Derailment of Leaders- Profiling Steve Jobs

The corporate world citizens operate on two myths – “We all are great leaders” and “We all have bad bosses”. We cling to these two fallacies with our dear life, most probably because if we let it go, corporate life may become unbearable. These two paradoxical statements make us feel better about ourselves as the delusional views cushion us from harsh realities.

The problem arises due to corporate world’s obsession with leadership. Interviewers question a 21-year-old fresher in the first interview about his/her leadership skills. After six months, s/he will give an opinion how the CEO doesn’t have adequate leadership skills. An employee will risk his/her career if s/he admits that they are good managers and do not have adequate leadership skills. This is despite the fact that most leadership surveys show that 50% of the managers are ineffective leaders.

On the humorous side it reminds me of Scott Adams definition of leadership – “Leadership is an intangible quality with no clear definition. That’s probably a good thing, because if people being led knew the definition, they would hunt down their leaders and kill them.”

On a serious note, I couldn’t help contemplating about Steve Jobs, considered the most successful CEO in our times. He is one of the few CEOs who was thrown out of the company he formed and came back to succeed beyond anyone’s expectations. On the positive side, people viewed him as a visionary, innovator and a driving force. Moreover, his negative traits were equally prominent. His teams said he suffered from “distorted reality”, bullied them no end and was extremely insulting. His professional career shows that in some ways he was an insufferable bad boss and an incredibly good leader. The complexities of his character make an interesting case study to assess leadership derailment.

I read his biography by Walter Isaacson and mapped his leadership skills to the traits mentioned in Michael James Benson’s research paper titled “A Walk on the Dark Side of Personality & Implications for Leadership (In)Effectiveness.” Briefly, it states that derailed leaders have same traits as successful leaders. However, they have additional traits and personality flaws that cause derailment. In Isaacson’s book, initially Jobs showed most of the traits that result in leadership derailment. In his second coming at Apple, he showed more maturity and balanced it out. A mellow version of his intense personality made him more successful.

It is important for risk managers to understand the derailment traits for leadership. Enron, WorldCom, Satyam are prime examples of leadership gone wrong. Prevalence of derailment traits and major personality flaws cause leaders to take unnecessary business risks, create dysfunctional work cultures and have low focus on corporate governance. As top management drives the risk culture in an organization, it is worthwhile for risk managers to assess their derailment characteristics.

In the following paragraphs, I am discussing five derailment traits and am exemplifying it with Steve Jobs life. Before you start reading it, remember all leaders have these traits. Leaders possessing these traits in low to moderate qualities continue to be successful. However, excessiveness of these traits causes derailment.

1.       Ego-centered

People close to Steve Jobs thought that he felt a strong sense of abandonment due to his adoption. This propelled him to consider himself special,  i.e. not required to follow norms of regular people. His ex-girlfriend Redse even thought that he had narcissistic personality disorder.

An amusing story about his employee badge showed his false sense of entitlement. On Apple’s formation, Scott assigned employee badge number #1 to Woznaik and #2 to Jobs. Steve demanded badge #1 and when he didn’t get it, he asked for  badge #0. He kept the badge, though Bank of America still processed his salary as employee number #2.

 His personality flaws showed in other small things. For example, he didn’t want a “reserved for CEO” parking slot, however parked his car in slots reserved for handicapped people.

 His ego-centrism drove Apple in murky waters. He wished to project the image that he didn’t work for money and took a salary of $1 per year as CEO. In 2000 when the board offered him $14 million stock options, he refused and asked for a plane. Subsequently, he demanded $20 million stock options. He received backdated stock options and although he didn’t make any monetary gains from it, Apple got some negative publicity as SEC investigated the case. Walter commented that – “On compensation issues in particular, the difficulty of defying his whims drove some good people to make some bad mistakes.”

 2.    Manipulation

 Everyone thought Steve Jobs was a master manipulator.  Sometimes, for him there was no difference between truth and lies. Bud Tribble one of his teammates said Steve doesn’t accept facts, which do not fit, into his picture. He said, “Steve has a reality distortion field. In his presence, reality is malleable.”  

 Another colleague Andy Hertzfeld said that even if one knew that Steve was manipulating, a person still was influenced. He stated- “The reality distortion field was a confounding mélange of a charismatic rhetorical style, indomitable will, and eagerness to bend any fact to fit the purpose at hand.”  

 Adding to the trouble, his teams complained that if their idea were a good one – “he would soon be telling people about it as though it was his own.”

 Apple employees though knew they had a difficult boss, still considered themselves lucky to be working for him. He inspired people to do what they thought was unachievable. Most probably because manipulators are great at cajoling, persuading and flattering people into complying with their wishes.

However, this did create a dysfunctional culture in Apple. Due to his oscillating behavior, his staff handled him like fragile glass. Most probably, Apple lost quite a few top performers because of this treatment given to them.

He definitely lost his job as a CEO because his manipulations caused turmoil in Apple in 1985. Apple board ousted him out and Sculley remained.

3.    Micromanaging

In some ways, Jobs can be categorized as a control freak. He chose to integrate hardware and software of his products to control customer experience. At one point of time, he banned download of applications to iPad and iPhone that defame people, were politically explosive or pornographic. He morally policed his customers.  According to him, he was providing his customers – “Freedom from programs that steal your private data. Freedom from programs that trash your battery. Freedom from porn.”

Throughout his career, he was at war with Bill Gates on open versus closed platforms. Gates promoted open systems while Jobs ardently opposed it. Though he professed to belong to hacker counterculture, he didn’t want people to be able to use Apple’s platforms without permission.

Even in designing and developing products, Jobs controlled every aspect of the decision-making. His teams while appreciating his capacity to go into the details, did resent lack of authority to some extent. He had the final say even on the look of the cord and sockets of the products. He ran the organization at 10,000 feet and zero feet.

The awesome bit is that with his ideas and approach he managed to change six industries and developed path-breaking products. In this, his customers were not complaining, his competitors were. His control philosophy made the technological world sit up and take notice. One has to marvel at it, and contemplate whether micro managing has benefits in some situations.

4.     Intimidating

Steve Jobs learnt his most effective intimidation trick from Robert Friedland in college. He unblinkingly stared intensely at others and them kept silent for a long time to unnerve opponents.

Moreover, if some project or product didn’t meet his “insanely great” standard, the product was shit and the guy was a bozo. His colleagues referred it to as “hero/shithead dichotomy”. He voiced his unedited opinions without the normal social graces that caused many of his teammates to breakdown emotionally. . His frequent unfiltered scathing comments were hurtful and created a fear factor. Although, known to be emotionally intelligent, he was unrepentant of mistreating others.

Though his behavior looked like my way of highway, he succeeded as he appreciated the people who confronted him. His teams could push back and if Steve found the person capable, he would respect the person. His Mac team gave an annual award to the employee who did the best job of standing up to him. “Jobs knew about it and liked it.”

However, in the second stint as CEO, his intimidating nature negatively affected independence of the board. For instance, he invited former SEC chairperson Arthur Levitt to join the board. But, when he read Levitt’s speech on independence of board, he withdrew the invitation on phone.

5.    Passive Aggressive

 Jobs was blatantly aggressive; hence, this trait didn’t fit his personality. However, his partner Steve Woznaik did show this trait to an excessive level. For instance, Woznaik was hesitant of participating in Apple in a leadership position. He said he was happy that – “I could stay at the bottom of the organization chart as an engineer.” He never attempted to be a manager or leader. He played the good guy image to the hilt. While he appeared satisfied for Jobs to take up the mantle of bad guy and fight the corporate battles.

Woznaik claimed in his biography that he did a job for Atari to remove chips and Steve cheated him of the bonus. He claimed  – “Ethics always mattered to me, and I still don’t understand why he would’ve gotten paid one thing and told me he’d gotten paid another. But, you know, people are different.” He further added – “I would rather let it pass. It’s not something I want to judge Steve by.”

 Steve Jobs on the other hand denied the allegation and said that he has always been fair to Woz. He said in his defense – “In mean, Woz stopped working in 1978. He never did an ounce of work after 1978. And yet he got exactly the same shares of Apple stock that I did.” It showed Woz avoided confronting Steve though didn’t mind maligning his reputation. Woz projected an image of childlike innocence. I suspect, without Steve Jobs driving force and personality Apple would have collapsed if Woz had become the torch-bearer.

Closing thoughts

Leadership is a complex phenomenon and the more I read about it, the more I think Scott Adams definition is accurate. There is a lot of truth in it. However, as risk managers we cannot take leadership derailment traits lightly. Excessive derailment traits create a dysfunctional organization culture. They are a harbinger of unprecedented risk taking activities. Uncontrolled behavior can put organizations in peril. Hence, risk managers need to devise ways to monitor it. They must ensure proper checks are incorporated in succession planning for early detection of derailment traits.

“One more thing”, what do you think it takes to become a Steve Jobs of risk management?


1. New Explorations in the Field of Leadership Research: A Walk on the Dark Side of Personality & Implications for Leadership (In)Effectiveness – By Michael James Benson

2. Steve Jobs – Biography by Walter Isaacson

2 comments on “Derailment of Leaders- Profiling Steve Jobs

  1. Excellent detailed post Sonia – well researched and insightful. I do think good leaders need to do the big picture thinking AND the small detail and that is often overlooked. I see this trait in artists such as Prince.

    Here’s my review of Jobs – not the person but his impact on the world

    My best to you


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