Questions to ask before someone drafts contracts you'll use for years

When you're about to hand someone authority to draft contracts your business will live by for years, the stakes are invisible until something breaks. A poorly written contract can cost thousands in dispute resolution, fail to protect your intellectual property, or expose you to unfair dismissal claims you didn't see coming. The key isn't finding the perfect provider—it's knowing which questions separate someone who'll truly understand your business from someone churning out generic clauses.

The conversation you need to have starts before you see a single draft. You're not just vetting credentials; you're testing whether this person will ask *you* the hard questions back.

Does your actual hiring process match what the contract assumes?

Ask: "Walk me through what you'll ask about how we hire, and what happens if the contract doesn't match." A strong answer doesn't default to boilerplate. They'll ask whether you have probation, what happens to remote workers or part-timers, whether you use independent contractors alongside employees, and how you handle promotions or role changes. They should explain why these details matter—for instance, a probation clause only protects you if it's actually lawful and your *practice* aligns with it.

An evasive answer: "We'll put in standard probation and notice periods." That's a red flag. Standard rarely fits, and misalignment between the written contract and what you actually do is fertile ground for disputes.

Ask what happens if your hiring practices evolve. Do they update templates, or do you pay again for new drafts? Clarity here saves friction in year three.

How do you stay current without making me an accidental test case?

Employment law in South Africa shifts. The Basic Conditions of Employment Act, Equity Act, and CCMA jurisprudence all move. Ask: "How do you keep up, and when was your template last refreshed?" Listen for specifics: Do they track CCMA awards? Subscribe to labour law updates? Attend training? Belong to a professional body that requires CPD?

Then ask: "If I sign this contract in January and the law changes in March, what's your responsibility?" A credible answer acknowledges they can't predict the future, but explains how you'll know if something's become risky and what your recourse is. Vague reassurance—"Don't worry, it's all compliant"—is the opposite of reassuring.

Don't accept that they've never had a contract challenged at the CCMA. Ask how many they've drafted, and what they've learned from cases they've seen or studied. Someone who's only read textbooks will miss nuances someone with real-world exposure catches.

What happens when the contract meets a real conflict?

Draft contracts in a vacuum. Real ones meet friction: an employee wants to freelance on the side, a founder's leaving and taking the customer list, someone claims they were promised something differently. Ask: "Give me an example of a restraint or non-compete clause you've drafted. Walk me through what it actually stops someone doing, and what it doesn't."

Listen for clarity. Can they explain why a blanket restraint might fail at the CCMA? Do they know the difference between reasonable and overreaching? If they waffle or lean on jargon, they probably haven't stress-tested their own clauses.

Also ask: "If one of my employees disagrees with a clause in this contract when they sign it, what do I do?" The right answer includes practical steps—signing under protest, a side letter, adjusting the clause—not a dismissal of the concern.

How much input do you actually need from me, and what do I brief badly?

Ask: "What's the most common mistake you see when clients brief you on what they want in a contract?" Good drafters will tell you: founders overstate what they can legally enforce, HR leaders forget to mention informal arrangements, and business owners assume a clause does more than it does.

Then ask: "Walk me through exactly what you'll ask me, and what happens if I'm vague." They should name the questions. Do they want org charts? Sample role descriptions? Details about your market and competitive position? This tells you whether they're building a contract that actually fits or one they can argue fit later.

Finally: "If I sign this and later wish something was different, can we adjust it?" Clarity on revision rounds, costs, and timelines stops expensive surprises.

When you're ready to move forward, verify they're up to date, ask for examples of past work (anonymised), and check references with other businesses like yours. On Strove, you can find verified HR consultants and employment attorneys who've been assessed against exactly these criteria—and you can compare their approaches before you commit.