Oesterreicher had not always been seen as the most promising of comers. As he rose through the ranks, nobody ever said that Jim Oesterreicher wasn't a decent guy. Nobody ever said he wasn't tough, either, whenever his responsibilities required it. And nobody ever worked any harder. Many, however, thought he lacked the leadership qualities necessary to become a top Penney executive. Still, at the end of the day, "the Farmer" had always gotten the job done.
Some called him that behind his back, less out of disrespect than as a warning. It was as if to say, "Be careful and don't pull anything fancy on this guy. He's basic. Go highbrow and he won't understand it and you're in trouble." And Jim Oesterreicher's interests did seem limited to the basics in his life: the business of retailing (not fabric, not style, not trends, but the business of retailing), plus family, church , and community service. Allen Questrom, the man who eventually replaced Oesterreicher at the top, once ran the Neiman-Marcus chain. Jim Oesterreicher would never have gotten to first base at Neiman's ” assuming the unlikely possibility of his even applying for management training there. 
As often happens, Oesterreicher changed when he became CEO, and shortcomings surfaced that seemed odd for a top man.  If the essential difference between a senior executive and the CEO is the difference between follow-through and decision making, Oesterreicher's inability to make important decisions until the last minute was a big problem. He also found it difficult to communicate exactly what he wanted. Sometimes it seemed as if he was giving clear instructions, but when the meetings were over, subordinates were often left grabbing at air. He did command immediate attention because he was quite self-assured and had always done his homework. But did he really have the vision or the soul of a leader? People wondered. He was quick with business platitudes and epigrams, but how about an idea?
Once, a rising upper-middle manager with access to the Golden Crescent sent Oesterreicher a memo politely requesting his thoughts on the most important aspects of an executive hire. She was making a presentation to an important outside body (a career boost) and wished to feature his quotes (clearly to be the meat of her piece). Later that week she met with a Golden Crescent executive on another matter. As she sat down, he regarded her with an unhappy chuckle and said, "So you're the one causing all this trouble."
"Huh?" was all she could reply.
He held up a copy of a memo. Hers. "This trouble," he said, sliding it to her. She saw that Oesterreicher had scrawled a note on it:
Copy this to Management Committee ”
What do you think?Pls give me your thoughts.
She produced a sheepish smile and mumbled, "Oh, m'god. I only wanted a couple of his own thoughts, whatever came to mind." She picked up the memo copy and indicated a sentence . "I made that clear."
"Ah, yes," said the executive. "And now I've got to put some people on this, have some meetings, watch over my own damn memo ”I mean report."
"I never dreamed."
"Well, now you know," he said. "It's always wise to think twice when you deal with Jimmy-O."
 Oesterreicher once said, "When I graduated I was married and had to get to work. The business school bulletin board had only two notices that made sense for me: selling vacuums and J. C. Penney. Vacuums paid better, but I thought that a big company like Penney was better for the long haul. And I had majored in retail, so that was that."
 Was this an illustration of Penney's insularity weakness? Would another CEO with such drawbacks be found among the Fortune 50? Probably not.