I have been very clear about this and have made the point on numerous occasions— workplace romances are almost always a bad idea. 

This isn’t some subjective observation on my part, but rather, what I have learned firsthand from managing people for the better part of 30 years. But one reader of this blog thinks I’m dead wrong on this subject and makes a very articulate challenge to my point of view.

Here’s what this reader, identified only as HR PS, had to say in response to my post titled “When an Office Affair Turns Into Fatal Attraction:”

“The problem with the examples here is that they typify the worst kind of sleazy behavior by married people with a substantial power differential between themselves and the people they’re having affairs with. All the office romance bans in the world aren’t going to begin to stop that behavior—the egos are too big and the sense of power too inflated.

“What such policies will do is push normal, healthy relationships underground, so that no real discussion with the employer can take place. You may call it prattle, but it’s unrealistic to believe that people won’t have workplace romances. The best policies I’ve seen accept this and deal with it an adult fashion instead of forcing the employees to try to fly below the radar.”

Now, let me be clear: I have never, ever called for a formal ban on office romances. In fact, here’s what I said about this last year at Valentine’s Day: Office romances have always been part of the equation in any workplace since the dawn of time, and there’s no evidence that the problem has gotten appreciably better or appreciably worse. Yes, sometimes office romances go bad, but the trend The New York Times was touting back in 2007 was to not get too worried or worked up about co-workers dating.

I certainly understand that very pragmatic viewpoint, but my own opinion on office romance hasn’t changed—hype, trends and surveys notwithstanding. It’s a bad idea. That’s because, in my experience, they go bad all too often. And, spoiled office romances leave the participants—and the co-workers around them, who have to live with the bitter, sometimes litigious aftermath—much worse off as a result.

Yes, I’ve written about the fallout from high-profile office affairs like the recent one with ESPN’s Steve Phillips (who just got fired for his bad judgment) and David Letterman before him. And yes, I agree with reader HR PS that these two examples DO “typify the worst kind of sleazy behavior by married people with a substantial power differential between themselves and the people they’re having affairs with.”

As bad as those are, the ones that drove me crazy were of the more mundane variety, like the three-month relationship between two co-workers who sat next to each other. When something like that goes sour, it affects everyone around them, generally for the worse. And, it’s a management headache I’ve had all too often.

But am I wrong here, as reader HR PS says? Can pragmatic office policies realistically deal with affairs of the heart, or are they just a Band-Aid approach to an emotional and hard-to-handle workforce problem?

Get my latest blog updates and workforce management news by following me on Twitter.

I love David Letterman. His late-night talk show is clearly the best of the bunch, and in my mind, he’s followed along in the footsteps of his mentor, the great late-night king, Johnny Carson.

But as much as I like Letterman and “The Late Show,” the news that he has been, as The New York Times put it, having “sexual affairs with staff members,” made me wonder: What the hell is this guy thinking?

It’s clear to me that David Letterman, highly paid late-night comedian and CBS talk show star, never heard (or conveniently forgot) one of the most basic managerial rules of all—don’t fish off the company pier.

Getting involved with your co-workers (sexually, romantically, or both) is not only terribly foolish, but can also be incredibly dangerous, as Letterman just found out. If you are powerful and highly paid like Letterman, it can open you up to $2 million extortion attempts.

And, although what Letterman was confronted with is extreme, there are numerous and regular examples of powerful executives who are tripped up by romantic entanglements that are just flat inappropriate and stupid.

Although many of the details are sketchy, there’s nothing that says what Letterman did was anything but consensual. One CBS Radio report I heard said Letterman was having sex with female staffers in his office, and as bad as that sounds, it’s still legal for consenting adults to engage in such behavior should they choose to do so.

That’s what catches me up, however. Why would any thinking, rational person—particularly someone of Letterman’s stature—choose to put themselves in a compromising position like that?

“While Letterman seems to be in no immediate risk of losing either his family or his job (ratings from last night’s telecast will likely be stratospheric), his troubles may not be over,” Time magazine says. “Having sex with people who were his employees or whom he managed could leave him, or CBS, open to a sexual-harassment lawsuit. It’s certain the comedian has given the network’s lawyers plenty of reasons to be up at night.”

Bosses getting involved with those who work for them is a trend that’s probably as old as the workplace itself. However, it’s fraught with peril and, in my long experience, is almost never worth the risk.

In fact, if you looked at this as a smart businessperson and examined the risk-reward potential, or the ROI of such a relationship, you probably wouldn’t get involved in such a deal at any level. But, that’s applying rational thinking to something that’s clearly an irrational decision.

Letterman has had a lot of drama and bad stuff to deal with in his life, but this is one that wasn’t foisted upon him; it’s trouble that’s self-inflicted. Even if the foiled extortion attempt turns out to be the worst of it, he’s left his many fans wondering just how someone who seems so smart and snappy on the surface can engage in such foolish (and some would say terribly bad) behavior when the office door is closed?

As someone who makes his living skewering other people and joking about their foibles, Letterman’s now going to become the punch line for a lot of manager and workplace jokes.

Who wants to be that guy? No manager that I know of. Yet Letterman, the guy who has publicly reveled in zinging Bill Clinton, Eliot Spitzer and many others for their sexual high jinks, is now going to become the poster boy for bosses behaving badly. That’s called karma, I believe.

And the jokes and zingers about this have already started. As Time magazine solemnly notes: “Letterman has also probably given truckloads of material to other comedians—or even his own writers. Let’s just say he may come to regret calling his company Worldwide Pants.”

Get my latest blog updates and workforce management news by following me on Twitter.

This may seem a little odd, but in my book, we should all celebrate June 25 as “Bad Management Day,” a day when we ponder all the terrible management decisions made each year by so many overpaid, puffed-up egomaniacs like former Chrysler head Bob Nardelli and current Tribune CEO (and foul-mouthed journalist hater) Sam Zell.

Why June 25? Well, it’s because one of the worst management decisions of all time was made back on June 25, 1876, by one of the most puffed-up egomaniacal executives of all time: Lt. Col. George Armstrong Custer, who made a fateful decision that day to engage more than 2,000 Sioux and Cheyenne warriors with only about 210 members of the 7th U.S. Cavalry along the Little Bighorn River in southeastern Montana.

Of such terrible management decisions is history made. So it was for Custer, who paid for his bad decisions with his life—and the lives of his men—in a battle now remembered as the Battle of the Little Bighorn, or “Custer’s Last Stand.”

How bad was Custer’s management decision-making that day?

Let us count the ways:

1. He wouldn’t listen to others: Custer was told to hold off on any attack and wait for reinforcements that were being led by Brig. Gen. Alfred Terry, but impatience got the better of him and pushed Custer to act. Terry and his reinforcements arrived one day after the battle, on June 27.

 2. He didn’t have proper respect for his competition: Custer was guilty of hubris, just like so many modern executives. He grossly underestimated the number of Indian warriors facing him, downplayed their talents and failed to understand the technological advantage the competition had. While Custer’s troops were generally armed with single-shot Springfield rifles, the Indians mostly had repeating rifles. A little less ego might have helped Custer to better respect what he was up against.

3. He focused on the wrong issue: Custer’s focus wasn’t on fighting and defeating the Indians who were itching to fight him at the Little Bighorn. His misguided concern was that he needed to trap them and prevent their escape. That’s why he split his forces into three parts, diluting his overall strength. The other two units of the 7th Cavalry, led by Capt. Frederick Benteen and Maj. Marcus Reno, survived a fierce two-day fight that ended when Terry’s reinforcements arrived.

4. He was badly outmanaged: Custer was overmatched by Indian leader Sitting Bull, who lured him into a fight on his schedule, in a place of his choosing, with a much superior force. And Sitting Bull had an able field lieutenant in Crazy Horse, who executed his leader’s plans to perfection.

5. He had incredibly bad luck: Benjamin Franklin said that luck is when preparation and opportunity meet, and that is certainly true for Sitting Bull at the Little Bighorn. The flip side is that Custer had the misfortune of deciding to engage the largest single concentration of Native American warriors ever assembled on the North American continent with an undersized and outgunned force that he stupidly split into three parts.

That’s not just bad decision-making, but also terribly bad luck.

With a couple of better management decisions and a couple of changed elements, perhaps Custer would have survived the Battle of the Little Bighorn. History would be very different had that happened.

That’s what we should keep in mind today, on Bad Management Day. Sometimes, in business and in life, there are only a couple of decisions separating glorious success and unmitigated disaster.

Get my latest blog updates and workforce management news by following me on Twitter.