The Tic-Tac-Tao of Legal Project Management

There are three ways to approach a skillset such as project management:

1. Have a specific rule to apply for every imaginable situation.
2. Analyze every situation anew, based on what you know.
3. Have a set of core principles that you apply as you recognize situations.

Let me offer an analogy. Let’s say I want to program a computer to play tic-tac-toe. I could do so using each of the three approaches above.

1, By rule: Tic-tac-toe is a simple game. There are only nine possible moves to start the game. For each opening move, there are but 8 possible responses, and so on. It adds up to a large but not unmanageable number of combinations. It’s an uncomplicated programming exercise, as well as a boring one. This appraoch works for tic-tac-toe, but the problem becomes impossibly huge for a more complex game such as checkers, let alone chess.

2, By analysis: Chess programs typically analyze each possible next move. They then examine various responses to those moves, responses to those responses, and so on. They look at what can happen one or two or three or more moves ahead. (I’m oversimplifying.) Not-very-good amateur chess players such as me do the same thing. However, chess is a lot more complex than tic-tac-toe. Tic-tac-toe is simple enough that a program can easily examine each move all the way to the end. That approach is reasonable for this simple game; it doesn’t take advantage of experience, but it costs almost nothing in computer processing time. However, there are far too many possibilities for this approach to work well in chess.

3, By principle: This line of attack would take the most programmer skil. In addition, there’s a risk of missing a good approach if the developer didn’t really think about the game.¹ The “principles” method would overcomplicate programming for a game as simple as tic-tac-toe. What about chess, though? Studies have shown that top players tackle games such as chess using principles (yep, oversimplifying again – it’s just an example). Programmers of the top chess programs are now trying to bring a “principles” approach to the computer.

Is project management tic-tac-toe, or is it chess?

It’s much closer to chess.²

I’ve known project managers who worked in each of these three styles.

The worst of them were those who used style 1, applying rules. Ironically, they tended to be educated in specific project management techniques without ever having been taught to truly manage projects. They had a rule for every situation. However, real-world situations are far more complex and nuanced than could be accommodated by the rules they’d learned. Project management would be much easier (and less interesting) if there were a simple set of rules you could apply, a magic wand you could wave. In reality, few projects in the legal world are as straightforward as tic-tac-toe.

I’ve known project managers who analyzed every situation before responding. They got most of their choices right, but they were often slow to respond, frustrating their co-workers. The “analysis” method comes up short when the project manager encounters something new or opaque, when she’s unable to figure out what’s really going on beyond what she see in front of her. In the legal world, most projects face an opposing party who considers it part of his job to make yours harder. (No, I don’t mean the client.) Opaque and unanticipated situations are the norm, and they’re often resistant to analysis.

The best project manages I’ve known worked from the principles they’d learned, often via the school of hard knocks. Like top chess players, they developed a “feel” for certain situations, recognizing patterns even when the circumstances were startlingly different. Sometimes they’d analyze a problem in depth, sometimes they’d apply simple rules to simple situations, but when necessary they could make sensible choices in new situations based on very incomplete data.

I remember one project manager I’d worked with as a colleague. At times we’d talk about the monster project he was working on. I’d ask why he handled a given situation the way he did, and sometimes he’d say, “It seemed the right thing to do.” When I’d press for details, most of the time he’d eventually figure out his own rationale; even though he was very self-aware as a person, however, such self-analysis wasn’t easy for him. I was often amazed at the intuitive leaps he made, and I think he himself enjoyed these mini after-action reviews as a way of building and codifying the principles of his style. He employed an approach to project management based on principles, following these principles even when he couldn’t immediately articulate them.

I think there’s a progression project managers go through. Most start off with a handful of rules. They quickly face a choice: Learn more rules as they recognize the increasing complexity of what they work on, or move up the chain to analysis and then to principles. The good ones realize that rules may provide the illusion of security but won’t be sufficient to effectively address complicated problems.

Simpler may sometimes be better, but simplistic rarely is.

That’s the Tao – or the tic-tac-Tao – of Legal Project Management.

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¹The traditional “rule” in tic-tac-toe is that the first player should start in the center. It’s the sure way to ensure a tie, but consider starting in one of the corners and then taking the diagonally opposite corner unless the opponent takes it first. Seriously. Try it.

²Actually, project management is more like bridge than chess. Both opponents and partners communicate via subtle signals, you know the set of pieces (cards) but not who will get what, the scoring system is incomprehensible to non-players, and there are multiple rounds (hands) in a session. In bridge, the opponents must explain honestly their signals and communication on request, while project managers have to figure out the veracity of the players in their game without really asking.