Knowing When To Embrace Leaderhip’s “Dark Side”

Self-confidence dialed too high can become arrogance. Too much attention to detail (a good thing) can become perfectionism (a not-so-good thing). But sometimes mitigating or attempting to control one’s weaknesses or flaws can have a deleterious effect.

Knowing When To Embrace Leaderhip’s “Dark Side”


Last week marked 6 months since the passing of Steve Jobs, and I and many others have finished Walter Isaacson’s well-crafted biography on the talented and complicated Jobs.

With the continued–and growing–interest in the leadership lessons of the former Apple leader, someone could make a lot of money selling WWSD (“What Would Steve Do?”) bracelets. In fact, a recent Wall Street Journal article described the phenomenon of business leaders trying to imitate Jobs in order to achieve Apple-like success.

Through Isaacson’s compelling book, we learn in great detail about the dark sides to Jobs’s leadership skillset. Yes, we knew he was brilliant. And charismatic. He was an intense and uber-focused master of both the big picture and the nitty-gritty. He was a customer-obsessed artist who built “insanely great” products and ultimately an extraordinarily successful organization (so far).

But he also exhibited many of what we call “executive derailers.” He was known to be dismissive, perfectionistic, arrogant, attention seeking, volatile, distrustful. He had an enormous need for control. He had a drive and set of standards that were off-putting to many people. He was parsimonious with praise and would have never been in the running for the “Mr. Empathy” award.

Despite all that, he changed our world, mostly in good ways. And he was able to achieve so much not despite his dark sides, but perhaps because of his dark sides. Yes, that’s provocative and sounds almost counterintuitive. But here’s the reasoning…

It’s a well-accepted principle that strengths when used in excess can become flaws or vulnerabilities. “Self-confidence” dialed up too high can become “arrogance.” Too much “attention to detail” (a good thing) can become “perfectionism” (a not-so-good thing).


But sometimes mitigating or attempting to control one’s weaknesses or flaws can have a deleterious effect on the strengths. One can write off Jobs’s obsessive attention to product and design detail as micro-management and failure to delegate, but there is no denying that the man’s almost fanatical need to approve much of the design minutiae helped make his devices coveted and cultish. Could a lower-level design team have achieved the same results? Would the ceiling of the Sistine Chapel be as exquisite if Michelangelo had some lower level apprentices paint some of the background texture? We can only speculate.

I’m suggesting that a less edgy, less intense, less arrogant, less dogmatic Steve Jobs would not likely have achieved the results he did. In fact, his towering strengths–the brilliance, the focus on being both aspirational and inspirational, the tenacity–could not have played out the way they did if he had controlled his “dark side.”

What makes an activity like bungee jumping so exhilarating is that is also simultaneously terrifying? Dial back the terror and you’ve dialed back the thrill. It’s a gestalt relationship, a package deal. So too, I think, with the temperamental artiste-technologist, Mr. Jobs.

This is not to suggest that we are all off the hook for trying to manage or mitigate our flaws and inadequacies, despite the tempting appeal of the “just focus on your strengths” crowd. It’s not okay to purposely park in handicapped spots because the rules don’t apply to you. It’s not okay to intimidate or browbeat or stare people down, and leaders who do so are erring if they think they are being Jobsian. They are likely just being jerks. It’s enticing to think that just by being intense and highly demanding and demonstrating a “reality distortion field” (as Jobs did) that we can indeed be like Steve. Um, not likely. And wearing the black turtleneck probably won’t get you there either.

What, then, is the “so what” about what we can learn–and apply–as leaders regarding the leadership lessons of Steve Jobs? My thoughts for consideration:

  • Avoid trying to cherry-pick Jobs’s prickly personal style and think it will work for you. Remember, he was also a life-long vegan, he abandoned his first daughter, and earlier in his life usually avoided both shoes and baths, so be careful of selective adoption of Steve-isms.
  • Read what Isaacson has to say on the issue in his recent HBR article about the leadership lessons of Steve Jobs. Isaacson provides 14 widely applicable wise practices, such as “Focus,” “Simplify,” “Impute” and “Engage Face-to-Face.” None of his suggested lessons were of the nature of “Belittle and Intimidate.”
  • Remember that Jobs was an individual who had a unique set of skills, personality traits, and life experiences and who played on a stage in a particular industry having unprecedented technical advances in a particular period of time. Jobs’s leadership and management style would not likely have had the same results in the insurance or oil exploration or agriculture industries. Even the “push for perfection” which was a Jobs trait is not apropos everywhere.

Derive the lessons–the right lessons–that will work for you in your world. And use those insights to help change that world. That’s what Steve did.


–Mike Hoban is a management consultant and can be contacted at

[Image: Flickr user Scott Smith]