I Killed Sears, And I’m Sorry

Today’s news that Sears has finally filed for bankruptcy protection has me thinking about my own role in the legendary retailer’s demise at the hands of the internet.

In 1995, along with a business partner in Chicago, I founded an “online presence” consultancy called Automatic Media Group. We consulted for businesses, connected clients to internet service and built websites with software tools that were incredibly primitive by today’s standards. A pair of technology-friendly creative types, we understood that the internet and the web were going to change how most businesses communicated.  We knew that the web would completely transform internal and external messaging and workflow for practically every business. We set out to show companies how to manage that change.

That decade, Chicago’s giant business sectors were retail, insurance, finance and logistics. We had friends working in some of these companies, and we could get meetings with decision-makers.  Sears — specifically its catalog production team based in Hoffman Estates — was a major target for us.  My partner and I had equal strengths in the print and creative worlds, and we were ready to talk to the makers of the world’s most famous mail-order catalog in their own language.

We could see the digital future: the Sears catalog’s pages would not be mailed in three-pound bricks of glossy dead tree to millions of postal customers. Those pages were headed instead toward the World-Wide Web.  And knowing this was half the battle, we were very sure.

But once we were in the room, the catalog’s future wasn’t the topic. Instead, the team asked us about something more modest: how to put internet email onto everybody’s desk. Two thirds of their hundreds of Mac computers weren’t on a local area network (LAN) and a third were on a hodegepodge of different, not-working-well-together network technologies. They asked: is email compatible with Aldus Pagemaker and Photoshop 4.0?

Yes it is, but first things first, I said. A bunch of things need to change, because the network itself is the point.

I then let them know that they were asking the wrong questions, not seeing the big picture.  Instead of talking about their email, I told them that the catalog team needs to create a LAN where everybody is on the same network, because the network is the point. That they should use 10Base2 NICs and AppleTalk and accounts from our ISP and…

Something was going wrong. I saw their eyes glazing over.

“We just need email,” they said.

I wasn’t getting through to them, so I doubled down on communicating the vision. “I think you need way more than that. Ultimately, your catalog pages need to be delivered to the world using the network, using the web, not paper mail. This is just step one.”

Long story short, we were shown the door.

It took time for me to see what had gone wrong. I was so sure of the future — so right — that had I more or less overlooked what the client was asking for. They were asking for X, which meant they were thinking about X. But I was looking beyond X, to its context. That was the big mistake. Being right about that context didn’t matter much at that moment.

In hindsight, we weren’t in the room because we were right. We were in the room to listen to the client.

Had I listened to them talk about their smaller problem, instead of fixating on their big problem, we could have solved the email on the team’s own terms, and, having stuck around, we might have let what would have naturally followed — e-commerce and all the disruption it brings — present itself for our likely involvement and guidance.

Today, I’m indulging in a bit of tongue-in-cheek — I obviously didn’t “kill Sears”.  But it is true that the once-powerful brands of Sears never connected in time to the serious technological and company-cultural guidance they needed to avoid today’s fate two decades later.  If I had known what I was (and wasn’t) doing that day, maybe we could have changed that at least a little.

In my defense, I was a very green twentysomething, and this was my first company. I was the first entrepreneur in my family. I was so inexperienced that  I didn’t even realize I was in a sales role, let alone that I was screwing it up.

Sorry, Sears.

You’re welcome, Amazon.