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Corporate Law Departments

Legal ops implementation: How we fell in love with a legal tool & had our hearts broken

Irene Liu  Executive in Residence / UC Berkeley / School of Law and Founder / Hypergrowth GC

· 9 minute read

Irene Liu  Executive in Residence / UC Berkeley / School of Law and Founder / Hypergrowth GC

· 9 minute read

In the new issue of Forum magazine, two in-house legal pros discuss how they fell in love with a legal tool that failed to deliver for them

This story begins like so many typical love stories: an introduction by a mutual friend that was just supposed to be coffee. Carried away by immediate sparks, we thought it was love at first sight.

Sparks & love at first sight

This casual coffee meeting was with the founder of a legal vendor looking for product feedback. His company and ours were both part of the same venture capital family so we felt obligated, and somewhat begrudgingly agreed to the meeting. There was no major sales pitch or attempt to convince us that we needed to buy something; he just asked questions about our experience with similar tools in their industry. We found we had plenty to say, slowly feeling more at ease and open about our past relationships with similar vendors and processes.

We shared our gripes and frustrations over our current legal and sales processes, and quickly discovered that this vendor seemed to address all our needs, at least from a demo perspective. Sure, it was a beta product, but it was user-friendly, polished and seemed to hit all our pain points! It looked like this vendor was definitely going to solve all our problems.

And yes, we did say beta product, but before you judge us too harshly, remember that sometimes love is blind! And because we both loved being technology-forward and data-driven lawyers, we thought this would be an opportunity to become early adopters of a hot new legal tool!

We conducted high-level diligence. We looked into the integrations with common sales tools, and we received general assurances that integration features were on the product road map. We saw a masterful sales pitch and more demos filled with promises of imminent features and functionality. We couldn’t worry ourselves about red flags. We were too in love with the streamlined features being shown to us. Sign us up, we said!

Giddy from our amazing find, we talked on the way back to the office about the increased productivity we were going to see. It didn’t cross our mind to evaluate other vendors. Why would we need to? We weren’t even looking before this meeting, but this was clearly the one. Finance approved our budget request and we emailed the vendor for their contract. We got a great deal, more than half off their list price. They liked us just as much as we liked them. Clearly, this was the beginning of an amazing partnership.

The short honeymoon

There’s always a honeymoon period, but ours was unexpectedly short. It lasted until we invited our director of Sales Ops to the first integration meeting. Granted, we hadn’t consulted him before buying, but he trusted us and could clearly see we were head over heels with our amazing purchase. He had some questions that needed addressing, and they quickly changed our outlook. It seems all those integrations we were promised weren’t as “imminent” as we had been led to believe. In fact, they were so far down the product road map there was no anticipated release date.

Immediately, the excuses started.

We had been telling our business partners that this tool was going to change the way they interacted with Legal, optimize turnaround time, enable the Sales team and transform our entire commercial process. We even conducted trainings before the integration was complete so that the team would be ready to hit the ground running.

Then we missed the first launch deadline.

Suddenly, our assurances to business partners of “just a couple more weeks and they’ll have that critical integration up and running” were met with doubtful looks and scrutinizing faces. We were losing credibility fast. It was time to define the relationship, to have The Talk. We called a meeting and asked our vendor whether they were ready to finally get serious and make this work. They asked for one more chance, just a little more time to fix things and meet their road map requirements. And we agreed.

It took us four months after signing with this vendor to admit to ourselves this relationship was not going anywhere. The integration was never completed. We never used the tool. It was time to admit to ourselves that we needed to break up. To the vendor’s credit, they were chivalrous about the situation and never invoiced us. We parted as friends but still carried some scars.

Lessons from our breakup

Every heartbreak, including a breakup with a legal vendor, is an opportunity for learning and growth. Looking back, it’s obvious that we fell in love too quickly. Here are a few key lessons from our breakup and the steps we’re now taking to evaluate new legal tools:

Identify top vendors… and pick more than one

Leverage your legal network to find the top vendors for the legal tool that you are seeking. Many in-house peers will generously point you to leading vendors and share the experiences they’ve had with them. Often, your peers will provide the most unbiased reviews of vendors both during the RFP process and post-implementation. Use their candor and experience to help find the leading vendors for the solutions you are seeking.


We often see requests for recommendations for leading contract management tools coming from groups like the Association of Corporate Counsel, the Corporate Legal Operations Consortium (CLOC) or other in-house networks. We frequently see the same vendors’ names repeated and recommended. And if you’re lucky enough to have a legal operations manager on your team, you can also utilize their CLOC network and conference to find leading vendors.

Make sure you identify more than one vendor so you don’t face the issue of falling in love too quickly with the first vendor, who can easily turn out to be a frog! And when you have more than one potential vendor, it can provide leverage for when it comes time to negotiate.

Align with key stakeholders & identify feature requirements

Once you have identified the vendors – but before you evaluate them – make sure you meet with your business stakeholders in IT, finance, legal, sales and other departments that will be using the new technology to better align the necessary requirements.

Sit down with them to discuss how the technology will be used, how it will be implemented and which top features they want in such a tool. Identify must-have versus nice-to-have requirements to ensure the tool is successfully implemented and used across the company. Use these recommendations to draft a vendor scorecard and evaluate the software options. Identify the business owners who can attend the demos with the legal team and help evaluate the vendors with the scorecard.

That way, you will have multiple business partners helping you objectively evaluate the tools to ensure the product meets your company’s business requirements before you hand the rose to your favorite vendor.

Conduct demos to evaluate vendors

To avoid a future heartbreak like ours, conduct demos with your top vendors so you know exactly what you’re getting yourself into. It’s not unusual to do multiple demos from the same vendor, so give yourself time to schedule these and to ensure that you have all business stakeholders in the room.

Utilize the scorecard that you developed to understand and assess your core feature requirements and score each criterion between 1-5 (1 for poor, and 5 for excellent). Include pricing as a criterion in the scorecard as your finance and procurement team will want to factor pricing in as a decision factor. You may also want to share your scorecard template with the vendor to ensure expectations align between all parties; that way, the vendors can focus on your core feature requirements and tailor their demos to your company.

Use these demos as your opportunity to learn how the system works as it relates to your company and its processes. Make sure you understand whether your core requirements are being met so that you won’t be disappointed later. If some of the features are not available, ask about their product road map and whether such a feature will be implemented and when.

But remember, they’re trying to sell you a product. A vendor may overpromise a feature on a road map so it’s important to understand that it’s never a guarantee.

Give the rose: Vendor selection & implementation

Once you have selected a vendor, negotiate the pricing and the commercial terms, and align with the vendor on the implementation timeline. Often, the vendors and your company’s IT department will each need work on their ends to implement the software. Build the implementation timeline into your launch schedule and use that time to set up training for the legal team and the business units who will be using the new legal tool.

Adoption is key to the tool’s success so it’s important that you offer training (and regularly repeat those trainings) to the legal and business teams to ensure effective adoption.

Once the tool is successfully adopted, evaluate the tool on at least an annual basis (after the honeymoon period) to decide whether the tool continues to meet the core functionalities that you desired. Use this opportunity to provide feedback to the vendors on the tools and on any recommended features. The healthiest couples have communications grounded in transparency and honesty. In the same way, be honest in your feedback with your vendors and they will appreciate you even more as a customer.

Like dating, we ultimately learned that you have to kiss a lot of frogs to find your prince. While we found one in the end, it wasn’t the smooth journey we had hoped for. We hope you will benefit and learn from our heartbreak story so that you can find your prince more quickly!

Neta Hamou, Director of Commercial Legal Affairs, at Checkr, contributed to this article.

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