The Foundation of Legal Firm Efficiency: Lessons from the (Server) Room

Paul Riley – April 11, 2025  – 6 mins read

If you’re reading this, there’s a good chance we’ve walked a similar path — maybe even tripped over the same cables. Core legal operations systems have been at the heart of my role for years, and like many of you, I’ve spent more late nights than I’d like to admit troubleshooting, evaluating, replacing, and defending tech decisions that ultimately shape how our firms operate.

Let’s be honest: keeping a legal tech stack humming is equal parts architecture, diplomacy, and damage control.

Moving from LEAP to Actionstep: A Strategic (and Sanity-Saving) Shift

One of the biggest transitions I’ve made recently was moving our firm from LEAP to Actionstep. LEAP served us well for a time — it’s lean, quick to deploy, and user-friendly on the front end. But as we grew and started integrating more tools (finance, CRM, DMS), we hit walls.

The tipping point? Integration fatigue. LEAP’s closed ecosystem became a bottleneck. Every customisation felt like we were fighting the system rather than extending it.

Actionstep, on the other hand, has been a breath of fresh air. Their support team doesn’t just answer tickets — they understand legal ops. We’ve built out custom workflows, integrated with Xero and NetDocuments, and even plugged in a lightweight BI tool — all without breaking the back end. Their modular approach let us scale sensibly without re-architecting everything. That flexibility has been critical as our litigation teams become more data-driven.

Lessons Learned (Sometimes the Hard Way)

Here are a few personal truths I’ve picked up, usually the hard way:

• Buy for the next 3 years, not just this year.
  A system that works today can become a liability tomorrow if it can’t grow with your firm. We learned that the moment we outgrew LEAP’s comfort zone.
• Integration > Feature Set.
  I’ve been seduced by shiny dashboards and features more than once. But at the end of the day, if it doesn’t play nicely with the rest of your stack, it becomes shelfware.
• Support quality is underrated.
  During our Actionstep rollout, I could Slack their team and get a real response — often from someone who’d been in a law firm before. That’s a world of difference from submitting a ticket into the void.
• You’re not just managing systems — you’re managing change.
  Adoption isn’t about features. It’s about lawyers feeling like their workflow is respected. Sometimes that means slowing down a rollout to get stakeholder buy-in — especially from the ones who still print every email.

What’s Working Right Now

• Document Management:
  iManage continues to be the gold standard for us. The integration with Actionstep has been surprisingly smooth, and their cloud offering has finally matured to where I’m comfortable running production-level work there.
• Time Tracking:
  Still the Achilles heel of most firms. We’ve started using Tikit Carpe Diem more aggressively — not just for capture, but to surface trends across practice groups. Seeing where we don’t bill has been just as useful as where we do.
• Matter Workflows:
  Customising workflows in Actionstep has been a quiet revolution. We’ve built logic that nudges teams to complete compliance steps, prompts reviews, and tracks key milestones — without nagging. It’s the closest we’ve come to invisible process enforcement.

The Human Side of IT Leadership

If there’s one thing I wish I’d figured out earlier, it’s that the best tech stack in the world won’t save you from poor communication. Your job — my job — isn’t just about buying tools. It’s about translating tech into confidence for the rest of the firm.

I don’t pretend to have it all figured out. But I’ve learned that clarity, responsiveness, and the occasional bit of stubbornness go a long way in navigating the weird (and sometimes wonderful) world of legal operations.

If you’ve recently made a core system shift — or are about to — I’d be genuinely interested to hear what drove your decision. We’re all working with the same toolbox, just building different things.

Let’s connect at the next Legal Digital Tools meet-up — the war stories are better when they’re shared.