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Can a customer of mine waive negligence caused by me when doing any business activity on assets/property? What if the property belongs to someone else, but I state that they take all responsibility as well? Provided that I am specific and the waiver is clearly written, is it enforceable? Can this replace the need for general liability insurance?

For an example, I pressure wash property for a living. While washing, I scratch a vehicle, however, the customer has signed a waiver that protects me from being sued/pay for damages. What if the car is leased, however, I state that they are responsible to pay X for all damages caused by my negligence?

All activities are based in Ontario, Canada.

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You can't enforce your contract with someone against a third party who is not a party to the contract. You can't agree with someone to take another person's rights away. If you're negligent, you're liable to anyone who didn't agree that you aren't.

However, you can add an indemnification clause to your contract. That could require your customer to defend you in court and cover your expenses. However, you would still be directly liable and if your customer refused to cover the damages (maybe alleging that you violated the contract somehow) or couldn't afford to cover the damages, you would have to pay the party whose property you damaged and then sue your customer.

The extent to which such indemnifications are honored depends on jurisdiction and public policy. You usually can't indemnify yourself against your own gross negligence as that would too severely reduce your incentive to be cautious, offending public policy. Ordinary negligence is usually okay. Check with a lawyer if you need specific advice.

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In your example, the car leasing company has a contract with the lessor (typically the driver of the car), so the car company would chase the lessor. How the damage occurred (car accident, someone washing cars, a neighbour's kid's bike rubbing against it) is of no interest to the car leasing company.

The lessor would then have to chase you because you would have a contract with them.

My understanding is few jurisdictions anywhere allow you to divest yourself of legal obligations. Thus, even a clause that dictates you are not responsible might be found invalid in court. So... if your poor judgement were to cause an obstruction which created a car accident, killing someone, then you would be liable, not your client. No amount of paperwork will redirect this responsibility elsewhere.

The way you manage the risk is via liability insurance - I currently have liability insurance that covers me for $5million per incident so long as I perform non-physical labour (thus I can work on computers, but cannot lift them). You can write various clauses into your contract that attempt to limit your liability, but if it goes to court, a judge might say the clause is unreasonable and strike it (or the entire contract) as being invalid.

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