Why the first click matters more than the feature list
How a legal team regained control of outside counsel spend by putting users first.
đ Hey there, Iâm Hadassah. Each week, 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
When we sat down with the Head of Legal Ops at a large transportation company, the challenge their team faced came through loud and clear: they had no real visibility into external legal spend. Invoices were scattered across departments, costs were being misclassified, and bills got buried in inboxes or stuck in accounts payable. Amid the chaos, nobody could answer a simple question: What are we really spending on outside counsel?
It wasnât for lack of trying. The team had turned to manual tracking, but even with a dedicated effort, the results were still incomplete and delivered little practical value. Leaning on Finance didnât help eitherâthey simply couldnât provide the detail the legal team needed. Meanwhile, firms were chasing overdue payments and the legal team was burning hours on a process that still left them blind. Without contextualised billing data, external spend couldnât be effectively tracked and managed.
Solution
The legal team quickly realised they needed a scalable way to regain control and cut costs. The turning point came when they drew a hard line: if outside counsel work wasnât authorised by Legal, it wouldnât be paid. That forced everything through one channel and gave the department more visibility.
With spend centralised, they began searching for a legal spend management systemâspecifically an e-billing platformâthat simplified invoice review and met the must-haves they had defined up-front:
Usability and user experience. The solution had to be intuitive for lawyers on the team; preferably one-click approvals to make it as easy as possible to use.
Invoice data accuracy. Data extraction had to reliably capture key invoicing fields of interest to the team and broader business.
Ease of implementation. The team was looking for a solution with a high go-live speed.
Integration with IT infrastructure. The solution had to align with existing infrastructure and security standards.
Flexibility and scalability. The solution had to scale with team needs over time, even if features went unused to start.
Support and training. The team was looking for a vendor that could provide strong adoption support post-onboarding.
Thatâs where Brightflag stood out. While other vendors risked overwhelming users, the team appreciated their solutionâs intuitive interface alongside its extensive set of features. They didnât need every feature on day one, but the accuracy, flexibility, speed, and usability they experienced testing the tool gave them confidence that they could grow into the system over time.
Results
By requiring authorisation from Legal before any outside counsel work could be paid, legal expenditures flowed through one channel, eliminating the chaos of fragmented approval paths.
The team moved from scattered, incomplete, and misclassified invoices to a centralised system that gave them clear visibility into spend, cut down on overdue payments, and improved their relationships with law firms.
Process
Procurement, IT, and Digital Safety were looped in early to clear compliance, security, and infrastructural hurdles. By the time investment was on the table, these functions were aligned and the field was narrowed. The broader legal team was shielded from overload: instead of endless demos, they saw only three pre-vetted finalists with brief updates in their inbox along the way.
But securing the investment itself wasnât straightforward. The first business case was rejectedânot for lack of merit, but because the organization was in flux: a new GC had just arrived, post-pandemic adjustments were ongoing, and leadership wasnât ready to greenlight something that looked like a back-office accounting project. The team also realised the initiative had a branding issue: calling it âlegal spend managementâ undersold its strategic value. On the second attempt, they reframed it as âoutside counsel managementâ, which signalled strategy rather than spend tracking. This time, the message landed.
They also aligned stakeholders upfront and ran a proof of concept with low-risk invoices, demonstrating savings and keeping expectations grounded. These tangible results built confidence, and Brightflag played their part by re-engaging when the timing was right.
With that groundwork in place, implementation took just 32 days from contract to go-live. A major enabler: the project team had day-to-day decision-making authority, avoiding the approval bottlenecks that often stall rollouts.
Go-live, however, was only the beginning. Despite initial buy-in, many lawyers logged in once, clicked around, and stepped back. Some didnât see invoice review as part of their job, others didnât grasp the business case, and unexpected system behaviour led to disengagement rather than questions.
Macro training sessions fell flat, so the team pivoted to individualised onboarding. One team member spent six months coaching lawyers one-on-one, walking through invoice approvals until the process felt natural. The first year was uneven, but by the end, adoption was strong: approvals happened in a click, usage was steady, and the data became reliable for decision-making.
The key lesson this team took? Fast implementation â fast adoption. Comfort levels with technology vary widely in legal teams, so success depends on meeting people where they are. This team found that addressing their biggest pain points, investing in hands-on support, and making sure the first click feels intuitive is criticalâotherwise, you risk losing them before you even begin.
Quick Wins
What made this solution work wasnât a shiny new piece of tech. It was the way the team approached the problem as well as the messy middleâcentralising approval flows, setting clear solution requirements form the outset, and doubling down on the user experience. Getting a new workflow off the ground is rarely about one big moment of success. More often, itâs about the small, practical wins that build momentum and keep a project moving forward.
For this legal team, those wins looked like:
Pre-training to build confidence before go-live. The project team ran short and hands-on practice sessions with dummy invoices so users could explore the system safely. They walked through the exact steps users would eventually takeâapprovals, billing-guideline checks, error handlingâand simulated common pain points so they could see the tool solving real problems.
The âfirst clickâ rule. The project team learned quickly that the first interaction sets the tone. If login feels clunky or navigation confusing, engagement drops. So they smoothened the path: simplified access, reduced friction at login, and made the initial touchpoint intuitive. They also paired each lawyerâs first use with a quick guided walkthrough to build early confidence.
One-on-one coaching. The team designated a super-user to work individually with attorneys, using real invoices so the system felt immediately relevant. Quick wins mattered: âSee? That took 10 seconds instead of 10 minutes.â Over time, repetition made the workflow second nature.
Be realistic about the timeframe. Adoption took months, not weeks. Progress wasnât linear, but steady reinforcement paid off. For this team, it took almost a year before usage felt natural and reliable. Patience and persistence are what ultimately turned sporadic engagement into sustainable habits.
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.