Original question from Quora:

If Steve Jobs were handed a pen and told, “sell me this pen”, how would he go about it in your opinion?

My Answer:

Steve Jobs was a smart, strong willed, persuasive dude. He also was a great entrepreneur and a terrible employee.

The question you are asking is essentially someone saying, “I don’t believe you know how to sell. Prove me wrong.” I never met Steve Jobs, but I’d imagine he’d basically tell the person to go to hell in so many words.

The most egregious problem with it is the fact that you are talking to Steve Jobs, the pitchman for Apple.

He made Apple the most profitable and successful company in the world.

Over the years, I watched Steve pitch many products and you knew that as long as the product wasn’t total garbage, he would do a good job selling it. Even if the product wasn’t great, he’d still sell the hell out of it to the Apple faithful.

Asking this question essentially is pretending that Steve Jobs has never sold anything before. It’s like asking Bruce Lee if he can throw a straight punch or side kick or if Brock Lesnar can do a suplex.

If you really want to know how Steve Jobs sold things, go back and watch him introduce the iPhone, iPad, Power Macs, iMacs, iPods, and so on. Seeing him in his element, doing his actual selling is more instructive than some kind of silly thought experiment about how Steve Jobs would respond to a lame interview question.

If you are wanting to know how to sell something like a pen or pencil like Steve Jobs does, I’d guess he would think about what you want and why you want it.

A great example is look at the magical Apple Pencil for the iPad Pro.

That is Apple selling a digital pencil. Look at how they sell it. They call it familiar, but revolutionary.

They sell what you want to do with it - draw and paint.

They sell the technology of having no lag and how amazing that truly is.

Most importantly, they are selling it to artists. Why is that the most important?

Here is why…

Artists are the most likely to buy this. Their profession is to create art, often digitally. So, this tool makes their job easier and potentially makes them more money.

If you are making $50,000 a year to create digital art, a $99 digital pen is a tool to make your life better. I can see how they are able to sell that well.

To people who aren’t artists and don’t live and die by their ability to take notes on a tablet, this product makes no sense.

Sell to people who want the thing in the first place. It’s so much easier.

You want to sell someone a pen? They better be someone who writes a lot with a pen.


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