I led a small marketing team at Sears briefly in 2015. The experience was so terrible that I quit ~5 months into the role (at great financial cost) and was so depressed that I took the same amount of time off to stop hating myself for ever getting involved.
Almost every person I worked with at Sears—from division presidents to middle managers to the janitorial staff—truly believed that Sears still deserved to be a leading American brand, and that the rest of the country just hadn’t figured that out yet. Things I heard all the time from people at Sears corporate:
I think this bizarre cognitive dissonance is the single largest driver of Sears’ failure. Sears waited for someone, anyone else to notice that the world isn’t working the way it should (as evidenced by their unjust decline). A significant chunk of the people I worked with at Sears had been with the company for more than ten years, and they held this attitude despite years of no compensation changes and benefits like 401k match disappearing. They kept this attitude as they bought SHLD shares at a slight discount through the employee stock purchase program (for roughly $25/share in 2015, worth $0.45 or so today). They maintained this attitude as they paid $1.25 per cup of drip coffee every morning (that they made themselves, via keurig, in the employee break room).
This was particularly frustrating for me as a B2B marketer. Business customers won’t hesitate to ask hard questions like “how will all the news about your trouble with creditors impact your ability to fulfill my orders?” and they expect real answers. If your value proposition boils down to “we promise we’re just as good as our competitors,” why should anyone care that you exist?