Why Is Buying CLM Systems So Much Harder Than Buying Shoes?

Let me know if this sounds familiar: Identify the business need. Six months gathering requirements. Three months crafting an RFP. Three months evaluating vendors. Shortlist to three vendor finalists. Make the final purchase decision.

Then here comes the really hard part - Implementation: 9 months to 2 years. Another year of training and rollout. And then? You realize it's too limited in functionality and too hard to use and rip it out.  Worse yet, the problems it was purchased to fix gets worse.  Big failure.

The Enterprise Purchasing Paradox

Here's the irony: enterprise purchasing is the only practice where nobody actually believes they're doing it right. The entire process revolves around "change management"—getting organizational buy-in, including all stakeholders as if they had any real choice in the first place.

The result? Multi-year investments that fail after multi-year rollouts. The system gets underutilized, the original team disbands for other projects, and you're back to square one shopping for vendors.

This is the CLM purchasing reality. Great intentions, bloated purchase cycles, and frequently making the wrong choice for the organization.

How You Buy Shoes - The Key to Happy Customers

Now let's talk about shoes. Most people buy shoes the same way:

1. See some ads or ask for recommendations

2. Walk into a store

3. Try them on

4. Check fit, comfort, and style

5. Buy them

Usually they're happy and keep them. If not? Return them for a full refund after reconsidering.

Simple. Efficient. Low-risk.  All with a much better customer experience.

Why Doesn't Legal Tech Work This Way?

Are we really that much more sophisticated when buying software than when buying shoes?

No. The difference is simple: they don't let you try it on.

Implementation costs are too high. Most vendors won't let you test their systems without a sales commitment. They don't want to waste resources on unqualified prospects. To try it means to buy it first.

Why Vendors Don't Let You Try

The reason most vendors resist trials is simple: if you actually try their system, you might not buy it.

The excuses vary, but they all sound the same:

• "It takes lots of resources to install"

• "Implementation takes a long time"

• "Configuration is complex"

• "Ingesting historical contracts is time-consuming"

  
  

The variations are endless, but the priority is always the same: lock you into a multi-year commitment upfront. Sales team wins. Vendor wins. Customer loses. Imagine how many costly multi-year mistakes could be avoided if you could simply try the system to assess whether it actually fits your organization.

The CLM Failure Epidemic

CLM system failures are so common that at CLOC or other legal tech conference, most people will tell you they hate their CLM. The only difference is why they hate it. 

The reasons are depressingly familiar: slower contract cycle times, poor user adoption, integration nightmares, data migration disasters. Then there's inadequate training, unrealistic expectations, unclear objectives, resistance to change, and lack of ongoing support. The list goes on and on.

The Contract Confidentiality Challenge

There is one legitimate difference with contracts: they're confidential and can't be shared with outside parties. So getting trial subscriptions to SaaS services won’t work for most organizations due to security concerns. They need the software deployed inside their own secure IT environments to properly evaluate it.

But that doesn't mean trials are impossible—it means vendors need to make deployment easy enough that trials become feasible and commonplace.

Customer Experience - Try Before You Buy Solves Change Management

The experience should work like buying shoes: Request three options. Deploy and try them with your own contracts. Ask colleagues what they think. Does it suit your needs? Does it do the job? Does it meet expectations?

It's simple, but it's never offered this way. Why? Because they know the actual product doesn't live up to those slick demos. Put it in users' hands, and the experience falls apart.

Here's the beautiful part: when people get to try systems before committing, "change management" stops being an issue. Stakeholders had a chance to test whether it fits. They're already bought in because they actually used the product, not just read about it in an RFP response.

Change Management - The Metrics That Actually Matter

Instead of focusing on feature checklists and crafting long RFPs, evaluate vendors on these time-based metrics:

• Time to Deploy Trial Can you get a working system quickly with minimal cost? Does it take months and significant investment just to install and test it?

• Time to Value How quickly do you realize the system's value? It should be instantly clear—demonstrating ROI and justifying costs while providing insights into how the product will work in your organization.

• Time to Configure How long does it take to set up additional features? Are you dependent on the vendor for every small change? Will they charge exorbitant service fees for simple modifications?

• Time to Operationalize How long until the system runs day-to-day operations? Is integration with other systems straightforward? Is it closed (only the vendor can make changes) or open? Do you need technical experts for basic changes?

• Time to Expand Usage How quickly can you roll out to more groups, other countries, additional contract types? What's the path from initial adoption to organization-wide deployment?

• Time to Update This is critical in the AI era: Can it leverage external tools? Can you easily update to new releases? Does it support the newest LLM models? Are new features accessible through simple software updates?

The Bottom Line

Next time you buy shoes, think about why the same thought process is not applied to buying systems and software.  The local shoe store understands customer experience better than most CLM vendors.