What Apple’s Triumphs And Failures Have Taught Us About Leadership

Wartime CEO vs Peacetime CEO.


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Last updated: November 16th, 2023

Apple leadership

Last updated: November 16th, 2023

Reading Time: 5 minutes

The iPhone turns 11 this year. Steve Jobs’ gift to the masses has become the world’s highest-selling gadget and, to use a hackneyed phrase, has changed the world.

He also left us with the iMac, iPod and iPad: All game changers—and all emblematic of the Jobs legend and legacy. But has Apple done anything remarkable since Jobs died?

Well, it did launch a super cool set of wireless headphones, which became an instant hit.

And the Apple watch, which even soccer moms are sporting to read texts from their kids without carrying their phones. Both are convenient. Yet…

Hardly Jaw-Dropping.

On Tim Cook’s watch Apple has made iterative improvements to its products, not revolutionary ones. Dare I say, safe. Boring?

To the point where Think Different has become more like Think Just A Little Different, But Not Too Out There.

So if a powerhouse like Apple—with the DNA of someone like Jobs—fails to innovate, what hope do the rest of us have? And, lest we forget the people component of the innovation equation…

(Related: Best 5 Types Of Feedback To Use In The Workplace).

Can You Innovate And Still Be A Good Leader?

Consider the quotes below from some Apple employees, many of whom see Tim as a much better all-round leader than Steve:

“The only thing that Steve cared about was creating great products. The company, the employees were only there to facilitate that goal. Tim is much more worried about everything at the company.”


“Steve was a wartime CEO, while Tim is a peacetime CEO.”

If you’re in the C-Suite (or close to it), which leader are you? And what would make it possible to create an iPhone equivalent at your company while you’re at the helm?

Given our Jobs/Cook comparison, being a revolutionary thinker versus an iterative thinker is tops.

(Related Article: The Key To Unlocking Your Leadership Potential).

What Does It Mean To Be A Revolutionary Leader?

Joshua Kendall, author of America’s Obsessives, claims that Steve Jobs, Thomas Jefferson, Estée Lauder, and Charles Lindbergh all suffered from the same mental illness.

And that this condition played into making them great innovators.

Obsessive Compulsive Personality Disorder.

Not to be confused with its run-of-the-mill relative, OCD (Obsessive Compulsive Disorder), where too many thoughts can paralyse the afflicted.

On the contrary, with OCPD, the sufferer thrives on the excess of mental activity. They are inspired by each and every conflicting thought, become control freaks, work addicts, and don’t care whose feelings they hurt in the pursuit of the revolutionary.

As the story goes, when Jobs built Apple’s first factory in 1984, he spent a lot of time on his hands and knees looking for dust and dirt. For him, these extreme measures were essential if the first Mac computers were to be a success.

Perfectionism As A Human Brand.

This obsessive perfectionism became one of his trademarks.

Pam Kerwin, marketing director at Pixar under Jobs, said he would go nuts if any document contained a single typo:

“He would carefully go over every document a million times and would pick up on punctuation errors such as misplaced commas.”

As the Managing Director of Arielle Executive, a high-end personal branding consultancy which, among other things, crafts top-notch resumes and personal websites, I understand this type of obsession very well.

And I don’t always see the line in the sand at which my high expectations of the team become excessive demands.

But it seems that Jobs took it to a whole new level.

Also as the story goes, he was a difficult and argumentative boss who had trouble relating to others.

But his OCDP gave him the ability to focus intensely on exactly what he wanted—which was to design “insanely great” products. And, as we all know, he doggedly pursued this obsession until the day he died.

So it seems that hard work, leadership skills and intelligence can take you only so far on the innovation spectrum.

To be revolutionary, you need that super-achiever’s disease that manifests as being just a little bit “out there”. Could it be, then, that Tim Cook—with his emphasis on teamwork, inclusion and transparency—is just too normal to lead revolutionary innovation?

Well, consider that “normal” is rarely a word used to capture the essence of the greatest leaders and innovators of our time.

Eccentric? Definitely.

Inspiring? In spades.

Crazy? Probably.

Normal? Never.

Some quick examples beyond Jobs:

  • Marissa Mayer (whose ability to lead and innovate has recently come into question) slept under her desk at Google, clocking 130+ hours of work per week. She was known to shower in the middle of the night when no one was around.
  • Mark Zuckerberg wears a “uniform” of grey t-shirts and jeans so he’s not faced with petty distractions like wardrobe choices.
  • Walt Disney willingly lost everything before he finally succeeded in building his empire.
  • The press called Alibaba’s Jack Ma “Crazy Jack”. His response was that he may be crazy but he’s not stupid.

Speaking of stupid, Jeff Bezos has been quoted as asking his employees if they’re “taking stupid pills”. And he’s known to start senior staff meetings by requiring them to read detailed single-spaced memos in silence.

(Related Reading: How To Create Employee Recognition Programs).

But if we take being a tad mad to a whole new level…

There’s Elon Musk.

  • He’s proposed to colonise Mars by 2024.
  • He stated that any human who takes that first trip to Mars should be prepared to die.
  • Eventually, he expects there to be everything on Mars we’re accustomed to on earth – from iron foundries to pizza joints.
  • He regularly debates whether humans exist in another civilization’s video game.

Now, one might argue that Musk is crazy in a good way.

A highly successful, productive brand of crazy that can’t help but innovate—a bit like Jobs on steroids.

But while you might have your quirks…

You’re Not Crazy.

What’s more, you’re proud to consider yourself “normal”, grounded and well-adjusted. Not to mention, a good leader.

You don’t want to take things to the crazy extreme. After all, Musk has been divorced 3 times and Jobs is, well … dead (and – arguably – may not have been, had his approach to work been less intense).

So, what qualities will inspire the best of your inner mad innovator?

Katherine Graham-Leviss, founder of XBInsight and regular HBR contributor, conducted a study that cites five qualities the most innovative CEOs display.

1. Manage Risk Proactively.

Yes, benchmarking and analysis are important. But the most innovative leaders set a time limit and don’t overthink decisions.

If you can live with the consequences, go for it. Hesitation kills.

2. Be Curious.

Stay open. Learn from your mistakes. Look at setbacks as opportunities.

Keep developing skills in new areas. Create an environment of learning for your employees. As they say in Zen, be the master with the beginner’s mind.

3. Lead Courageously.

Remember the quote about Jobs being a war-time CEO and Cook being a peace-time one?

Don’t be afraid to walk into conflicts with confidence and authority. Make the tough decisions and be accountable. Be humble enough to recognise the leader in others.

(Related: How To Develop A Strong Executive Presence).

4. Seize Opportunities.

Consider the obstacles without over-analysing.

Spot the advantages in changing circumstances. Recognize what intimidates you and work to overcome fear. Don’t go it alone. Have the guts to rely on your best people.

5. Stay Strategic.

Know your employees. Know your customers. Know your competitors.

Know the sweet spot where you maximise the best that each of them has to give. Live there and explore. Maintain order and avoid chaos (a real challenge for true creative thinkers).

And this last bit of advice comes straight from me to you…

Write A Personal Mission Statement.

For example, Richard Branson’s mission statement is “To have fun on my journey through life and learn from my mistakes.”

Your statement or phrase should be a succinct expression of your core DNA.

Knowing yourself and what you stand for will go a long way in boosting your confidence when you find yourself ambling about on the razor’s edge, feeling unsure and alone.

Still wondering if you have what it takes to be a great innovator in your own right?

Consider what Steve Jobs said to Tim Cook on his deathbed about how best to take Apple forward:

“No matter what, don’t ask yourself what Steve Jobs would do. Trust your heart and your gut. The rest will take care of itself.”

– Irene

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