Big Sis Briefing: The CLM Implementation That Survived COVID (and What I'd Do Differently)

Three months into our CLM implementation, I was sitting in a project review meeting when someone asked the question I'd been dreading: "So, what's the adoption rate looking like?"

I pulled up the dashboard. Twelve percent. After three months of work, countless training sessions and a significant budget, twelve percent of our stakeholders were actually using our shiny new system.

The room went quiet. I'd heard the horror stories about CLM implementations that never took off: systems that cost hundreds of thousands but sit unused, teams that spend months on setup only to watch people revert to email and shared drives. I just didn’t expect it to be our story.

But here's the truth: it doesn’t have to end like that.

Luckily, I can now say that I led the implementation of a well-known CLM tool at a global tech company and it worked. Not overnight, but eventually. 

The eventual success didn't come from picking the perfect tool or having an unlimited budget. It came from learning what actually matters when you're trying to change how an entire organisation handles its contracts and legal advice matters. Oh, and patience too!

I shared the full behind-the-scenes story in Episode 18 of my podcast Counsel if you want more behind-the-scenes details.

The Lessons I Learned (Some More Painful Than Others)

Lesson 1: The "Why" Can't Be Vague

Looking back, our first attempt at defining success was embarrassingly generic: "make contracting faster." I thought that was specific enough. I was wrong.

Three months in, when the sales team complained that the new system was actually slower than our old hodge podge way of engaging with them, I realised we'd never really defined what "faster" meant.

Faster approval cycles? Faster contract creation? Faster signature collection?

The breakthrough came when we got brutally specific. Instead of "faster," we said: "Reduce time from initial contract request to signature from 12 days to 5 days for standard agreements." Suddenly, everyone knew what we were building toward.

We had published service level commitments and we reported against them weekly.

Lesson 2: Change Management Isn't Optional (Neither Is Perfect Timing)

I made the classic tech person mistake: I thought if we built something intuitive enough, people would naturally adopt it. I also made the classic overachiever mistake: I thought I could manage a major system implementation while maintaining my full caseload as senior legal counsel.

Our rollout was scheduled for mid-March 2020. You can probably guess what happened next…

Just as we were launching our beautiful new CLM system, the entire company suddenly went remote. The sales team that had been collaborating around whiteboards was now scattered across home offices with spotty Wi-Fi. Our legal team that relied on hallway conversations was trying to figure out Zoom. And here I was, attempting to train people on a new contract system while we were all learning how to work from home at the same time.

It wasn't exactly a disaster, but it wasn't the smooth rollout I'd envisioned either. People were dealing with kids interrupting calls, makeshift home offices and the general chaos of a world turning upside down. Learning a new CLM system wasn't their top priority.

The real lesson though? I'd bitten off way more than I could chew. Running a major implementation project while trying to keep up with my day job as senior legal counsel was ambitious to the point of being reckless. I managed to pull it off, but not entirely unscathed. (Though I'll admit, it looks pretty good on the CV now.)

The turnaround came when we stopped focusing on the tool and started focusing on the people. We identified champions in each department, adapted our training for the new remote reality and created feedback loops where people could actually influence how the system worked.

Lesson 3: Feature Creep Is the Enemy of Adoption

The vendor demos were seductive. AI-powered clause analysis! Blockchain integration! Advanced analytics dashboards! I wanted it all.

But when I stepped back and looked at our actual pain points, they were embarrassingly basic: Where are our contracts? When do they expire? Who needs to approve what?

The most successful parts of our implementation were the simplest: centralised storage, automated reminders and clear approval workflows. The fancy features we initially got excited about? Half of them are still unused two years later. But the basics stuck.

Lesson 4: Your Users Will Surprise You

I thought I knew how our team worked. I'd been there for years, sat in the meetings and watched the processes. But when we actually started mapping workflows, I discovered we had three different approval processes that nobody had documented and two teams that had been doing the same work without knowing it.

The real eye-opener came during our pilot. I'd assumed procurement would be the power users and sales would be the reluctant adopters. Turned out to be the opposite. Sales loved the transparency and speed. Procurement was more resistant to changing their established review processes.

What I'd Do Differently

If I were starting over tomorrow, here's my playbook:

Don't try to do everything yourself: This seems obvious, but when you're the one who understands both the legal needs and the technical requirements, it's tempting to take on the whole project. Get proper project management support and delegate what you can.

Start with detective work, not vendor calls: I'd spend the first month just observing. Shadow someone through their entire contract process. Time how long things actually take. Ask everyone (not just legal) what drives them crazy about the current system.

Build your non-negotiables list like your budget depends on it: Because it does. Every feature you don't absolutely need is a distraction during implementation and a complication during adoption.

Run a real pilot, not a demo: Use actual contracts, real deadlines and genuine consequences. If something breaks during the pilot, you want to know about it then, not during the full rollout.

Plan for the unexpected: We couldn't have predicted a global pandemic, but we could have built more flexibility into our rollout plan. Have backup training methods, alternative communication channels and realistic timelines that can absorb disruptions.

Design for your least tech-savvy user: If the system isn't intuitive enough for this colleague, it's too complex.

Measure what matters: Don't just track system usage. Track business outcomes. Are contracts actually moving faster? Are fewer deals falling through due to legal delays? Are people happier?

The Plot Twist

That painful project review meeting? It became our turning point. Instead of doubling down on training people to use a system they clearly didn't want, we went back to the drawing board.

Six months later, we hit 85% adoption. Not because we'd bought different software, but because we'd learned to build around how people actually work, not how we thought they should work.

The failed CLM implementations you hear about aren't usually technology problems, they're process problems. Process problems can be solved.

You're not behind. You're not doomed to repeat others' mistakes. You're just one good plan away from a CLM that transforms how your team works.

The success stories are out there.

Yours can be one of them.