July 01, 2019 July/August 2019

Smashing Through Your Barriers to Breakthroughs

Self-inflicted limitations to your practice can be broken by including your clients and a broader, portfolio view.

Dennis Kennedy

Lawyers are trained to think in ways that can be the opposite of good innovation practices. We spot issues and potential problems, with an emphasis on the problems. We focus on process, procedure and precedent. Saying that something “has always been done this way” is seen as high praise.

At the same time legal work often is creative, innovative and forward-thinking—on legal matters, but much less so on the actual practice of law, new business models and big ideas about the practice itself. As a result, implementation of change, technology and big, bold new ideas too often either doesn’t happen or happens at a glacial pace. However, the combination of these two aspects of lawyers—conservative practice approaches and creative legal approaches—holds the key to identifying and smashing through barriers to breakthroughs in the practice.

Pinpointing Barriers

Let’s see how many of the following barriers are familiar to you.

I’m too busy.

How many long conversations have you had with lawyers in which they tell you in painstaking detail how overbusy they are and that they have no time for anything—except, seemingly, to tell you at length how busy they are. Michael E. Gerber, author of the book The E-Myth Attorney, says that we should spend as much time working on our practices as we do in our practices. The move to massive minimum billable hours has had a corrosive effect on the practice, especially in reducing the amount of time available to rethink and make changes to how lawyers work. Are there really not enough hours in your day?

Legal exceptionalism.

Many lawyers believe that everything they do is unique and cannot be standardized. Sometimes this belief is summed up by saying that law is a profession, not a business. There is a tendency to see every aspect of legal work as customized and unique. From fussing with fonts and margins on invoices to a wide variety of arcane procedures, many lawyers insist on long-standing personalized approaches appreciated only by them rather than moving to more efficient and standard processes that can be delegated to others. Is everything you do in your practice actually a “legal” process?

No one else is doing this.

Lawyers sometimes need to feel the comfort of knowing that they are not the first to try something and that other lawyers are doing the same things, especially in technology. There is an interesting pattern in legal technology where certain software tools become prevalent in certain cities. The fact that others are doing something helps lawyers get comfortable that a change is not too radical. This approach tends to make many lawyers followers rather than leaders. Are you making sure someone else you know has implemented a new idea before you decide to look into it for yourself?

Someone else is doing this, so we can’t.

The interplay of this barrier and the previous one, which sometimes can occur in the same conversation, is fascinating. If a competitor is working on a new approach or technology, some lawyers will say that they don’t want to copy it. They might also say that if John Doe is doing it, it must be a bad idea because he isn’t so smart. This reaction might not be a bad thing if it pushes you to act and explore different options, but, too often, it shuts down the change process. Is the “not invented here” mindset slowing you down?

Not asking the client.

Clients, especially corporate clients, are on record as saying that they want their lawyers to bring them new ideas and innovations. Truth be told, many lawyers do not like to have direct conversations about their work with their clients. Many lawyers hate to send bills, let alone suggest new approaches and changes to the existing relationship. The key to innovation is getting the client involved and solving the client’s real problems, not assuming that you know what the client wants. On at least an annual basis, are you sitting down with key clients to talk about improvements to the relationship and work processes?


I once had a law partner who asked his estate planning clients about the “atomic bomb dropped on the family reunion” scenario to get them to focus on the absolutely final disposition of their estate to contingent beneficiaries. Lawyers are really good at finding worst-case scenarios and playing devil’s advocate. It’s a key part of risk assessment. When it seeps into looking at new practice ideas, however, it can become a significant barrier, especially if done reflexively and automatically. “If we try this new technology, everything else will break, we won’t be able to do any work and we will have no revenue for six months.” “If we suggest flat fees on certain matters to a client, they will fire us on the spot.” Risks fall within a set of ranges. Are you too often going to the worst-case scenario when considering a big new idea?

Thinking in isolation—compared with what?

There’s a famous philosophy problem about whether it’s best to push one person into the path of a train to save five people on the track or to save the one person and have the train hit the five people on the track. It often gets raised in the context of self-driving cars—how can the programming of the car resolve this dilemma? Our attention focuses on the rarity rather than the reality of 40,000 highway deaths a year in the United States. It can be difficult to step back and look at your practice and your systems in a critical way. It is much easier to look at a new system and compare it to a mythical ideal. Context is important in making big idea decisions. If you were to start over, would you implement your existing system or the new one that you are considering?

Discomfort with standard innovation techniques.

I was recently at a CLE seminar, and there was a session on improvisation for lawyers. The room all but emptied before the session began. I’ve heard lawyers and other legal professionals complain about and dismiss every innovation and design thinking technique in common use elsewhere—from brainstorming to whiteboards to, particularly vehemently, Post-it notes for capturing ideas. It is important to, as they say, think different. Are you refusing to try standard techniques?

Quality over quantity.

The statistics vary, but it looks like you can expect 90 percent of start-ups and new initiatives to fail. Many other efforts change drastically. Companies often “pivot” to new business models based on customer feedback. Twitter, originally a podcasting company, is a classic example. In brainstorming exercises, the goal is quantity of ideas—getting lots of ideas expressed and captured. In brainstorming, a primary goal is not to criticize ideas as they get generated. Lawyers tend to want to highlight quality ideas and, because of that, experience stress over quantity. Given the 90 percent failure rate, the odds of identifying quality at an early stage is low. There are better frameworks than quality. Are you uncomfortable with generating lots of ideas before judging their quality?

Moving too quickly from why and what to how.

This barrier is similar to the previous one. The evidence indicates that if you can focus on the actual problems of clients, the jobs they need to get done, and what reduces their pain and increases their gain, the likelihood of great results is enhanced. Lawyers tend to move too quickly to the “how” to accomplish something. Lawyers like processes and procedures. There is great value in remaining patient at the “why” and “what” stages before moving to the “how” stage. Are you moving to solutions before you fully understand the underlying problem to be solved and what approach addresses that specific problem?

Not looking at other businesses and professions.

I’ve noticed recently that doctors have done a great job with online portals. I can make and change appointments, look at test results and get other medical information easily and conveniently online. I dread calling into voicemail systems for doctors and always prefer to use the portals. They benefit both the doctors and the patients. There are many innovations happening in professions and businesses similar to law and also in those not similar to law: online portals, productization of services, use of video, self-service of all sorts and much more. Sometimes a fresh perspective is required. How often do you look at the changes in your other customer experiences and wonder how you might try them in your practice?

Not killing bad ideas.

There are many reasons not to recommend being in meetings with lawyers. Looking back on my legal career, I recall the many times—in hiring decisions, technology decisions, motions for action, nominations of officers, etc.—where it’s clear that there are several excellent options and several that aren’t at the same level, have no support and can be dismissed. Far too often there will be lawyers who want to give the options that don’t make sense a thorough discussion so that “we are sure we are right about them.” The end result is exactly what you would expect, and valuable time that could be spent on the best options is wasted. Are you able to move forward and decide on options ruthlessly and without sentimentality?

I suspect that you can add a few items of your own to the list and that you have your own examples from the categories above. It’s quite an obstacle course of barriers. Can you smash through these barriers?

Getting Through (or Around) Barriers

Here are a few recommendations of ways to break through barriers to big ideas.

Surface your biases.

We all lapse into several of the biases mentioned in this article. We also tend to have a bias toward the status quo and inaction. Identifying and diagnosing your biases will help you move past them. When considering a new idea, use a framework that helps you test your reactions to an idea or proposal against these barriers. Are you analyzing smartly and critically, or are you simply falling back on biases and old methods? A simple checklist or grid might be all you need.

Involve your clients.

It is so easy to assume that lawyers know what our clients want without talking to them. The best innovations come out of a thorough understanding of client problems. Identify your clients who are likely to be most interested in new approaches and schedule time to talk to at least two or three of them.

Find some standard techniques you like.

There are lots of standard design and innovation practices. Some you will hate, but some you will like. That’s a good thing. One I’ve found quite valuable recently is the Value Proposition Canvas, which lets you map out in a simple way the job your client needs to get done, the client’s pains and hoped-for gains, and then how your service fits that job, reduces the pains and creates the gains. Check it out.

Look at what works elsewhere.

Start to pay attention to your customer experience in other settings. Your doctor’s online portal might be an eye-opener. What frustrates you? What do you like? Can you try something like that in your practice?

Take a portfolio approach.

I’m a big fan of the modern portfolio theory of investment, which says that it’s prudent not to invest just in cautious and “safe” investments but to diversify and spread your investments across asset classes and risk categories, all in accordance with your own risk tolerance. In simplest terms this approach means that it is both necessary and wise to mix some higher-risk, higher-potential-return investments in your portfolio. The same reasoning applies to innovation and change. Are you creating more risk for yourself by playing it too safe? A simple chart mapping out your innovation “investments” and where they fit in terms of risk is a great approach to thinking about innovation as a portfolio.

Closing Thoughts

It’s easy to get overwhelmed when hearing about big new ideas, transformation and “change or die” predictions. Lawyers have a lot of barriers, some psychological and some self-imposed. Often the answers to questions come in the opposites. How do I work on big ideas and smash through barriers? With small steps, patience and resilience. 

Dennis Kennedy

Dennis Kennedy is a well-known legal technology author and speaker. He advises legal organizations on their innovation and technology efforts and co-hosts The Kennedy- Mighell Report podcast on the Legal Talk Network. dmk@denniskennedy.com