Jeff's Daily Dose: Don't Get Eddie Bauer'd

I grew up on Eddie Bauer.

My first real winter jacket was an Eddie Bauer down parka. It was the color of a school bus (and roughly the size of one too!) But it was indestructible. I wore that thing through college in Philly, through winters in Chicago, through years of abuse it had no business surviving.

Yesterday, Eddie Bauer filed for Chapter 11 bankruptcy. Again. For the 3rd time.

The CEO said the team "could not implement changes fast enough to fully address the challenges created over several years." Read that sentence again. They saw the problems. They knew what to do. They just couldn't move quickly enough.

Sound familiar?

That's not a retail problem. That's a leadership problem. And it's the same one sitting in your conference room right now ... wearing a lanyard & pretending AI won't change their job.

Every leader knows their cash runway ... the number of months before the money runs out. And your team has a skills runway too. It's the amount of time before the way they work today becomes irrelevant.

Eddie Bauer's product development team had a skills runway. It expired. Their supply chain team had one. It expired. Their marketing team had one. You get the picture.

Most leaders have never calculated this for their own teams. Don't let it happen to you.

This week: Run what I call an "Obsolescence Audit" ... Not on your products. On your people's workflows.

Pick 1 department. Sit down with the manager. Go through every recurring task that team performs weekly. For each one, answer 2 questions.

(1) Could AI do 80% of this task today? Not perfectly. Not autonomously. But 80%. If yes, mark it red.

(2) Does anyone on the team know how to use AI to do it? If no, mark it red again.

Any task that's double-red is a ticking clock. That's your skills runway shrinking in real time.

This isn't about replacing people. Eddie Bauer didn't go bankrupt because they had bad employees.

They went bankrupt because their people were doing 2019 work in 2026. The brand was sturdy. The skills weren't.

Most upskilling programs fail because they train people on AI Tools instead of Workflows. Teaching someone to use ChatGPT is like handing them a sewing machine & expecting a jacket. Doesn't work that way.

Instead, take your double-red tasks and build a 30-minute workflow around each one. Input, prompt, review, output. (Here's my step-by-step on how to do it). Make it a documented, repeatable process anyone on the team can follow. Not a training session ... a recipe card.

One documented AI workflow per week. That's it. In 90 days, you'll have a dozen processes that are faster, cheaper, better. And a team that doesn't feel like the rug is being pulled out from under them.

Eddie Bauer had 100 years of brand equity. Didn't matter. The parka couldn't save them. Neither will yours. Don't let your team's skills expire before you notice.

The leaders who layer up on upskilling now won't end up in Chapter 11 of their own transformation story.

0 comments