Lessons Learned from Working with Steve Jobs by Ken Segall

For 12 years, it was Ken Segall’s job to make people love Apple. As creative director for NeXT and Apple, Segall worked closely with Steve Jobs to pivot Apple from near bankruptcy to a value of $153 billion within the course of a decade. Segall has documented the secrets to Apple’s success and how other companies can apply them in his New York Times bestseller, Insanely Simple: The Obsession That Drives Apple’s Success, and his follow-up book, Think Simple: How Smart Leaders Defeat Complexity.

SPEAKING.COM: Why do you say “simplicity is the most powerful force in business”?

SEGALL: Because I can! I think we can all agree that every human being is born with a preference for simplicity. We all choose the simple over the complex—and this is a preference that can be monetized by any business.

Customers react positively to simpler products, simpler services, simpler websites and simpler marketing. Employees are more motivated and fulfilled when they’re not burdened by complexity.

Steve Jobs demonstrated these things in the most spectacular way by guiding Apple from near-bankruptcy to “most valuable company on earth” in just 14 years. Of course, Steve had many talents, but at the core of his business philosophy was his love of simplicity. You could see that in Apple’s products, packaging, marketing, retail stores, internal processes and even its corporate structure.

That said, being simple is not simple. As Steve himself put it, “Simple can be harder than complex … but it’s worth it in the end, because once you get there, you can move mountains.”

SPEAKING.COM: Why do you think simplicity can be so difficult?

SEGALL: I believe it’s because simplicity is such an obvious, seemingly instinctive thing that many people take it for granted. They assume if something’s simple, it can happen on its own, but it rarely does. If we don’t make the effort to create and nurture simplicity, complexity quickly grows through the cracks. It takes the form of unnecessarily complex products and product choices, confusing websites, squandered resources, and internal processes that grow more tedious, frustrating, and even destructive over time. Too often, as companies expand, new processes and workarounds take the place of fresh thinking and employees who work in complex environments tend to become demoralized or de-incentivized.

SPEAKING.COM: What are the signs that your company has crossed the line from simplicity to complexity?

SEGALL: There are two sides to the simplicity story—what customers experience and what employees experience.

It’s important to assess complexity in both places. The best way to do that is to look through the eyes of others. As a customer, see how you feel about the entire customer experience, from advertising to purchase to learning and using the product or service. Ask yourself one critical question: is the experience so good that you’d actually tell friends, family or colleagues about it? If not, why? For example, if the buying process seems confusing, it might be that you’re offering too many choices, which can actually backfire, freezing customers into inaction.

As an employee, do you have a clear vision of the company’s mission and values? Are you frustrated because internal processes are too long and complex, or involve too many opinions, or require too many levels of approvals? If you can’t get a good picture of that yourself, ask your employees. Trust me, when it comes to making things simpler, they’re more than eager to help.

SPEAKING.COM: What was “simple” about the way Apple as a company operated in comparison to other organizations?

SEGALL: I had an interesting experience in contrasts. At one point, after working in the Apple world for many years, I moved across the country to work on Intel’s marketing and it was a shock to my system. I had become used to working in a world where the goals were well-defined and product strategies were simple, as was the process of creating advertising. In the Intel culture, nothing came easy. We spent more money over a longer period of time, and ended up with work that was noticeably of lesser quality. Years later, I returned to the world of Apple, and it was as if a thousand-pound weight had been lifted from my shoulders.

One major reason it was simpler to work with Apple was that the ultimate decision maker was involved in every major project from the very first briefing. At Intel and many big companies, that person might not appear until the very end of the process. At that point, a thumbs-down means that weeks or months of work have been wasted.

Apple was also unique in the way it gave responsibility to “small groups of smart people.” Small groups feel a sense of ownership in a project and become emotionally invested in a positive outcome. In other words, they’ll work crazy hours for the company’s success if necessary. However, in many big companies, project groups can be overpopulated to the point where progress becomes difficult and people feel like cogs in a wheel.

Smaller is always simpler—and often far more effective.

SPEAKING.COM: Steve Jobs is one of the most covered and artistically depicted business figures in modern history. What have some of those depictions gotten right about Jobs’s professional side and what have they perhaps omitted or misconstrued?

SEGALL: Most of the articles, books and movies about Steve put his personality first. They highlight his quick temper or his often brutish behavior. All of us who worked with Steve would agree that he had those traits, but we’d also agree that this wasn’t the “whole” Steve. He was far more complex. I don’t condone his negative behaviors, but I can offer a little insight.

First, his outbursts weren’t as frequent as most people imagine, given the press. When he did have an outburst, it was triggered by something specific—an unexpected setback, substandard work, disappointing design, needless complexity, a deviation from Apple values, and so on. His flaw was that he was so passionate about these things, he couldn’t control his temper when obstacles were thrown in his path.

Overall, working with Steve was unlike anything I ever experienced elsewhere. It was simultaneously surprising, exciting, inspiring and even fun (yes, he had a great sense of humor). And of course there was a bit of danger mixed in, because there was always pressure to perform, and you knew what would happen if you didn’t.

Another of Steve’s positive attributes was accessibility. I could call him any time, day or night, in the office or at home. In fact, my favorite interactions with him were our late-night conversations. That’s when we’d go over ads or scripts, talking about concepts and details, right down to particular choices of words and phrases. Steve was an excellent writer, and his opinions often led me to make changes. On the other hand, he could be swayed by a good argument, so I never felt that he was “micromanaging;” he just wanted to make his opinion heard. It felt like we were collaborating to make the best possible product—which is how Steve interacted with his engineers and designers as well.

How he found the time to pay attention to so many things in a day is something I will never understand. Bear in mind that at this moment in time, Steve was working three days a week at Apple and two days a week at Pixar, where he was also the CEO.

SPEAKING.COM: You have a keynote called “Working the Steve Jobs Way.” What are some principles of Steve’s management style that anyone can adopt—and what are some aspects that maybe only worked for him because of his unique level of talent?

SEGALL: Over the years, Steve managed to retain the mindset and energy of a young person building a business. No doubt, his way of running a company would have been shunned by most big-company CEOs.

I think Steve’s philosophy can be traced to the days when Apple operated out of his father’s garage. He loved entrepreneurial adventure and he hated bureaucracy. In Steve’s thinking, committees were poison, small groups of smart people could accomplish anything, and great ideas needed to be nurtured and protected.

None of these things are out of the reach of any smart business person. The reason we don’t have more Steve Jobs types in the world is that Steve was unique—a charismatic blend of visionary, artist, humanist and businessman. In rebuilding Apple, he had another big advantage—he was the founder who embodied Apple’s values, and he was returning to reignite the company’s spirit. He had license to revolutionize and a personality that could seemingly allow him to accomplish things by sheer force of will.

You and I don’t have these advantages. Trying to emulate Steve Jobs’ personality isn’t likely to get us too far. Yet we can still embrace the principles that helped Steve guide the rebirth of an iconic American company.

SPEAKING.COM: Now that you can look back, what do you see as the critical turning points for Apple?

SEGALL: There are many key moments in Apple history—the first Macintosh, iMac, iPod, iPhone, and so on. For me, one moment towers above all them. It wasn’t a product, it was a philosophy.

Steve believed that it was important to “do fewer things better.” He demonstrated that in a historic way on the day he unveiled the first iMac. At that time, Apple was making more than 25 distinct products—desktop computers, laptops, laser printers, scanners, cameras, Newtons, you name it. None were exceptional, yet together they were eating up Apple’s resources for R&D and marketing. So, minutes after he introduced the iMac, Steve announced that Apple was literally killing all but two of its many products. He put a simple four-box grid on the screen, and explained that from that day forward, Apple would make only four products—a home and pro version of a desktop and laptop. Only the home laptop was missing, and he promised that it would arrive soon after. Not only did he eliminate most of Apple’s product line, he also killed dozens of products that were then in development.

This was Apple’s “fresh start,” and it changed the company in the most profound way. There would be no more mediocre products. Every Apple product would be a leader in design, quality and functionality. Steve believed that people would pay more for a product if they perceived it was worth the price. By doing fewer things better, Steve turned around a dying company and established a philosophy that would guide Apple into a new future. The rest is history.

SPEAKING.COM: How has Apple changed since the passing of Steve Jobs?

SEGALL: Given that Steve Jobs was unique, I don’t believe Apple can ever be the same without him. The question is, can it still be great? By all accounts, Steve did a superb job of burning his values into Apple’s DNA, so that it could continue to thrive without him. In his last days, he encouraged Apple’s leaders not to guess what he would do, but instead think in line with the company’s values.

How has that worked out since Steve passed away? Honestly, it’s been spotty. Employees might avoid asking “what would Steve do?” but it’s natural for customers to ask and in recent years, Apple has given people good reason to wonder. Some key products have gone neglected for uncomfortably long periods. Software quality has been questioned, ads have become more ordinary and announcement events are less exciting.

This is disappointing to me, but it’s not exactly surprising. It’s tough to replace Steve’s judgment and taste. In addition, the competitive landscape has changed dramatically, and audiences have become bigger and more sophisticated. 20 years from now, I imagine Apple will be an entirely different company, just as Disney changed so radically in the decades that followed Walt’s passing. Time marches on, customers evolve, opportunities arise and obstacles appear. That’s business. I’d like to believe that Apple’s most cherished values will remain intact and it won’t lose its ability to delight customers with things they never imagined.

SPEAKING.COM: You’ve written that Steve was the most demanding client you’ve ever had. What is your advice for people who are working for a demanding client or boss, particularly when that person in unhappy with the work you’re doing?

SEGALL: I learned one very important lesson in my first years in advertising, and I believe it even more today. That is, business is about relationships, and relationships create trust. If you don’t have that kind of relationship with your client or boss, you will forever be pushing the boulder uphill (or failing to push it at all).

You can’t expect to build this relationship until you have a few victories under your belt. That client or boss needs to see the evidence before they can believe in you. Also, you need more than business skills to succeed with difficult clients and bosses: you need people skills, and some of the brightest people struggle with that. I’ve known brilliant creative people who flamed out because they were incapable of creating positive relationships that moved business forward.

Unfortunately, sometimes you must deal with people who are immune to positive relationships. To them, you will forever be an order-taker. They’re not interested in joining forces to do great things. If you’re in a situation like this, you need to be happy for whatever victories you might achieve. If you are to succeed on a grander level, you’ll likely have to do it elsewhere.

SPEAKING.COM: You are the person responsible for that iconic “i” in the name of so many breakthrough Apple products. What was your inspiration for this and how were you able to convince others that it would be a winning move?

SEGALL: The concept behind the very first iMac was “the easy way to the internet.” Remember, back in those dark days, getting onto the internet meant that you had to buy a modem, find an internet provider, go through a configuration process, etc. iMac was designed to make it easy. You’d just power it up and follow the prompts.

So the name iMac didn’t take too much digging—i for internet and Mac for Macintosh. Of course, nothing came easy in the world of Steve Jobs. He harshly rejected the iMac name once and then not-so-harshly rejected it a second time. It was only after he put the name on a model that he started to warm up to it. As he would later explain, he thought it looked great on the machine—it was short, simple, and gave the radically designed computer some personality.

Naming any product is tricky. As this story implies, it is unwise to be locked into your first reaction. Imagine how you might have reacted if one of your people brought you the name “Google.” It’s pretty goofy, yet it turned out to be one of the most memorable and identifiable names in business history. The debate over names is both intellectual and emotional. One of our arguments to Steve in support of “iMac” was that the i could be a foundational element for future product names. Imagine that! But at that point, Apple made only computers. We weren’t envisioning the full potential of that little “i.”

SPEAKING.COM: Your first book, Insanely Simple, focused on Steve Jobs and Apple. What was the motivation to write your newest book, Think Simple?

SEGALL: When Insanely Simple was published, I started to speak about the principles of simplicity behind Apple’s success. It was gratifying to see audiences eager to apply these principles to their businesses. Following my speeches, many asked, “Where do I start?” I then realized that I needed to dive deeper into my topic. Understanding the principles is one thing—putting them to work is another.

Think Simple was my way of closing this loop. I interviewed more than 40 business leaders in different countries and different industries to talk about the power of simplicity. I wanted to learn exactly how they put simplicity to work in their companies. I wanted to know what was missing in their business, and how simplicity helped solve their problem. My goal was to inspire readers to action, shining a light on the methods used by business leaders in very different circumstances. My research convinced me even more that in a complex world, simplicity is a powerful competitive weapon—and learning from others’ success is a wonderful way to create one’s own.

To bring leadership and marketing speaker Ken Segall to your organization, please contact Michael Frick at: Mike@Speaking.com