I mountain climb. I climb rocks, 20,000-foot peaks, and ice. Climbing is a superb physical workout that simultaneously provides a spiritual and emotional high that leaves me totally refreshed and recharged when I return to work.

But, as the legendary climber Ed Viesturs wrote in his book, No Shortcuts to the Top, a climber has to know when to say "when." He has to objectively assess his strengths and weaknesses, and make sure they're perfectly aligned with the summit he seeks to climb. To do otherwise is to court disaster.

The same thing is true in business. I know because I was once the right climber trying to climb the wrong mountain.

Eighteen years ago, I accepted a position as president of a $100-million division of the legendary ad agency, J. Walter Thompson. I was promised by the 65-year-old CEO that, after a brief interregnum, I would inherit the throne. 

But, then, everything went wrong. I'd seriously misjudged the mountain:

  • My outgoing, self-deprecating sense of humor continually clashed with the autocratic chief executive's no-nonsense approach.
  • My management-by-walking around style didn't sit well with the CEO's "us vs. them" mentality. He despised what he saw as my "fraternization" with the troops. I still remember being called on the carpet and told, "Look, you're one of the patricians. Stay away from the plebeians." Imagine his response when I chuckled and said, "But, Jim, I don't look good in a toga."
  • My continuous searching for "what's new" was at odds with the chief executive's old school ways. He saw no reason to embrace a then newly emerging thing called the worldwide web. He said it was a fad and would disappear.

Needless to say, I didn't last too long at JWT. In fact, I still call it my 15 months in hell. But, it provided a critically valuable lesson: An executive must be sure her values and strengths are in alignment with an organization's before making any sort of move.

Here are three leaders who, like overly confident mountain climbers, chose the wrong mountain to climb:

  • Carol Bartz and Yahoo. Bartz's blame game and foul-mouthed, longshoreman-like strong arm tactics ran 180 degrees to the warm-and-fuzzy company culture she inherited. Bartz angered existing employees while alienating analysts, the media and the board. When her decisions didn't improve the stock price, she was fired.
  • Jimmy Carter and the Oval Office. Carter will be remembered as one of America's worst presidents yet, thanks to his charitable work and peace brokering, perhaps the best ex-president. His focus on minutia and Debbie Downer personality during the oil and Iran hostage crises, respectively, were exactly what Americans didn't want or need. Ronald Reagan's upbeat, positive, and powerful personality was the perfect match for a down-in-the-dumps electorate and he crushed Carter in 1980.
  • Terry Francona and the Boston Red Sox. Francona lost his job as manager last season because his values and style didn't evolve to stay aligned with a new cast of players. Francona had piloted the Bosox to two World Series championships with a laid-back, let-the-players-play style. But, as fresh blood replaced aging stars, Francona didn't keep his finger on the pulse of the clubhouse. So, while he stayed cool, the players drank, caroused, and did everything but stay focused. As a result, the Sox staged one of the greatest late season collapses in baseball history. And, well, Francona was fired. 

Great climbers update their mental checklist with each new climb to be sure they're the right climber climbing the right mountain. Great leaders do the same: Jack Welch at GE, Steve Jobs at Apple, and Herb Kelleher at Southwest Airlines come to mind.

The single biggest mistake I made was in not conducting proper due diligence prior to joining J. Walter Thompson. I'd argue that every executive, whether they're looking for a promotion with their existing employer or contemplating a move to a new setting, should list their strengths and values and then compare them with those of the organization. If anything's amiss, don't climb. As Ed Viesturs would tell you, "There's always another mountain that will be the right one."