Good Afternoon, Tom, said the A.I.

There’s nothing quite like getting an email addressed to Tom when your name is Jim.

Or even when the name is right, getting content like:

  • Subject line: “We want to work with you”
  • Opening: “Hello. I hope all is well.”
  • Opening: “Hello Jim, I just wanted to check, have you checked my previous e-mail?”
  • Or, “Hi Jim, free Thursday afternoon?”

The trouble with automation is automation.

In one scenario, I arranged a meeting with someone who sounded like he had an interesting product. I was speaking over Zoom with someone pitching me without any visual except our names on the screen, when I finally had to ask, “Jerome, are you a robot?”

Jerome burst out laughing and I knew he was human. He had been on a roll, pitching off a script, excited to have “gotten through” to a human being with his automated solicitations. But his tone was all wrong. His reactions to my questions had that “pause” that makes you think there’s something automated going on in the background, like that feeling you get when talking on a phone to a computer. But, when he laughed, he proved he was a human.

Automation has its place, but…

I was speaking to a very smart associate who was telling me about his company’s latest foray into automation. They were going to try to automate the entire specification process for a building by buying and integrating technology companies.

He was very excited about it. Genuinely.

When he concluded, I asked if saw the movie Taken and if he remembered the scene where the bad guys took the hero’s daughter. The hero, on the other side of the world, was a CIA killer. He (Liam Neeson) was talking on the phone to the bad guy. He told him if he let his daughter go, nothing would happen. But if he didn’t, he would find him and kill him. The bad guy answered Liam with two words: “Good luck.”  Then smashed the phone.

I replied to my friend with the same two words about his company’s idea.

You can’t automate everything.

I heard a presentation by Imran Chaudhri, the designer of some of the automated products many of us use daily, including the iPhone (he invented the user interface for the iPhone). You should listen to it. He spoke of a world driven by devices that all of us can connect to anytime, anywhere. “Beneficial AI” is what he called it. Trust the device. His company believes technologies should be trust based.

His example was someone running. Music you listen to is scored to where you are. Or another example where you are about to give a presentation, and you are advised meditation will help you calm down.

Technology will handle everything for you, instantly, allowing you to remain in the moment.

The question I would ask is: who is doing the advising? If technology, I would ask why trust technology to advise you of anything?

When you look at a sunset, are you “in the moment” or do you need technology to do something to put you “in the moment.” Can a device appreciate or understand a sunset?

But that is exactly what automation does. And the more we trust it, the more freedom of choice we give up.

And therein lies the challenge – for all of us. How much choice do you want to give up? What kind of choices do you want to give up? What is choice anyway when you don’t know “who” is defining your options?

How Much Do, Could, Would, Should We Automate?

I reminded my friend in our conversation of something Dostoevsky said: “Man is not a math formula. Sometimes he just likes to break things.”

Human behavior is complex. Perhaps more complex than anything on the planet, including climate.

The more complex the thing, the less you can automate it. Even when you think you’ve figured behavior out, something happens that throws your calculations off.

When Deep Blue, the system built by IBM beat world chess champion Garry Kasparov, the promise of machines seemed to get locked in.

But chess is a closed system: there are only so many moves you can make to checkmate the king.

Life isn’t like that. Marketing isn’t like that.

And when you get solicitations like the ones in this post, well, who wants to talk to (or work for) a machine?

Nothing beats a human being researching a target, learning about the target’s needs, and then creating a pitch to win the business.


But all of that takes time, and the promise of all automation is to save time. But unless you put in the time, all of your relationships will be superficial. A Tom will be the same as Jim or a Bill or a Jerry. Empty words in an email string that’s been merged and purged.

Would love to hear your thoughts on automation. Thanks for reading.

For more insights follow interlinejim@twitter

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