Digitalizing your Legal Department: Three Questions to Consider Before You Get Started 

The pressure is real. Contracts pile up, deadlines get missed in spreadsheets, subsidiary data sits in filing cabinets across three jurisdictions. Finance has its ERP. HR has its HCM. Sales has its CRM. Legal, too often, is still running on email threads and shared drives.

But technology doesn’t fix a poorly defined problem. Teams that rush straight to vendor demos — without answering a few foundational questions first — tend to select the wrong tool, or implement the right one badly.

Are you looking to follow suit and digitalize your legal department? Before taking your first steps into this new project, here are the three key questions you should be asking yourself.

1. What does my legal department’s day-to-day operations look like?

This is the first question to consider before launching into any digitalization project. After all, the aim of the project is to improve existing processes, meaning that you will first need to have a good understanding of how they work. Realistically, discovering this will require a full audit of all your legal department’s practices. This analysis can be broken down into several questions:

• What does a typical day or week in the legal department look like?
• What duties and responsibilities do the employees have?
• What are their daily practices and routines?
• What tools do they use?

The more precise and quantifiable the answers to these questions are, the simpler and more targeted the implementation of your project will subsequently prove to be. At this stage, there is no need to identify the challenges being faced by the staff; the idea is merely to gain an understanding of how the department operates.

The question regarding tools is particularly important, as it points you in the direction of what the legal team’s technical requirements are. Gaining an understanding of existing tools will help you find a better fit when implementing future solutions.

2. What are the areas for improvement and the main challenges faced by the teams?

This second question is crucial, as it will determine the direction of the entire project: the choice of legal tech solution and how it will be implemented.

Digitalizing legal departments actually assists in addressing the daily challenges of not only the lawyers themselves, but also the various other departments they interact with (marketing, purchasing, human resources, etc.).

Read also: Digitalizing Legal Departments: Tips on Implementing Your Legal Tech

Identifying these difficulties should be as precise and comprehensive as possible. With this in mind, any needs and sticking points should be sought out and identified both within the legal department and with the operational staff who assist it. After all, any new tools introduced will have an impact on all departments.

Legal tech tools are, in actual fact, used a great deal more by the operational staff than by lawyers themselves.

Some examples of things you can do to collect the staff’s reflections on the issues they encounter include:

• organizing workshops in each department, being sure to carefully follow the agenda;
• conducting interviews with individuals or in small groups, by team;
• sending out online questionnaires.

Workshops and interviews have the advantage of humanizing the preparation of the project, opening up opportunities for discussion. Online questionnaires, meanwhile, are an ideal solution for gathering as much data as possible in a short space of time. It is up to you to choose the method that best suits your constraints, requirements, and available time.

The pain points worth cataloguing

When mapping challenges, teams tend to cluster around a few recurring themes. Recognizing them early makes the selection process sharper:

• Contracts: approvals take too long, deadlines are missed, obligations tracked in spreadsheets
• Legal entities: subsidiary data scattered across jurisdictions with no central view
• Matters and external counsel: costs hard to track, workload invisible, escalation unstructured
• Board and governance: meeting prep manual, documents circulate by email, minutes take days to finalize

Each of these maps to a specific category of legal tech tool. Knowing where your friction is heaviest will save time during vendor selection, and help you prioritize which module to roll out first.

Ready to map your department’s challenges?
Download our Guide “How to Choose Your Legal Operations Software: Key Considerations and Expert Tips“, covering audit steps, selection criteria, and implementation phases for in-house legal teams.

3. What are the goals of the digitalization project?

Digitalizing a legal department is a project with specific aims, which usually revolve around the idea of efficiency. Any well-executed project must be guided by at least one clear, fixed, and measurable objective, which must be established in advance. Analyzing how the department functions and collecting details of the challenges they face should provide a clear indication of what these objectives are. The more common a difficulty is and the greater its impact on the staff, the more the project should focus on rectifying it.

At this stage of your planning, it is important to involve senior management, as the objectives of this digital transformation are a key element in any strategic approach. The idea is to address the day-to-day issues faced by both legal and operational staff while also integrating the project into the company’s overarching strategy.

Generally speaking, the goals our clients often set for themselves are:

• improving the performance of the various departments;
• saving time in day-to-day operations;
• improving visibility of ongoing commitments;
• helping exchanges and collaborations to run more smoothly.

To better manage your digital transformation, we recommend listing these objectives in order of priority. Then, when it comes to integrating the tool, this will allow you to determine the highest-priority actions to be implemented (which features to roll out, staff training, etc.).

Read also: What Are the Main Challenges of Contract Management?

Measure before you launch

One practical step many teams skip: establish your baseline metrics before go-live. Contract approval cycle time, missed renewal deadlines, external counsel cost per matter, hours spent preparing board packs: track these before the tool is live, and you’ll have real numbers to show three months after implementation.

Teams that define KPIs at the outset find it far easier to demonstrate ROI and secure budget for the next phase.

Bonus: How do you plan for adoption?

Even the right legal tech tool fails without adoption. Legal professionals are risk-averse by training, and new workflows rarely sell themselves. This is the planning question most teams ignore. And it’s often what separates a successful implementation from an expensive one.

A few things that make adoption easier in practice:

• Appoint a project owner inside the legal team, not just an IT contact. Someone who understands both the workflows and the internal dynamics.
• Start with the highest-pain, highest-volume process. Quick wins build momentum. They also reduce resistance across the team.
• Involve operational departments early. Sales, procurement, and HR will use legal tech daily. Their input at the design stage reduces friction at rollout.
• Communicate results regularly. When the team sees that contract approvals now take two days instead of two weeks, they become advocates rather than skeptics.

Change management doesn’t need to be a separate project. It does need to be deliberate.

Still managing legal workflows manually?
See how legal teams reduce contract cycle times, centralize entity data, and automate board meeting prep, without a lengthy IT project. Explore the DiliTrust Suite →

How to choose your legal tech solution

The answers to the three questions above will lay the groundwork for your digitalization project. The way your legal department functions, as well as the difficulties encountered by your employees, will help you to establish one or more big-picture objectives that will determine which solution you opt for.

To select the legal tech solution that will be best suited to your needs, you should ideally run a benchmark of the various tools available on the market. This benchmark should be guided by multiple criteria linked to your teams’ requirements.

The four legal tech categories to know

Modern legal platforms typically cover one or several of the following workflows:

Category	What it addresses
Contract Management (CLM)	Drafting, approval workflows, obligation tracking, renewals
Entity Management	Corporate structure, subsidiary governance, compliance filings
Matter Management	Case tracking, external counsel spend, workload oversight
Board Portal	Meeting prep, board packs, minutes, governance workflows

Some teams start with one module and expand over time. Others look for a single platform that connects all four, particularly useful when an entity feeds into a contract, or a contract dispute escalates into a matter.

The criteria your benchmark should cover

Beyond features, your evaluation should cover:

• Collaboration and remote access: Can teams work on contracts and documents simultaneously, from any location?
• Automatic monitoring and deadline alerts: Does the tool track contract expirations, renewal dates, and compliance deadlines automatically?
• Document storage and classification: Is there a centralized, searchable repository for legal documents, with version control and access permissions?
• Data security and sovereignty: Where is data hosted? What certifications does the vendor hold? For cross-border teams, data residency matters.
• Electronic signature: Can contracts be signed directly within the platform?
• Integration with your existing tools: Does it connect with your CRM, ERP, or productivity suite (Microsoft 365, Google Workspace, Salesforce)?
• AI capabilities: Can the platform review contracts against your standards, summarize documents, generate meeting minutes from audio, or answer natural-language questions across your legal data?
• Scalability: A tool that works for a 5-person legal team should be able to grow with the organization, without migration or re-implementation.
• Time to value: Ask vendors directly: how long does implementation typically take? The best platforms can be operational in 1 to 3 months.

Of course, this list is by no means exhaustive: it is up to you to determine your key criteria, accounting for both the needs of the staff who will use the tool and the constraints put in place by management.

AI as a selection criterion

AI has moved from a differentiator to a practical expectation in legal tech. When evaluating platforms, look past the surface claims. Useful AI in a legal context means:

• Contract clause analysis against a pre-approved playbook
• Automated document summaries before meetings or reviews
• AI-generated board meeting minutes, adapted to your format
• Natural-language queries across your own contract and matter data

The best implementations embed AI at the platform level, built in rather than bolted on. DiliTrust’s Lini AI engine is built across all four modules of the Suite: Risk Detector for contract review, Document Summarization for fast document prep, Audio Transcription and Minutes Generation for board meetings, and Ask Lini for queries across your legal data. Your data stays in your environment; there’s no dependency on an external AI service.

Frequently asked questions

See how in-house legal teams centralize contracts, entities, matters, and governance in a single platform.
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