(CBS) More than four years after he retired as manager of the Cubs, Lou Piniella has some advice for new manager Joe Maddon regarding the question that every new Chicago skipper seems to get.

Do you know what you’re getting yourself into?

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“The magnitude of the job is all-encompassing,” Piniella said Friday on the Boers and Bernstein Show. “It really is.”

In a wide-ranging and thoughtful interview, Piniella had lofty praise for Maddon — a friendly acquaintance of his — but also emphasized he’s wading into a whole new world that will challenge him in a way he never imagined. Maddon spent the past nine seasons managing the small-market Tampa Bay Rays, leading them to great success — six winning seasons, four playoff berths and the 2008 World Series.

It’s different vibe in Chicago, where the Cubs haven’t won the World Series since 1908 and you’re under a microscope every single day — in a tiny, cramped clubhouse to boot, Piniella noted.

“It’s not easy,” Piniella said.

“Joe will find out that this is a little tougher job than the Tampa Bay job that he came from … The amazing thing about the Cubs is you win three or four in a row, you’re ready to win the World Series. You lose three or four in a row, the season’s over. It’s the darndest thing in the world.”

That said, Piniella believes Maddon will find success.

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“Joe is a savvy guy,” Piniella said. “First of all, he’s an excellent manager. He did a really, really nice job here in Tampa Bay. He does a really nice job of facing the media. I think he’ll be really good with the young kids the Cubs have there. And I think he’ll bring a winner back to Chicago. I really do.

“Now, is this going to be an easy job or as easy job as the Tampa Bay job? I don’t think so. I don’t think so. You know, there are a lot of expectations in Chicago. Look, I was there four years. In the four years I was there, we had three winnings seasons. We won two division (titles). I don’t think the Cubs have done that in a long time in their history.”

In reflecting on his time in Chicago — which saw the Cubs get swept in the NLDS in 2007 and 2008 — Piniella said he had just one regret.

“If I had to re-do my four years there in Chicago, the only thing I would have done differently … is when we went to the postseason, I should have had a meeting with the team and said, ‘Fellas look, nobody expects anything. Let’s go out and have some fun. Let’s do the best we can, and whatever happens, happens,'” Piniella said.

“I come from a different culture, managing the Yankees and managing in Cincinnati. And I didn’t feel that we had to do that in Chicago. But looking back, I think that was probably the right approach.

“I didn’t do it, and I kick myself in the butt from time to time when I look back at my four years there.

“Unfortunately, we just didn’t get the damn thing done in the postseason.”

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Click here for the full interview with Piniella.