This team was reviewing freelancer compliance one case at a time
Until a simple scoring model turned legal judgment into a scalable, self-serve workflow.
đ Hey there, Iâm Hadassah. Each month, I unpack how in-house legal teams use AI to enable the business, protect against risk, and free up time for the work they enjoy mostâwhat works, what doesnât, and the quick wins that make all the difference.
Before we dive in, a quick note: this is just one example of a legal team solving an operational bottleneck. There are plenty of ways to approach these kinds of problems, and the right solution will always depend on your specific needs and context. My goal is to give you some food for thought as you define what that solution should be.
Problem
This week, weâre joined by the Head of Legal Ops at a large enterprise company in retail and consumer goods. For years, the company relied heavily on external IT specialists to deliver project work that couldnât be fulfilled by internal staff. Every engagement required a compliance check under national labor law to ensure freelancers werenât being treated like employeesâa process that Legal and Procurement handled manually, case by case.
What looked simple on paper (Procurement submits a request, Legal reviews it), was a slow, judgment-heavy process in practice. Legal repeatedly interpreted the same case-law criteria, asked clarifying questions, and documented a defensible result. Similar cases often produced different outcomes depending on who reviewed them, and even the same lawyer might reach a different conclusion months later.
Volume and workflow friction made things worse. On average, at least one new request came in every workday (often more!) and each required 30â60 minutes of focused review plus back-and-forth for missing details. Requests sat in the ticket queue until someone found time to start them, delaying Procurementâs SLAs and frustrating requesters.
The legal team had no scalable way to deliver consistent, timely decisions; they needed a solution that would standardise judgment, reduce manual effort, and accelerate turnaround without relying on IT.
Solution
The project team built a self-serve compliance engine using the Microsoft suite the company already had access to. They started with a simple Excel model and later evolved this into a fully automated workflow using Forms, Power Automate, and SharePoint.
The insight was simple: even though each case varied in context, the underlying legal criteria never changed. The project team translated the fixed legal criteria into a weighted scoring system, delivered through a yes/no questionnaire. Conditional formatting calculated a total score and rendered a result: compliant or non-compliant, based on a predetermined threshold. A hidden worksheet protected the scoring logic, allowing Procurement to triage straightforward cases while preventing requesters from shaping answers to reach a desired outcome. This MVP helped Procurement triage requests and escalate only edge cases to Legal.
As usage grew, the manual steps in this new workflow became a friction point, prompting the project team to automate the entire workflow. Requesters now complete a Microsoft Form, which they can also use as a self-serve pre-check before going into the formal procurement process; Power Automate applies the same scoring logic; and results are emailed back, along with a compliance checklist clarifying what they may and may not do during the engagement. Each submission is automatically stored in SharePoint, creating a full audit trail for Procurement, Legal, and Compliance. The principles stayed the same, the delivery just became faster, cleaner, and more scalable, all while using tools the company was already paying for.
Results
Consistent decisions across similar cases, removing subjective variation across reviewers.
Faster turnaround, improving Procurementâs SLA performance and reducing requester waiting time.
Reduced legal workload as Procurement can now process compliant results independently.
Automatic documentation captures every assessment, enabling Compliance to conduct spot checks without manual filing.
Higher compliance overall as Legal is able to assess a greater number of cases than before, demonstrating greater organisational control.
Process
The shift from manual reviews to a fully automated workflow happened iteratively, shaped by collaboration and continuous refinement. It started with a legal counsel translating case-law criteria into a simple Excel modelânot to be perfect, but to create a repeatable baseline. Procurement tested it in live requests and quickly revealed that a key challenge wasnât technical, but linguistic: requesters often misunderstood terminology, prompting several rounds of rewording with heavy input from teams who hired external consultants most frequently.
Once the first version proved itself, the project team took over and rebuilt the workflow using Power Automate. No one on the team had an IT background; they learned through tutorials and experimentation, staying within the governance constraints of the companyâs Microsoft environment. Keeping IT out of the build was intentionalânot for lack of trust, but to avoid landing at the bottom of a long backlog.
Adoption grew naturally; Procurement gained faster cycle times, Legal gained consistency, and Compliance gained a clean documentation trail for post-approval spot checks to verify real-world adherence.
The harder shift was getting the project team to move from perfectionism to an 80%-first mindset. However, as the workflow improved with each iteration, early adopters began proposing their own automation ideas. This signalled a broader transformation, from one-off assessments to a legal function capable of building scalable operational systems.
Quick Wins
This teamâs success in resolving a long-standing operational bottleneck was not driven by a flashy new tech stack. Instead, they started simple, expanded capabilities incrementally, and let user feedback lead the way. The small, practical wins that built momentum and kept the project moving forward included:
A lightweight MVP that proved the concept. Rather than waiting for a perfect solution, the project team translated case-law criteria into a lightweight Excel-powered scoring system that immediately delivered consistent results and proved the concept quickly.
Iterating question wording based on user feedback. Testing the form with colleagues who regularly hired external consultants surfaced misunderstandings early, helping the project team refine âyes/noâ questions into language non-lawyers could reliably answer.
Procurement-driven triage. With the scoring model in place, Procurement could handle compliant cases without escalating, freeing Legal to focus on more complex cases.
Using existing tools to avoid delays. By building with Excel, Forms, Power Automate, and SharePoint, the project team stayed out of the IT backlog and maintained full control over timelines and iteration speed.
Adopting an 80% mindset. The project team embraced the idea that a solid, working solution could launch before every edge case was solved. This approach accelerated learning and helped the workflow mature over time.
Now itâs your turn. If your team is dealing with something similar, I hope this story sparks a few practical ideas you can put to work.
And⊠if youâve been through something similarâor solved a different operational challenge altogetherâIâd love to hear your story and spotlight your win.