Most lists of pet sitter questions are written by sitters, so they start with “Are you insured and bonded?” Insurance matters, but it doesn’t tell you what someone will do when your dog won’t eat on day two, or when they can’t reach you from a 2 a.m. emergency vet.
These are the questions that do. Ask every candidate the same twelve, by phone or at the meet-and-greet, and listen for specifics.
Free printable: all 12 questions, with boxes to tick solid answers, are in the free Pet-Sitter Vetting Kit. Get the kit →
1. “If my dog gets hurt or sick and you can’t reach me, what exactly do you do?”
Start here. A good sitter names a vet or 24-hour emergency clinic, how they’d get there, who they’d call next, and asks you how much they’re allowed to spend.
Red flag: “I’d figure it out.” A sitter without a plan will be inventing one at the worst possible moment.
2. “How many other pets will you care for during my dates?”
Listen for a specific number and how they split their time. “A few” isn’t an answer. An overbooked sitter is how a “check-in” turns into five minutes at the door.
3. “Where will my dog be, and who else will be there?”
The exact place, plus any other people, kids or pets. For in-home sitting, ask whether anyone will visit. Surprises here, like a roommate or three more dogs, are a common source of trouble.
4. “How often will you send updates, and what will they include?”
You want a set schedule, with photos or video, sent without being asked. Agree on it now so that a missed update means something.
5. “What would you do if my dog won’t eat?”
A thoughtful answer says when they’d start to worry and when they’d call you or the vet. One skipped meal can be normal; two days isn’t.
6. “Has a dog ever escaped or been hurt in your care? What happened?”
Listen for an honest answer and what they changed afterward. Blaming the dog, or the owner, is a warning sign.
7. “What’s your backup plan if you get sick during my trip?”
The most-skipped question, and the one owners most wish they’d asked. You want a named backup person you can meet. “That won’t happen” is not a plan.
8. “How do you handle doors and gates with a dog that bolts?”
The answer you want: leash on before any door opens, gates checked every time, no off-leash time unless you approve it. Some of the lost-dog stories owners tell begin at a front door left open for a moment.
9. “Can I keep my pet camera on? How do you feel about that?”
A good sitter says yes comfortably. Hesitation, or asking you to turn it off, is a red flag.
10. “Can you show me how you’d give my dog’s medication?”
They should watch you once, do it themselves, and ask what to do if a dose is missed or spat out.
11. “Can I talk to two recent clients?”
Names and numbers offered readily, ideally from longer trips. Ask each reference: Would you hire them again for a long trip? Did anything go wrong, and how did they handle it? Were updates on time without reminders?
12. “What’s included in the price, and what costs extra?”
Written rates, plus any extra fees for meds, holidays or vet trips, and how a vet bill gets paid if one comes up.
After the interview: do a trial run
Book a short paid trial, an overnight or a few hours while you’re nearby, before the real trip. Watch three things:
- Did they send an update without being asked?
- Does your dog greet them relaxed, or wary?
- Did they follow your care sheet exactly, or “close enough”?
If any answer worries you, you still have time to find someone else. That’s much easier now than mid-trip.
Book earlier than you think
The best sitters and boarding places fill up first, especially around holidays. Starting three weeks out gives you time for an interview, a trial run and a backup. Last-minute is where most owners end up taking whoever is free.
Get the printable interview script
All 12 questions, the red-flag checklist and a ready-to-sign care agreement. Free.
Please read: This guide is general information, not veterinary or legal advice. Trip-Ready Dog doesn’t screen or endorse any sitter or boarding business, and no checklist can guarantee your dog’s safety; you’re responsible for who you choose. In an emergency, call your vet or a 24-hour emergency vet. See our Terms of Use.
