Donn Denman

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CW: The conversation today is a little different. Rather than talking with a leader with a lifetime of experience building and leading teams. This time, we’re looking from the other perspective. Today we’re talking with Donn Denman, a longtime veteran of Silicon Valley. Donn was an early Apple employee and is now an engineer at Google.

In our conversation, Donn shares what it was like to work with one of the true luminaries of the tech world, Steve Jobs. He talks about how Steve drove the details of the development of the iconic Macintosh, and what it was like to work with him. He also talks about his work at Google, and the culture, his attitude toward the old guard of the valley.

Through Donn, we learn a lot about vision and passion and how they combine to change the world. And that’s what this is all about.

This is Leading Smart, the show about managing in the brain power 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 time we talk with a longtime engineer in the tech world. This is Episode 230, my conversation with Donn Denman.

I’m sure dedicated listeners of this show will think it’s more than coincidence, but like several others, we’ve heard from Donn Denman grew up in Ohio. He lived in Yellow Springs, the home of Antioch College, where his father was a professor. Antioch is a work study school with lots of internships. And while pursuing his degree in math and computer science, Donn came to Silicon Valley to search for an internship.

DD: In December of 78, I came to Silicon Valley and looked for a job. And in January of 79, I went into the lobby of Apple, and I asked to see Steve Wozniak or the VP of engineering.

And the minute I stepped in, there was a receptionist who was constantly saying, Apple Computer, can you hold please, Apple Computer, can you hold please? That went on for several minutes before she would talk to me. But then she said, I could sit down and wait for one of these people.

And long story short, I was able to get a real interview the next day and got hired as an intern. Because it’s easy to sell yourself as an intern, I’m either going to be great, you can rehire me when I graduate, or I’ll be terrible, and I’ll automatically go away.

CW: So was that internship was that the between years in college like between high school or between junior and senior year or something?

DD: Basically, you know, we had internships all throughout the year, year after year, so they didn’t have to be summer internships. And I had room in my schedule for another internship, even though I didn’t really need one. And I said, Well, I’ll pretend I just graduated and go look for my dream job. And I ended up at Apple. And so they gave me an offer to come back full time.

CW: What originally got you to Silicon Valley from Ohio? Did you just sort of know that’s where the center of the world was and you wanted to be there?

DD: That’s right. And my computer science instructor coached me and he said, I have a graduate who lives over here in Silicon Valley, you should go you know, live with him until you can find a job. And he said he he’s been working at this little town is this little dot on the map called Cupertino and so I went to Cupertino. That’s where Apple was. At the time that I arrived at Apple that day. It was all in one building Bandly one and Bandly was literally a dead end street. And all of Apple was in one building with production in the back half. And

CW: so that was sort of like a light industrial complex or something where they had a garage Bay in the back. And they were building things in the back.

DD: Yeah.

CW: So you mean, so you had to be in the first couple dozen employees? Right?

DD: No, I was employee 228.

CW: So okay, so there were more people than I thought,

DD: Yeah, a couple 100 people. And that first day, when I was sitting in the lobby waiting for somebody to come talk to me, the VP of engineering. Somebody sat down next to me, and talked to another visitor and said, “Apple sold more computers in the month of October than in the previous year.” And I thought to myself, I want to join this company. But I wonder who this guy is. He wasn’t wearing a tie or anything. turned out he was the president of apple. I didn’t know that then. But that’s the way Apple was the culture was a little different.

CW: Yeah. And what did you start working on when you got there?

DD: I was working on a version of BASIC for the Apple II, that would be subsequent to the Apple floating point BASIC, which was a Microsoft BASIC. And I worked on some numerical functions for that BASIC, but it never shipped.

CW: Okay. And then later, when you’re working you, you actually were the guy who wrote Mac BASIC.

DD: That’s right, the interpreter. Mm hmm. I worked on Mac BASIC, I was the lead for that. And I had to help her most of the time. And it was originally scheduled to be part of the original Macintosh launch. But one of my co workers quit.

And so I wasn’t able to make the schedule. And so then it was supposed to come out a year afterwards. But there was a high profile deal between Microsoft and Apple in which they killed it.

CW: was most of your work in those first few years on language on the on the on the BASIC language?

DD: That’s right. Yeah. The Apple II BASIC that I worked on for as an intern, and evolved to an Apple III BASIC for the Apple III. And because I was the main BASIC guy, and they wanted BASIC on the Macintosh, they recruited me to join the Macintosh team. So I did and started the Mac BASIC project.

And Steve often said, I want Mac BASIC to be lean and mean. And that is the primary guidance that I got on what to build and how to do it.

CW: Those first early years. I mean, you’re there is, you know, the first couple 100 employees are around. Was it everything that we’ve all heard about the valley at the time, sort of the wild and crazy bunch of kids getting to get, you know, let’s play Defender all night kind of world.

DD: Yeah, yeah, I would say it was, especially working on the Macintosh, there was a lot of pressure. We got t shirts at one point that said 80 hours a week and loving it. And that was in the year or two before the Macintosh shipped. We really pushed hard to make that work. And there literally was a Defender machine in the lobby. And there’s some good stories about that.

CW: Yeah, I think I recall seeing a good story or two about that.

DD: Part of the experience was, you’d be programming away, you’d get tired, and you needed something to reinvigorate you. And there’s nothing like going to a video game and struggling for your life for a minute to get that adrenaline going, then you go back to work.

CW: So at that time, both Steve and Steve, were there. How did the management and the leadership of projects go at that time? Was it? Was it fairly well structured? Or was it pretty loose?

DD: So it was fairly loose, I would say, with the Apple II, Steve Jobs was the marketing guy and Steve Wozniak was the real brains behind the whole thing. He basically built both the hardware and the software of the Apple II.

And what happened after that was an engineering organization to support that had been built and decided to do the Apple III. And Steve was still mostly in marketing, but part of the marketing role is sort of defining what the product should be. And so he did make some significant changes in what the Apple III should be. And that ended up ultimately really making the apple three a quite a failure.

I remember distinctly that the Apple III was designed to be an Apple II plus more stuff. The Apple II part was a physical hardware emulation mode. And Steve came into the engineering area one day and said, “I have this great idea. Can we do emulation in software instead of hardware, we could remove 20 chips off of the motherboard, we could reduce the cost by all this.” And we thought to ourselves, oh, my God, we are almost done with this thing. This is a little late to be, you know, asking for changes like that. And so ultimately, that did not happen. But he asked for other changes that caused the single motherboard to have to be split. The RAM was separate and it didn’t have good connectors. And so the machine was not reliable, and it became a complete flop.

CW: Yeah. Do you remember how the birth of the Mac came about? Do you remember the germ of the idea?

DD: Yeah, yeah, so… there’s another piece, it’s critical that people have really mostly forgotten, which is the Lisa computer. And of course, Lisa was named after Steve’s daughter. And it was a project that I think Steve helped to start. But once the real engineering infrastructure came up behind it, it needed to… you know, Steve lost some control there.

And it also took a direction, that probably was not a good direction, it was basically a mini computer that was for your desktop. So it was expensive. And there were some other issues with it. So around that time, Steve decided to split off a little sister to Lisa. And he saw that Jeff Raskin, who was a brilliant user interface guy, had a little project called the Macintosh.

And so Steve really came over and stole the Macintosh, from Jeff, and started up his own little fiefdom where he could hire the people that he wanted to and control the engineering of it. And the rest of the company basically said, the reason we have a Macintosh is to keep Steve out of our hair.

CW: Okay.

DD: Yeah. And so, of course, what the Lisa and the Mac shared was the GUI, these are the first commercial products that featured a GUI as the primary user interface and had a mouse.

And so there was a high end one and a low end one. And the Mac was really designed to be just all in one, very inexpensive and for the masses.

CW: Was was there a clear vision for the Mac? I mean, was, was it obvious or and and not for the Mac? But for the GUI as a whole? Was there a clear vision was that really well understood in the whole company, what it needed to look like and be like?

DD: Not at all, there was inspiration from Xerox PARC. At one time, a group of people went and saw the Alto at Xerox PARC and saw what a GUI could be. But we had to bring that back and refine it, and distill it into something that really worked well for a small black and white screen. And the Lisa team was doing its own similar development on the GUI. We knew we needed drop down menus, but we didn’t know how they should look, should you be able to invoke a menu from a keyboard and how, you know, what is the Command key like? And how do you reflect that in the menu. The actual title bar of a window, how that looked in, is laid out with the title and then some, you know, graphical stuff to make it look heavy and a close box and all of those things evolved. And often there was animation, like if you started to click on the close box, it would turn into an app strip show you that, yes, you are actually clicking on it. And it was ready to do something if you let the mouse up.

And so I was privileged to be part of that team and see the cycle of innovation between Steve and the key developers of the Mac operating system, primarily Andy Hertzfeld, and the people that were working on the Finder and Bill Atkinson, who was working on Mac Paint and so the pieces came up little by little, and Steve would come in and say show me the, you know, show me the title bar, show me the drop down menus. And then he would say this is s**t! And usually the engineer would say, No, this is great. And here’s why it’s great.

And the fact that Steve pushed them and criticized them, got them to defend themselves and articulate what was great about their design, and then they iterated. Often, there would be a new, better path forward that was designed on the spot there. And then the engineer would say, I’m gonna do it tonight. I’ll show it to you tomorrow.

And Steve would come back the next day. And he’d look at it. And that cycle of evolution continued. And, you know, that’s why we were working 80 hour weeks is because you had to get it done for Steve the next day.

CW: Was that style of of sort of iterative working …? Do you feel like that was intentional? Or was that just sort of how it happened to develop?

DD: I think it’s a combination of both? That is an excellent question. I think it started out as Steve’s style. And I think he saw that it was working. And so he built off of it and refined it.

But nobody else worked that way. As far as I knew I’d never had that sort of experience. But it really worked between Steve and the real innovators on the team.

When Steve came to me and said that was s**t. I would cower, I wouldn’t say, No, it’s not. And so I, I couldn’t respond in the same way. And I think most people couldn’t respond in the same way. But the the key people that Steve had built a close working relationship with, the people with strong enough egos to really feel like they knew what was right and could articulate that and stand up to Steve, that really worked well for them. And that’s how, you know, the genius was built. That’s one of the real special sauces that Steve had and was able to apply.

CW: Was that a part of a culture that got emulated by I mean, did other leaders in the company try and do that I try and be like, Steve, and try and try and be that sort of aggressive challenge, kind of leader?

DD: No, I don’t think anyone else tried to do that. Steve was able to make this work because he had power. And the way he did it made him an ass****. Everyone knew he was a jerk. And yet, the power and the willingness to be a jerk, contributed to that ability to really push people and know how hard you could push them, and still have them respond and go in the direction you want them to go.

But nobody else had the power. Nobody wanted to be like, Steve, nobody wanted to be a jerk. And he really was a jerk back then.

CW: I worked with a lot of people who I could classify as jerks and but incredibly smart jerks. Some of the way in which those people got away with that, or were able to make that work was because they had deep respect from people because they were so smart. They were so talented, they were so visionary. I’m assuming that that’s the way people looked at Steve also and knew that he was right and knew that he was or was it just him wielding around like a 300 pound gorilla?

DD: Yeah, he would come in like a wrecking ball sometimes. But the most amazing thing about Steve, which is really why we all love him is his ability to paint a vision and then inspire you to believe in it. He was able to paint a vision that was so clear and detailed, that you envisioned it clearly yourself. And then that made it seem real. And these were the famous reality distortion coils that he applied, reality would really shift to Steve’s will. And you knew that he had the power to actually make these things happen. And so you believed in it.

CW: And, and there was a feedback loop, right? I mean, it would you would do it, it would work that would make you feel better about doing it. The vision would become clearer, you would do some more I mean, right?

DD: Yes. Yeah, that’s really true. We, we saw that what we were building was really amazing. And we would bring people in and show it to them. And about two thirds of the people would see “wow, this is really amazing. You can point to any pixel on the screen and just change it. That is amazing.” And then about a third of the people just didn’t get it. They would come and they would look and they would go, you know, “okay, this is nice, but…” We really drank the Kool Aid, we saw that this was going to change the world, we believed we were going to change the world. And under Steve’s leadership, we really did change the world significantly. And it took the world a while to catch up.

CW: So the Mac came out. You were at Apple about about five years when the Mac came out, but you were at Apple for 14 years. So So after the Mac came out, and you know, what it did you continue to work on languages, or did you go to do other things as well?

DD: I worked on a keyboard macros facility. That was a good effort, but not a great effort. After Mac BASIC was canceled, that was a real blow to me. And it was hard for me to put my whole heart and soul into anything.

And after that macro project, I worked on Apple Script. And we put together a really great team. And we made some really innovative contributions to languages.

For instance, there was a record mode that allowed you to start recording and then when you directly manipulated things script would get created. And the script was in an English like language, but you could convert it from that English representation of an internal form into a Japanese representation, or a C representation of the same internal structure. So it was incredibly innovative at it for its time, and it is still in use today as a system for automating other applications. So I am really proud of that.

CW: At this point, in our conversation, a crew showed up to work on the remodel of a bathroom in Dawn’s home, he retreated to the quiet of a car in his garage to conclude our conversation.

One of the things that is is sort of legendary in Apple’s culture is the is the incredible secrecy that the company I mean, today, it’s you know, it’s CIA level, was that always something that was part of the company culture early on this keeping it all tightly coupled inside the company,

DD: Early on, Apple was a very open place. And they didn’t have that culture of secrecy. There weren’t silos, there were different teams, but they were able to talk with each other and be very open. And that really helped foster innovation, I think.

But around the time after the Macintosh shipped, and the Mac was clearly becoming dominant, Steve was in power again. And Steve said, “you guys from these other teams, I don’t want you coming by and bothering my engineers, stay away from the Macintosh team.” So that was the way he began to build those silos.

And when you think about it, it makes some sense that Apple is siloed. Because if you are open, then something else can be built that plugs in in that open way. And because Apple is proprietary, they need to control those things. And and so it has become incredibly siloed. After I left Apple, it was in the process of becoming somewhat siloed. But my brother stayed on for many years. And he was frustrated by how siloed it became.

CW: So tell me about how the culture of the company changed when Steve left. I mean, both both before he left, and when he came back later, Apple was, in many ways driven by his vision, so did it did the company go visionless when he left?

DD: Yeah, it did it. It realized that it was primarily a hardware manufacturer. And so Windows and PCs were just beginning to dominate. And people saw that having a standard and being able to have multiple manufacturers build to that standard was winning.

And so at that time, Apple tried to license the design and have third parties start building those machines. And I think that would have been a reasonable way to go, if we saw that it wasn’t all about the hardware, it was really about the software. But we didn’t sell our software, our software came with the hardware. And so there wasn’t a way to put value on the software. and the value was clearly there on the hardware. And so hardware drove it. And that’s not where the vision of computing really comes from. So I, I realized it was time for me to go.

CW: Donn left Apple after almost a decade and a half and spent some time working on interactive TV, and in the world of open source software. In 2008, he followed his friend and mentor Andy Hertzfeld, one of the leads of the Macintosh project, to Google, where he’s been for over a decade.

DD: When I got to Google, I felt like an older engineer, because there were so many younger people. And so I shaved my beard and tried to act and look young. And I felt like that would help me fit in.

And it took me a couple of years, before I realized that there were a significant number of older Googlers. And that, without exception, they had invented something amazing. You know, the inventor of the internet, the inventor of Java, those people work at Google, and they are not young. And I thought to myself, ha, I fooled them. They think I invented something amazing. And all I did was I had an amazing catastrophe with Mac BASIC.

And it literally took me another year or two, before I remembered Apple Script and said, Wait, I did build something amazing.

And this is human nature, we get obsessed by our failures. And we downplay our successes. And that played out with me over a course of several years.

CW: And and so when you finally managed to be proud of your work on Apple Script at Google, did that get you some cred?

DD: It gave me the confidence to try to do my own projects.

CW: And what kinds of things did you work on?

DD: Well, for the last five years, I’ve been working on Chrome for Android. And I built a little feature called touch to search that lets you touch on almost any web page on plain text, and then it will select that and do a search for that.

And the smart thing is it can look at the page context, if you’ve given it privacy permissions. And so you can figure out that Chris is part of Chris Williams, and then it can look up, you and then give you a little icon and more information.

CW: You you were at Apple really early on you, you then, you know, got to Google in a fairly early stage. Were the cultures of those organizations similar in in their early phases? Was that something, you know, the same sort of open collaborative culture kind of thing.

DD: I think the culture at Google very much reflects the culture that was at the early Apple innovative period, and the openness and the sort of hero culture. That that has been a big thing at Apple, when you have a hero like Steve Wozniak, then you end up with these, you know, heroes, one person or two person projects that can change the world.

And I think that also was at Google for a while. But then it became clear that bigger teams needed to be built. But the team still had the same spirit of openness and changing the world and being innovative.

And Google has taken one aspect of that sort of the hacker culture, the the personal projects to demonstrate brilliance and possibilities, and formalized it as the 20% time. And so any engineer at Google can decide what to do that is best for Google with 20% of their time, and they don’t have to get approval from anyone.

And that, I think, really has been a force for innovation. There’s some famous projects that came out of that, like Gmail. And I saw some amazing projects at Apple that were through the same spirit. There was a project called Alice that was like an Alice in Wonderland on the chessboard that was built for the original Mac during that original Mac development time. And there are so many things like that, that were really inspiring.

CW: So how does the 20% thing work? Do you? Is it I’m I use Fridays? Or do I? Or does it is it sort of an honor system about how what 20% really is?

DD: I think it is an honor system and it’s flexible, you can spend the time as you see fit. They do not want you to sort of stack it up and say I haven’t done that 20% for two years. So now I’m going to take two months working on X, that doesn’t work. But other than things like that, your manager supports you in that.

And what I have found over the last few years is that it really plays out in two ways. In one way, because engineering time is scarce. If an engineer volunteers to do a specific thing, then all the infrastructure kind of lines up behind that, you know, the UX, and the testing team and the management and the processes. And so you can actually make projects, you can bring something to life and get evaluated if you can contribute the 20% time. And often, those innovative ideas will gather other 20%ers so you can put together a whole team and actually make something start to happen.

But that is quite uncommon. What normally happens is everyone just decides they would be best off doing their normal work for their 20%. And so nothing ever gets done.

But occasionally, people will say I’m thinking of switching teams, I want to go join this other team. And the way they do that is they do 20% work on the other team. And that allows people to get to know each other, and to decide whether it’s a good fit culturally, on both sides. And then that really greases the wheels for the transition.

CW: Yeah. Does the 20% do things pop out of the 20% and grow into full blown, you know, orchids?

DD: Yeah, absolutely. In fact, I started a little project on Chrome for Android. And it is a real project. Now, it hasn’t launched yet. But if it gains traction, it can get, you know, official blessing. And then…

CW: so so you get you, you get the attention of your manager or people who might be interested in it can sort of split out from the 20% into the real world as it were.

DD: Yes, yeah. And the way it works at Google is we have OKRs objectives and key results. And we put those on a list. And those are our formal goals every quarter and every year. And if something is showing promise, as a 20% project, then often it’ll just get put in the OKR for the next quarter. And now it has become a legitimate project that is an official goal for the team.

CW: You’ve experienced a wide range of different styles and, and models of leadership. And in fact, earlier you had suggested that, that, you know, Steve’s confrontational style was uncomfortable for you. Do you… Do you feel like you work better with a given type or style of leader? Or is there a Is there a way you you feel you work better?

DD: I think for me, I get inspired to bring something to life, to take an idea and make it reality. And that really excites me. And so if I can work on projects that have that aspect, then I’m happy to put in a lot of time and effort. But with almost any project, there’s some grunt work that has to be done. And I’m not very good at doing that grunt work. So a manager that can set goals and deadlines for me and allow me to sort of intersperse the grunt work with the the inspiring stuff that really works for me.

CW: Yeah. One of the things you said when we were talking on the phone was absolutely fascinating, you said that, that you you likened leadership to, to raising children expound on that.

DD: You know, leadership. We often think of it as being the person that motivates an entire group. That there are certain qualities and unique aspects of the leader so that they can get an entire group to work together and head in the same direction.

But that same set of qualities is needed just for you to do something simple like go on a hike, you have to decide where you’re going to go, you have to get inspired, and then you actually have to go do it. And you have to decide along the way, whether to follow through with that decision, or to make changes when new data comes in. And I think that’s one of the hardest things about leadership is knowing when to stick to your decision. And when it’s okay to change.

And some things were very difficult for me with leadership because I was a little brother. And so I was naturally a follower, I think many of us are natural followers. So for me, I’m a natural follower. And just doing something like learning how to dance with my wife. And being the lead in the dance partnership was very difficult for me to do.

But learning leadership through little ways, like that little ways where it’s okay to fail, I think teach you how to become a leader in the bigger ways. Like once you have children, now you’re leading or co-leading a family making decisions, like where you’re gonna live, in, what job to do, and how to raise those kids, as best you can.

And so we have real challenges in leadership in our everyday life. And I think that grows and spills over into our abilities as leaders, as company leaders and business leaders too.

CW: Do you feel like, the more you’ve experienced different styles of people in your work leadership life that’s helped you understand more about yourself?

DD: I think it has Yes, I hadn’t thought of that until you asked me that. But when … leadership is a challenge for many of us. And so we learn what we can do, and we learn what styles we can take. And I was lucky enough to not only have an amazing dad, who showed me how to lead a family, but also amazing technical leaders within the business organizations.

And I could not have led the project that I lead. Now. If it wasn’t for me saying to myself, “when things get tough, I’m just going to make the decision than I thought my previous leader would do.”

CW: Working by example often work, doesn’t it?

DD: It does. Yeah.

CW: Cool.

DD: And there are times when we feel like we can’t do it. But we can play one on TV. I can. I can put on a persona that I think would work. And then it slowly becomes part of you.

CW: Like so many things in life part of part of getting through it is to at least play the part to see if it works, right?

DD: Mm hmm.

CW: Yeah. Hey, Don, this has been a blast. I really enjoyed this.

DD: It’s been a pleasure for me to.

CW: Thank you so much.

DD: You’re very welcome.

CW: Donn Denman has had a fascinating experience working for two of the seminal companies in Silicon Valley. I want to thank him for his time and for sharing his insights with us.

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. The next episode concludes the series on communication as a leader will broach a very touchy subject, swearing in the workplace. I hope you’ll listen. Until then, please remember that each of the several dozen decisions you make today are part of Leading Smart.