How Technology can Help Change Bad Habits

Last time she checked, there were over 400 email messages related to the case in her inbox. Generated by a group that included seven or more lawyers in the firm. Finding just the right email, at just the right time, was somewhat problematic. The fact that most of the relevant information and communication about the case lived in email in the first place? Very problematic.

However, the norm for her practice group is communicating via email. Or in meetings. Too many meetings, that last too long. And when she’s in one of these meetings, she can’t be completing any of her tasks related to the case in question. Which leads to added stress. And much longer work days (because she has to stay even later to do her actual work thanks to the multiple, too-long meetings).

And the tasks? Maybe they’re sprinkled throughout the 400+ emails. More likely, they live on someone’s legal pad. Which necessitates another meeting to bring the rest of the team up to speed because only the person with the legal pad knows exactly what the case status is at any given time.

The bottom line: instead of supporting the team’s work, this method of case (mis)management is hindering everyone’s success. And it’s causing burn out, too. The team has already cycled through a handful of associates. And each time a new one comes on board, it’s a tedious process to bring him/her up to speed.

Habits. Bad Habits.

So if the workflow isn’t functional, team members are frustrated, and no one is even close to optimally productive, why does this method of management persist?

Because it’s habit. It’s become the norm for these lawyers, for this practice group, and for others in this mid-size regional firm. And for many other lawyers and firms. It’s status quo. It’s case management on auto-pilot. This way of working has become habitual for its perpetrators.  And habits are hard to break. Especially when we lawyers are faced with heavy workloads, mammoth client expectations, and pressure to increase collectible billings. All of these pressures put lawyers in reactive mode, instead of supporting a proactive way of working. We simply don’t have the time or energy to disrupt the status quo (which is what’s required to break the habits). So we maintain and perpetuate habitual behaviors, instead of breaking and replacing them with more productive workflow habits.

The above example? It’s of a real firm, and real lawyers, and an active case. I know because the lead lawyer on the case talks with me often about this broken system of management.  It drives her crazy. And exhausts her. And others on her team. Yet nothing changes.

There are also a few obstacles to breaking bad workflow habits that warrant a mention. The most common for lawyers and firms (in my experience): poor communication about the change process; inadequate support by firm/practice group leaders; inconsistent application of the change; pushing a change too quickly; and failing to take into account individual lawyers’ predisposition toward change. The good news? These obstacles can be planned for in the strategy used to achieve a shift in workflow habits.

But it doesn’t have to be this way. Change can happen. In fact, this firm already has a nifty software platform for managing cases. That takes the workflow out of email and the status off of legal pads. It makes it easy for those using it to access communication, documents, and status quickly. But no one is using it.  At least not effectively.

Why? Well, remember that point about habits? And the fact that they’re hard to break? The answer is really that simple. No one on this team has taken the time to figure out how to use the firm’s (feature-rich yet complicated) practice management platform. With deadlines looming, the team sticks with the dysfunction of what they know. They remain on auto-pilot.

The solution isn’t as simple as just forcing people to use a practice management (PM) platform. But it’s not really complicated, either. And the solution is somewhat one-size-fits-all, meaning it’s as applicable to the two-person firm as one with 500+ attorneys in multiple states.

I’ve worked with a small firm whose lawyers ignored their PM platform’s most useful tools for the very same reasons the mid-size firm lawyers in the above example do. They all say the same thing: it takes too much time to change how (and where) they do their work, so they stay stuck.

Technology Answer: Collaborative Software

Just so we’re all on the same page, here are a few reasons why anyone and everyone should be using some form of collaborative PM software:

  • Important information and communication doesn’t belong in email. Period. In addition to the obvious ethical issues, it’s simply not efficient or productive to spread this content out in emails, regardless of how neatly you organize your Outlook folders.
  • Documents can and should be organized in a functional way, and in a place where everyone who needs them can access them. And not by trolling through their email inbox, or even a circuitous server-based file system. Antiquated methods of organizing and sharing documents have no place in an efficient, modern law practice.
  • Case status should be transparent, easy to update, and easy to access. Which all happens when status lives in a maintained PM system. Status should not live within the sole control of any single person, even if that person is using a digital tool instead of a legal pad. Which leads to the next point …
  • Meetings should only happen because they’re really necessary. They shouldn’t happen because this is the only way to bring everyone up to speed on status. Or because communication is otherwise so poor or convoluted that  a meeting becomes necessary. When communication, task status, documents, and case information live in a PM system, the number of meetings required diminishes considerably. This, I promise. (And, as an aside, those meetings that must be held? Please, please learn and use the principles for conducting effective meetings. This is not taught in law school, but it’s not too late. You, too, can do it.)

Three Ways to Change Bad Habits

So if we accept that we need to break these bad workflow habits, and that habits are hard to change, what do we do about it?

Classic change management principles apply, with a twist. A successful shift within a firm happens on a very granular (personal) level: one lawyer at a time.

  1. PM system needs to be simple to use. So simple that it doesn’t require a consultant to make it work or to help lawyers understand how to make it work. Intuitive, in fact. Think Asana, a task-based project management platform that is dead-simple to use. Know how to use email? Then you can figure out Asana, quickly. A simple system means that people actually use it. Sadly, this principle does not apply to most PM systems that firms invest in. But it should.
  2. Lawyers need to buy into the truth that using the platform will improve the quality of their work, their work lives, and by extension, their lives generally. While I don’t have a one-size-fits-all checklist for how to achieve buy-in, I can tell you that getting one person to use the platform and model for others the positive impact it has on his practice, productivity and general happiness is incredibly effective. Yes, a firm must model the behavior it seeks of its people, one person at a time. These people become the change agents, who pave the way for wide spread adoption. Knowing that this works, a firm can be strategic in how it recruits and supports its change agents. This isn’t hard. It’s common sense.
  3. Use of the PM platform must be consistent. In other words, once you change, you can’t go back. Research tells us that old habits don’t die. Instead, they remain dormant, waiting for us to regress. To thwart regression, we’ve got to be consistent in our continuing use of the new “habits” that form a well-managed workflow. And this kind of consistency is fed directly by reaching an optimal percentage of buy-in within the practice group or firm. Which, again, happens one person at a time.

These three steps can help any firm launch a successful PM platform adoption process. And while they’re not the only factors controlling success, I know from many experiences within firms that they work.

Want to kick the bad habits of managing your work in email, endless meetings, and poorly managed task lists? You can. Successful change starts with one person. You can be the change you wish to see.

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About Caitlin Moon

Caitlin Moon
5th generation lawyer | legal tech co-founder + COO/CDO | design thinker After representing startups and creative businesses for 18+ years, Cat now applies tools like agile project management and human-centered design thinking to the creation of legal technology. She believes that the delivery of legal services will be revolutionized when we put clients at the center of all that we do — and that a lot of this will be done on a blockchain. Reach her at

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