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DH is a self-employed General Contractor, and has typically taken jobs that only require him to complete or that he can sub-contract out to others who are also in business for themselves.

Does he currently obtain (annually) certificates of insurance (COI) for liability and workers' compensation from these sub-contractors? A COI is basically a document the subs would give your DH to show they have current & adequate coverage.

But this morning, he brought up the fact that he's thinking about hiring a kid from the local vocational school to help him over the summer. Right away, bells went off for me as this is not the same thing as sub-contracting, and these are not people I could put on a 1099 as he will be training them and highly supervising them. So what I do need to worry about as far as paperwork and such.

What type of work would the employee be performing? Liability concerns are very different for someone who would be entering an occupied residence as opposed to being a laborer for a brick mason on a construction site (for exampe).

The things that immediately came to mind is that he would probably need to change his liability insurance to cover workers...

At least four insurance issues immediately come to mind. General liability insurance, completed operations insurance, workers' compensation insurance, and business auto (assuming this employee might drive on company business). Is your insurance agent an Independent Agent? Talk to him/her - responding to questions like yours is what the insurance agent does to earn the commission.

Anybody have any insight or tips on this?

Is your DH familiar with OSHA 1926 - the Standard for Construction? In what state are you located? Does your DH have a safety program?

I will also call the state as they are typically very helpful, but I thought I'd be able to get some good opinions and input here.

Get help where you can, but be careful. There are likely a number of state agencies that would have impact on your operations and a person at one of those agencies may be clueless about the function of other agencies.

For example, someone at the state department of revenue may tell you "everything" you need to know about income tax reporting without mentioning licensing, insurance, OSHA, overtime and other considerations.

Could you provide a bit more information? How old is this student? Full or part-time? Will the student drive to the job site or will you transport him to the job site? Will the student ever be allowed to drive your vehicle or drive his own on company business? What type of work will the student be performing - residential, business, new, remodeling?

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