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Forging a Path Forward

Forging a Path Forward When Legal Tech Fumbles

  • Legal Operations
  • 4 Mins

The use of legal technology is up 53 percent as more legal departments are searching for new ways to use these tools to manage their workflows, according to the Thomson Reuters 2023 Legal Department Operations Index. This is not surprising as innovative tools continue to enter the market and there is more eagerness across the board to derive the benefits. Smaller and medium sized organisations are joining larger organisations in the building of their legal operations teams and tech stacks to enhance their environments with foundational tools such as contract management and matter spend management.

But what happens when a technology initiative does not live up to the expectations? This a common refrain amongst many corporate legal leaders. A lot of time and resources are spent on tech investments, so underperformance can be disheartening. It can be difficult to determine the underlying reason for the investment going off course.

It often is also tricky to determine the best path forward. Is it time to scale down the tech the department already has in-house? Would revamping current usage with new processes and efficiencies be a better option? Is it time to throw in the towel and start over with a new tool?

To answer these questions, it is first crucial to pinpoint why a tool is underperforming. Then, how to determine whether to optimise existing technology or start over with a new solution.

Common Obstacles

When diving deeper into why a tool is not living up to expectations, it frequently becomes clear that the technology itself is not the issue. 

Here are three alternate reasons to consider when researching the root cause of a seemingly failed legal tech investment.

  • The business case projections may have been too ambitious. A reassessment may show that an extended timeline or refocused use cases would lead to better results.
  • The manner in which the vendor implemented the tool was not up to par with what the organisation needed for it to thrive. It is important to thoroughly vet partnerships and have discussions around implementation beforehand in order to appropriately align expectations.
  • The internal processes around using the new tool were weak or unclear. Change management can be hard. Even the best tools in the market can underperform without proper usage, training, and stakeholder involvement. This leads to people giving up and sticking with the old ways of completing tasks.

Considering the above will often show that the technology was not a failure at all. Instead, it is time to evaluate tech performance through a different lens to pinpoint valid feedback and determine where implementation or utilisation fell short.

Cultivating Successful Outcomes

There is one questions that ensues: is it time to turn back or push forward? At this point, it should be clearer how the organisation is actually using current technology and it is time to set some goals for the future. Whether to optimise current tools, drop them, or invest in new tech will be the focus. Best practice is to optimise what the department already has, then look to new solutions if necessary. Optimisation versus new investment costs, need for data migration, internal compliance, and change management sentiment will all feed into this assessment.

Three factors will guide this decision: technology roadmaps, process mapping, and stakeholder engagement.

Technology Roadmaps

Having a functional detailed plan is crucial. Building a legal technology roadmap with clear goals in mind leads to improved operational performance management. When a tool underperforms, it is time to dive deeper. It may become clear that it is time to redefine the roadmap in order to determine the best path forward. While all roadmaps are unique and require room for change, consider including the following characteristics:

  • Define a phased timeline that supports iterative development and leaves room for evolution. A major roadblock to successful implementation is attempting to accomplish too much too quickly.
  • Focus on the tool’s enhancement capabilities instead of strictly looking at the functionalities.
  • Consider the broader technology stack and architecture for both the legal department and entire enterprise. This will help avoid siloed operations and disjointed technology integration, while also shining light on other potential opportunities.

If these things were not done at the outset, it may be why the technology did not live up to the set expectations. Redefining the roadmap to incorporate these factors may provide an opportunity to push forward with the investment and avoid the need to be reactionary when something goes off track. Always include room to reprioritise.

Process Mapping

Teams may avoid mapping out processes before integrating new technology because it can be time-consuming. However, failing to do so can lead to confusion over how to effectuate meaningful change and achieve uniform adoption. Process mapping will show how the department operated before the new tool came aboard and throughout the integration process. This can inform decisions about how teams can do things differently using the current technology investment, where gaps exist, and whether it is time to take a new path.

Stakeholder Engagement

Take a look at the level of stakeholder engagement during the tech planning, implementation, and follow-up phases. These individuals need ownership and say for a tool to thrive. When key stakeholders are involved, it is easier to get the resources and training necessary for teams to effectively integrate new solutions into their workflows. A huge roadblock to effective change management is when there is lack of stakeholder involvement and commitment to helping carry out the change.

Stakeholders should be ready, willing, and able from day one to embrace everything that goes into adopting and successfully integrating new technologies. To attain this, consider these best practices:

  • Identify stakeholders and determine how much support and influence they can offer for the project. Build an initial strategy around getting the right stakeholders on board and well-positioned to effectuate meaningful change.
  • Perform change impact and change fatigue assessments. These bring to light how many different areas across the enterprise that changes to technology and process will touch, how significant the impact will be, and where to proactively create mitigation strategies.
  • Create a clear vision so there is a collective understanding of how to achieve success. Hallmarks of a successful plan include specific and actionable goals, considering the entire organisational architecture, and engaging pertinent stakeholders optimally at each stage of the process.
  • Thoroughly communicate what each business unit needs to do before a new tool launches and schedule trainings.
  • Create a continuous operational improvement plan to keep on track, measure success, receive feedback, and make revisions based on user input.

All of these steps will be more impactful with informed and engaged stakeholders taking purposeful actions to ensure a new tool thrives.


Following the steps above will help legal departments better evaluate their legal tech stack and make more strategic decisions in the future. In many cases, they will likely find room to optimise – at least to some degree. There are also external legal business advisory resources that can help navigate tech initiatives and redefine strategies with ease. All of this will make everyone happier and create an internal culture of more informed and tech-savvy individuals.

The contents of this article are intended to convey general information only and not to provide legal advice or opinions.

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