Every founder knows the feeling. A deal is as good as done, the other side has agreed everything on a call, the contract has been sent out…and nothing happens for weeks.
Sometimes, speed and momentum are key to signing a deal at all which means slow contract processes and excessive redlines can stop them in their tracks.
Often this is put down to lawyers being lawyers and that’s just how it is. Increasingly, it’s AI tools over-lawyering straightforward documents, giving the impression of speed to mark-up a document while actually slowing the wider process down. Either way, the problem is in the process, and that means the fix doesn't require a bigger legal budget, but a smarter approach.
Here are five levers you can pull to compress your contracting cycle, starting now.
1. Open with reasonable terms
If your opening position is heavily one-sided, you're not starting a negotiation, you're starting an argument. Contracts that open in a reasonable place tend to close faster, because there's less ground to cover before both sides feel comfortable. That doesn't mean giving away your position; it means not manufacturing friction before you've even begun.
2. AI-proof your terms before you send them
You can bet that every time you send out a contract, the other side is asking Claude or ChatGPT to do the first review. While it speeds up the process for them, these tools often red-flag fixable issues and can slow the wider process down. Before your contract lands with the other side, run it through an AI tool from your counterparty's perspective. What issues does it surface? Which clauses are likely to attract pushback? You might find that some of those concerns are easy to address without giving anything away, and resolving them pre-emptively removes rounds of negotiation before they happen.
3. Track what actually gets negotiated, then fix it
In most contracting processes, 20% of your clauses generate 80% of the back-and-forth. The same issues come up, deal after deal. If you're not tracking which provisions consistently cause friction, you're solving the same problems on repeat. Monitor your redlines, identify the patterns, and ask whether those clauses can be re-written to reduce the resistance without weakening your position.
4. Build a playbook for your most common positions
Don't guess at the answer every time a counterparty pushes back. Document what you'll accept, what you won't, and how to defend what matters. A well-structured negotiation playbook covering your key fallback positions and the rationale behind your most important terms means your team responds faster and more consistently. AI tools are particularly useful here, both for drafting the playbook and for keeping it current as your business evolves.
5. Clarify who owns each decision
Confusion over roles is one of the most under-appreciated causes of slow contracting. If it's not clear who can approve a change to a liability cap, or who needs to sign off before a redline goes back, deals stall while people work it out. A simple RACI setting out who can agree to changes and who signs off removes that ambiguity and keeps things moving.
Contracting speed is a competitive advantage, particularly in markets where buyers have options and patience runs thin. The good news is that most of these levers can be pulled without touching your legal budget. A founder I once worked with hammered into the team that a frictionless on-boarding process is part of the product. Get that right, and the deals will follow.
If you need support in fine-tuning your contracting process, we offer fixed-fee support delivered by experienced GCs. Get in touch below.
