary things. And so I looked for not just ability, but character, commitment, leadership abilities, how they worked as a team.

Well, I like diversity too. I wanted a mixture of talent and types on my teams. Some people, they’re not visionaries, but they get stuff done. They’re just incredible at the execution side. And when you have a big vision to build a product, you don’t sell, you have to sell the vision to the world. But if you have to ship a product, there’s got to be a great product and you need people who are capable of managing schedules and keeping track of all the various different teams and seeing all the parts from different teams come together and do that in a fair and capable way, you want to see people get treated well, but also challenged and held to a high standard.

So you need, you need the creative thinkers you need. Sometimes they can be a little, you know, hard to manage. But, you know, they stir the drink, you know, they need people who kind of trigger the sand in the oyster, that can be stirred things up a little bit, but they get the creative, they tell you what’s possible what, what the product really could be. Sometimes those people are capable of also building it, like, you know, somebody like Anders. More often it’s not, they’re not more often you need to build a team around them that can actually go off and execute it.

So you need need some leaders, you need, you know, a blue collar guy, or folks that roll up their sleeves and get stuff done and people with good character because any project is going to have some setbacks and especially, the more ambitious the vision of the product, the more setbacks you’re going to have along the way. And it has a lot of ups and downs and you need people who are optimistic, who are committed who are there for each other, that when things go badly, you know that people are gonna be there for you. That you can be open and honest with your manager, your co workers and you don’t have to worry about that being held against you, that you can be yourself.

And I found, if you create that environment of trust, I would say trust is where it all starts and trust is a two way street. That when manager or leader gives trust, that trust is repaid 10 times over. When an individual fields trusted, feels respected feels given an opportunity for themselves to be able to contribute to the product in a meaningful way and see part of themselves in that product.

People don’t like to just be given specs thrown over the wall and say go implement this, they want to see. They want to see their own initiative, their own creativity, their own their own selves in the product. So I was a big, big proponent of pushing responsibility down into the organization. Shaping, this was what we’re trying to accomplish the vision of the product, make sure that that gets well communicated so that everybody on the team knows what it is. In fact, I would do a lot of walking around and ask people, okay, what is this product stand for? Or I would ask my managers to do the same thing. And if you don’t hear a consistent message, then you know you’re not doing a good enough job of communicating that message or the message isn’t the right message. That you need to hear it from the bottom up that what you want to hear from the top down and communicate that message very clearly. And then give people that provides take it the next level down in terms of the set of features, whatever that they can use to make decisions for about the product. And then turn them loose.

And the best thing about manager can do is to be an enabler and not a decider. And that’s probably the biggest lesson I learned. For my first job as a manager at Analytica to where I was at Microsoft is your job is to help other people be successful. It’s not for you to make the decisions and have other people be an extension of you. And I think that’s what a lot of mistake a lot of first time managers make is okay, now they work for me, I get to tell them what to do and that doesn’t end well.

CW: One of the most exciting parts of being a manager and a leader is watching someone get excited by the vision for the project, and then realizing they can have a crucial part in realizing that vision. Helping people to grow in this way is the reason many people love leadership.

BS: They discover a potential that they didn’t even know that they had. It’s not just helping them achieve their potential but it’s discover a level of potential that they didn’t even know they had. And once they go through that, they taste that you never forget him. Yes, never. It’s intoxicating. like wow, look what we look what I accomplished. Look what we accomplished as our small team. Look, are we accomplished as a bigger team and we did it together? Because we all believed we believed in the vision. We believed in the product, which is two different things. You could believe in a vision but the product itself may not Be faithful or good enough implementation of vision. That’s where some of these, you know, people that can actually get stuff done, David Cole was way better managing the dev team than I ever would have been. I was happy to let David do that, he’s better than me.

And that’s another part of being a manager is to recognize and embrace the fact that there are people who work for you who do their jobs better than you would do them. A lot of first time managers or even CEOs think that they can do your job better than you can do it. And don’t want to hire people who will do their job better than you can do it. Managers feel threatened by that. And I embraced it. I realized, especially at Microsoft, there’s people here who are so much smarter than me. And if you let it, you can be intimidated or threatened by it. They’re just they’re just way smarter than me. They’re just way better at certain things than I ever could be, I could never even conceive as being as good as a lot of people who worked for me, were in their jobs and you embrace it, you let them do all that stuff and be the best they can be, and you try to be… so you’re like a conductor, you have to orchestrate it. You’re not the one playing the violin or the cello, but you help orchestrate everybody to
be their best.

CW: A very difficult lesson for many leaders to learn. And honestly, there are some that never learn it, is that there will almost always be people who are better at some things than you are. That these people aren’t threats, but rather their assets. There are people you shouldn’t be afraid of. But you should learn to attract.

BS: You have to you have to trust you have to let go. You have to hire people better than you and feel. And feel okay about that. I actually was super excited about it, I was like, great. And I can spend my time on other things if I don’t have to worry about that area. I mean, I was trust but verify was kind of my management philosophy that when somebody was new or, you know, I’d be very close to it and make sure that they knew what they were doing. But once I’ve had a lot of confidence in it, I left them alone. Let David alone, left John Ludwig alone, left Brad chase alone, worked very closely with them, but still there was a lot. We built a lot of trust between us.

CW: Communication in leadership is another challenge. If what you hear is only what your team wants you to hear, you can develop what Brad calls the “headquarters mentality”.

BS: And I also work very hard to maintain close relationships with people all up and down the organization, individual contributors, the testers, the admins… And I wanted them to feel comfortable coming to me with any kind of issue because otherwise you create this kind of headquarter mentality where top managers get isolated. And they they only hear what’s happening through their direct reports. And well, that’s a highly biased and filtered set of information. Nobody wants to go to their boss and talk about problems or am not really doing a great job of managing my organization, or the morale in my organization is pretty bad. You don’t really hear that directly from your, from your directs.

I’ve wanted to really have my finger on the pulse of the organization at all different levels so that I could get early warning for areas that would need attention, to work with managers on improving this or improving that, or having to move some pieces around if that was the right solution to the problem.

I think that’s really important, otherwise you can get very, very isolated. And you get completely wrong and misleading data about the health of your organization or the health product and tried to be be very accessible to people throughout the organization. And I think that was also key to being empathetic to people and they could feel connected to management and not feel like management is off in, you know, some other building, disconnected from what’s happening on the ground or out in the field. I think that contributed a lot to people really feeling part of part of the team.

CW: If you listen to the first episode of my conversation with Brad, or the series of episodes I did in Season One on the topic, you know that vision is a crucial management tool. Having a clear, crisp vision is something that distinguishes all great leaders. They use it to rally and focus the team. And it helps them to make important decisions in their projects.

But what struck me as I spoke to Brad was his unique clarity of vision. It’s as if he knew the future and made life changing decisions based on that.

One of the things that you and I have talked a bunch about in the conversations that we’ve had has been, you know, this passion for vision and how important having a vision for a product is and, and you’ve just discussed it at great length with how vision is important. One of the things that strikes me in this conversation though, is you have an unbelievable clarity of vision that I see through I mean, throughout your career. For example, you you really have this passion for personal computing, you really saw that the graphical user interface and the that was really important to you, you made a life changing decisions based on that.

And and I’m thinking back to the conversation that you and I had when you were trying to leave Microsoft or trying to decide whether or not you wanted to leave Microsoft. And we were talking about this the other day, and you said that one of the things that was really key was that you didn’t think Microsoft really figured out what the internet was about, and that you really knew the internet was going where it was going. How do you have this, this, this clarity of vision about where things are going? I mean, you were clearly right at that time, and you left Microsoft in a part because you didn’t feel it was going in the right you know, I didn’t have enough passion for the internet. Where does this clarity where does this prescience, this vision of yours come from?

BS: You know, it’s a gift I have. I was able to see personal computing be able to, as a history major, and then see what was happening at Xerox early on and say, Wow, that’s just incredible. But it shouldn’t just be on these $10,000 or $30,000 machines for the special few it should be for everybody around the world. And I was also very much of I wanted to democratize computing and want to put the tools and I just saw how it helps people achieve their personal, personal potential, create community, reach out to friends around the world, make new friends.

So I saw that with Windows and then I saw early on early 90s, about the internet that I had to be using the ARPANET while I was at SRI. And I saw how that enabled scientists around the world to connect and and saw the value of that community. So I was one of the early people at Microsoft to identify the potential of the internet.

And it was the internet. There was also another group of people inside Microsoft who saw it as the Information Highway, which was Microsoft proprietary set of protocols and formats

CW: that was the NETBUI versus the NETBUI versus TCP IP world arguments, correct?

BS: Yeah, and it was MSN 1.0. It was all proprietary formats. It wasn’t HTML. They have their own formats for a parallels for everything up and down the internet stack. They had proprietary formats and protocols for. They wanted to create a closed world that Microsoft owned and controlled and I really was a big believer in the internet, the opportunity potential of the internet and this open architecture. connect people around the world. And I was a huge believer in it.

So I was in a big rush to ship windows 95 so that I could then focus full time, on the internet stuff. I had the Internet Explorer group inside my team starting in I think 93 or 94, Ben Slivka was running that team. I actually had another team before Ben that, in I think 93 working on the initial web browser, and it wasn’t making the progress I thought it should be making, so I replaced that leader with Ben who was passionate about it, and then worked on that.

And so I was very, I really saw that, that the internet was going to be the successor to personal computing, it was kind of the logical outcome of all these things that we were doing. This is where it led to next. As an end user, the ease of use of the Internet was just sit in front of our web browser. Anybody can figure it out. You don’t need to go to classes for a week, learn about config.sys and all this other stuff of learning how to use a PC as easy to use as Windows 95 was compared to Windows 3.1, using a web browser was dramatically easier. You put a five year old kid in front of a computer with a web browser and they’d be productive right away. So I saw that as the fulfillment of the vision of making computing easy to use for people around the world. That’s why we put so much effort into Windows 95 with the tech mode TCP IP stack and adding DHCP to make it easy for anybody to use, connect to the internet, PPP stack to be able to dial up and put the underlying plumbing for the internet that previously it really took an IT professional setup. To put it in the hands of anybody.

CW: I feel the need to remind listeners that Brad is talking about the early 1990s more than 25 years ago, long before most of us, even those of us in the industry, had even used a web browser. Yet Brad has this stunning clarity. Where does this come from?

BS: It probably is a background I had in history and my particular area of interest in college was modern European histories say, from the French Revolution on through First World War. I could see how technology, innovations, which shape the entire world stage. They would change politics, they would reshape economics, they would cause revolutions around the world they would upset the existing social order. turn our society from agrarian to industrial societies and create working classes and middle classes that would all want political power and cause redistribution of resources around the world.

And I saw, I saw the internet and PCs is having that same type of potential as much as you know, when Whitney invented the steam engine, and how it changed, changed the world, how the railroads changed the world. The impact technology and technology innovation has to change, change and upset, cause revolutions and change the world.

And I saw the internet as having that type of potential and I had the same type of fervor and believe in and the potential opportunity of the internet. And the flip side, which was particularly apropos at Microsoft as you know, Microsoft, saw the world through two two sides of a lens. One was opportunity. And then once Windows was successful, it also saw the world as a bunch of threats. I saw the internet as an incredible opportunity for Microsoft to be able to step out and become a leader just as we had with graphical user interfaces, and be able to help shape that new internet world and be a full participant. I also saw it as an opportunity for Microsoft to say, improve its corporate culture and the way it related to the outside world.

That there were aspects of Microsoft that was fairly adversarial with the outside world. And I felt the internet had an opportunity to improve and transform Microsoft into perhaps a more kinder, gentler, cooperative, engage with the outside world without it… But you know, there’s a threat to we wouldn’t have the same level of proprietary protection we had with Windows and so it put more pressure on Microsoft to be more innovative and stay ahead of the game and, and not be able to rest on our existing laurels. So there was risks with it too.

But I was excited by and I was committed to helping evolve the company towards internet first company, shall we say? When. you know, I think the latter half of the 90s after the initial successes we had with particularly IE 3 and IE 4, there was, I think a sense, okay, we won the browser wars, that threat is put away, we can go back to business as usual with Windows of being a Windows-first company. Which is completely understandable in the mid to late 90s. If you own windows, life is good. The world revolves around you. You are the center of the universe and everything that happens, you know, emanates from from Redmond. Why would you want the world to change? It’s completely understandable why, you’ve got an incredibly high margin successful business. And the way the stock market is priced is priced on expectation of future performance and you know the stock price did really well in the 90s. We all did very well.

And as a result, there’s a real premium for being a leader and not just for revenue, there’s a real premium for being a leader, the leader in industry, not just a revenue multiple, but a strategic multiple, and we were the beneficiary of that. And I felt that that would be a risk that if we weren’t the leaders, I felt the internet was gonna be the next transformational technology that would have impact on the world, similar and beyond what windows had had. But similar to the industrial revolution of the 1800s. I got pretty frustrated in the last half of the 90s as I felt the company had kind of gone into more “Protecting the Empire” than towards creating exciting new future. A future oriented around the internet and being able to contribute. And we also saw the world through Windows eyes.

CW: In this period of the later 1990s, Microsoft was wildly successful. Windows 95 and its successors had taken the world by storm. Microsoft Office was dominant in the productivity space, the company’s stock seemed inexorably on the rise. Life was good.

And yet, here comes Brad trying to convince the company that it needed to embrace the internet. That just like they saw the future with Windows, it should see the world through the internet. But the company largely saw the internet as a threat to the core business. They were making a fortune selling windows to original equipment manufacturers or OEMs. And they weren’t about to give that up. Brad was growing frustrated.

So some of that was also though, a change in leadership. Because right at about that time Bill was moving out and Steve was moving in to run the company. And Steve was significantly more practical and less visionary. Right? He was very much the sales guy who had had made the world out of OEM and all that and, and was a less visionary sort. So do you think that had an effect on the way Microsoft responded at that time?

BS: I get your premise, but I’ll say no.

CW: Okay.

BS: Because I think, well, there were two things. One, the antitrust trial was going on and Bill was very consumed with that. And second, fundamentally, Bill was committed to a Windows-First future. That’s that strategy was led by Bill even after Steve became CEO, if you look at the overall company strategy, especially in the first couple of years, it was still led by Bill and Bill’s commitment was to keepin’ the good days. The good times rolling. And that was the Windows-First strategy and not the internet-first strategy.

And there are a number of decisions that were made that made it clear. I mean, I was leading the Internet Explorer group independently because I felt it was important to decouple our development from the internet. From the Windows team, the Windows team was, at that point, pretty, not just pretty, for the most part. Certainly, there were pockets that were different, but from the top down, they were very anti-internet. They saw internet as a threat. Certainly groups within the team that were excited about the internet and built some strong internet components, but fundamentally, they were anti-internet anything that might threaten Windows was was the enemy.

I was strongly in favor of keeping the Internet Explorer team and the internet work that I was doing independent of that, partly because we had to ship on different schedules. There was the notion of internet time then. If you weren’t shipping frequently, you’re gonna fall behind. If you’re tied to an OS schedule. OSes shipped every 2, 3, 4 years. Well, the world is racing off in one direction, you can’t be on a three, three year ship schedule, you gotta be gotta be in the arena. You got to be playing by the new rules and doing a better job of that. So we needed that level of independence.

When the decision was then made to move Internet Explorer into the Windows group… I knew that was the death of Internet Explorer. It was over. They were going to kill it. And they did. And that was you know, IE 5, IE 6 time a time when we had leadership in the industry. We had the most industry standard browser, we had the fastest, most capable browser, leading the world and helping very active and productive on the W3C, and all the industry standard committees that all went down the tubes and Internet Explorer was neglected and, and left, you know, just kind of left there on side of the road to die. And then came Firefox and then Chrome and Microsoft lost the position that it had a 90 plus percent share of, because of the commitment to the internet was not was not there.

My strength is my weakness, which is I became very passionate about Windows. I became passionate about in the early 90s passionate about Windows and that everything I had in my team into building, building Windows 95. I’m very passionate about that and that passion kind of comes through and bleeds through the team. A team reflects that and I was very happy with the way Windows 95 turned out. It defined computing for a generation, we really made a difference to the world.

But then I had that same passion towards the internet. And that passion I had towards the internet was pretty all consuming and some of the folks that I had worked with at Microsoft, John Ludwig, Tom Reardon, a bunch of other folks… we had that same passion as “this is the future”. Ben Slivka, we saw it. Ben wrote a memo came out 25 years ago,

CW: 25 years ago yesterday, I think so…

BS: 25 years ago yesterday, the internet’s an active platform, you read that memo and like, he nailed it. He absolutely nailed it. And that really, to me painted, this is a roadmap for the future. Another one called three years later called Neptune that was even more prescient. He laid out the roadmap for Microsoft for the next two decades, and company chose to go down another path.

And when you’re that passionately committed to something and then be told no, we want you to manage Office instead? I couldn’t do it. I couldn’t do it, Chris, I am an all or nothing type of person. That’s if my heart’s really not in it, I’m not going to do a great job. I’m going to want to go bicycling instead of burning the midnight hour on compuserve answering questions from our beta testers.

And so I left.

CW: That was when Brad and I had that conversation in my office that I’ll never forget. Brad had taken a sabbatical to ponder the future. I had followed my passion for people and leadership to move from the world of technical leadership into human resources. He came to my office to discuss his return and the role he would take. It was one of the most powerful conversations I’ve ever had in the workplace.

Brad’s passion for both the internet and for the company was all-encompassing. The direction seemed so obvious to him. The company he had grown to love and help to make incredibly successful was going to miss the next big wave. That Bill and Steve couldn’t or wouldn’t see it was killing him.

Brad was part of the front edge of a wave of senior people leaving the company at that time. The skyrocketing stock price had minted a whole layer of people who had “walking away money”. They began asking themselves and me, “why am I working 70 to 80 hours a week?” Brad and I talked for an hour. We both adored the company, but he clearly saw the world with more clarity than I did.

By the end of our talk, it was clear he was going to leave. He saw no other choice. It was so very depressing. One of the first but certainly not the last time I shared some tears with a senior leader making that very difficult choice.

In the next and final episode of my chat with Brad, we talked more about his choice to leave and his entry into the world of venture capital. And Brad once again peers into the future to talk about a post COVID world

Leading Smart is from me, Chris Williams. You can find out more about the show and discover other resources for leaders at my website,

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That’s it for this episode. Next episode we wrap up the conversation with Brad Silverberg. We explore leadership and venture capital and the future of a post-COVID world. Until then, please remember that each of the several dozen decisions you make today are part of Leading Smart.