Legal Law

Getting To No – Above the Legislation

stop sign businessman holding up hand stop gestureThe attorney mindset is cultivated, not born. I’ve met hundreds of attorneys in my life. The breadth of personalities across our profession is immense. I’ve known successful, skilled attorneys both extroverted and introverted, liberal and conservative, playful and serious, optimistic and pessimistic. Yet when the time comes to put on our lawyer hats and counsel clients, we all reliably fall back into a similar set of mental habits and techniques.

Given that the vast majority of practicing attorneys in the U.S. went through an ABA-approved law school curriculum, this is perhaps unsurprising. Law school, as they say, is less about teaching law than about teaching students to think like a lawyer. As described by Edward Levin in his 1948 article “An Introduction to Legal Reasoning,” thinking like a lawyer is all about “reasoning from case to case,” from precedent to present. A lawyer sees a problem and finds a similar case from the past. They extrapolate a rule of law from that past case, and then build an argument as to how they should apply that rule to the case before them. We’re taught from the first day to rely on precedent at a fundamental level.

The actual process of developing that attorney mindset can, at times, be a brutal and ruthless one. The Socratic method that many schools use for part or all of their curriculum is a harsh, Darwinian environment for ideas. We’re forced to advance arguments and then have all the flaws implicit in them dragged to the surface. Over time, we learn to be careful, skeptical, and reflexively critical of ourselves and others. We see the flaws in our arguments and avoid them before we voice them. By the time exams roll around at the end of the first semester, most of us have developed strong senses for spotting legal issues and using them to develop precedent-based arguments.

That legal mindset is invaluable to our actual practice. Clients bring us their problems. We spot the issues and advise them on how to proceed based on precedent. We fit our clients’ troubles into pre-existing boxes. We draft agreements using polished language and well-vetted structures. We cite case law and statutes, and make today’s troubles look like yesterday’s solutions. No matter who we are as people, that’s the mental framework every lawyer uses to do their job well.

And that crucial, necessary mental framework is absolutely killing our industry.

Good Lawyering Can Be Bad Business

The legal mindset in many ways is the opposite of what you would see from a successful entrepreneur or business leader. If entrepreneurs based their entire business model on what’s worked before, they’re failing at actual entrepreneurship by definition.

If being a lawyer is about seeing how the present connects to the past, being an entrepreneur is about visualizing a future. It’s about finding something that isn’t being done and trying to do it differently. It’s about a cycle of cheap, measurable experimentation, followed by almost certain failure, followed by learning and refining, followed by another round of experimentation, until eventually the business takes off or runs into the ground. Failures along the way are expected, a fundamental part of the DNA of creating something new.

To be clear, the entrepreneurial mindset in isolation would be a terrible approach to the practice of law. When we’re being entrusted as fiduciaries to solve our clients’ problems, we shouldn’t be focused on experimentation. We shouldn’t be hoping to fail fast and cheaply for the sake of seeing if an alternative approach works better. Our clients come to us for reliability and predictability, and they’re the ones whose rights and legal budgets are on the line. Lawyers think like they do for a reason.

But the practice of law and the running of a law firm are two very different things. Yet we as attorneys often expect the techniques of successful lawyering to somehow translate to successful navigation of a complicated, competitive marketplace. Slow, steady, risk-averse practices might thrive in the short term, but they tend to get outmaneuvered by entrepreneurial management styles over the long run. Any firm that doesn’t want its lunch eaten by its competitors needs to embrace the entrepreneurial mindset for its actual operations.

Getting Past No

While most of the business world is focused on Getting To Yes, lawyers have trained themselves for decades on the fastest ways to avoid trying new things. No matter the circumstances, leave it to most lawyers to figure out a way to get to no. If entrepreneurship is about “Yes, how?,” lawyering is about “No, because … .” Entrepreneurs see a far-off goal and go for it, figuring they’ll solve problems as they arise. Lawyers tend to spot a pothole ahead and decide that’s a good reason to just stay put.

So how is management supposed to cultivate entrepreneurship in firms composed of attorneys who have had most of the basic components of entrepreneurship deliberately drilled out of them? It starts, as always, at the top. Law firm leaders need to cultivate operational cultures where innovation, experimentation, and failure are norms to be celebrated, not shunned.

The first step is all about education and coalition building. Get out in the firm, both formally and informally, to let people know that innovation is something you care about, and that the firm is happier failing at something daring than succeeding at something boring. When conversation inevitably moves toward lawyers’ comfort zones of issue-spotting and pessimism, redirect it into thoughts of the future. Take ideas from all levels of the organization and start quick, cheap, and measurable pilot programs to see what works.

Fight the urge to pilot your programs quietly, out of fear of failure. Take opportunities to announce and highlight your experiments, whether they’re on track for success or appear headed for failure. In fact, highlight them especially when they’re not working out as planned, because failure is when organizations and individuals learn the most valuable lessons. When we punish failure, we stifle future innovation. When we celebrate it as a necessary part of growth, we encourage our teams to find that next big idea.

When you’re lawyering, be a lawyer. Be cautious and skeptical, work within precedent, and advise your clients carefully and thoroughly. But when it comes time to run your business, do it like a businessperson. Get creative, get your hands dirty, and don’t be afraid to deviate from precedent and get to yes.

GoodnowJames Goodnow is the CEO and managing partner of NLJ 250 firm Fennemore Craig. At age 36, he became the youngest known chief executive of a large law firm in the U.S. He holds his JD from Harvard Law School and dual business management certificates from MIT. He’s currently attending the Cambridge University Judge Business School (U.K.), where he’s working toward a master’s degree in entrepreneurship. James is the co-author of Motivating Millennials, which hit number one on Amazon in the business management new release category. As a practitioner, he and his colleagues created and run a tech-based plaintiffs’ practice and business model. You can connect with James on Twitter (@JamesGoodnow) or by emailing him at

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