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The Singapore Law Gazette

Future Proofing Your Practice

Key Considerations for Technology Pilots in Law Firms

In an era of rapid legal evolution, how are law firms reviewing new technology? This article examines the necessity of technology pilots for law firms alongside key considerations to ensure these new tools not only fit within the existing digital landscape but also propel firms towards efficiency and competitiveness in a digitally driven world.

The rapid evolution of legal service delivery mandates that lawyers stay abreast of technological advancements such as Generative AI, document automation, contract lifecycle management, and process automation.1Law Society of Singapore, “Future Proofing for Lawyers 101,” These innovations are not just buzzwords but pivotal elements driving discussions on enhancing legal practices. Law firms are increasingly investing in their tech stack, digital infrastructure, and even reimagining their physical workspaces to foster collaboration and streamline operations.

However, with the pace of technology moving so swiftly, it’s a challenge to keep up. Every week brings news of another technological breakthrough, making it easy to be swept up in the excitement of the latest offerings that promise to resolve various legal process challenges. To avoid the allure of every new “shiny object” and ensure a pragmatic approach, law firms must adopt a disciplined strategy of conducting comprehensive technology pilots.

What is a Tech Pilot?

A technology pilot is essentially a small-scale, short-term experimentation of new technology that can allow a firm to understand how it might benefit or work for the organisation. It enables the firm to identify risks and deficiencies, test hypotheses before substantial resources are committed towards onboarding this new technology.2GeeksforGeeks, “Pilot Testing in Software Testing,” In many instances law firms leave it up to the vendors to direct these pilots and this can potentially lead to user dissatisfaction, wasted resources, and ultimately a rejection and replacement of the tool.

How do we then develop a systematic approach? This article seeks to highlight some key considerations when piloting new technologies and how a firm can prepare itself before any engagements with vendors.

The Firm’s Digital Profile

A good starting point before any engagements with solution providers is to first develop a good understanding of the firm’s digital profile, maturity and readiness to adapt to new technology.3Cygnet Digital, “Digital Maturity Model to Drive Business Transformation,” With this information ready at hand, conversations with vendors become much more efficient, focused and productive. Here are some questions and tools for self-analysis and evaluation:

Digital Profile

  • How does the firm manage matters digitally at present? (From inception to closure)
  • What is the firm’s current tech stack and how do they align with the firm’s strategic goals and matter life cycle?
  • Who are the key decision makers in the organisation with regards to technology and operations?

Digital Maturity

  • Does the firm have baseline digital infrastructure for effective case-management?
  • Are there systems in place for managing, storing, and analysing data?
  • Has the firm leveraged technology to enhance client engagement and satisfaction?

Digital Readiness

  • Do employees of the firm have the baseline skills to adopt new technologies?
  • Is there a culture of innovation that encourages learning and adoption of new technologies?
  • Does the firm support and incentivise innovation amongst employees?
  • How does the firm manage change and transition within the firm when implementing new technologies?

With these considerations, the firm’s representatives would be able to communicate the firm’s digital profile, structure, and readiness clearly. This in turn, would provide vendors with a good context of who they’re working with, whether their product would be a good fit and how they can potentially tailor their solution or service.


In the legal industry, adoption of technology requires solutions that seamlessly integrate into lawyers’ workflows, emphasising the principle that technology should adapt to users, not vice versa. The effectiveness of technology pilots is significantly amplified when they target specific, yet often undiscovered, pain points within legal practices.4MakeIterate, “How to Write a Problem Statement for Design Thinking,” Understanding these challenges necessitates a deep empathy towards the users, which can be effectively fostered through storytelling. By capturing and sharing lawyers’ personal experiences and struggles, storytelling becomes a powerful tool in human-centered UX (User Experience) design, enriching the technology selection process with genuine insights into the users’ needs and preferences. This narrative approach not only deepens the understanding of lawyers’ perspectives but also showcases the varied experiences across practice groups, guiding the implementation of technologies that truly address users’ issues.5MakeIterate, “How to Empathize in Design Thinking: Practical Tools and Techniques,”

Observing daily practices, and engaging lawyers in the evaluation of new technologies are critical steps in developing an empathetic, user-centric tech ecosystem within law firms. This empathy-driven approach ensures that technology adoption is both meaningful and aligned with the actual needs of legal professionals, ultimately enhancing efficiency and satisfaction.

Clear Responsibilities and Processes

A tech pilot should ideally involve key stakeholders of within the firm i.e. Legal Ops personnel, IT reps, and actual end-users of the application. This would allow for consideration of different perspectives and feedback collected would be well-rounded. It is crucial for each participant to be clear about their role, whether it’s gathering feedback, analysing test results, liaising with vendors, or conducting the tests themselves. To facilitate a smooth and efficient pilot process, establishing clear protocols is crucial. Questions such as “What are the duration and cut-off dates for testing?”, “How will the testing be conducted?”, “Where will the results be compiled?”, and “How will escalations be communicated to the software provider?” need to be addressed before the pilot begins. Answering these questions in advance will help avoid potential friction and ensure that the pilot is well-organised and effective.

Metrics and Parameters

Testing new tools or technologies may take place for either one of two reasons: Implementing a brand-new system or replacing an outdated legacy system. The agreed metrics for testing and validation may differ slightly for each reason. When replacing a legacy system, it is easy to measure and record pain points as well as time taken on related processes. Using this frame of reference, the replacement solution can be tested accordingly. Testing a new technology on the other hand may require some thought put into how success of the pilot is measured. Are there any current processes potentially affected? How will a new workflow be adopted by users? Are there any potential side effects of implementing this new tool or technology? With the answers to these questions, choosing the right metric would become clearer.

Here are some useful pointers:

  1. Measure user-satisfaction: Using a numeric value (e.g. on a scale of 1 to 10), end users should be able to communicate how they feel about their experience using the tool (Was it easy to learn? Was the interface user-friendly? Would they recommend this tool to other users? Do they see themselves using the tool frequently?).6Jeremy Devray-Benichou, LinkedIn, “5 Metrics to Help You Measure Success in a Pilot,”
  2. Tangible and measurable critical success factors: Not all costs and benefits of the tool or technology can be tied to a value within a numerical scale, however, in aiding the decision-making process, factors that define how the pilot project is judged need to be measurable and straightforward. For example, if assessing a new document automation tool, “document should be generated quickly” is a poor critical success factor as it is subjective and open to interpretation. Instead, “Upon completion of questionnaire, document should be generated in less than 10 seconds”, is a much clearer objective and does not allow for any room for unambiguity.
  3. Define the scope for testing: Tech solutions often include a vast array of features, but given the short lifecycle of a tech pilot, it is impractical to test every available feature. Depending on the firm’s requirements and lawyers’ must-haves, parameters should be drawn to define what are the areas that will be included for testing and what will not. Consequently, each feature should then be tied in with a target metric as well as a pass rate percentage value to determine if it has met or exceeded expectations.

Identify Potential Risks

Before giving the green light to conduct a tech pilot, a risk analysis conducted could be vital in preventing any potential harm to the firm.7Managing Projects Successfully. Bloomsbury Business (Business Essentials), 2022. Within the context of a tech pilot, some suggested areas for assessment are as follows:

  1. Reputation: Will public perception of the firm be harmed if the firm engages with the technology or provider? Does the provider or tech solution have any history of data breach? Firms should be wary if the provider had previously been involved in any negative press.
  2. Operational: Would the rollout of the new tool increase the volume of work (incurring cost) in another area? Would a new department have to be formed to support the new process? Would there be a need for reorganisation of departments?
  3. Technical: Does the tech solution integrate well with the firm’s current tech stack? Is it flexible and scalable? Does the tool overlap with existing technology within the firm? Is personal data being hosted securely on the cloud?

Conducting the Pilot

In the execution phase of the pilot, staying organised is key. Leveraging a collaboration platform, such as a “Teams Channel”, is instrumental in ensuring that all relevant information – including site URLs, tester log-in IDs, and technical guides – is centralised and easily accessible to all participants. Despite the inherently brief duration of the pilot phase, it’s critical to allocate ample time for several key stages: pre-testing orientation to familiarise testers with the system, onboarding to ensure smooth access and setup, actual testing to assess the solution in action, feedback gathering to capture users’ experiences and insights, and finally, an internal review to evaluate the pilot’s outcomes against its objectives. This structured approach not only facilitates a comprehensive assessment of the tech solution but also enhances the overall effectiveness and efficiency of the pilot process, laying a solid foundation for subsequent phases and eventual full-scale implementation.

Post-Pilot Evaluation

Did it pass the test? Following the conclusion of the pilot, a thorough evaluation is essential to determine the technology’s impact and its potential for firm-wide implementation. This evaluation should assess whether the technology met the predefined success metrics, its effect on workflow efficiency, user satisfaction, and any unforeseen outcomes. The decision to scale the solution should be based on a balanced consideration of these factors, alongside a plan for addressing any gaps identified during the pilot. This stage is critical for transitioning from a pilot to a full-scale implementation, ensuring the technology aligns with the firm’s strategic objectives and user needs.8SHI Resource Hub, “Put your technology to the test: Steps for achieving a successful pilot program,”

Change Management

Implementing new technology is as much about managing people as it is about managing the technology itself. Effective change management strategies should be integrated into the pilot process to facilitate acceptance and minimise resistance. This includes clear communication about the benefits and impact of the technology, involving users as change champions to advocate for the pilot, and managing expectations throughout the firm.9Forbes, “Five Steps to Successful Technology Change Management,” A proactive approach to change management helps to ensure a smooth transition and greater adoption post-pilot.


In conclusion, future-proofing a law firm’s practice through technology pilots is an essential strategy in today’s rapidly evolving legal landscape. As this article has outlined, understanding the firm’s digital profile, fostering empathy towards end-users, establishing clear responsibilities and processes, setting measurable success criteria, and conducting thorough risk assessments are critical steps in ensuring the effective piloting of new technologies. These considerations form the backbone of a structured approach to technology adoption, enabling law firms to navigate the complexities of digital transformation with confidence.

The success of technology pilots hinges not just on the technological solutions themselves but also on the firm’s readiness to embrace change, the alignment of technology with strategic goals, and the seamless integration of new tools into existing workflows. By prioritising user-centric design, clear communication, and meticulous planning, law firms can mitigate risks, enhance efficiency, and improve client satisfaction. Ultimately, the goal is to adopt technologies that not only address immediate needs but also position the firm for long-term competitiveness and growth.


1 Law Society of Singapore, “Future Proofing for Lawyers 101,”
2 GeeksforGeeks, “Pilot Testing in Software Testing,”
3 Cygnet Digital, “Digital Maturity Model to Drive Business Transformation,”
4 MakeIterate, “How to Write a Problem Statement for Design Thinking,”
5 MakeIterate, “How to Empathize in Design Thinking: Practical Tools and Techniques,”
6 Jeremy Devray-Benichou, LinkedIn, “5 Metrics to Help You Measure Success in a Pilot,”
7 Managing Projects Successfully. Bloomsbury Business (Business Essentials), 2022.
8 SHI Resource Hub, “Put your technology to the test: Steps for achieving a successful pilot program,”
9 Forbes, “Five Steps to Successful Technology Change Management,”

Legal Technology Analyst
Allen & Overy
[email protected]

A qualified lawyer from Singapore who has dived into the world of LegalTech, Harry Kishen has always been keen in exploring new and promising technologies with the aim of alleviating the dreary aspects of practice. Having worked in various law firms over the last six years, he understands that for practice-culture to change, we must increase awareness of and receptiveness towards new technologies and its applications. With experience from a legal technology startup and in his current role at Allen & Overy, he has honed his expertise in diverse aspects of legal technology, including product development, implementation, technology adoption, process analysis, document automation, and project management. His vision for LegalTech is to empower lawyers to deliver their services efficiently, cost-effectively, and peacefully.