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Randy Bishop

5 Legal Tech Adoption Challenges (And How To Overcome Them)

Are you struggling with adopting legal technology? You're not alone. 

In fact, 47% of legal times find themselves struggling to integrate legal tech

While technology can help simplify a legal team’s day-to-day, actually implementing it is often tougher than you think. 

In this post, we'll outline some specific challenges and share some practical strategies and insights to help you navigate the adoption process with ease. From overcoming resistance to change to ensure seamless integration with your existing workflows, we're here to help you make legal tech work for you. 


  • The 5 most common hurdles for tech adoption are: embracing change, training teams, protecting client trust, integrating with existing workflows, and setting clear goals.
  • There are 7 things you can do ahead-of-time for painless adoption later (read on).
  • Know how to evaluate legal tech tools and when to say no if they don't add value.

Types of Legal Tech 

Legal professionals have a ton of different tools at their fingertips that can simplify processes, enhance accuracy, and help serve clients better. From managing contracts with ease to speeding up the research phase, let's delve into the diverse world of legal tech.


  • E-signature software: These platforms allow individuals and organizations to securely sign, send, and manage documents online.

  • Legal research tools: These tools are designed to assist legal professionals in finding legal resources such as case law, statutes, and secondary sources.

  • E-discovery platforms: These tools help identify, collect, and produce electronically stored information (ESI) for evidence in lawsuits and investigations.

  • Legal analytics tools: These platforms provide data-driven insights to aid legal decision-making. 

  • AI-powered legal assistance: Artificial intelligence (AI) tools assist lawyers in tasks such as contract review, predicting legal outcomes, or even drafting legal documents.

  • Case management software: These platforms help legal professionals manage and track the progress of their cases and often include features like scheduling, document storage, and client communication tools.

  • Billing and time-tracking tools: This software aids lawyers in tracking their work hours and generating invoices. 

  • Dispute resolution: These digital platforms assist in resolving disputes between parties without litigation and might include online mediation or arbitration tools.

  • Business development: These tools and platforms aid legal professionals in expanding their client base, tracking leads, and managing relationships. It could include CRM software, marketing automation, or analytics tools tailored for legal firms.

How to Overcome the 5 Biggest Challenges in Legal Tech Adoption

Embracing legal technology can significantly boost efficiency and accuracy, but it's not always a straightforward path for many legal teams. The reluctance often lies in concerns over disrupting time-honored processes (“we’ve always done it this way”) or the daunting task of setting up these tools (“I don’t have time to start all this over”). 


After all, adoption goes beyond simply implementing a new tool into your workflow. To truly realize its benefits, you’ll need to integrate its use across your organization and make it an integral part of daily operations.

Ahead, we'll delve into the specific challenges legal teams encounter and provide insights on how to navigate and overcome them with ease.

overcoming-challenges-in-legal-tech-adoption (1)

1. Embracing Change

With its deep roots in tradition, the legal sector can be reluctant to embrace change. This is particularly true when technology, especially AI, promises to transform tasks that have always been human-centric. 

And it’s not exactly without reason.

Recently, a pair of lawyers found themselves in hot water after using ChatGPT in a case. What went wrong? Well, the generative AI tool cited a number of cases that, unbeknownst to the lawyers, didn’t actually exist. 

Setback aside, legal technology offers some undeniable benefits, including: 

  • Efficiency and speed: Technology, especially AI, can drastically reduce the time it takes to review documents or draft contracts, enabling lawyers to focus on more strategic tasks.
  • Cost savings: Contract automation and streamlined processes can lead to significant savings in the long run.
  • Enhanced accuracy: Contrary to the ChatGPT mishap, well-trained AI systems can be incredibly precise, minimizing human errors in repetitive tasks.
  • Data-driven decision-making: Technology enables better insights through analytics, allowing legal professionals to make more informed decisions based on historical data and predictive modeling.

The challenge, however, lies in managing the balance between change and tradition.

To truly leverage technology while mitigating its risks, consider the following approaches:

  • Double-check everything: Technology's outputs, like any tool, should always be checked by a human. 

  • Engage transparently with tech vendors: Understand the capabilities and constraints of their products.

  • Communicate and customize: Ensure the solutions are tailored to the unique needs and concerns of the legal domain and your business.

  • Test and adapt: Before full-scale adoption, trial the technology to identify potential integration challenges and areas that might require human intervention.

As the legal sector evolves with technology, the key to success lies in balancing human skill with the efficiency of tech.

As the sector undergoes this digital transformation, it's the harmony between human expertise and technological efficiency that will dictate success.

2. Training Teams 

In the legal field, precision matters and the stakes are high. Sometimes, introducing new tech can be a double-edged sword. 

Without proper training, technology might lead to errors, like data loss or operational mishaps, which could have legal and financial consequences.

To turn technology into an asset rather than a liability, consider these strategies:

  • Adopt bite-sized training sessions: With packed schedules, short, on-demand training modules allow legal professionals to learn at their own pace, ensuring they grasp key features without being overwhelmed.

  • Ensure continuous support: Real-time tech support, user-level training, help centers, and webinars from the software provider not only alleviate user frustrations but boost confidence in the tool's reliability.

  • Invest in comprehensive training resources: Build your own training repository. Every class, software walkthrough, and any related documentation should be readily available for team members to reference or catch up on if they missed the original training session. 

With the right strategies, legal professionals can seamlessly merge tradition with innovation, maximizing both efficiency and precision.

3. Protecting Client Trust 

Today's interconnected digital environment has put security and privacy in the spotlight. 

Picture this: A legal team, having just adopted a new AI contract management tool, discovers that a third-party vendor is refining its model using confidential client information. The consequences of such breaches, both in terms of reputation and potential legal action, can be immense.

Beyond the immediate concerns, there's the added complexity of international data protection regulations like GDPR or HIPAA. 

Legal professionals must grapple with ensuring their tools not only provide an advantage in their work but also strictly adhere to these regulations.

As with previous challenges, the answer is not to retreat from technology but to wield it judiciously. Here’s how: 

  • Conduct robust security audits: Before integrating a new tool, carry out comprehensive security assessments. Ensure it's equipped with state-of-the-art encryption, multifactor authentication, and other advanced security measures.

  • Opt for certified solutions: When it comes to legal tech, certifications matter. Look for tools with privacy compliance certifications, signaling their adherence to global data protection standards.

  • Don’t forget cloud-based safeguards: While cloud solutions offer flexibility and scalability, it's essential they come with end-to-end encryption and regular backup protocols.

  • Collaborate with tech experts: Forge a close working relationship with your IT team. Together, review and understand the intricacies of how data is stored, transferred, and accessed. 

  • Understand how AI is used: Ensure clear understanding of AI applications in legal tech, including data usage, ease of human verification of AI outputs, and AI's role in backend processes.

By prioritizing security and privacy from the outset, legal professionals can harness the power of tech while upholding the trust placed in them by their clients.

4. Merging New Tech With Existing Workflows

“If it ain’t broke, don’t fix it.” You’ve probably heard that before — perhaps even when pitching some new tech. 

Established processes, honed over years, aren't just the fruit of habit — they are the carefully constructed workflows of invested stakeholders. These aren't just ways of doing things; they are the underpinnings of how a firm or legal entity functions. And there’s a real risk to messing with the status quo.

The legal software realm is vast, with tools ranging from e-signature tools and customer management software to specialized litigation support systems and contract management solutions. Migrating to new technologies means making sure that tech is compatible and customizable so you can integrate it with what’s already working well. 

And that doesn’t mean just getting the software with the most features. It means ensuring the features you get align perfectly with your requirements, eliminating unnecessary functionalities and automating the fundamental tasks that will free up precious time for legal professionals. 

When all the stars align, legal tech can enhance workflows rather than disrupt them. It can automate routine tasks, scale with your firm, and adapt to rigorous regulatory environments. Here are some strategies to focus on to make sure everything goes smoothly: 


  • Map out your current processes: Before integrating tech, have a clear blueprint of existing processes. This aids in understanding where and how technology can fit in.

  • Create feedback loops: Regularly engage with end users. Their on-the-ground experiences with the technology can provide invaluable insights into areas for improvement.

  • Start small: Kick off the integration with a smaller team or a single department. Let them be the pioneers. As they familiarize themselves with the new tech, they'll likely identify potential hitches and provide feedback that can be used to improve the larger rollout.

  • Check for compatibility: Before full-scale implementation, ensure that the new tool can integrate with existing systems. This might involve liaising with the tech vendor or bringing in IT specialists for a comprehensive compatibility audit.

  • Engage stakeholders: Their involvement ensures that the tech aligns with the processes they've built and trust. Demonstrate the potential benefits and returns on investment.

  • Look for robust support systems: Choose tools that come with thorough support. Whether it's 24/7 tech support, regular webinars, a help center, or training modules, having a robust support system can smooth out the integration process.

  • Create internal evangelists: As you roll out new tech, identify and nurture internal champions. These individuals have mastered the tool and can provide hands-on support to their colleagues. Their success stories, showcased internally, can spark enthusiasm and drive adoption.

As legal firms adopt new technologies, their success will depend on how well these tools integrate with existing processes, enhancing rather than disrupting their work.

5. Setting Clear Goals 

A frequent misstep in the legal tech adoption process is venturing into the technological realm without clearly defined goals. This approach can lead to wasted resources, staff frustration, and inefficiencies — ironically, the very issues technology seeks to resolve.

Here are some things to keep an eye out for: 

  • Purposeless adoption: The sheer array of available tools can be tantalizing. Firms may find themselves investing in tools without a clear understanding of the specific problems they're trying to solve. 

  • Inability to measure success: Without predetermined objectives and KPIs, determining whether the tech adoption is successful becomes challenging. Firms may have spent significant time and resources on a tool, only to find they have no metrics to gauge its impact or ROI.

  • Misaligned resources: Without set objectives, firms might misallocate resources. For instance, they might provide excessive training for features that are not vital to their needs or neglect crucial functionalities due to a lack of awareness.

To ensure a successful tech adoption journey, legal teams need to clearly identify what they hope to achieve. 

  • Define what success looks like: With no benchmarks, how do you measure progress? Establish tangible KPIs. It might be "reducing contract review times by 30%" or "increasing client communication efficiency."

  • Set realistic milestones: While the ultimate benefits of a tech tool might be realized in the long run, setting and celebrating interim goals can keep the momentum going and prevent disillusionment.

  • Be flexible: Goals should be concrete but not rigid. As firms delve deeper into the functionalities of a tool, they might discover new potential advantages. Revisiting and tweaking goals is as crucial as setting them.

  • Review regularly: Periodic evaluations ensure the firm remains on track. It's an opportunity to assess if the tool is meeting its objectives and a chance to recalibrate if necessary.

  • Know when to say no: Legal teams often face pressure to adopt new tools from other parts of the organization, but they’re not always adding any value. If a tool isn’t helping your team, don’t be scared to push back so you can put adoption resources where they’ll actually help. 

A tech tool, no matter how advanced, is only as good as the strategy behind its adoption. By establishing clear, purpose-driven goals, legal teams can harness the full potential of their technological investments, ensuring they sail smoothly toward their desired horizons.

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