A Playbook for Your First AI Win
The idea of launching an "AI initiative" can feel overwhelming, expensive, and abstract. So don't.
Instead, focus on getting one, single, tangible win. A successful pilot project is the most powerful currency you have for building momentum and getting buy-in for a broader strategy, and depending on where you focus it can be accomplished in days or weeks, not months.
Here is a simple, 5-step playbook to guide you.
Step 1: Identify the Migraine As we’ve discussed before, start with the most acute and universally acknowledged pain point. What is the one task that, if you solved it, would make your team visibly happier and more productive? It must be specific, measurable, and painful enough that people are desperate for a fix.
Example: "It takes 40 hours per month for our senior paralegal to manually review invoices for compliance with our billing guidelines."
Step 2: Define "Fixed" How will you know if you've won? Be ruthlessly specific about what success looks like. These metrics will be your north star when evaluating any potential solution.
Example: "Success is reducing manual review time by 75% (to 10 hours/month), catching at least 10% more non-compliant charges than our manual process, and having the paralegal approve, not hunt for, the data."
Step 3: Run a Small, Controlled Pilot Resist the urge to launch a department-wide solution. Select a small, representative sample of the problem to test. For an invoice tool, that might mean running one month's worth of invoices from your three most strategic law firms through the platform. This limits the risk, cost, and complexity, allowing you to learn quickly - literally in days if you use data from the past few months.
Step 4: Measure and Gather Feedback Once the pilot is complete, measure your results against the success metrics you defined in Step 2. But don't stop with the numbers. The human feedback is just as important. Talk to the people who used the tool.
Was it easy to use?
Did it actually save them time?
Did it make their job less frustrating?
What suggestions do they have?
Step 5: Scale or Scrap You now have a data-driven decision to make. If the pilot was a success—if it met your metrics and got positive feedback—you now have a powerful business case to scale the solution. You've proven the ROI on a small scale, making the request for a larger investment much easier. And if it failed? That’s also a win. You’ve learned a valuable lesson with minimal cost and can now pivot your strategy without having wasted significant time or political capital.
Securing that first win is everything. It proves that AI doesn't have to be a scary, abstract concept. It can be a practical tool that solves real problems, and that success will be the foundation for everything that comes next.
I explore this playbook and the broader strategic considerations for a sensible AI rollout in much greater detail here in an article called Sensible AI Roll Out: Start with Spend Management for Low Risk and Clear ROI published by Legalverse Media.
