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Ken Segall is the author of the New York Times bestseller Insanely Simple. Working with Steve Jobs as his ad agency's creative director for twelve years spanning NeXT and Apple,[…]

Have you ever wondered why your iPhone has an ‘i’ at the front? The iPod, the iMac, iPad, iTunes? Allow us to introduce you to Ken Segall, a veteran creative director and manager of Apple’s ‘Think Different’ campaign, who worked with Steve Jobs for 14 years.

When Jobs was looking for a name for the 1998 computer that would save the Macintosh company, he wanted something that would connect instantly with the Macintosh brand, and show that this computer was built for the internet – for the future. Ken Segall pitched five name ideas, and among them was his personal frontrunner, iMac. Segall pitched it to Jobs twice, but never heard back on a formal decision until the name was printed onto the product, ready for unveiling. There are rumors that Jobs initially wanted to call it the “MacMan”, and what a different world we’d be living in if that was the case. Segall’s simple, effective formula gave way to the entire ‘i’ product suite and lifestyle, and at the core of its success was a beautiful plainspoken-ness, which has become synonymous with his work.

But how to you do simplicity? Where does simple come from? Ironically, simplicity turns out to be quite a complex beast. Segall explains that in business and art, what might look short, quick and simple – whether it’s a product, a business, a work flow, a philosophy, a website, a store – has probably been through a long distillation process; a smooth, nice thing that’s chiseled out from a bulking block.

One practical tip for steering towards simplicity is perspective. Steve Jobs took something seriously that many managers only think of as a pesky obligation: the user experience. Segall says that Jobs put himself in the shoes of the nightmare user – critical, brutal, unforgiving. He focused on the experience of the product, from the first ad you would see, to what the store you bought it in looked like, to the packaging, to opening the box, to reading the instructions, to intuiting its functions. That was his amazing strength as a visionary. The difference between that mindset and a regular attitude is the phrase, ‘Well, that’s close enough.’

This critical mindset is as useful in business as it is in a person’s social life – and here we can perhaps no longer be inspired by Jobs. The kind of self-analysis Jobs embodied in business can translate to self-awareness in friendships and relationships too. What’s the perspective you’re not seeing? Consider people’s experiences with you and how they could be improved. It also extends to the design of the space in which you live. Can you crystalize your home into a simple state? Segall leaves that branch of simplicity more up to Marie Kondo, but he has a lot of wisdom on the art of simplicity. Watch above and learn.

Ken Segall’s most recent book is Think Simple: How Smart Leaders Defeat Complexity.

Ken Segall: How does one define simplicity? Very good question. To me it is just a distilled thought; something that registers quickly; doesn't require a lot of explanations; seems intuitively obvious that kind of a thing. And I think a lot of businesses out of there tend to put things in terms that require more thought study or whatever and I think what made Steve Jobs such a genius was that he had this belief in the power of simplicity and he wanted to ensure that his products embodied that and the way the company communicated with people embodied that. So I think simplicity is this this thing, it's a concept really that gets applied to so many different things. It's not just oh look it's a simple product, it's the whole structure of the organization, the belief system, all that stuff is based on this idea that human beings have a built in desire for simpler things, we just don't like to labor over complex issues. And when someone has something to share with us, whether it's a product, it's service or whatever that the people who really understand that simplicity is a very powerful thing, those are the people who establish an emotional connection with their customers, which is something that Apple is very, very good at doing.

I do think that simplicity is one of the hardest things you can do. And it is deceptive in that way because it looks simple. The way I like to put it is that there is no such thing as simplicity, there is only the perception of simplicity, that every simple thing we see in this world, whether it's an iPhone, obviously years worth of research goes into making the little things that make an iPhone, but you can look at a simple website and we all know, we who create such things know that this beautifully simple site that you've built could have been a result of weeks or months of anguished debate and differences of opinion and arguments and whatever and you end up with something that's simple.

So what's really important is the perception of simplicity. If someone walks away from the experience and feels that it was simple, that's mission accomplished. But I think getting there is really, really hard. It requires all that commitment and energy. It doesn't come easily I guess that's the point, but when you do get there it becomes very worth it. In fact there's a great Steve Jobs quote, it's always about Steve Jobs is in it? He said "It takes a lot of hard work to make something simple but it's worth it in the end because once you get there you can move the mountains." And I think those are great words to live by. H e understood that that was the challenge for Apple was to take really cool products and really cool capabilities and put them in a form that people could so easily relate to and take advantage of without thick manuals and that kind of thing. So that's the real work is making great things simple.

The big question is how do you do it? Where does simplicity come from? And that's a question I hear all the time. I have some humble suggestions on that topic. I think because simple is such a simple thing it comes along with some simple advice. And I think that one of the most important things you can do is simply step back and look at what you're doing through the eyes of the customer. I believe that that was Steve Jobs' amazing strength that he looked at this experience that Apple was creating and he looked at it with a super critical eye what would he think as a customer. I think that a lot of company leaders don't do that as well as Steve. And I think you can criticize your own products and services and your website and all that stuff, you can excuse your own lapses by saying yeah well we did the best we could because we had these certain issues and that's how he dealt with it. But that's the difference between a regular person and a Steve Jobs kind of a person. Steve was on I'm sorry no compromises allowed and if you suggest to me that we're going to compromise your future here is probably not very good.

He believed that the user experience was all important. So I always tell people the best place to start for me is to just be the customer and look at every part of the customer experience from the very first ad they might see to the website to what the retail experience is like and how hard it is to order, when you get product what does it feel like to open it up and start experiencing it and then, of course, the design of the product, the interface, when you need help how easy is it to get support, the whole bit. So you create this experience that is simple for people and fails to confuse them in a very good way. So you look at all the choices some people provide to their customers with all the best intentions. You might go to a website and there are 20 different products to choose from, whereas a company that really believes in simplicity might say here are three and we thought it all out. There are three kinds of people here. There's the small, medium and large or whatever it is that make it easy for you to make a decision rather than force you to think too hard and then wonder after you made the purchase whether you might of made a big mistake, that kind of a thing.

So I think Apple, again, has been very good at doing that kind of a thing so it's customers go away feeling pretty confident that they got the right thing and they enjoy the experience. But all along the way all these decisions that must be made need to be looked at with a kind of brutal bit of self-analysis that is the experience so good that you would actually tell your friends about it and say you got to look at this thing with me; I love this thing and you're going to like it too? Or is it just kind of like okay I buy it and I'm not sure if I would tell anyone about it but it worked for me, that kind of a thing. And I think in the world of Steve Jobs it was always about make the experience like amazingly good and too many people are willing to compromise that away. Simplicity requires that brutal assessment of what is really, really good versus what's good enough and what's good enough isn't good enough, it's got to be really, really good.

Okay so you're Mr. simplicity, what about your personal life? How simple is that? And the answer is not at all really and I'm working on it. But I think simplicity is something that works in business and it should work in your personal life as well. And it's a gratifying way to live and work I think. There's something very satisfying about having this kind of space in your life and the order and the lack of clutter and the firm direction. But life is complicated and it's because life is complicated that simplicity stands out so we got to take the good with the bad. We live in this complicated world but that actually gives us an opportunity to be more noticed by being simple. So whether it's business or personal, simplicity has that kind of power.