“You can’t connect the dots looking forward” – Steve Jobs & Simon Sinek on “Why”

career vision, leadership

Simon Sinek’s “Start with why” and Steve Jobs’ vision

I have a confession: I am no Apple fanatic. I also think Steve Jobs was overrated as a ‘leader’ in the traditional, managerial sense. Of course, he was a charismatic polymath of colossal work ethics and fanatical commitment to UX. But I think his success came more from his supernatural vision than his chequered leadership. Simon Sinek’s “Start with why” than Steve Jobs’ homemade leadership style.

I actually think he was the first real theorist and practician of the now famous “Start with why” approach. 

His own life was a sustained vision that he shaped, growing up adopted by parents who could not afford to send him to college. Turning obstacles into enablers.

This makes his address at Stanford in 2005 a particularly poignant motivational speech. In it, he applies the genius of his vision looking back and joining seemingly disconnected dots. 

Zen Buddhism, the randomness of adoption and biological parents demands, calligraphy, personal computing, dropping out of college. Love, dropping into college, getting sacked from your own company. Meaning. Death. The grit to succeed despite severe obstacles.

Thing is, as he says “You can’t connect the dots looking forward.” You can’t solve that one. You can’t plan this one out. You have to commit on passion and vision, but trust yourself to listen. To become more connected. More aware emotionally also, of customer feedback. Of the Zeitgeist. 

Steve Jobs’ Leadership vs. Vision


Jobs was a leader, and a great one in some respects, but there were plenty of better ones.

He seemed too big for this life in many ways, too bright to explain or train. Too obsessed with quality to care about party politics even they threatened his entire company.

  • He was said to frequently obliterate staff when giving “feedback” and openly question their intelligence. Some valuable staff left unable to cope with the humiliation or constant fear.
  • He also had a reputation for not doing much training or mentoring or nurturing staff or execs at Apple. He had received little training himself and simply wanted the best experts out there, all the time, anytime. 
  • Ex-Apple staff often underline that he could attract the very best. But that ideally, these experts should also like things just the way he did. “Get it” (his vision) naturally. Not suggest too many things, Jobs occasionally sacked staff who had taken initiative. 
  • Ironically he could sometimes be catastrophically indecisive. He kept John Sculley in the boardroom, despite persisting signs that Sculley did not understand Apple’s culture. Who went on to cobble enough internal support to have Jobs sacked. A cruel low for Jobs. But there again when you love your work and it rests on a sincere, existential “why”… You’ll always come back. 
  • His sense of secrecy when it came to product development led to the creation of silos at Apple. He did not always communicate expectations clearly. This also led to leading to frictions with key execs such as Ron Johnson, the retail genius behind Apple stores.

His leadership on the better side also rested on his total commitment to customer experience. Canning products that had cost millions to develop at the last minute. Or “Get so close to your customers that you tell them what they need well before they realize it themselves.” And do just that.

It is interesting to note that modern digital / inbound marketing enables also just that. Most SME’s cannot afford expensive poll-based research. Those who implemented a successful inbound activity have found that social media feeds them a lot of intel on the market. 

And that the more authentic they are themselves living out their “why” the better the feedback. For one great benefit of social media implementations well done, but often under-reported is that the voice of your customers will come much closer to you, internally.

And that helps at every floor, from product development to sales. 

Simplicity whenever possible. Acting boldly, confidently. Never ceasing to innovate. Drive change. Challenge the status quo.

When you take a step back you see most of his leadership actually rests not on technical skills but attitudinal beliefs and vision. 


Think differently. Start with the why. In many ways, his leadership style was that of cult leadership: An unattainable, otherworldly force of nature that sought the very best and attracted it in its orbit in pursuit of a centralised vision of near-spiritual dimension.

And you don’t build that fanatical engagement with pension perks.

It all rested on very few ideas. Be fearless and passionate. Be creative and invent new ways and new products through intuition rather than endless polling and focus groups. Never, ever compromise. Always exceed expectations at each price point. 

No wonder that kind of corporate culture, authentically expressed, yields amazing results. 

The brand value of Apple beat multiple consecutive world records. In 2016 it as estimated at $145.92 Bn. Only recently was it dethroned by Google, but that might change back to Apple leading when they start really monetising the iPhone X.

His vision of current or future trends single-handedly revolutionised or created entire industries. Personal computing (the Mac, iMac, MacBook Air). Consumer electronics (iPod, iPad). Music (iTunes). Movies (Pixar). Even advertising (the legendary 1984 ad https://goo.gl/rwcrx8).

Nobody could read the Zeitgeist as well.

Contrary to popular belief Jobs did not really invent the modern UX interface in personal computing, with mouse and windows.

Xerox’s Palo Alto labs did.

But he was the only one hopping around in the room with excitement when he saw the prototype run. He even shouted out to the demo engineer “Why are you sitting on this??? Why are you not using this??”

Starting with why and connecting the dots

Simon Sinek’s “Start with why” is now accepted standard marketing ordonnance in terms of digital, content, inbound and social media marketing. That anyone venturing out online to create content and build inbound, relevant traffic on social media, will need to have something genuine to say and live out.

It is however not always that simple to figure out this simple “why”.

Most clients we work with, and it’s entirely normal, never really thought of it. They focus on profit and growth almost entirely and their actual “why” is never thought about, let alone documented anywhere. And it gets drowned under classic brochure-speak, that still make up a majority of companies’ business communication.

Yet it is worth thinking about. To shake off the shackles of glossy, impersonal brochure-speak. To favour risk-taking and foster authentic communication in your company. 

The benefits are deep and lasting. Some are intangible such as increased employee satisfaction and retention. Others are hard, coruscating, cascading cash: Your potential customers buy more for emotional reasons than rational ones. That is, expressly, also the message of “Start with why”.

Does that remind you of any Mac fetichist talking to you about how he was overjoyed to spend £1500 for a Mac laptop? That it is “actually better value for money over the lifespan of the laptop than a PC” etc?

Admittedly, not everyone is Steve Jobs

Apple has hit a much deeper nerve in their customer base than most companies will ever dream of. most of their clients are rabid followers and promoters. They don’t just provide them with a great product, they also provide them with a great “why”.

One that resonates at an existential level with millions. 

Nobody could connect the dots better, see what the deeper need was, or what the deeper need could be. No one could so effortlessly combine the minds of an engineer and that of an artist, to connect dots and shape them into the best product ever devised (if it existed at the time).

He could not explain himself always perfectly for everything seemed so obvious to him. When he first saw a demonstration of the Xerox’s first Graphical User Interface (and mouse!) in 1970’s, he was the only one leaping around with ecstasy in the room, having understood the watershed development this was going to be. And he brought the fire of the gods, to the everyday personal computer user.

Jobs always said you had to do something you like, find someone you like, find a career that you like. That there is no substitute for any of these things, they are entirely worth vesting time and money into, and never letting go. The dots will connect at some point. He showed how thinking differently can be thinking brilliantly if it rests on a vision.

His vision was not just in grasping technological trends. It was also in bringing something to his fellow man, in that vision, it was bringing simplicity and solutions to the overworked individual. Spare him learning DOS. Use a mouse to drag and drop intuitive icons. Funky iMac colours that brightened many interiors.

He was not the best management leader, but the strength of his vision gave him leadership.

He was not the best corporate leader, but he rallied the best around him, and he knew perfectly where to go. And it mattered to him to get there. His vision was the fuel for his job satisfaction. 

As he said in that Stanford speech:

 “You have to find what you love. And that is as true for work as it is for your lovers. The only way to be truly satisfied is to do what you truly believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. And don’t settle.”

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