Long-Lost Leadership Lessons from Steve Jobs

Shortly after Steve Jobs died, Walter Isaacson’s authorized biography came out. It was an influential book. Unfortunately, the lesson many entrepreneurial types took away was; you gotta be an asshole if you want to get things done. While Steve’s personality was the stuff of legend, I don’t think it’s why he was so effective. It really was his uncanny judgement.

I worked at Apple in the late 90s when Jobs returned as the CEO. Back then, it was a much smaller company, and one of the guys I worked for reported directly to him. So I had a chance to see him operate up close.

Following, are some of the leadership lessons I learned and contexts in which they took place.

  1. If you have a reputation for being mean, the few times you’re nice is more effective. I never experienced his legendary temper, but I did see him get prickly with people. He was aware he made people nervous, so he acted pretty casual when things were going right. He was pretty funny too, which disarmed those who expected the worst.
  2. Make demands that matter. I was on a team that had to pitch Steve ideas for his keynote speeches. He liked to do demos that showed Macs were faster than PCs. He needed 3 screens and the conference told him he’d have to do it with one. He didn’t come right out and say it, but he was ready to pull out if they didn’t accommodate his request. He had leverage and used it. Not just because he was Steve, but because it made for a better experience for the audience.
  3. Answer tough questions with tough answers. Back then, people didn’t think Apple was going to survive, let alone prosper. Those of us who stuck around or weren’t laid off had put up with pay freezes, lost benefits etc. Steve would have town hall meetings where you could ask him anything. This one woman who had a reputation for asking the tough questions. She asked Steve when can we expect to see things improve for the employees. His response, “The Valley is hot. So why are you still here? Those who stay will do it because they love the company and the mission.” At least he didn’t insult our intelligence. Instead of a sanitized answer, it was the painful truth.
  4. Get rid of people that aren’t behind the vision. Before the iMac shipped Steve asked for sales forecasts. One guy didn’t believe the iMac was right for his market and went with existing product lines. He had a chance to reconsider, and didn’t. He was gone. Steve was betting the company on the vision of the iMac. Had the existing products been cutting it, we wouldn’t have needed a big bet.
  5. Give blunt, flippant answers to blunt, flippant questions. We were in a Customer Advisory Board meeting full of execs from big companies. Steve had laid out a simple explanation of his plan to get the company back on track. One of the guys asked, “I’m not just a customer, I’m an investor. How are you going to ensure me that you’ll be around next year?” Steve replied, “I just told you.” Unsatisfied with the answer he pressed on, and said, “But how?” Steve said, “How about not losing a fucking billions dollars for starters. How’s that?” That’s when I knew we were in good hands. For too many years, Apple was run by people who listened to guys who cared more about the stock price than what we actually made.
  6. Explain unpopular decisions. For a brief moment in time, there used to be Mac clones on the market. Steve killed the clones and a lot of people were unhappy about it. Instead of avoiding the topic, he brought it up during his keynote speech at Seybold. He not only spelled out why it was bad for Apple, but why it was bad for everyone. Whether it was the right thing to do is debatable, but at least he explained his decision and owned it. (Bonus YouTube clip of the speech).
  7. Listen to your customers, just know which ones are wrong. Steve understood the difference between economic buyers and users. At the aforementioned Customer Advisory Board, the audience was made up of economic buyers. They wanted the same thing from Apple that every other PC manufacturer was offering – cheap homogeneous boxes that could be centrally managed. In that same meeting Steve questioned why we were even talking to one of the guys who admitted he doesn’t even use a Mac. Real users weren’t asking Apple to be more like Acer, Gateway, or Packard Bell (the leading makers of commodity PCs back then). They wanted more of what made Apple different in the first place.
  8. Take advantage of your position. One of the first moves that started the turnaround of Apple was the $150M investment from Microsoft. I don’t know what happened between Steve and Bill Gates, but he leveraged his personal relationship. It was a unique move, not just anyone could pull off.
  9. Court objections. When people told Steve “no” directly, and indirectly, he would ask “why not” and follow up with plenty of “what if” questions. Before Apple had their own retail stores, Macs were poorly represented in various retail outlets. One store, CompUSA, told him why they didn’t even try to sell Macs. So Steve said what if we took over the experience and the store-within-a-store concept was born. Mac sales went through the roof at those stores. They may have said no, but he questioned whether they were thinking big enough.
  10. Be focused and tell others how it’s done. Steve mentioned the book, “Focus” by Al Reis in a meeting. I was excited because I had read it and had unsuccessful explaining it to co-workers. Steve summed it nicely. If we’re not the best at something, we shouldn’t be doing it. He used printers and servers as an example. We sold both at the time, but weren’t first in either category. To get this level of focus he used a 10-3-1 rule. He’d ask people to list their top 10 priorities. Then of those 10, which 3 are most important. Finally, he’d ask which 1 are you going to do. His point was you can’t do 3, let alone 10 things simultaneously well so don’t even try.