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I’ve Made a Huge Mistake! Why Legal Tech Fails

Written by Darren Fancher, Originally published by the American Bar Association The Business Lawyer, Vol. 36, No. 5, Fall 2019 Legal professionals are reluctant to admit.

Darren Fancher CEO Headshot

Written by Darren Fancher
Originally published by the American Bar Association
The Business Lawyer, Vol. 36, No. 5, Fall 2019

Legal professionals are reluctant to admit defeat, but when it comes to software, I’d wager that at one point or another, most of us have stared at our computer screen, dropped our face into our palm, and admitted, “I’ve made a huge mistake.”

Whether it was prematurely jumping on a failed bandwagon, holding out for an upgrade to an antiquated solution, or entering into a long-term contract for something that never gets used, expensive and time-consuming mistakes are made every day with results that can stifle your practice and productivity.

The good news? You can bounce back.

There are strategies to help improve software outcomes, whether you choose to stick with your existing solution or adopt a new one. As an attorney and the CEO of a legal technology software company, I’m familiar with both sides of the conversation when it comes to technology selection, implementation, and use.

Below, I’ve outlined three common software implementation mistakes—along with fixes to improve your existing software and practical advice if you plan on starting over.


It is frustrating and costly for a firm to deploy a case management software solution, only to see that six months in, no one is using it. And if no one is using it, then all the promises of improved reporting, increased productivity, and greater accountability are lost. Managing partners may choose the software, but it’s the staff who will use it most.

Buy-in from staff is critical if you want a high return on investment. And while it would have been ideal to involve your team in the decision-making process, it’s never too late to improve staff buy-in and increase user adoption.

There are two common reasons why firms fail to get buy-in. First is a failure to demonstrate the value of the system. If your staff doesn’t think the system will help them, they won’t be motivated to use it. What matters most here is their perceived value of the technology: If the staff believes the product will streamline their daily work flow by saving time and effort—they will be motivated to use it, provided it works as promised.

The second common reason for a failure of buy-in is misaligned expectations. Even with well-performing software, a successful data import, and adequate training, you will find that implementing new technology takes time and requires appropriate expectations for rollout, timing, and adherence from management. It undermines the management /employee relationship if staff isn’t given appropriate expectations by the management team.

Fix the mistake if you’re keeping your software

Achieving buy-in for an existing product is often more difficult than getting buy-in for a new one. However, if you believe you have the right system, pursuing buy-in at this stage may be the best choice.

– Retraining: Your software provider has a vested interest in your success. It’s never too late to work with their support team to gain higher adoption. Have your team identify their challenges and schedule a call with the vendor to remedy issues, learn best practices, and highlight the merits of the software. Retraining also helps to reiterate to staff the reasons behind the software adoption. It helps them see the bigger picture of why they should be learning to use the technology.

– Positive reinforcement: I’ve seen firms successfully turn to positive reinforcement, rewarding staff for making good use of the current system. It’s amazing what can be achieved with a stack of Starbucks gift cards.

Avoid the mistake if you’re starting over

– Get your team involved as early as possible: When selecting software, engage your team and listen to feedback about what they would like to see in a new program. Involve key staff members in your conversations with vendors. Employees will be more invested in a project when they feel they’ve contributed to it.

“When selecting software, engage your team and listen to feedback about what they would like to see in a new program.”

– Identify a “champion” early in the process: You should have at least one person in your firm who is knowledgeable and enthusiastic about your new system. This person’s enthusiasm will rub off on the rest of your employees and encourage the use of the software. Your firm’s “champion” often becomes the go-to person for software questions, which frees up more of your time.

– Hire an outside consultant: Understandably, some business owners find it difficult to evaluate their business critically. A legal consultant can bring a fresh perspective, offer invaluable insights, and provide you with meaningful solutions to existing problems. Consultants should be able to work with your team to determine and define expectations and help ensure staff buy-in.


When it comes to software, it’s not uncommon for law firms to have buyer’s remorse. Life often looks better in the movies, and the same can be said for some software demonstrations. Time is limited, and less scrupulous salespeople will highlight the best features while glossing over the shortcomings of a product. As such, even before the contract is presented, management has already formed images of complete, robust reports and graphs seen in a well-seasoned demonstration account—only to find, in reality, reports are incomplete and results are inaccurate.

Although this mistake often stems from a software’s sales team making promises they can’t deliver, sometimes the product is, simply put, not user-friendly. The most successful technology and social media platforms, such as Apple and Facebook, are powerful and effective because they are user-friendly and intuitive for users.

Your legal software shouldn’t be any different. Complex products that require lengthy training to be useful won’t achieve rapid adoption, are time-consuming, and make staff more likely to return to their previous or outdated methods. As a result, the new software’s reports won’t get the data they need, and firm leaders will regret their software decision.

Fix the mistake if you’re keeping your software

– Talk to your salesperson: If you’ve recently deployed the software and things aren’t working as expected, you should immediately approach the salesperson with your concern. A good salesperson who is concerned about her company’s reputation will be more than willing to shepherd you to the right resources.

– Talk to customer support: If you’ve been using a product for some time or are committed to a long-term contract, reach out to the customer support team. More than ever, support teams are focused on client retention. Usually, your call won’t be the first they’ve received on the matter. They should be able to offer training or another suitable resolution, lest they may lose a client.

– Start by identifying your firm’s needs, procedures, and priorities: Identifying the right legal software begins with identifying your firms special needs. Before looking at new software options, sit down with the intended users and make a master list of what procedures your firm already follows and what you’re looking for in a new system. Once you have your list, assign priority to the items on the list. Make sure you understand the difference between what your firms needs and what it wants.

Why Legal Tech Fails-03

Avoid the mistake if you’re starting over

– Be thorough in your research: Ask questions and hold the software provider accountable for promises made. Check reviews, ask to talk to their clients, and ensure there is sufficient customer service and training available. Set realistic expectations with the software salesperson and their customer support team as to what the software can do before and during its implementation.

You and your team will want to look beyond an introductory demo of the product and really see the screens and features you will be using on a daily basis. If things look good, be sure to kick the tires in a demo account or free trial, and make sure you and your team actually test it. Importantly, never sign a long-term contract, no matter the discount. The software company should constantly strive to earn your business, and if the company is trying to lock you in for the next several years, it may be for a reason.

“Never sign a long-term contract, no matter the discount. The software company should constantly strive to earn your business, and if the company is trying to lock you in for the next several years, it may be for a reason.”

– Look for software made for your practice area: Some case management solutions are practice area specific. For example, CASEpeer was specifically created for personal injury firms and was intentionally designed to support personal injury workflows, so it’s not surprising that clients often tell us, “this is exactly how I think about things.” Aim for that kind of fit with your software selection. Software that focuses on your practice area can be an easy shortcut to a “custom fit” for your practice.

– Understand customization vs. out-of-the-box solutions: Proceed with caution when it comes to software requiring a lot of customization. Customization takes time and money and often delays the onboarding for your firm. On the contrary, out-of-the-box solutions can be tailored to your practice area and should already contain necessary data fields and work flows to effectively manage your firm. If there is something missing, tell your provider.

If you chose to customize, it is important to ask where your custom data goes after it’s entered into the system. Can you find it in a useful report? Extensive customization can often lead to what I call the “data dumpster,” in which data can be entered into the system but cannot be utilized in meaningful ways or reports. Which leads to mistake number three. . . .


There are a lot of articles published about the value of data, data analytics, and data-driven decisions, but most authors don’t address the reality that many data sets are not as useful as they would have you believe. Data entry is usually done in a hurry by staff responsible for capturing names and details while on a call or transcribing information from one location to another.

Imagine transcribing the name of an insurance carrier from a call— AAA Insurance could also be recorded as American Automobile Association, American Auto, or Triple A. Unless your software has a way to manage this, you won’t be able to effectively drive reporting from all your prior cases with AAA Insurance. Most established law firms planning a software upgrade do so with a data transfer in mind.

“Your satisfaction with the end result will depend heavily on the quality of data entered into your existing system.”

Initially, data preservation may seem like an issue where more is more, but in our business there is a saying: “junk data in yields junk data out.” Your satisfaction with the end result will depend heavily on the quality of data entered into your existing system. Some firms may actually be better off starting fresh if the data isn’t salvageable or useful.

Fix the mistake if you’re keeping your software

– Junk data? Call for help: Your software provider wants a happy client. If you’re struggling with junk data as a result of bad data entry or a failed import, talk to them about your options for a data cleanup and be open to suggestions. They may have tools at their disposal that can help find and merge redundant or incorrectly entered data.

– Establish consistency: Work with your team to come up with procedures to ensure data fields are used consistently. Some products offer a lookup feature to cross-check an entry against prior entries before allowing you to add something new. Plan to review data regularly to confirm compliance.

Avoid the mistake if you’re starting over

– Evaluate existing data: Conduct an honest evaluation of your existing data. If data fields are used inconsistently, then importing the data into a new solution will result in equally useless reporting. If your data needs help, you can talk to your new software provider about potential strategies. You may even want to engage a consultant who specializes in this kind of data cleanup.

– Start early: It is tempting to think that the next software solution will resolve your data problem, but delaying your review and improvements to the process simply means more work and more stress later. You can start your data review anytime, conduct a cleanup, and establish improved procedures that will make the transition to new software an easier one.


Successful software implementations outnumber the failed ones, but mistakes can and will continue to happen. Before hitting the eject button, take a moment and learn from a failure. This rejection can serve as an opportunity to improve your processes, engage and reinvigorate your team, and either improve usage of existing software or replace it with something better. And whether you salvage your current solution or shop for a new one, setting reasonable expectations for the product and your team will ensure success moving forward.

© 2019 Published in The Business Lawyer, Vol. 36, No. 5, Fall 2019, by the American Bar Association. Reproduced with permission. All rights reserved. This information or any portion thereof may not be copied or disseminated in any form or by any means or stored in an electronic database or retrieval system without the express written consent of the American Bar Association or the copyright holder.

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