Most CLM evaluations go wrong before the first demo. Teams compare features, pick the most impressive AI, and a year later sales is still emailing legal for every NDA.
The demo usually wasn't the problem. "Most of these shiny demos that you see are not lies," said Sabrina Pervez, Head of GTM for EMEA at SpotDraft. Rollouts fail at implementation and adoption, which a feature comparison never tests.
That was the premise of The Buyer's Guide to Contract Management: 5 Questions to Ask, a webinar hosted by SpotDraft and MangoCloud. Sabrina moderated, joined by Naomi Thompson, Founder of CatalyNT, and Mpho Chitapi, Group Legal Technology Head at Nedbank. Here are the five questions they said to answer before you look at a single feature list.
The most common mistake Naomi sees is going to market before defining the problem. Lost contracts, slow approvals, legal buried in admin and missed renewals each call for a different tool. A demo can't tell you which one you have.
Mpho's advice: map your contract journey, find the friction points, and define measurable outcomes before you speak to a vendor. Then test every tool against them. Clear use cases also make adoption easier, Sabrina added, because the rollout can target exactly what you bought the tool to fix.
The takeaway: Write down two or three outcomes that would make the purchase worth it, and how you'll measure them.
Legal owns the process, but sales, procurement, finance and HR are the heaviest users. Their priorities are different. "A contract is not number one on their KPIs," Naomi said. If the tool feels slow, sales will sign on its own paper. The audience agreed: in a live poll, ease of use ranked first, ahead of AI and integrations.
Two things help. First, involve the business while you write requirements, not after you buy; even a two-line update at an all-hands builds buy-in. Second, meet people where they already work. That's why integrations were Mpho's top priority. Sales should request contracts from their CRM, and lawyers should redline in Word.
The takeaway: Design for your busiest, least patient user. If they won't use the tool, legal won't get the benefit either.
Contracts live in SharePoint, inboxes, old systems and, Naomi admitted, sometimes a physical cupboard. She called migration the point that most often makes or breaks a rollout. Contracts with live obligations need to come across, but not every document from decades past. Her advice: don't "eat the entire elephant at the same time." Start with critical, high-risk and recent contracts, because "you only have one opportunity with your business stakeholders to get their buy-in."
Mpho's vendor questions on data:
The takeaway: Treat migration and data exit as part of the buying decision, not implementation details. "Data is really the crown jewel of your organisation," Mpho said.
"Do you have AI?" is the wrong question, Sabrina said. Ask what it does for your team. Naomi looks for AI that works from your own playbook and fallback positions, and that turns your contract portfolio into business insight. "Legal sits with some of our organisation's most valuable pieces of data," she said.
Sabrina gave an example of what a specialist CLM can do that a general assistant like Copilot can't. If your team accepted its second NDA fallback every time last quarter, the system can suggest making it the first position, saving a negotiation round on every deal. Grounding AI in your own contracts also answers lawyers' biggest worries about hallucination and data leaks. That matters, because lawyers who don't trust AI won't use it.
In demos, Naomi asks vendors to show the tool adapting to her requirements, handling both buy-side and sell-side work, and reviewing contracts from her industry, not a simple NDA. Better still, run a pilot. "When you have a demo, it's easy to just watch and see and miss some of your critical points."
The takeaway: A demo shows what a tool can do. A pilot on your own contracts shows what it will do for you.
Vendor support often fades after go-live, just when users are forming habits. If a salesperson's day-one question takes 24 hours to answer, "by that time, sales has given up," Sabrina said. A real person replying within 15 minutes is often the difference between adoption and abandonment. Naomi also urged building the business case early so finance is on side before the fee comes up.
How do you know it worked? "The use of the tool," Naomi said. Her test: if you announced you weren't renewing, would people protest? Then check the KPIs from question 1, such as faster turnaround, higher close rates, fewer negotiated clauses and a business that no longer goes around legal.
The takeaway: Ask about post-launch support as carefully as features, and agree success metrics before you sign.
Buyers who start with features end up judging demos. Buyers who start with these five questions end up judging fit, and fit decides whether a CLM is still in use a year later.
Working through these questions now? Book a conversation with SpotDraft to see how we approach evaluation and rollout.
