Hillary Clinton's Penn-Ultimate Leadership Mistake

The worst mistakes I've made in life and leadership have always involved waiting too long to fire someone.

Whether I'm hanging onto a relationship long after love is gone or hanging onto an employee long after positive value to the organization has diminished beyond the point of return, my loyalty tends to trump my better sense. And like most women, including it appears, Hillary Clinton, I always think I can fix the situation. That I can retrain, redo the job description, or refocus the person's priorities so his or her performance will magically improve. After all, maybe it was my fault; I didn't provide sufficient direction or support to tease out their talents. Surely if I did, Ms or Mr. X would shine again.

Women are particularly sensitive to the connective filaments in the web of relationships that make up our organizations, just as we're sensitive to them within our families. We counsel our kids to eat Aunt Ida's hideous orange jello, carrot, and horseradish salad because she's such a good soul after all. Past contributions, we think, deserve to be recognized, good intent respected

These qualities serve women well, until they don't, as has been the case with Clinton and her top advisors. Many said she kept Patti Solis Doyle as her campaign manager out of loyalty (and perhaps fear of what the firing would do to her relationships with Hispanics) long after Solis Doyle's effectiveness had waned.

And then there's Mark Penn.

Penn is obviously a smart guy. After all, he's global CEO of the enormously successful public relations firm Burson-Marstellar and has a best-selling book that lays out his notions of a microtrend-focused political strategy designed to appeal to the maximum number of voters by speaking to each psychographic in its own tongue. He's intricately connected within the web of Clinton supporters, and has a full throated commitment to her candidacy.

But in no small part owing to his boorish personality which he too often flaunted on prime time TV, Penn's full-throated comments needed to be shut off long ago.

Penn's advice, while perhaps valuable when the campaign was forming based on the political landscape of 2006, soon became a net negative. He was too rigidly wedded to it, couldn't flex and pivot when the young upstart Barack Obama shifted the earth beneath them and created new environmental conditions within which the campaign would be waged.

Seems the sophisticated techniques of segmenting the electorate and moving the parts with wedge issues, so effective for Karl Rove to move the ideological Republican right during the past several elections, proved less likely to move Democratic and Independent constituencies in this election cycle. A simple unifying message that elevates voters' sense of patriotic mission -- much like messages JFK and Ronald Reagan were so good at delivering whether or not they could ultimately deliver the goods -- is once again the requisite new new thing to propel a candidate to victory.

The last and latest arrow in Penn's capacious quiver of insults to the campaign's integrity was taking the Colombian government on as a client to lobby for a trade agreement that Clinton opposes. That astonishing degree of boorishness and bad judgment finally had to break even the most loyal boss's back.

Sadly, to many voters, it doesn't matter now how brilliantly Clinton has mastered the enormous range of policy issues desperately needing attention in our beleaguered nation. It doesn't matter that her health plan comes closest to universal coverage or that she is more seasoned on the international diplomacy front. It matters not that she has endless capacity for the hard work required to bring politicians together to create those "solutions that work," as her slogan touts.

What matters to the 2008 electorate is that Obama speaks in words that make people feel like they themselves are being brought together, that they are elevated above the mundane, slogging work of finding wonky solutions. Where Penn says there are "hundreds of America's," which may be accurate social science, Obama makes the electorate feel good about themselves by assuring them there is one America.

However realistic it is to believe that good feelings will translate into the concrete change we need, it's where the people are today -- miles from the cautious beaten path where Penn's strategic advice led Clinton.

Clinton should have cut Penn loose when it became evident early on in the campaign that he wasn't serving her well. I'll bet the love faded long ago and she was hanging onto the relationship for a web of other reasons. That she finally fired him as chief consultant -- though strangely retaining him as pollster, not realizing that failure to fire cleanly is as bad as not firing at all -- is a Hail Mary pass, but it's the best supporters can hope for. Sometimes miracles happen despite the odds; otherwise there would be no buyers for lottery tickets.

Pennsylvania's scorecard will tell us definitively whether the clock had run out before this long overdue firing decision was made.