Every small business should have an endorsement on their insurance policy called Hired & Non-Owned auto insurance. This is coverage for your business when you tell "Sally" to run the bank deposit to the bank for you. Or you tell "Bob" to go to Office Depot to pick up more envelopes.
You see, when you ask an employee to use their own vehicle to runs errands for your business, it could put their own auto insurance in jeopardy. Some personal auto insurance policies could deny coverage for using their vehicle for business use. I've seen it happen, not often but it does happen. If you are the business owner, you don't want to see an employees auto accident get denied when doing you a favor.
So just know there is a way to not get into this mess by adding hired/non-owned auto coverage on your small business insurance policy. As you can see in the example above, it doesn't cost that much money.