All of us like to flatter ourselves into thinking that our careers have been the result of careful planning and that we regularly sit down and map out the next few steps in some master strategy. Would that it were so.

In this column, I want to concentrate on a potential career hazard. It happens when we focus so much on the current situation that we lose our perspective. This kind of management myopia has killed a lot of promising careers. By heeding the advice in this column, you can keep that from happening to you.

From quarters to paychecks in 15 minutes
Back when I was in college, I worked in the evenings as a cook in a restaurant. One nice thing about the place was that almost all the employees were obsessed with sports. Consequently, we bet on just about everything: Super Bowl, NCAA tournament pairings, World Series—you name it, we bet on it.

Except for one guy I’ll call Daniel. He was a nice guy, but we could never get him to bet on anything, not even to cover a single square on the Super Bowl sheet. When asked, he would politely (and correctly) note that we were wasting our money.

One night, things were pretty slow in the kitchen. Julius (another cook) and I were flipping coins for a dollar at a time. To play, we each flipped a coin in the air at the same time, and one person called “odd” or “even.” If I called “even,” and both coins came up either heads or tails, then I would win, and Julius would owe me a dollar. On the other hand, if one coin was heads and the other was tails—well, that’s “odds” and I would owe Julius a dollar.

Pretty tame stuff, you might say, and I’d agree with you. Anyway, Julius and I were playing, while Daniel was in the corner prepping salads for the next day’s lunch and watching us intently. He asked us what we were up to, and we explained.

After a few more minutes, he said tentatively, “I guess there’s no way that three people could play, is there?”

Julius and I smiled at each other and explained that certainly three people could play. With three players, no one has to call anything. All three of us would flip a coin at the same time, and if one person got something different than the other two, he would be the winner and the other two would each owe him a dollar.

After hearing the rules, Daniel agreed to play. We each flipped a coin. Just like in the movies, beginner’s luck rules, and Daniel had heads while Julius and I had tails. We flipped again, and he won again. We kept playing and keeping track as to who owed how much to whom.

About 10 minutes later, I was able to break even with both of them and dropped out, since I was due to get off soon. Julius and Daniel kept playing, and eventually Daniel was up five dollars on Julius. He was pretty excited about it too.

Then he ran into a cold streak. Eventually, he and Julius were even. At that point, Julius suggested they quit, but Daniel wanted to go for a few more rounds. Julius continued to win, and Daniel was down a dollar, then two, three, four, and finally five dollars.

“Double or nothing!” Daniel roared.

“Are you sure?” Julius asked.


They flipped again. Daniel lost. He was now down $10.

“Double or nothing!”

He lost again. Down $20.

Daniel got a funny look in his eye and growled, “Let’s settle this once and for all. We got paid today—let’s flip for our paychecks!”

To his credit, Julius refused, asking Daniel, “What comes next? You going to flip for the pink slip to your car?”

I had never seen anything like it. From abstainer to gambling addict in less than half an hour—that’s all it took.

Understanding the stakes
As he left the restaurant that night, Daniel must have been wondering, What the heck happened? One minute I’m shaving carrots and blanching romaine, and the next I’m betting my paycheck away. And on what—the toss of a coin? How did I get there?

One thing is certain. Daniel didn’t wake up that morning expecting to finish the day by betting away his paycheck.

That’s the point I’m trying to make. To carry the gambling analogy a step further, I’ve seen too many otherwise talented managers throw away their careers by doubling down on a bad hand. They continue to throw more and more chips into the pot, refusing to back down even when the stakes become ruinous. One minute they’re fine, and the next they’re tapped out, with an expression that says, what the heck happened?

Of course, as IT managers, we don’t run into this problem while flipping for dollars. It happens when a meeting or a phone call or an e-mail thread suddenly takes a wrong turn, and before you know it, you find yourself saying things you didn’t think you would ever say. All the while, you’re thinking, what the heck happened?

You know the kind of thing I’m talking about. Don’t we all know a gifted technical manager who suddenly blew up in a meeting, arguing over the merits of a particular implementation approach, and alienating everyone in the room? What about the application development manager who signs up for a ridiculous deadline, trying to make a point about the utility of a pet programming language? How about the help desk manager who loses his temper at an admittedly stupid end user—who just happens to be the CFO?

I know the phrase “pick your battles” is a cliche. But sometimes cliches get to be cliches because they contain an important truth. Whether it’s a conference call or an e-mail thread or a meeting, events can spiral out of control if you’re not careful. Nobody plans for such things.

I have some suggestions on things you can do to avoid becoming a victim of your own inflexibility. Of course, these are mostly common sense, but as we all know, when you’re in one of these situations, you lose your ability to think clearly.

Try to put your ego on the shelf
Ask yourself if your blood pressure is shooting through the roof because the other person’s comment was objectively stupid or because you felt some kind of personal affront. If it’s the latter, put it aside and deal with it later. Concentrate on the merits right now.

Have an exit strategy
Don’t act like a character in a Chuck Jones cartoon, climbing out on a limb and sawing it off behind you. No matter how contentious the issue, give yourself a way to climb down.

Give the other party a graceful out
Unless you’ve really gone around the bend and you’re arguing with yourself, you’re not the only one in this dispute. To make sure things don’t get out of hand, you not only have to preserve an exit strategy for yourself but also keep from boxing in the other person.

Slow things down
There are lots of ways to keep a potential management hurricane from reaching land. For example, when an e-mail thread starts to get hairy, walk away from your desk for a while. When you return, short-circuit the debate by sending an e-mail along the lines of, “As we can all see, this issue is pretty complicated. Rather than hash it out in e-mail, we should probably meet face to face to discuss it.” If the parties work in remote locations, suggest a conference call. If you’re having a face-to-face confrontation, make sure you pause before replying, even if you have a devastating riposte ready to go—in fact, especially then.

You might also try my old boss’s technique of playing for time in a tough discussion by first reformulating what he had just heard: “What I hear you saying is [insert the other party’s point here]. Is that right?” This allowed him to calm himself down before countering. It also protected him from misinterpreting the other person, preventing several blowups over the years.

Ask yourself if this is a battle worth fighting
This is the real question. As a manager, as a human being, sometimes you have to make a stand on principle. The important thing is to pick your battles and fight on ground of your own choosing. Don’t back into a dispute that threatens your career simply out of carelessness or spite.

That isn’t to say you might not have to bet your career on a project or a technology or even a principle—you probably will, more than once. The key is for you to pick the times when you push all your chips into the center of the table and bet everything on a single hand. Don’t let yourself be duped into doing so.

Play smart
None of this is rocket science, of course, if you’re thinking clearly. Unfortunately, too many of us turn our brains off during this kind of confrontation. However, if you’re smart and cautious, you’ll never end up asking yourself, what the heck happened?

From the IT Leadership Web log

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