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Steve Jobs and Critical Thinking

Quotes from Becoming Steve Jobs: The Evolution of a Reckless Upstart into a Visionary Leader. Bold text in quotes is my emphasis.
Given his uncertain position at the time, it wasn’t surprising that Steve was the more volatile participant. He was willing to admit a few mistakes, even allowing that Bill was correct in saying that Apple should have taken the IBM PC more seriously. Then he took that thought further. “The singular event that defined Apple’s place in the industry in the 1980s was actually not the Macintosh,” he announced. “That was a positive event. The negative event that defined Apple’s place was the Apple III. It was the first example I’d seen in my career of a product taking on a life of its own and developing way beyond what was necessary to satisfy customer demand. The project took eighteen months more than we’d planned and was overdesigned and cost a little too much. It’s interesting to speculate what would’ve happened if the Apple III had come out right, as a lean, mean upgrade to the Apple II that offered incremental features that made it more suitable for business. [Instead,] Apple left a real hole.” Later, he made clear that much of the blame could be laid at his feet: “One of the reasons that the Apple III had problems was that I grabbed some of the best people from that project to do research on how to turn what I saw at Xerox [PARC] into reality.”
Steve admits mistakes, Bill doesn't. Steve doesn't get credit. It "wasn't surprising" because of Steve's external circumstances. This is an example of quality critical thinking.
It was a fascinating admission. Steve was never much for looking back at his own mistakes, and yet during this very public conversation with a friend whom everyone but Jobs now acknowledged as the leader of the computer industry, he was downright contrite. Later in the conversation, he even pulled out a story he’d ripped from the pages of Newsweek to make sure that Bill wasn’t offended by the author’s claim that Steve was no longer his friend. “I tore this out and I was going to call you before I knew we were getting together,” he said, brandishing the page like a trial attorney. “This is not true at all, and I have no idea where they got that.”
This is the very next paragraph, after talking about Steve looking back at his own mistakes in a serious and thoughtful way, and making comments like how it's "interesting to speculate" about such matters. And what does the author do? Declare, without example, and contrary to the examples he just gave, that Steve "was never much for looking back at his own mistakes".

And with Bill, he implies Bill did not admit mistakes during the conversation, but because he expected that he doesn't criticize Bill over it. He's holding Steve to a different standard for no apparent reason. (People who are less succesful admit more mistakes? Bullshit. It can go either way. The guy on top might think he's in a strong enough position he can admit to some mistakes. External circumstances like these simply don't dictate who admits what mistakes.)
Theirs was a quiet, sincere friendship, enabled in great part by Catmull’s maturity. “Steve and I never argued,” he says. “We had disagreements; I won several and he won several. But even early on, when he wasn’t particularly skilled at dealing with relationships, I always felt that he was talking about a topic, not about who was right or who was wrong. For a lot of people, their egos are tied up in an idea and it gets in the way of learning. You have to separate yourself from the idea. Steve was like that.”
Again we see Steve has critical thinking skills others lack. He's called not skilled at dealing with relationships – meaning social graces and appeasement of irrationality – but at the very same time it's admitted he was superior at purely good skills (rather than mixed compromises) like focusing on ideas instead of making things personal.
The two men would eventually know each other and work together for twenty-six years. Catmull says he saw enormous changes over the years, but allows that this, too, was something Steve would never acknowledge. “I look at Steve as someone who was actually always trying to change, but he didn’t express it in the same ways as others, and he didn’t communicate with people about that. He really was trying to change the world. It didn’t come across as him being personally introspective.”
This is another passage with a strange duality. On the one hand it says Steve was good at something. But then it criticizes Steve, on that very topic, somehow. In this case it says he hid his virtues rather than bragging. Normally that'd be praised as humility rather than arrogance. Yet somehow Steve has a reputation for arrogance, and stuff like this is not used to dispel it. Instead, nonsensically, the lesson the book tries to convey here is not to hide your virtues from people around you – the very same virtues the book quotes people who knew Steve talking about, because they were not in fact hidden (which is somehow overlooked).
[Steve Jobs] believed that Amelio, who ascended to the CEO position after just one year on the board, had maneuvered himself into the gig by positioning himself as a turnaround expert. “But how can he be a turnaround expert,” Steve asked me, “when he eats his lunch alone in his office, with food served to him on china that looks like it came from Versailles?”
A nice anti-prestige comment. Steve is held up as this arrogant asshole who thought he was above the rules. Someone like Gil Amelio doesn't get that kind of criticism (partly because no one cares about him, but also partly because he's seen as normal and people don't see much to criticize. he just lacked the mysterious "greatness" quality, which isn't his fault or something that can be controlled – people falsely believe).

But really, Steve was more down to Earth. He interacted with people at his company, he could sully his hands with regular dishware, he was fundamentally more approachable and more a part of the regular world.
The four men became the core of what Catmull calls the Brain Trust—a collection of Pixar writers, directors, and animators who provide constructive criticism to the director of every Pixar movie. It’s a unique idea—the Brain Trust has no authority whatsoever, and the directors are only asked to listen and deeply consider the advice of its members. It became a powerful tool, helping to reshape movies like The Incredibles and Wall-E. But Steve was never a part of it. Catmull kept him out of those discussions, because he felt that Steve’s big personality would skew the proceedings.
Steve Jobs was the best critical thinker of the people involved with this. And he was kept out of the group that provides criticism, because he was too good at criticizing – intellectually – and most people don't actually like criticism and only want limited criticism.

Even with his stature, prestige, reputation, money (he owned 70% of Pixar when it split away from Lucasfilm, I don't know how much later but still a lot), people still had very mixed feelings about Steve because he was especially good at critical thinking.

How valuable is a critic like Steve?
Steve had his own misgivings about Toy Story’s commercial potential, mainly based upon what he was hearing from Disney’s marketers. “Disney came to do a big presentation to us about the marketing,” remembers Lasseter. “They told us they had a big promotional plan with Sears. Steve looks around the room and goes, ‘Has anybody in this room been into a Sears lately? Anybody.’ No one raises a hand. ‘Then why are we making a deal with Sears? Why are we not going for products we like? Can’t we be doing a deal with Rolex? Sony high-end audio equipment?’ And their answer was basically, ‘Um, um, this is what we do!’ He poked holes in every one of their ideas. He was just so logical. Why associate ourselves with products we can’t stand?” (In the end, the most prominent sponsor would turn out to be Burger King.)
You may think that sounds easy, he hasn't done much in this anecdote. And yet, it took Steve to get up and say this. It's a skill worth billions of dollars. The vast majority of people, for one reason or another, are unwilling to be like this. Steve would challenge things and criticize. Yeah not every criticism is super hard to think of, so it's deceptive – a big part of the skill is being willing to think of and say criticism at all, rather than being scared of being declared an asshole and excluded from the Brain Trust and other things.
In early 1998, just a few months after his return to Apple, he asked his chief information officer, Niall O’Connor, to come up with a proposal for an online store where Apple could sell its computers directly to customers, much like Dell Computer was doing then with such great success. O’Connor asked Eddy Cue, who was then an IT technician in the human resources division, to sketch out an initial version of what the store might look like from a programmer’s perspective. “I don’t think Niall thought I was his best person,” says Cue, “but he did think I could deal with Steve, for some reason.” Cue, who had never met Steve and knew little about e-commerce or retailing, sought advice from a number of people, including head of sales Mitch Mandich. “Give him your best ideas,” Mandich told him, “but it won’t matter because we’ll never do it. It would piss off the channels [the stores and distributors that had traditionally sold Apple’s computers].” One week later, Cue, O’Connor, Mandich, and others attended a meeting to review the initial proposal. Cue handed his presentation to Steve—he’d made it visual, because everyone had told him that Steve preferred visual presentations, and he’d put it on paper, because everyone had told him Steve hated sitting through slides, especially in small meetings. All the research seemed to have gone for naught. Steve looked at his pages, handed them back, and said, “These suck.”

Despite his gruff initial reaction, Steve asked the others in the room about Cue’s proposal, and about the basic idea of selling direct to customers online. The executives around the table started to talk about all the problems they could foresee with an online store—tying customized purchases into a manufacturing system that had been built to create computers with standardized configurations; not having any research indicating that customers actually wanted to buy computers this way; and, most worrisome, the potential for alienating Apple’s existing retail partners, like Best Buy and CompUSA. Mandich, who was senior enough to know that an interesting discussion was developing, kept silent. Finally, one of the senior guys opposing the idea spoke up. “Steve,” he asked, “isn’t this all pointless? You’re not going to do this—the channel will hate it.” Cue, who didn’t know any better, turned to him immediately. “The channel?” he exclaimed. “We lost two billion dollars last year! Who gives a fuck about the channel?” Steve perked up. “You,” he said, pointing at the senior exec, “are wrong. And you,” he continued, looking at Cue, “are right.” By the end of the meeting, he had asked Cue and O’Connor to create an online store where buyers could customize their purchases—and to have it completed in two months.

The online store went up on April 28, 1998. As Cue prepared to drive home that evening, he walked past Steve’s office to tell him they’d sold more than a million dollars’ worth of computers in just six hours. “That’s great,” said Steve. “Imagine what we could do if we had real stores.” Nothing would ever be enough, Cue realized. He liked the challenge.
Eddy Cue is now a Senior Vice President at Apple, and has done great work. That wouldn't have happened if the company was run by normal anti-critical people, instead of by Steve who appreciated Cue's critical thinking.

Even though critical thinking is worth billions of dollars, people still don't like it, to the point of excluding even Steve Jobs from things – and it's much harder for most would-be critical thinkers who don't have Steve as their CEO.

Elliot Temple on April 17, 2015

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