Leadership and Career Success—On Purpose: An Interview with James Whittaker

James Whittaker will be presenting three seperate presentations at  Agile Development Conference & Better Software Conference West 2014, which will take place June 1 through 6, 2014. James is presenting two half-day tutorials titled "Giving Great Presentations: The Art of Stage Presence" and "Leadership and Career Success—On Purpose," as well as a keynote titled "Beyond the Web and Apps: The Domestication of Knowledge."

About "Leadership and Career Success—On Purpose":

Line up all the successful people in the world. Take away the pedigree and the prodigies—you know the people who are going to succeed no matter what. Remove the brown-nosers and right-time-right-place lottery winners. And whom do you have left? People who succeeded on purpose. Study these folks carefully, and you’ll find their paths to the top have common themes. James Whittaker exposes the career strategies of the ultra-successful and analyzes them in detail. Learn about personal strategies for identifying high-payoff activities and gain insight into being more effective as an individual contributor, manager, and leader. Discover how to identify and interact with the right set of career mentors and role models. Being successful doesn’t have to be an accident. Join James and learn how to succeed—on purpose.

About "Giving Great Presentations: The Art of Stage Presence":

Every hour of every day in every country where business is conducted, the same scene plays out―dozens of well-paid people sitting in a conference room being bored senseless. Death by a thousand slides. This mind-numbing, soul-crushing, grotesquely expensive experience ends here and now! James Whittaker reveals the secrets to conceiving, building, and delivering a great presentation. Whatever your level of presentation skills, this tutorial will hone them. Learn how to build a compelling story from the ground up. Receive advice on how to remember and recall that story as you deliver it. Learn how to use oratory and literary instruments to make the story come alive for your audience. Do your part to put an end to crap presentations―attend this tutorial.

About "Beyond the Web and Apps: The Domestication of Knowledge":

Since the dawn of computing, we've invented only two ways to get work done―the web or apps. We hunt for information on the web or we gather functionality from the app store. In each case, users must take the initiative to find the information they need. We've become used to this life of hunting and gathering, but its time is ending. A new era of domesticated information and functionality is dawning. In this new world, the web's information comes to users when and where they need it. Apps won't have to be installed and updated; their functionality will simply find its own way to users when it is needed. James Whittaker describes the technologies that are enabling this new era of domestication and describes how both developing software and using computers will fundamentally change the world in which users—and especially developers—live and work. New knowledge APIs and cloud functionality are waiting to make your apps more capable than ever before. Come hear about it. It's going to affect us all.

Cameron Philipp-Edmonds: Today we have James Whittaker, who will be speaking at Agile Development Conference & Better Software Conference West 2014, which is June 1 through June 6. James Whittaker is a technology executive with a career that spans academia, start-ups, and top tech companies. With a PhD in computer science, James worked for IBM, Ericsson, SAP, Sysco, and Microsoft. In 1996 he joined the faculty at Florida Institute of Technology, where his work in Y2K testing and software security earned many awards. James' first stint at Microsoft was in Trustworthy Computing and then Visual Studio. In 2009 he joined Google as an engineering director and led teams working on Chrome, Chrome OS, Maps, and Google+. In 2012 James rejoined Microsoft to build the Bing information platform. Of his five books, two have been Jolt Award finalists. Did we catch everything, James?

James Whittaker: Yeah. You caught some things I didn't even know about or I forgot.

Cameron: Now, you're giving three presentations at Agile Development Conference & Better Software Conference West 2014.

James: Yeah. They're wearing my ass out, man.

Cameron: You're giving a presentation called "Giving Great Presentations: The Art of Stage Presence," another presentation called "Leadership and Career Success—On Purpose," as well as a keynote titled "Beyond the Web and Apps: The Domestication of Knowledge." You are also somewhat of a testing legend. With that being said, I have a few questions regarding that. The first question is, with a career that includes experience with start-ups, work at industry-leading tech companies, and spans of time spent in academia, you have certainly made your mark on testing. However, what do you feel your legacy is to testing?

James: I purposefully exited testing twice, really. In the 1990s testing was really a necessary evil. We had serious quality problems. The industry wasn't that good at software development. Software was becoming really important, and bugs were just absolutely prevalent. No one knew how to test for them. It was a really noble profession in the 1990s because somebody had to step in and figure it out. There weren't a lot of people with development skills going into testing in the 1990s, and so those of us with a development background really had a pretty big impact on how to do it, what to do, what were the important problems and really laying a lot of the foundation for the work that continues today.

So I don't know. You asked about legacy. I don't think anybody can determine their own legacy. That's going to have to happen over time. I was one of the original thought leaders around model-based testing, understanding input and output structure, and how those sorts of things can be used to test software. I think I was also one of the people who really started looking at the code itself and trying to understand what is it that's going wrong, what are the patterns in code that people are continuing to get wrong.

Especially now, but even in the early 2000s, testing was beginning to lose its luster and, in fact, really beginning to become a self-fulfilling prophecy. The more testers you hire for a project, the more testers you're going to need, which means the less developers have to have skin in the game. That really became a problem.

I actually got out of testing and into computer security in the early 2000s because I just felt like testing had become less of a problem. We had solved it. We had given developers all the tools that they needed. By staying around and continuing to do testing, we were preventing those developers from having to actually grasp those tools and learn them. I wish more people would have abandoned software testing in the early 2000s, because I think it would have sped the industry along.

There are still people in the testing industry preaching the same things they were preaching a decade ago, two decades ago. I think they've done the field a disservice. Software testing is not a role. Software testing is an activity, and it's an activity that PMs and developers need to have on their radar. That's why I say the more testers you have on a project, the more testers you're going to need. The lack of quality will become a self-fulfilling prophecy.

I moved out of testing, moved into security, and then moved out of security, and now I guess the area I'm in is knowledge and big data.

Cameron: You also have done a lot of writing. In an article you actually wrote for StickyMinds in 2012, you wrote about the importance of connecting testers and coordinating work. Why is communication really that important to testing?

James: I wrote that article a decade before it was published. They wanted a testing article. I love StickyMinds. I love Software Quality Engineering. I've been speaking in their conferences for a long time, so I gave them that. It was very old. Something about four horsemen and the apocalypse. I don't remember what the title was. Anyhow, I'm ready to move away from the testing subject, because I just don't think about it that often anymore. Let's talk about some of my newer work. Is that OK with you?

Cameron: Yeah, sounds great. You're doing a session titled "Leadership and Career Success—On Purpose," and that speaks to the ability to identify leadership traits in others so you can leverage that knowledge into becoming a more effective leader and gaining career success. With that in mind, when you think of leaders who have catapulted their leadership skills into successful careers, who really comes to mind?

James: I haven't modeled this lecture after any specific leader. Part of developing your own leadership skills is finding people who you admire and can lead. I'm giving two tutorials at Better Software. The first one is on stage presence, and the second one is on leadership. Mostly they came out of people asking me, "How do you do this stuff?" Actually, the request on stage presence, "How do I give a good talk?" I'm actively giving that lecture now at Microsoft. It's a monthly internal thing. We get fifty, sixty people together. It's a two- or three-hour presentation/course because it's both. It's a ton of fun.

The leadership one was actually supposed to be a management course. I was asked to put down some ideas about how to manage people because I managed a lot of people at Google. I had, I think my peak was 110 people under me and then when I was in Bing, I think it was 450 or so people under me in my report chain. The idea was how do you manage people. When I began to look at these two subjects, stage presence and management, the stage presence one was fairly easy. I've been giving talks for a long time, so I know what has worked for me and where I've screwed it up royally. In the course I don't talk about the screwups; I only talk about the good stuff.

The management stuff was a lot more difficult because I found that I'm actually not a very good manager when I really began to look at my activities. I always got rated highly as a manager, but I don't think it was because of managing. I think it was because of leading. I have always preferred to lead people in the right direction and then just get out of their way, which is almost the exact opposite of management. It became a leadership course because I realized I wasn't very good at management, and I don't want to teach a course on something that I’m not very good at.

Cameron: You spoke about being a leader and being a manager. In your tutorial you talk about how leadership and leadership skills allow you to not only be a better manager, but also to be a better contributor. How does it make you a better contributor?

James: It makes you a better contributor by understanding what's not being covered. Leading a project means understanding every aspect of the project, understanding what are the hard parts of the project, what are the easier parts of the project, and where the gaps are in getting work done. I think good leaders are good at understanding those gaps and then stepping in and doing some work. It's very rare that you have a great leader who can't contribute in some way. If you look at Steve Jobs—great leader and a great contributor. He had ideas that not only founded the project but made it successful.

If leaders don't have the ability to contribute, they're not really leading. They're dictating. They're doing something that's not leading. Keeping your individual skills sharp in some form or fashion, whether it's design, whether it's in development, whether it's in seeing the future, whether it's in taking control of some aspect of the project, is really important.

It's also important to get your followers to continue following. No one wants to follow a leader who doesn't have any relevant skills. I've reported to people before that didn't have any relevant skills. All they could do was talk about stuff or all they could do was push people and micromanage. No one wants to work for somebody like that.

Keep your skills relevant in some area. Your skills are going to go down. I'm not the developer that I used to be, I'm not the tester that I used to be, because I don't concentrate on those things as much as someone fresh out of school who's doing it ten, twelve hours a day.

You've got to have the ability to contribute in some form or fashion. If you don't, you're not a leader, and you should step aside and allow somebody else who still has relevant skills to do it.

Cameron: You also talk about the need to find the right mentor and the right role model.

James: There's nothing more important, seriously. You're born with a certain amount of DNA that's going to take you so far. Everything else are things that you learn from someone else. I am a mixture of all the people that I have learned from over my whole life—teachers in high school, teachers in college, my older brother, who's really had a strong influence on my personality, my PhD adviser Harlan Mills, my current boss, who really has been one of the better managers that I've had over the years. I am a mixture of all of these different people. You've got to recognize that and you've got to understand that you have choice here. You can choose who you want to be like. You don't have to just take whoever you have.

Back in the '60s and '70s and '80s, you had no choice. You just couldn't connect to a lot of people. Your line of sight from your desk represented every mentor you could choose from, and you were stuck with these people. Not anymore. The world's a much smaller place. I am currently being influenced by people in other countries. I'm being influenced by people I've never even met before just through social networking and online. I've got Twitter relationships with people who I think I'm having an effect on and they're having an effect on me. It's not just one mentor. It's lots of mentors.

For any given person it's just a piece of their personality or a piece of their leadership skills or a piece of their technical ability or a piece of their insights. It's this idea of collecting mentors and composing from lots of different people, their ideas and their thought processes, that's the perfect mentor for you. You are who you learn from. Choose wisely and make sure that you're doing this consciously and it's not just happening on your behalf.

Cameron: You talk about choosing wisely. Are there certain traits that you look for that someone else should definitely look for when they are choosing a role model?

James: They've got to have something to teach you, man. You've got to be really good. It's so crucial that you take control of this. You literally are who you learn from, and you have control of that. You just can't take what's given you. You take the good with the bad, and you throw the bad away and you really learn from the good. It's a process—it's really important that you're in control of it and that you're doing this consciously.

Cameron: You talk about how leadership isn't something that happens by accident. It's something that you make happen. You go out and you find role models and you find people to mentor you and you find knowledge to gain. Let's have a little hypothetical here. Let's say somehow you stumbled into some success. Is there a way to keep that success rolling by doing something? Is it as simple as throwing away the bad stuff and holding onto the good, or is there another trick to the component there?

James: I have certainly stumbled into success before. I have made some bad moves, known they were bad career moves, and they turned out to be good moves through a series of accidents. Sometimes it's who I met. Sometimes it's a project I'd get assigned. Sometimes it's the role on the project I'd get assigned that I ended up turning into something good.

It's very important to be conscious of yourself and understand, are you in this failure mode right now, are the things that are happening bad to you, are the things that are happening good to you? And understand why. If you don't understand, "Hey, this particular part of my career is not good for me," then you're going to be stuck there.

You really have to be consciously and constantly introspecting. What am I doing right now? Is it good for me? What am I learning? Is there anything that I can take away from this, or is this just one of those experiences that I need to try to get out of as quickly as I can? You need to be conscious, constantly introspecting yourself, constantly introspecting your situation, and understanding what you're learning from it.

Ultimately we are a collection of lessons and a collection of stories that happened to us in our lives. Every lesson can be good if you approach it consciously and understand whether or not it's good or bad for you and digging out the lessons from that.

Cameron: You did say earlier that you also are giving a presentation on giving great presentations. It's titled "The Art of Stage Presence." What do you really hope that attendees take away from this tutorial?

James: Let's face it. We are boring the s*** out of millions of people every single day sitting through just dull—I mean, we call this death by PowerPoint, right?

Cameron: Right.

James: We don't call it discomfort by PowerPoint. We don't call it slightly irritated by PowerPoint. We call it death. There's nothing more permanent than death. If nothing else, I'm hoping that the people in that class can stop this. I have a little subtitle, "Putting an End to S*** Presentations Since 1989"—something like that.

We need to set the bar higher. This is a painful, expensive, huge waste of time having all these people sitting around being bored to death. I want to get an army of good presenters out there that just set the bar higher. I want people in the audiences to understand, "Hey, this is a waste of my time. This is boring. This is demotivating and I demand better." That's the way I think it's going to start. It's kind of what I did in software testing. I got audiences around and I said, "Look, this is important. Let's start taking this seriously. Let's start doing this right."

Stage presence is really needed out there. I could ask any of these courses I've ever taught, "How many people have sat in a boring presentation?" Everybody raises their hand. How many people have sat in a boring presentation in the last week? Everybody raises their hand. How many people have sat in a boring presentation yesterday? Everybody raises their hand. Then I tell them, "If this gets boring, walk out. Vote with your feet. Get the hell out of here." No one's ever walked out on me. I thought they did a couple of times, but it just turned out they had to pee and then came back and they weren't bored.

This is important. We're spending a lot of money wasting a lot of people's time, and it needs to end.

Cameron: This is really good for anyone of any sort of speaking skill set. If they're new to speaking or if they've been speaking, actually, for a long time.

James: Look, I can't turn you into Steve Jobs. I can't turn you into me. I can't turn you into Martin Luther King. But I can make you better. I can make anybody better.

Cameron: Fantastic. You also mentioned that it's really important to not only tell a story but build your presentation from the foundation up. Why is it really important to build from the basics and tell a story?

James: The storytelling is the most important part of that. How you build your presentation, whether it's from a ten-thousand-foot view down or whether it's from the details up, I'm flexible on that. The storytelling piece of it is crucial. It has to have a contiguous whole. It has to have a strong start. You have to stick the landing, and the pieces in the middle have to be right, and they have to be on point. I lay out the structure. How you build it, front to back, top to bottom, I don't really care. I lay out the structure of a good story in this talk. It's actually my favorite presentation to give. I gave it this week and really enjoyed the hell out of it.

Cameron: You also mentioned the importance of literary and oratory instruments that can be used to help build that story. What are some of those ...

James: I've stolen from the literary, right? Literary means writing. We're not writing these down. Oratory instruments are literary instruments that are taken out of the literary realm and put into the speaking realm. It's really crucial because they make a story come alive. You can take a story and tell it in a very boring way. You can take a story and tell it in a very interesting way. A lot of times the difference between boring and interesting are those oratory instruments. I do it partly by demonstration, where I'm speaking and presenting and then I stop and go back and talk about the instruments that I use. I also showed some videos of people who are really, really good at using certain types of oratory instruments, so we build the catalog through example.

Cameron: You have some great advice and you have a lot of great knowledge and wisdom as far as making people better leaders . . .

James: Keep saying great. This is good, man.

Cameron: OK. And making them greater presenters, and you're just making them greater overall. What is some advice you would give to someone who is a young business person, someone who's just now starting out?

James: You mean to make them successful, or to make them a better orator, or . . . ?

Cameron: Really anything. Let's say better career success.

James: First of all, my advice is do something that's worthwhile. There is enough picture-taking apps out there. There's enough social apps out there. I know they're worth a lot of money, but at the end of the day, do something that's going to make humanity better. There are hungry people out there. There are brain researchers that need good technical talent. There's some really important problems out there that are being solved.

I feel like a lot of the start-up industry right now is just going for the dollar, and it depresses me. Big companies buying small companies and making them go slower or taking them off the market I think is a real shame. The real innovation for the future is going to come from small companies. People need to solve problems that are actually important to humanity. We have so many of them. Better ways of taking pictures of our cats and various body parts isn't particularly high on my ranking of a contribution to humanity.

Cameron: You talk about giving presentations. What if someone's very nervous? A lot of people get very nervous when giving presentations. What are some tips ...

James: No, I cover that.

Cameron: OK.

James: No hints, man. Go to the presentation and you'll understand how to tame your nerves. I was nervous. I've been a nervous presenter, and I still deal with nerves even though I present all the time. It's not only a matter of dealing with nerves, it's a matter of turning them to your advantage, which can be done.

Cameron: Is there anything else you'd like to say to the attendees of Agile Development Conference & Better Software Conference West 2014?

James: Yeah. In advance I'll tweet what bars I'm going to be hanging out if you want to buy me a drink—important stuff, got to keep the vocal cords loose for all these talks.

Cameron: Once again, this was James Whittaker. He'll be speaking at Agile Development Conference & Better Software Conference West 2014, which is June 1 through June 6. Thank you so much, James.

James: Yeah, you're welcome. See you in Las Vegas.

Cameron: All right, sounds great. Thank you.

James Whittaker is a technology executive with a career that spans academia, start-ups, and top tech companies. With a PhD in computer science, James worked for IBM, Ericsson, SAP, Cisco, and Microsoft. In 1996, he joined the faculty at Florida Institute of Technology, where his work in Y2K testing and software security earned many awards. James’ first stint at Microsoft was in Trustworthy Computing and then Visual Studio. In 2009, he joined Google as an engineering director and led teams working on Chrome, Chrome OS, Maps, and Google+. In 2012, James rejoined Microsoft to build the Bing Information Platform. Of his five books, two have been Jolt Award finalists. Follow James on Twitter @docjamesw.