Contract management software is like a gym membership - don't waste yours

Every January, gyms sign up a wave of hopeful new members. By March, most of them have stopped coming, and their monthly fees are quietly paying for the treadmills of the people who still show up. Nobody joins a gym planning to waste the money. They join because the place looked great on the tour.

Buying contract management software can go the same way. The demo is the tour. There are clean dashboards, an AI that summarises a 40-page agreement before you've finished your coffee, and a workflow diagram tidy enough to frame. 

Then the contract gets signed, the licences go live, and six months on, someone in Sales is still emailing Legal a Word file called "FINAL_v7_actually_final.docx".

A better demo won't fix that. Better questions might. Here are five worth asking before you sign anything.

1. What are we actually trying to fix?

"We need a CLM" isn't a problem. It's a shopping list. The real problem is usually more specific, and a lot more annoying: nobody can find the signed MSA, approvals drag on for three weeks, Legal is buried in admin, or nobody remembers what was promised once the ink dried.

It's tempting to skip this step and go straight to technology. Vendors fall for it too. 

Shashank Bijapur, SpotDraft's CEO and co-founder, talks about the company's very first product: an automated NDA grader that struggled to get its accuracy right. The bigger lesson was that grading one document was never the real problem. The team ended up building the place where legal work actually happens instead, with the editor, the workflows, and the repository. 

The clever feature mattered far less than the work around it.

So map the work before you go shopping. How do requests reach Legal today? Email, chat, a phone call, someone leaning over your desk on the way to lunch? Who approves what, and where do signed contracts end up? 

The answers can surprise you. Akshay Verma, SpotDraft COO, talks about teams who assumed Legal was the bottleneck, only to find that much of the delay was sitting with the counterparty. That's a very different problem, and it needs a very different fix.

Once you know what's actually broken, rank your wishlist, and don't let any two features tie. If a product is missing a must-have, cut it, however charming the rest of it is. It also helps to keep one line from SpotDraft's CLM Buyer's Guide somewhere you'll see it: automating a bad process only makes the bad process faster.

2. Who actually needs to use it?

Legal may own the contract process, but it doesn't live there alone. Sales wants the deal closed this quarter. Procurement wants to catch renewals before they roll over. Finance wants to know what was committed, and HR wants the offer letter out before the candidate says yes to someone else.

When people outside Legal ignore a new tool, the easy conclusion is that they don't like change. Akshay has argued the opposite: resistance to technology is often a design problem, not a people problem. If raising a contract means learning yet another system, people will keep emailing Legal, and it's hard to blame them.

So look for software that meets people where they already work. Contracts that start from Salesforce or HubSpot. Requests raised in Slack or Microsoft Teams. Offer letters that pull details from Greenhouse. Sign-in through Okta or Azure. 

In the demo, ask to see what a sales rep sees, not just the lawyer's view. If the answer is "they'll log in to our platform", picture your sales team's faces.

3. What happens to everything we already have?

Nobody starts with a clean slate. Contracts are scattered across shared drives, inboxes, an old system nobody remembers setting up, and the personal folder of a colleague who left two years ago.

Ask how legacy contracts get in: bulk upload, OCR for scanned PDFs, AI that reads and tags key terms. Then ask the better question. Not "where will our contracts live?" but "what can we do with them once they're there?" 

A repository is a filing cabinet. You want a library with a very good librarian: searchable metadata, linked records, renewal alerts and reports you can build without raising a ticket.

4. What can the technology actually do?

Every platform has AI now. Asking "does it have AI?" is like asking a restaurant if it serves food. The useful question is what it does for your team on an ordinary Tuesday afternoon.

Bring your own contracts to the demo, not the vendor's polished samples. Ask the AI to suggest redlines against your playbook and see whether a lawyer would accept them. Check that formatting survives the trip to Word, and that approvals can follow rules, like anything above a set value going to Finance.

Then ask two things that vendors rarely volunteer. What does the product do today, and what is still on the roadmap? And where does a human stay in charge? Good AI drafts, flags, and summarises. It should not quietly sign off on your indemnity clause. 

While you are at it, ask about security, access controls, and multi-factor authentication before your IT team does.

5. What happens after we buy it?

Signing with a vendor is not the finish line. It is the starting gun.

Decide who on your side will run the implementation and who has the final say on approvals. Ask the vendor about timelines, training, change management and support after go-live. Then agree upfront on how you will judge success at six and twelve months: faster turnaround, more contracts generated by the business without Legal, renewals caught before the deadline. If you cannot measure it, you will never know whether you bought a tool or a very expensive bookmark.

Questions before features

The best buyers do not arrive with the longest feature list. They arrive with the clearest problem, the right people in the room, and a plan for life after go-live. Features matter. They just should not come first.

If you are evaluating contract management software, or expect to be soon, join us for The Buyer's Guide to Contract Management: 5 Questions to Ask webinar on 5 November 2026, 08:45 to 09:45 SAST. Sabrina Pervez, Head of GTM, EMEA at SpotDraft, will be in conversation with Mpho Chitapi, Head of Legal: Group Technology at Nedbank, and Naomi Thompson, Legal Innovation Strategist and Founder of CatalyNT. 

SpotDraft is hosting the session with MangoCloud. Register here. Think of it as the gym tour where someone finally asks about the cancellation policy.