The Deadly Virtues

“C’est magnifique, mais ce n’est pas la guerre”

-Pierre Bosquet

Oh, but it was magnificent. I wish you could have seen it. Let me describe it to you.

Behold a group of men (they were all men), boldly united in singular commitment to an ambitious cause. Their purpose was clear, their focus complete. They were not afraid of hard work; on the contrary, they were ready to put everything they had into the task before them. They were prepared to make sacrifices, to set aside family time and even sleep to achieve their tasks. They believed deeply in themselves, and in the inevitability of their success. Theirs was a boundless optimism, a reverence for the power of the individual. Men of will, they believed in the power of heroic effort. They believed in the power of will itself. They believed in the transformative power of belief itself. They were ready, and being ready, they committed themselves to the task at hand. The work began.

And after several weeks of glorious striving, the project crumbled in the most abject and embarrassing form of failure.

No really, they shit the bed. Complete humiliation. A failed project, a furious customer, a million dollar contract now hanging by the slenderest of threads, the air thick with recrimination and despair.

How did this happen? How did an effort so deeply infused with all that we normally deem potent virtues end in the most pathetic form of ignominy? These, dear reader, are the wages of optimism. I’m happy to say that this wasn’t a project in which I was closely involved, and to protect the innocent and guilty alike, I’ll share no details, but to sketch the outlines should be sufficient. In the simplest terms the men that I described took on an ambitious technical project on which the fate of a significant business transaction depended. And they blew it in the worst imaginable way. They could not have done otherwise. The effort was doomed from the start, and it was doomed by the very virtues they possessed. Let’s consider each in turn.

First, confidence. Each of these men was a successful professional with an excellent track record. They’d all achieved difficult things before. They’d all failed before too, but that wasn’t any fun to think about. Each of them could think of at least one comparable, hail-Mary effort from somewhere in his past, and if he’d done it once, he could do it again. And given that, why waste any serious time on estimation or risk assessment? To look closely at the feasibility of the project, to identify potential points of failure, was just negative. Men of prowess don’t have to think about things like that. It only muddies the waters.

Which feeds into the second deadly virtue, which is heroism. Each man understood that something would probably go sideways at some point – they weren’t fools. But what can’t be achieved through the heroic power of an individual? If they hit an obstacle, they’d power through it. And just as importantly, they’d be rewarded for doing so. Their heroism would be celebrated. It might hurt, it might take a couple of late nights, some clever thinking, but they’d be showing the group what they could do. They’d be a man. Their deeds would be sung. Hell, think about it the right way, and it would almost be a shame if something didn’t go wrong. Who wants a layup? Any risk or friction lurking in the project plan was just an opportunity to strut their best stuff. Why in the world would you let that hold you back?

Taking these things together, an optimistic outlook only seemed to make sense. Sure, the project looked difficult from the outside, but there was a path to success. That path required a long series of improbable things to come together perfectly, but that’s okay! It’s a path! It could happen! I get this too, I really do. I won’t say what conversations I was personally part of surrounding this specific item (not a lot, truthfully), but I’ve been part of many others. Time and again I’ve seen an exasperated executive say, “Guys, yes or no. Is it possible to get this project done?” To which some young underling (occasionally it’s been a young me) says, truthfully, that there is. Because the underling has been asked a yes or no question, he is not free to add, “Yes, it is possible, in the sense that getting hit with a meteor in the center of your forehead at exactly 2:17pm on your 57th birthday is possible, just not really way up there in terms of probability.” But that’s okay, that’s not what the executive wanted to know. And neither did the men undertaking this project. There was a way to be successful. There was a path that could be conceived in the mind of a very confident and cheerful man, and that was enough. Probability is complicated. Optimism is simple. Simple things feel good. This was enough.

So what went wrong in the end? I mean, pretty much everything. Confident in their ability to execute, the men started working without really defining the work to be done. The client, aware of this, encountered no barrier to adding new work to the mix. No one really knew which piece of work needed to be done in which order, and at any rate this project was about individual effort, so the men worked at cross-purposes for a long time before discovering that their tasks didn’t align. Several high-risk elements had never been identified as such, so when the risks became live issues affecting the project, no mitigation strategies were in place. There had only ever been a plan A, no plan B had been contemplated. And plan A, if we’re honest, was pretty loosely defined. The client, as  a result, found meaningful status excruciatingly difficult to get. The client got frustrated. Then the client began to get scared, which is worse. Pressure mounted. Deadlines began to flicker by, goals unmet.

At last the time for real heroism had come, and that’s when things really got bad. The hero, striving mightily, pushing forward against all odds, had no way of admitting that he couldn’t succeed. He worked all night, he worked all day, trying to find something to throw at the problem that could achieve the necessary breakthrough. Valiantly, he never abandoned hope. And because he did not abandon hope, neither did the team. Meaning, the team continued to tell the client that the deadline would be met.

And in due course, the deadline came. The deadline passed. The hero had nothing. The team had nothing. The project was weeks behind plan with no path for recovery and no revised delivery date for the client.

Okay, so what do we learn? Let me be clear about something. Deadlines are part of business. They’re part of life. And they’re part of client delivery whether we like it or not. You’ll be handed challenging projects and they’ll have money riding on them and that’s life in the big city.  My point here is not that you can’t get difficult things done. But as I’ve said before, difficult things get done by difficult people. The first step to success on a tough project is the moment when a savvy, pessimistic leader pulls the team together and says, “People, we’re probably screwed here. We need to get some realistic options on the table. Let’s start with a list of everything that can go wrong.”

See, two things define my career, as I look back on it. One is an exceptional record of getting things done. My track record on complex delivery is one of the best around, and such success as I’ve had has had everything to do with that. The second defining thing is that in every organization I’ve been part of, there’s been a profound reluctance to move me into the higher levels of leadership. Difficult things get done by difficult people, and the conversations I find most important are the conversations most people least enjoy. In the totally of my career, what I have is a winning record. I will never have the seductive sheen of doomed, heroic virtue.

I mean, I guess I could try. I’m just not optimistic about it.

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