Politeness makes owners soften these questions, as if checking a sitter's paperwork implied distrust. Professionals expect every one of them, and the hesitant answers are data too. You are not interviewing a friend for a favour; you are hiring someone to hold your dog's welfare, your house keys and possibly a vet bill in the same pair of hands, possibly while you are on another continent with patchy signal. The time to discover how that person handles scrutiny is a calm afternoon in your kitchen, not a crisis phone call from an airport.
Insurance, Asked Without Embarrassment
Ask plainly what insurance the sitter holds, and ask to see it. The cover that matters protects three things: animals in their care if one is injured or escapes, your home if they are staying in it and something is damaged, and the sitter themselves if your dog injures them or a visitor. Ask what the policy excludes, because exclusions are where pleasant assumptions go to die: some cover stops at a certain number of dogs, some excludes particular situations, and some lapses the moment care happens in the owner's home rather than the sitter's.
Ask how an emergency vet bill would be handled in the first hour, before any insurer is involved. A sitter who can pay upfront and claim later, or who holds a clear agreement with you about who pays what and when, removes money from the worst moment of the booking. A sitter who has never considered the question is not being modest; they are telling you the plan does not exist, and you should believe them and plan accordingly.
References You Actually Call
Ask for references you can actually contact, and then contact them. Choose, where the sitter offers several, the owners of dogs like yours: similar size, similar energy, similar quirks, because a glowing report from the owner of a placid senior says little about your adolescent escape artist. Ask each reference what went well, what went less well, how communication felt mid-booking, and whether they booked again for a longer trip, since rebooking is the review nobody can fake.
Ask one question owners forget: what did the sitter do when something went wrong, however small? Every long booking contains a mishap: a chewed shoe, a missed walk in a storm, a dog off its food for a day. References remember how problems were reported and fixed far more clearly than they remember perfection, and a sitter whose references describe early phone calls and sensible fixes is showing you their character under load.
The Day the Sitter Falls Ill
Ask what happens if they fall ill mid-booking, and refuse to accept a wave of the hand. The answer you need names a person: a backup who steps in, and that backup must have met your dog before the booking, ideally at the introductory visit, so a stranger's arrival does not become the dog's second emergency. Ask how you would be told, how keys and instructions pass across, and whether the backup knows your vet, your routine and your dog's particular fears already.
Consider what the alternative looks like without one: a sick sitter, a dog alone longer each day, and you arranging emergency cover from a departure lounge. For a short booking with family nearby, your own network may be the honest backup, and that is fine if it is agreed in advance rather than assumed. What is not fine is discovering, mid-booking, that the contingency was optimism. If illness strikes mid-booking, another Care Pass through KinsLe can be issued to the named backup, time-boxed to the days they cover.