Every great pet sit starts with a proper conversation. The homeowners who feel most relaxed on their holidays are almost always the ones who asked the right questions beforehand and got specific, honest answers. Here are the 15 questions we recommend working through with any prospective sitter, whether that's over messaging, a video call, or a meet-and-greet.
About Their Experience
1. Have you cared for a pet similar to mine before?
Not all pet experience is the same. A sitter who's comfortable with small dogs may have little experience with large breeds, reactive animals, or cats who need daily medication. Ask for specifics: breed, age, any challenges they navigated.
2. What's the longest sit you've completed, and how did it go?
Duration matters. A sitter who has done well on three-day sits may not have been tested on a two-week trip. Understanding their longest sit, and what they handled during it, gives you a useful reference point.
3. Have you ever had an emergency during a sit? How did you handle it?
This question tells you a lot. It reveals problem-solving ability, composure under pressure, and honesty. The best answer isn't 'nothing has ever gone wrong.' It's a specific story about a challenge and how they managed it calmly.
About Their Approach to Care
4. How will you handle my pet's feeding schedule?
Routine matters enormously to pets. A good sitter will ask about your schedule and commit to following it, rather than adapting your pet to their own preferences. Consistency with feeding times makes a noticeable difference to anxiety levels.
5. How often will you be out of the home each day?
This is especially important for dogs. Many dogs struggle with more than four hours alone. Understanding the sitter's daily schedule, including remote work, social plans, or day trips, tells you whether the sit will actually meet your pet's needs.
6. How will you communicate with me while I'm away?
Agree on frequency and format before you leave. Daily photo updates? A message each evening? A video call after the first night? Setting this expectation upfront means neither of you is left guessing.
7. How comfortable are you administering medication?
If your pet takes any medication, even occasional supplements, you need a clear answer here. Ask them to describe how they would administer tablets or drops to an animal who resists.
About Practical Logistics
8. Who else will be staying in or visiting my home during the sit?
This is a completely fair question, and a good sitter won't take offence. Partners, friends, family members. You should know everyone who will be in your home and agree on boundaries clearly.
9. Do you have your own transport?
For regional or suburban sits, and especially for any situation where your pet might need a vet visit, having a car matters. Confirm they can reach your nearest emergency vet if they need to.
10. What would you do if my pet became ill or injured?
Walk through the scenario together. Your dog shows signs of distress at 11pm. What's the plan? The answer should include contacting you immediately, knowing where your vet details are, and being willing to seek emergency care. Any hesitation here is worth following up on.
About Their Understanding of Your Expectations
11. Do you have any concerns about anything in the listing?
An experienced sitter will have read your listing carefully and come prepared with specific questions or concerns. Someone who says 'no, all looks fine' to everything may not have engaged with it as deeply as you'd want.
12. Are you comfortable with my home's specific requirements?
Go through anything non-standard: alarm systems, pool maintenance, specific appliances, outdoor areas, neighbour arrangements. Document all of it in your handover notes.
13. Have you read the Sitterly Community Guidelines and Sitter Agreement?
A professional sitter knows the platform's expectations. This isn't a trick question. It's a signal of how seriously they take the responsibility.
The Final Two
14. Can I contact your previous homeowners for a reference?
Strong sitters will say yes straight away. Profile reviews are great, but a direct conversation with a previous homeowner, especially for a longer sit, gives you a level of reassurance that no rating system fully replaces.
15. Is there anything you'd like to ask me before we confirm?
This is your closing check. A sitter who asks nothing at the end either already knows everything they need, or hasn't quite thought through what they're taking on. The best sitters close the conversation with their own list of questions.
Write It All Down
After your conversation, put the agreed answers in a written handover guide. Email it to yourself and your sitter so there's a clear record for both of you. The best sits have the clearest paperwork.
