Contract Automation: Technically Brilliant, Behaviourally Broken

Introduction: The Automation Paradox

Contract automation is one of legal tech’s most seductive promises: generate contracts in minutes, reduce drafting errors, and free lawyers for strategic work. Technically, the potential is almost infinite. With rule-based templates and logic-driven assembly, automation can produce agreements so accurate they save thousands in negotiation time.

But here’s the paradox: what’s technically possible collides with human behaviour. Unless users can plug all their requirements into the system in less than two minutes, they won’t use it. Legal teams abandon automation workflows halfway through because the “upfront interview” feels like effort — even if the output document is flawless.

This is not a technology failure. It’s a behavioural one. And it’s killing ROI for one of the most promising areas of legal transformation.

The Promise: Why Automation Matters

Contract automation promises:

◼️Speed: Generate contracts in minutes, not hours.

◼️Accuracy: Apply pre-approved templates and clauses consistently.

◼️Scalability: Handle high volumes without proportional headcount increases.

◼️Risk Control: Embed compliance into drafting logic.

On paper, this is transformative. For NDAs, procurement agreements, and sales contracts, automation should be a no-brainer.

The Reality: Why Adoption Fails

Here’s the hard truth:

◼️Behavioural Resistance: Users hate upfront data entry. If they can’t complete it in two minutes, they bail.

◼️Attention Deficit: Legal tech competes with swipe-generation culture. People expect instant gratification.

◼️CLMS Limitations: Most CLMS platforms have substandard automation logic. They offer template libraries, not true dynamic assembly.

◼️Technical Complexity: Building robust rules requires deep process mapping and legal judgment.

◼️ROI Mirage: Tools promise savings, but adoption bottlenecks kill the business case.

PAA:

Why do most contract automation projects fail?

Because user behaviour sabotages adoption and vendors overstate capabilities.

GLS Insider Story: Two Rounds of Painful Lessons

At GLS, we’ve invested heavily in automation — twice. Both times, the technology worked beautifully. Our systems could generate contracts so accurate they saved thousands in negotiation time. Numbering, cross-references, clause prioritisation — all perfect. The output was “on the money”.

But adoption? A disaster. Why?

◼️Users wouldn’t complete the upfront interview.

◼️They abandoned workflows halfway through.

◼️They defaulted to old habits: copy-paste from Word.

The lesson? Automation is not just a tech challenge — it’s a behavioural one.

The Weirdness of Legal Tech Behaviour

This is a strange corner of legal tech. The capability is almost infinite — but user attention spans are finite. Automation competes with swipe-generation culture, where people expect instant results. If the system asks for 10 data points, users revolt — even if those inputs unlock a flawless draft.

It’s irrational. But it’s real. And it explains why automation adoption lags behind its promise.

Why CLMS Platforms Fail

Most CLMS systems claim automation. Reality?

◼️They offer glorified template libraries.

◼️They lack dynamic logic for clause prioritisation.

◼️They can’t even generate numbered contracts — a basic requirement for professional drafting.

Without numbering and cross-referencing, automation is a gimmick. Negotiators need structured documents, not Frankenstein drafts.

The GLS View: Automation Is Essential — But Needs Reinvention

Despite the pain, we believe automation is essential. Why?

◼️It reduces drafting time dramatically.

◼️It enforces compliance and consistency.

◼️It frees lawyers for strategic work.

But success requires rethinking the user experience. Automation must feel effortless. Data capture must be minimal. Interfaces must be intuitive. And adoption strategies must address behavioural barriers, not just technical ones.

Practical Advice for Legal Teams

◼️Start Small: Automate NDAs or low-risk contracts first.

◼️Simplify Inputs: Minimise upfront data entry.

◼️Design for UX: Make workflows feel like consumer apps, not enterprise software.

◼️Train for Adoption: Explain the ROI of completing the interview.

◼️Avoid CLMS Shortcuts: Dedicated automation tools outperform bundled features.

◼️Measure Behaviour: Track abandonment rates and iterate.

PAA:

How do you prepare for contract automation?

By mapping workflows, simplifying inputs, and designing for user behaviour.

The Future: Where Automation Needs to Go

For automation to fulfil its promise, it must:

◼️Deliver Instant Gratification: Minimal inputs, maximum output.

◼️Embed Intelligence: AI-driven clause suggestions and risk scoring.

◼️Support Complex Drafting: Numbering, cross-references, and prioritisation as standard.

◼️Integrate Seamlessly: Plug-and-play with CLMS and workflow tools.

Until then, expect incremental progress — not perfection.

Why This Matters for Legal Transformation

Contract automation is not optional. It’s the foundation for scaling legal services. But adoption will remain elusive unless we solve the behavioural paradox: users want automation, but they resist the effort it requires.

People Also Ask (PAAs) 

1. What is contract automation?

Technology that generates contracts through rule-based templates to reduce drafting time and error rates.

2. Why do contract automation projects fail?

Because user behaviour sabotages adoption and vendors overstate capabilities.

3. Does contract automation replace lawyers?

No. It handles routine drafting but requires legal oversight for complex agreements.

4. What is rule-based contract assembly?

Logic-driven selection of clauses based on inputs like jurisdiction and contract value.

5. Can contract automation integrate with CLMS?

Yes, most platforms offer APIs for seamless connectivity.

6. Is generative AI ready for contract automation?

Not yet — reliability and accuracy remain issues.

7. What is the ROI of contract automation?

Depends on adoption; gains take time to materialise.

8. Are contract automation tools expensive?

Costs vary; ROI depends on configuration and usage.

9. Does contract automation improve compliance?

Yes, by enforcing use of approved templates and clauses.

10. Will contract automation become standard?

Yes, as tools mature and user experience improves.

Conclusion: The Balanced View

Contract automation is technically brilliant — but behaviourally broken. The tools can deliver flawless drafts that save thousands in negotiation time. But unless users can complete the upfront interview in two minutes, they won’t use it. This is not a tech failure. It’s a human one.

Our advice? Invest in automation, but design for behaviour. Simplify inputs. Train users. Measure adoption. And remember: the future of legal tech isn’t just about capability — it’s about psychology.

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© The GLS Group - Law Rewritten