Smart Lawyers Who Feel They Know Less

What is a good lawyer? What is a smarter lawyer, for that matter?

How we evaluate ourselves, and our colleagues, may have historically been based on outdated notions of an encyclopedic knowledge of the law. But in the era of search engines and legal databases, the utility of such skill sets are not nearly as useful as in the past.

Harvey Schachter of The Globe interviewed Edward Hess on how workers can improve in an era balancing on the precipice of machine learning:

…start to change your mental model of what “smart” looks like. We have been trained to believe it involves knowing more than the next person. So the goal is to keep accumulating knowledge. Not knowing the right answers has traditionally – and still is – a big blow to the ego. But in a search-engine era, we can look many things up. “Being smart is using our best learning, thinking and collaboration processes. To do that, we need a quiet mind. We need to tell people what we believe and check whether it’s right,” he says.

Hess is the author of Learn and Die, which explains how individuals and organizations can foster continuous improvement, operational excellence and innovation. He posits that human learning emerges from a Pavlovian search for cause and effect in an environment of survival, identifying and finding the cues in our social and physical environments which best helps us thrive.

The heuristic patterns which emerge differ from the computational models we develop in a lab through emotions and consciousness, elements that artificial intelligence still struggle with and may never truly achieve. These mental models are not always an asset though, in particular in their resilience against change, even if that change is beneficial.

Our various life experiences often dictates how we respond to new information. Hess writes,

People with different histories of experiences likely attend to and process a different subset of stimuli arising from the same new data. Each of us focuses on what seems particularly relevant in the data and can be effectively blind to the rest. Two employees working for the same company may be exposed to the same new data, but unless there are rigid organizational mental models in play, each will process information in ways that confirm his own existing knowledge. Having a diverse group can be a learning enabler by helping identify cognitive blind spots.

Hess also challenges the supposed dichotomy between logic and emotions in humans. Emotions can help people make bad decisions, but it can also help people make good decisions. Emotions are not the antithesis to rational decision making.

Fear of change or of the unknown, and the pride or ego of being wrong or simply the certainty of erroneously being right, are particular emotions which operate as significant barriers to learning. The use of mindfulness, which is also used extensively for stress reduction, can help channel emotions to assist rather than inhibit openness. Positive emotions even enhance our abilities to relate to new information and develop alternative interpretations.

Much of Hess’ book focuses on developing a learning organization and fostering a learning environment. These organizations are the ones which will survive the best in the new economy.


Charles Darwin’s often misstated “survival of the fittest” could actually be better understood as where there is enough variation in a species in extreme conditions, some of the individuals in that population will be more likely to successfully adapt to those changes.

Tim Kastelle extends this analogy to industry:

If we apply this to innovation, you might think of it this way: products are like individuals and organisations are like species. To do well, products need to be the best at getting some job done for some group of customers.

However, for an organization to do well over time, it needs to be adaptable. This means that unless its environment is unusually stable, it needs to generate variety. Even though economic evolution is directed by the choices that people make, we still don’t have much control over which ideas work and which don’t. Or over which take off, and which never really click.

The best workers, and the best lawyers, are the ones most willing to change and learn new ways of doing things.

Hess spent much of his early career practicing law. His experiences, and frustrations in practice, must have influenced his passion for understanding change. But it also helped him appreciate constructive criticism:

My early experience practicing law also greatly influenced how I reacted to negative feedback, which helped me to shift away from a performance mindset. I had a mentor, a partner, who was “Mr. Feedback.” He taught me that negative feedback was necessary to become the best in a field. (Thank you, Peter.) He taught me to pause and reflect rather than automatically defend, deflect, or deny. He taught me that it wasn’t about me, but rather about producing the best legal memorandum or brief that could be written in a particular case. As I advanced in my career, I came to realize how difficult it can be to get this kind of constructive feedback. Rather than getting the kind of specific, constructive feedback that can help us improve our skills, most of us will receive guarded or politically correct feedback that is fairly useless in practice. Thoughtful and constructive feedback is a valuable thing, especially when you can foster your mindset to absorb and not deflect it.

The feedback for the legal industry is that quite bluntly the skills learned in law school and the early years of practice are not what will make the best lawyers of the future.

In an era of automation and information overload, the best lawyers will be the ones who hold on to what makes us most human – our compassion, understanding and ability to empathize with others.



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