Engagement letter automation - Top three challenges and how to overcome them

And beyond risk management, the economics are also compelling. Engagement letters are high volume and typically already templated to some extent. Any efficiency gained is a direct saving to the firm.

On paper, it’s a ‘quick win’. In practice, however, engagement letter automation projects can be surprisingly challenging - a typical Engagement Letter project involves well over 900 pieces of automation logic. Therefore, whilst the documents are relatively short, the automation can involve as much complexity as we would see in a much larger project.

In this article, we explore where those challenges arise - and how to approach them.

Challenge: Agreeing the “right” template

Engagement letters have a wider user base than almost any other document type. They are drafted across the entire firm, and different practice areas (sometimes different teams within them) will have developed their own approaches over time. Variations in scope wording, liability positions, and tone can all reflect legitimate differences in practice.

This creates a fundamental challenge: what exactly are you automating?

Reaching a firm-wide position typically requires:

• Strong central coordination
• Genuine leadership-level buy-in
• Input from multiple practice areas and functions

Without this, projects tend to fall into one of a few different traps:

• Stalling completely, while stakeholders debate what the “right” template should be.
• Delivering a lowest-common-denominator solution that no one fully supports, and therefore no one uses, or that delivers so little in terms of content or automation that it does not address the key aims of the project.
• Automation explosion, as teams try to separately automate all of the disparate templates, creating a management and maintenance monster.

There is also a more subtle technical challenge. Engagement letters are typically not designed to be ‘modular’ documents. Unlike contracts, which are separated into clauses, definition tables and related schedules, engagement letters instead rely on a consistent narrative flow. Capturing that in an automation can be surprisingly fiddly and requires careful structuring.

Top tips

Securing buy-in for a firm-wide project can take patience and persistence. In the meantime, thoughtful automation can help build that support:

• Start small. A single team with high volume and genuine enthusiasm can help validate a choice of technology and delivery model ahead of a firm-wide rollout.
• Anticipate precedent needs. Take advantage of a project with more limited scope (a few teams or offices) to refine a template approach that can be scaled firm-wide. For example, can small changes (such as content ordering) be made to support flexibility whilst simplifying maintenance?

Challenge: Maintaining the automation

All automations require some level of ongoing development and maintenance to keep them current and useful. In our experience, engagement letters are among the most frequently updated document types, driven by:

• Changes to standard terms and conditions
• Evolving approaches to scope and pricing
• New practice areas or specialisms
• Updates to rates or regulatory requirements

These changes are often time sensitive. Firms may agree updates internally that need to take effect from a specific date, not when automation resource becomes available.

This creates a tension if maintenance sits solely with a central automation team balancing multiple priorities.

Top tip

• Plan for maintenance from the outset. Be explicit about ownership, resourcing, and turnaround expectations. If you have started with automation in a single team, use that data to help understand the maintenance requirements at the firm level. You can also look at historical updates to templates to set a baseline for update frequency, and budget resources to meet that need once the automation goes live.

Challenge: Workflow automation

Engagement letters are rarely created as standalone documents. They sit within a broader process that may include:

• matter opening
• fee scoping and pricing; and
• client onboarding and KYC.

This raises a key question: where should automation sit within that workflow?

For example, it might seem logical to generate an engagement letter as part of matter opening. But in practice:

• matter opening is often done early, sometimes speculatively;
• the person opening the matter (e.g. an assistant) may not have the information needed to complete the letter; and
• key elements like scope and team may still be fluid.

In these cases, forcing full automation too early can add friction rather than remove it.

Alternatively, generating the letter later in the process allows for greater accuracy, but may make it harder to reuse data between steps.

Top tips

• Design for the real user. Be clear who will generate the letter and what information they are likely to have at that point.
• Don’t over-engineer early stages. If key information isn’t available, focus automation effort where it will have the most impact.
• Decouple where needed. You don’t have to wait for perfect integration with your practice management system to move forward, especially if you already have alignment on the precedent.

A high-impact opportunity - with the right approach

Despite these challenges, engagement letters remain one of the most valuable areas for automation.

They combine:

• clear risk management improvements;
• high volume; and
• immediate efficiency gains.

But success depends on recognising that this is not just a technical exercise. It requires:

• alignment on content;
• ongoing ownership; and
• thoughtful integration into existing workflows.

At Clarilis, we’ve delivered automation projects for a huge range of firms, and our lawyer-led managed service approach is a particularly strong fit for engagement letter projects. We take care of implementation and ensure your automation scales from single team to firm-wide. And following launch, our ‘unlimited amendments’ service means the automation is always up to date.

Are you considering an engagement letter automation project?

We’d love to hear from teams that are considering engagement letter automation. Get in touch with us here if you’d like to explore this further.