Rex Harrison as the Doctor in the 1967 20th Century Fox film Doctor Dolittle

5 Reasons to Become a Doctor Dolittle of Lawyer-Client Communication

The first of the beloved Doctor Dolittle children’s books appeared in 1920. Hugh Lofting authored the series. A British civil engineer, he started writing letters to his children during World War I as an alternative to telling them about the horrors of the war. The letters became books and his legacy is the Doctor Dolittle series.

The main character of the series is, of course, Doctor John Dolittle. The books are set in early Victorian England and the good Doctor practices medicine in Puddleby-on-the-Marsh in the West Country. Doctor Dolittle has the unique ability to converse with all manner of animals. Preferring animal patients to humans, Doctor Dolittle and his animal friends, including Gub-Gub, Jip, Dab-Dab, Chee-Chee, and the pushmi-pullyu (surely a metaphor for a lawyer: a beast with two heads who can talk with one while eating with the other allowing it to multitask) go on a variety of adventures.

Much of the stories’ charm lies in Doctor Dolittle’s serving as the linguistic intermediary between the animal and human worlds.

Today, when lawyers speak with corporate clients, we frequently don’t have Dolittle-type moments when there is real communication.

Many factors, including increased specialization, time pressures, and sometimes just a lack of interest, have led to a gap. Lawyers speak law and clients speak business. We need to develop in all lawyers a Dolittle-like ability to bridge the worlds of business and law. The challenge is broader than just one of vocabulary. By understanding the language of business clients, lawyers delve deeper into the world of real client problems and can do a better job of delivering broader problem solutions.

The Devolution of Lawyer-Client Communication

There was a time when lawyers and clients spoke a common language.

Law had not become the specialized collection of topics and subtopics it is today, where lawyers focus on narrow legal topics and build deep substantive knowledge. Business also was not as structurally complex. Fewer managers had to spend their time building unique skill sets to demonstrate their value to corporate employers. With less specialization and related jargon, lawyers and clients could discuss problems and solutions using a shared vocabulary.

When I first started practicing law, I was something of a generalist. I worked on large corporate transactions, major lawsuits, employment matters, and general commercial matters. My in-house contacts had general management or executive positions. We talked in broad terms about the problems and solutions, only getting deep into technical topics when absolutely necessary. Each of us had some experts to help on certain questions, but those were marginal points and the experts communicated directly, sharing their own specialty jargon.

For the most part, we had the Dolittle ability to bridge law and business.

Many years later when I became a general counsel, you could feel the gap that had developed between clients and lawyers. Clients began by phrasing their business problem as a proposed legal solution. They did this in part to show they weren’t coming to the lawyer empty handed. They also did it in part hoping to fast-track the legal solution. Of course, some did it because of a growing familiarity with legal services, even though the solution often didn’t fit the problem.

A typical discussion could start as “I need a contract” or “We should file a lawsuit” rather than “What is the best way to reflect a new commercial relationship?” or “How can we manage this escalating dispute?” Lost clients might start a conversation by saying “We need to subpoena the other side to find out what they know about our products before we start negotiating the deal.”

An in-house lawyer on top of her game moved the discussion back to the client’s turf by focusing on the business goal and the client’s real problem. “Why are we developing this relationship?” or “What is driving the dispute?” were typical rejoinders. She was learning business language and felt comfortable carrying on conversations in financial, marketing, and logistics speak. Outside lawyers often become bored during this part of the discussion.

Often, I heard outside lawyers ask to be excused from the conversation and invited to rejoin it only when the conversation turned back to specific legal topics within their domain.

While today, fewer outside lawyers would ask to be excused (for many good reasons and some financial), it is clear many struggle to follow the discussions. Lawyers who recently moved in-house also find themselves awash in a world of business jargon, acronyms and, to use a technical term, gobbledygook. We all suffer through those moments when someone wants to “operationalize the transformative paradigm shift to drive impactful results.”

The rejoinder questions were not just clever ploys to make the client feel at ease. Lawyers really wanted to shift the focus from law to business. It is this shift in vocabulary as a means for deeper understanding that I think is the real reason for developing the Dolittle-type business and law communication bridge.

The Doctor Dolittle Lawyer

The more lawyers present themselves as discrete legal-issue technicians and not as business problem solvers, the more they run the danger of irrelevance. We have all heard the dangers of technology becoming more adept at taking work away from lawyers.

Technologists will have the earliest and greatest success replacing lawyers who do only legal technician work.

But there is a better reason to focus on problem solving. Increasingly, clients want to work with those lawyers who know at a substantive level what the clients’ businesses are all about, understand what challenges they face, and can build creative solutions to today’s problems while mitigating future risks. Lawyers who speak law and not business are at a significant disadvantage in meeting those needs.

These are the major reasons I see for becoming a Doctor Dolittle lawyer:

  1. Meeting the client where the client is.
  2. Framing discussions around business objectives.
  3. Challenging lawyers to think slow, not fast.
  4. Considering the full spectrum of options.
  5. Nemawashi (根回し).

Nemawashi often is translated to “going around the roots,” as in something done in preparation for planting a tree. It comes from a business practice at Toyota and has grown to become part of well-run lean thinking organizations.

Let’s explore each of these reasons in detail.

1. Meeting the client where the client is.

Lawyers want clients to use them to help solve problems. To get clients to use lawyers, we must get lawyers to go to where the client is, not expect the client to come to where the lawyer wants to be. The internet has helped by making law more accessible to lay persons. Clients can pre-shop legal solutions just as we all can pre-shop our buying decisions. But lawyers can and should do more to make clients want to bring their problems to lawyers. Meeting the client where he or she is helps eliminate barriers.

Clients feel more comfortable and confident on their home ground and are more likely to open up when in their comfort zones. When clients are more comfortable, lawyers learn more from them. Some of the things lawyers learn, the client might not have shared if the conversation were on legal ground. Sometimes, we learn a lot more of the backstory.

In one particularly challenging situation, I was asked by a manager what he should do with a competitor’s pricing information. He had received the information, before it was released to the market, in a plain tan envelope sent through the mail. Rather than just answering “throw it away,” I shifted to a discussion about business practices. That discussion led to the backstory. For many years, the manager’s predecessor and a manager at the competitor had been sharing pricing information before it was released to the market. The manager’s predecessor was promoted, so the next envelope came to the manager at my company (for those not familiar with U.S. law, this falls into the zone of a “go to jail” offense).

At other times, moving to where the client is simply shows that the client is more important than the lawyer.

When lawyers speak law it sends a message to clients that lawyers are superior because they are experts in an area unfamiliar to clients.

While admittedly, there are times when this is a useful message, most of the time it simply puts a barrier between client and lawyer.

2. Framing discussions around business objectives.

As much as lawyers might wish it were so, clients do not wake up in the morning and shout gleefully, “I have a legal problem so I must go see the lawyers today!” In my experience, it’s more of a, “I’ve tried to think of a way to do this without the lawyers, but I haven’t succeeded so here I am.”

Framing discussions around business objectives makes meeting with lawyers seem like less of a chore and more of an opportunity to improve a business strategy.

When lawyers use their analytical skills as part of business discussions with clients, they can help clients work through ideas to find the best fit for achieving business objectives. The person talking to you may want revenge for a perceived wrong, to cover a serious mistake, or to make a point to competitors. While that may be the person’s goal, and it may be backed by budget or performance evaluation concerns, the business probably has other and better goals.

Revenge might make the person feel good, but it might damage a broader and very valuable commercial relationship. Addressing one person’s mistake may reduce its impact, but cost the organization far more than the mistake itself. Sending a message may deter others from making a challenge, or it may teach the market or potential customers that the client is “difficult.”

One manager approached me with a request that our company immediately bring a lawsuit against a business partner for breaching a contract. Rather than discussing the lawsuit, we talked about the contract and the relationship. After a long conversation, the client opened up and explained that he had misread the contract years ago and had been overpaying the other party to the contract. The business person on the other side came into the relationship after the contract had been signed and just accepted the payments without checking the contract. After investigating a bit further, I called the general counsel of the other party and we were able to work out a solution fairly quickly.

3. Challenging lawyers to think slow, not fast.

Lawyers are lazy thinkers. They aren’t lazier than clients, but they aren’t more energetic. When working with clients, lawyers should resist the urge to let their lazier selves take over.

Over the past 20 years, cognitive psychologists have taught us new ways to understand how our brains handle thinking and problem solving. Our brains use two systems, called System 1 and System 2, to process requests. System 1 is on most of the time, quick to respond, and has many tools to help it respond quickly, but it does’nt think deeply. System 2 comes on infrequently, is slow to respond, requires data and energy to operate, but thinks very deeply. All people are lazy, preferring to let System 1 run things than to do the heavy work required for System 2 to operate.

If you ask a lawyer a legal question, she will give you a quick response — and miss an opportunity to answer the more complicated underlying business question which requires slow thought.

Clients want an expert who can give the fast answer, because business moves quickly and that time clock is ticking in the background. Having the answer right at the tip of your tongue shows the lawyer knows her stuff. For the client, it confirms he made the right choice in coming to the lawyer. That quick answer comes from System 1 and that is the problem — System 1 isn’t the deep thinker.

System 1 is fast because it uses a long list of heuristics (rules) to get to those fast answers. Going through the list is well beyond the scope of this post (read Nobel laureate Daniel Kahneman’s book Thinking, Fast and Slow), but one example will make the point.

System 1 uses the “availability heuristic,” which leads to biases and systematic errors. The availability heuristic works like most heuristics System 1 uses. When confronted with a problem, System 1 looks for an easy way out so it can give you that fast answer. Complex problems aren’t easy and require System 2, so System 1 uses a substitution trick — it looks for an easier question to answer, answers it, and gives you that back as the answer to your question. Most of the time, you don’t know that System 1 used its trick.

What fun would it be if System 1 said, “Hey Ken, that is a tough question. So, I skipped it and found another question I could answer and gave you that answer as a substitute. Now you think you have an answer to the first question, but I really gave you the substitute answer, which may be the completely wrong answer to your tough question.” Brains like to have some fun too.

This whole System 1 / System 2 and substitution thing may seem a bit abstract, so let’s look at a concrete example. Your client wants to buy a business and has asked you to represent him. In your discussion, he tells you the name of the lawyer and law firm representing the seller. He asks you if it will be easy or difficult (meaning quick and less expensive, or drawn out and more expensive) to negotiate with the opposing lawyer and firm.

Answering the client’s question will be difficult. Even if you have negotiated against the firm and lawyer, you would want many examples across many variables to make a good prediction if this particular negotiation will go the same way as the prior ones. Apart from things like knowing how motivated the seller is to sell and what instructions the seller gave its lawyer, you would want to know the mood of the opposing lawyer on negotiation day. A cynic might say it could even depend on whether the opposing lawyer is under pressure to bill more hours. Answering your client’s question is definitely going to be a lot of work and something System 2 would have to handle.

But, System 1 isn’t going to stand by and let System 2 take over. System 1 jumps into the fray by saying: “We know the opposing law firm is well-respected. We also know that the opposing lawyer went to a top 10 law school and has been doing these types of deals for over 20 years. We’ve heard good things about him from other lawyers in our firm. So, we can jump to the answer: the other lawyer and his firm are well-regarded professionals who are unlikely to negotiate just for the sake of negotiating and who know their stuff, so doing the deal should not be difficult. System 1 comes up with a quick answer to the substitute question, “do the opposing lawyer and law firm have good reputations?” Lawyers and firms with good reputations don’t unnecessarily complicate negotiations, so you tell your client the deal negotiations should go smoothly.

System 1 gave you an answer to the substitute question and System 2 never woke up. But, you didn’t really answer the client’s question. In fact, if you had surveyed lawyers on the other side of deals handled by the opposing lawyer, you would have found that of the past 10 deals, opposing counsel said the lawyer and his firm were incredibly difficult to negotiate against nine times. In other words, had you stopped to gather data and let System 2 process the question, the correct answer would have been quite different than the quick, but not fact based, System 1 answer.

I have heard outside lawyers often respond to the “will negotiations be difficult” question with the reputation answer. Lawyers hate to give “I don’t know” answers and since System 1 can supply the reputation answer quickly, they prefer to tell clients the reputation answer rather than say “I don’t know and it would be difficult to get the information needed to give you a data-based answer.” Many clients have, of course, been trained to accept the reputation answer and don’t push for more.

When framing the discussion with the client around business objectives, lawyers kick System 2 into action. System 2 requires data and time, and so it slows down the discussion. Lawyers have to think deeply about the issue the client raised and how it relates to what the business’ objectives. The lawyer is taking the discussion out of System 1’s hands. The lawyer starts asking for data and pushing to understand the connection between what the client wants and those business objectives. While not as easy as letting System 1 do all the work, lawyers slowing things down and using System 2 get to much better quality answers. Working with the client to get the better answer, not the fastest answer, is a mark of a lawyer focusing with emotional and business intelligence.

4. Considering the full spectrum of options.

Clients may come to lawyers, but that doesn’t mean the answers to their problems are in the law. Those problems involve issues crossing a wide range of disciplines and often can be solved through many approaches. To use an obvious example, many disputes can be resolved through money without lawyers playing any role, or at least a minimal role.

But, to borrow from Arthur Maslow, if you go to a lawyer and his only tool is the law, then every problem will require a law solution.

Many lawyers I encountered approached client problems with legal solutions — period. If you asked about other solutions, the lawyers would decline to discuss them. Many lawyers disclaimed expertise (I don’t know finance, I’m not an operations person). Others would reinforce their silo (I’m a tax guy, I’m a securities gal). Far too many would head for the lawyer versus business person oldie — I’m a lawyer and that is a business question.

The last one irked me — and by the way, really irked my clients when I was in-house counsel — the most. Clients know that lawyers are lawyers, not business people. But, there are still some clients around who believe that lawyers are astute analysts who can help them break down problems and come up with practical solutions. They also understand that sometimes those solutions are business solutions not legal solutions (I’m still not sure what that means, but I’ll go with it). The risk of a client suing you for malpractice because together you reached a business solution and it later turned out poorly says a lot more about your relationship with the client than it does about the state of malpractice law.

Of course, you need to think about and point out key legal points (statutes of limitations, for example).

But clients want help solving problems and if you can’t think beyond law, expect the clients to turn elsewhere for help (many are).

Consider this well worn phrase in corporate America — “We’ll bring in the lawyers when it is time to document the deal.”

5. Nemawashi.

The Toyota Production System, the genesis of what we call lean thinking in other companies, includes many principles as well as methodologies. One of those principles is embodied in nemawashi. According to this principle, we involve all the affected players in the process leading up to a decision. We prepare the foundation for the decision, just as we smooth and prepare the ground prior to planting the tree. Toyota shares information relevant to decisions and solicits opinions of those who will be affected.

The goal is to reach a more informed decision supported by everyone, rather than a decision formed at the top and then crammed down on those affected.

When lawyers meet with clients, various styles emerge. When I first started working in law firms, lawyers had a lot of mystique and power. They had few in-house counterparts and often the in-house lawyers had very limited roles. The clients did not view them as real lawyers and looked to outside lawyers.

Over the past 35 plus years, I’ve seen the styles of in-house and outside counsel evolve. Lawyers in corporations have steadily grown in power and today they have commanding roles in their companies. Clients look to and trust in-house lawyers, whom they work with every day, while outside lawyers are treated as service providers to the in-house lawyers.

Outside lawyers have become gun shy. Whether it is fear of malpractice claims or something else, outside lawyers often tremble when clients ask for their opinions. I have seen this happen often across many top-tier firms and lawyers. The client must choose language for a contract provision and when asked, the outside lawyers don’t guide. They simply say, “You must decide that, I can only offer you options for the language.”

Clients perceive that answer, and rightly so, as the lawyer failing to partner with the client to find the best solution. Sophisticated clients (that is, corporations) understand they have the final call and bear responsibility for the decision. If they ask for a legal opinion on the language, they expect the outside lawyer to stand behind it. But, if they ask for the lawyer to provide input into a judgment call, the answer above screams, “I’m not a member of your team.” It doesn’t reflect the spirit of nemawashi. The lawyer is hiding behind an artificial “law versus business” wall.

For each of the 5 reasons above, you may think the examples I gave were picked for dramatic purposes, but not typical of what clients encounter. Unfortunately, no. While dramatic, the examples also were mainstream. As concern over legal fees has risen and trust between clients and lawyers has dropped, lawyers have run for cover in the law and seem less willing to engage in business conversations. In-house lawyers are less prone to falling into this trap, for obvious reasons, but it still affects lawyers inside and out.

Curing the Lawyer-Client Communication Problem

When I teach workshops with in-house and outside lawyers, the faculty sometimes asks the participants to make a list of all the things going well in the relationships between clients and lawyers and a list of all the things not going so well. When discussing things not going so well, the primary reason raised by both parties for things is poor communication. Many factors drive poor communication, including frequency, content, and vocabulary.

If clients talk business and lawyers talk law, the communication quality will be low.

In the lawyer-client relationship, the burden is on the lawyer to be the Doctor Dolittle. The lawyer must learn the vocabulary of business clients, become fluent in it, and use it when speaking to clients.

If the lawyer can’t translate a legal concept into something the client cares about from a business perspective, then the lawyer isn’t doing a good job of communicating.


Since I’m an evangelist, I should bring you good news.

The good news is that learning to speak business is fun and will boost your legal career.

As much as clients hate lawyers who only speak law, they love lawyers (or at least what passes for love in any commercial relationship with a lawyer) who speak business. They want to consult those lawyers more often, they listen to their advice more closely, and they are more likely to stick with that advice. The lawyers have become part of the team, and teammates like to protect the team. In a world where clients find so many reasons to distrust lawyers, why give them one more? Learn to speak the language of your clients and build the type of lawyer-client relationship you — and your clients — really want.