Don't be afraid to ask if daily updates and the like are an established policy and specifically how they are handled, and what time frames they adhere to for pet sitting visits throughout the day. 'Is this your full time career, or is pet care something that you do in addition to another job?' If the latter is the case, it doesn't hurt to inquire how they manage a work schedule and a pet sitting schedule.
Which approaches do they use or recommend to give medications to pets?
(One family reached out to me to ask how their pet sitter handled getting in
Knowing their recommendations and preferences on dog walking equipment (leashes, harnesses and other tools) is an excellent view into their knowledge about best practices and safety. Ditto for knowing how they would handle a situation with an off-leash dog that is making an unwanted approach or if a dog fight ensues.
Whether or not they require vaccinations and how often they scoop the litter box and asking, 'I'm wondering how I'd know if my dog has tapeworm?', 'My friend's dog has a cough, I wonder if I should be concerned about my own pet', and 'If my dog or cat or displaying unwanted behavior, how do you address that?' can be great leading questions about their basic knowledge into areas of health and animal behavior.
More experienced pet sitters have seen their share of difficult situations and have had to navigate them. Picking their brain about what the most challenging situation they've had to handle professionally is—and how it played out is an excellent question.
To go further, if you're considering boarding services for your pet, ask to view where your pet will be housed, allowed to play and how many dogs are boarded on any given date. Ask about their sanitation practices and flea/tick preventative, heartworm testing and vaccination policies. Does the area or home smell foul? Does it look clean? How many pets are present, and how do they behave? How do the owner or handlers supervise canine interactions—any questionable practices? It's helpful to know if the caregiver (or trained staff) is on site 24/7, and if the facility or home is climate controlled.