Cogs Agency recently co hosted another Books for Breakfast event with the author Ken Segall talking about his latest book, Insanely Simple – The Obsession That Drives Apple’s Success.

If you don’t know who Ken is, he was a World Wide Creative Director at Chiat/Day LA  and was a member of the team that created Apple’s legendary ‘Think Different’ campaign.  He was also responsible for that little  ’i‘  that’s part of Apple’s most popular products.

We had the pleasure of throwing a few questions his way for our blog and, as he’s a proper gent, he was only too willing to respond.

If you haven’t read his book yet we can highly recommend it.

So, the questions….

How did you get your first break into the industry?

Ken: After trying to make it as a drummer, a friend in advertising industry suggested that I give it a try. Honestly, I didn’t know a thing about it. I didn’t even know that there was such a thing as a “creative department.” So I took a job at Chiat/Day LA in the production department. When I figured things out, I took some copywriting courses on the side. After just six months in the production department, I followed my girlfriend to NY to begin searching for my first writing job. I started with a list of eight names supplied by my copywriting teacher, and that grew into a list of over 60 names. I interviewed with almost all of them. It took me six months, but I finally met someone who was actually looking for help, and who thought I had the right spirit. Within three months, that agency was swallowed by a bigger agency, but I survived all the cuts simply because my salary was so meaningless.

What’s the hardest interview question you’ve ever asked or been asked?

Ken: One of my favorites is “tell me about the worst boss you ever had and how you dealt with him.” That’s a tough one because you don’t want to look like a complainer, yet you’re being asked to revisit a negative time. Rather than go off on a rant about what a horrible person I had to deal with, I would only speak in general terms about my ex-boss — and focus instead on how I tried to turn a bad situation into a better one. It’s about being a positive person. With every question, you want to come off as a smart creative person, not just a creative person.

What advice would you give a you creative who is now trying to start a career in the industry?

Ken: I was advised to put together a portfolio that showed I had a wide range: travel, beer, cars, technology, whatever. What got me a job turned out to be the opposite of that. After five months of frustration, a headhunter suggested that I choose one category and show how to market a single product in many different ways. I chose technology (surprise!) and blew out about 20 different approaches to selling a product. I did keep the other ads in my portfolio, but they were demoted in importance. By displaying a passion for one category, I became a person of interest to agencies who had clients in that category. I didn’t worry about being typecast because (a) it was my first job and there would be plenty of other opportunities ahead, and (b) technology was my passion and there are a zillion opportunities within that category. Bottom line: if you really love a category, it’s hardly “limiting” — and it helps to show off your passion.

What should people be looking for in a potential boss of new company to work for?

Ken: That’s an easy one. You want to work for someone who has a great creative reputation and whose work you truly admire. As important, you should do your research to learn more about the personality of the person you’ll be working for. Some very talented people are perfectly capable of making your life miserable. You’re not looking for a life of leisure, but neither do you wish to work for a psychopath.

How important is winning creative awards?

Ken: Depends. It’s gratifying when your work is recognized by the industry and your peers, plus it does give you some credibility points. Plus winning awards can do wonders for your self-confidence. But honestly, I never hired anyone because they won a bunch of awards. I hired people because I liked the way they think and believed that their personalities would be a good addition to the agency.

What could we learn from other industries?

Ken: What I love about our industry is that it’s a combination of so many different skills — from creativity and craftsmanship to strategy and relationships. It’s art with deadlines. What we do is probably more akin to a NASA launch than any specific industry, since we normally work in project groups consisting of people with varied backgrounds, working together to achieve a goal. NASA is a great example of groups of people starting with nothing more than an idea, who then turn it into a spectacular reality.

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