How to Choose a Trusted Dog Sitter: 10 Questions to Ask Before Booking

Leaving your dog with someone else is one of the more anxious moments of dog ownership — and that anxiety doesn't go away just because a sitter has a nice profile photo. Your dog can't tell you what happened while you were gone. That's why preparation matters. In this guide, you'll find the 10 essential questions every owner should ask before booking a dog sitter, including what a great answer looks like and which responses should send you running.

Here are the 10 questions at a glance: (1) Are you insured? (2) Do you have experience with my breed? (3) How many dogs will you have at once? (4) Where will my dog sleep? (5) What's your emergency protocol? (6) Will you send updates during the stay? (7) Can we do a meet & greet first? (8) What's your cancellation policy? (9) Can I read verified reviews? (10) How do you handle separation anxiety? Read on for the full breakdown.

Why Choosing the Right Dog Sitter Actually Matters

Handing your dog to a sitter isn't like dropping off a houseplant. It involves trusting another person with the physical and emotional wellbeing of an animal who depends entirely on you. A sitter who seems friendly online but lacks experience, preparation, or accountability can cause real harm — stress, injury, or worse.

Animal behaviour experts recommend approaching the sitter selection process with the same seriousness you'd give to choosing a babysitter. That's not an overstatement. The quality of a caregiver directly impacts a dog's emotional state, particularly in dogs with separation anxiety or rescue backgrounds.

The reassuring news: identifying a trustworthy sitter is entirely doable if you know what to ask. The responses you get in the first 15 minutes of a conversation will tell you more than any platform badge or star rating.

The 10 Questions to Ask Before Hiring a Dog Sitter

1. Are You Insured?

This is the single most important question on the list, and it should be your first. A responsible dog sitter — whether professional or hobbyist — should carry some form of liability insurance that covers accidents involving animals in their care. If your dog is injured on their watch, or if your dog injures another animal or person while in the sitter's custody, you need to know who bears the financial and legal responsibility.

Good answer: "Yes, I have liability insurance that covers accidents with animals in my care. Happy to send you the details."

Red flag: "No, but I've been doing this for years and nothing has ever happened." The absence of insurance isn't just a legal gap — it signals the sitter hasn't thought through risk scenarios at all.

2. Do You Have Experience With My Breed or Size of Dog?

An excellent sitter for Labrador Retrievers may be completely out of their depth with a reactive Malinois, a giant breed like a Great Dane, or a brachycephalic dog like a French Bulldog with specific health needs. Working breeds, large dogs, and dogs with known behavioural challenges require sitters with specific knowledge — not just a general love of animals.

Good answer: The sitter names specific breeds they've worked with, shows photos or reviews from comparable dogs, and can describe how they adapt their routine to different sizes or temperaments.

Red flag: "I'm great with all dogs." This is a warning sign, not a reassurance. No one has experience with every breed, and a good sitter knows that.

3. How Many Dogs Will You Have in Your Care at the Same Time?

Your dog needs genuine one-on-one attention, not diluted supervision. A sitter managing six, eight, or ten dogs simultaneously cannot meaningfully monitor each animal's stress levels, eating habits, or physical condition. Beyond quality of care, larger groups also increase the risk of conflicts between dogs — and an overwhelmed sitter is slower to notice the early warning signs.

Good answer: A specific maximum — typically two to three dogs at most — or a willingness to tell you exactly how many dogs will be present during your booking period.

Red flag: "As many as people need" or "I don't have a limit." A sitter who prioritises volume over individual care is prioritising income over your dog's wellbeing.

4. Where Will My Dog Sleep and How Much Space Will They Have?

Environment shapes behaviour and stress. A dog used to sleeping in bed may become anxious if crated overnight. An active breed needs real outdoor space, not a two-metre balcony. Asking about space also gives you the natural opening to request photos of the actual area — which is entirely reasonable and should be readily offered.

Good answer: A specific, clear description of sleeping arrangements, outdoor access, what other animals live in the home, and how introductions between pets are managed.

Red flag: Vague responses ("just at my house, it's fine") or reluctance to share photos of the space. A sitter with nothing to hide will be happy to show you exactly where your dog will be.

5. What Happens If My Dog Gets Sick or There's an Emergency?

This is the question most owners forget to ask and most regret not asking. A good sitter doesn't improvise in a crisis — they have a plan. They should know the nearest emergency vet, be prepared to act without waiting for your call back, and have a clear protocol for reaching you at any hour.

Good answer: "I have a 24-hour emergency vet clinic [X minutes away]. If something happens, I act first and call you immediately. I'll keep your vet's details from day one."

Red flag: "I'd call a vet" with no further specifics. No named clinic, no timeline, no protocol. Vagueness in an emergency scenario can cost your dog its life.

6. Will You Send Me Photos and Updates During the Stay?

Regular updates aren't neurotic owner behaviour — they're a sign that the sitter is engaged, present, and proud of their work. A sitter who genuinely cares about the dogs in their charge will send photos proactively, because they know it matters to you. If updates feel like an imposition, that tells you something important about their attitude.

Good answer: "I send a morning photo and an evening update every day. If anything interesting or unusual happens, I'll message you straight away."

Red flag: "If you need it, sure." This passive, conditional answer signals that communication is a chore for this sitter, not a natural part of how they work.

7. Can We Do a Meet & Greet Before I Confirm the Booking?

The meet & greet is non-negotiable. It lets you see the actual space your dog will sleep in, observe how the sitter interacts with your dog without you directing the situation, and gauge whether there's a genuine connection. Your dog also has a vote in this decision — watch their body language carefully during the visit.

Good answer: "Absolutely, I consider it essential before any booking. It gives us both peace of mind and helps your dog get comfortable with me first."

Red flag: Resistance, excuses, or an offer to "just do a quick video call instead." If a sitter doesn't want you to see their home or meet them in person before you hand over your dog, ask yourself why.

8. What Is Your Cancellation Policy?

Plans change. Flights get cancelled, family emergencies happen, travel dates shift. You need to know the financial terms before you pay — not after a cancellation becomes necessary. A professional sitter has a written, clearly communicated policy. Ambiguity here nearly always leads to awkward conversations and unresolved disputes.

Good answer: A clear, specific policy stated in writing — how far in advance you can cancel free of charge, and what applies after that.

Red flag: "We'll figure it out if it happens." Informality around money is a professionalism red flag, especially when you're trusting someone with your pet.

9. Can I Read Reviews From Your Previous Clients?

Verified reviews from real clients are the most powerful trust signal available. Even better when they appear on a platform that confirms the reviewer's identity and validates that the booking actually happened. Be cautious of sitters who can only offer WhatsApp screenshots or Facebook group comments — these are easily fabricated and impossible to verify.

Good answer: An active profile on a verified review platform (like My Tails) with at least five detailed, specific reviews from real dog owners describing concrete experiences.

Red flag: No reviews at all, or exclusively five-star reviews with no text. A flawless but empty profile is often a sign of an incomplete or manufactured history.

10. How Do You Handle Dogs With Separation Anxiety or Special Needs?

Many dogs have behavioural quirks that require patience and specific knowledge: separation anxiety, fear responses, reactivity toward other dogs, daily medication, or reduced mobility. A good sitter knows these cases exist, has encountered them before, and has genuine strategies for managing them. A poorly equipped sitter will minimise the problem or assume the dog will simply "settle in."

Good answer: Specific techniques are mentioned — gradual introductions, maintaining the dog's existing routine, positive reinforcement, experience with medicated or senior dogs.

Red flag: "Dogs are dogs — they all adapt eventually" or any dismissive framing of behavioural needs. Indifference to a dog's individual needs is incompatible with responsible care. If your dog struggles with being left, read our guide to dog separation anxiety before you book.

Green Flags: What to Look for in a Dog Sitter's Profile

Beyond the questions, there are indicators you can evaluate before you even make contact:

• Real photos of the sitter's home and outdoor space, not just selfies with cute dogs

• Pet first aid training — increasingly common and a strong marker of professionalism

• Registration as an animal care activity with the local council (required in some Spanish cities)

• A detailed, specific profile that explains their routine, limits, and what they actually offer

• Fast, detailed responses to initial messages — how someone communicates before you book predicts how they'll communicate during the stay

• They ask questions about your dog before accepting the booking. A sitter who asks is a sitter who cares about the fit, not just the fee

All sitters on My Tails go through an identity verification and profile review process before they can accept bookings. Find the right sitter for your dog at mytails.eu.

Red Flags: When to Walk Away From a Dog Sitter

Sometimes the right answer is no, even if the photos look great and the price is right:

• Refuses the meet & greet or offers excuses instead of a date

• No verified reviews, or reviews that are all five stars with no descriptive text

• Only communicates via WhatsApp and avoids platforms that create an auditable trail

• Evades or deflects the insurance question

• Pressures you to book quickly before you've had time to think or ask questions

• Asks nothing about your dog — a sitter who accepts any animal without questions isn't thinking about what's best for the animal

Remember: a sitter's urgency to close the booking is inversely proportional to the peace of mind you'll have once you leave.

The First Visit: What to Observe During the Meet & Greet

The meet & greet is a tool, not a formality. Come prepared to observe, not just to chat. Key things to look for:

The space: Is it clean and hazard-free? Are there loose cables, toxic plants, or escape routes? Is there genuine outdoor access? How is it fenced?

How the sitter interacts with your dog: Do they crouch to the dog's level, or immediately try to grab or hug? Do they wait for the dog to approach, or force contact? Is their voice calm and steady?

The general dynamic: Are there other animals in the home? How are introductions handled — controlled and gradual, or chaotic?

Your dog: Watch for gradual relaxation, curious exploration, or persistent stress signals (tucked tail, excessive panting, seeking exits). Your dog's read on a person is data you should take seriously.

First Time Dog Sitter Checklist: Before You Confirm

Before hitting "book," verify these points:

• Sitter's identity verified (platform verification or in-person ID check)

• At least 5 detailed reviews from verified real clients

• Meet & greet completed in the actual space where your dog will stay

• Vaccination requirements confirmed and met

• Complete care card left with the sitter: vet details, allergies, daily routine, emergency contact

• Cancellation policy received in writing

• Number of dogs in care during your stay confirmed

Once you've chosen someone, our step-by-step guide to preparing your dog for a pet sitter covers the care card, the scent trick, and how to handle the goodbye.

Frequently Asked Questions

How do I know if a dog sitter is trustworthy? The three strongest indicators are: verified reviews on a platform, active liability insurance, and a willingness to do a meet & greet without hesitation. A genuinely trustworthy sitter doesn't wait for you to ask — they offer these things proactively.

Is a meet & greet really necessary before booking? Not legally required, but strongly recommended for your dog's welfare. Without a prior visit, you haven't seen the real environment and your dog has had no chance to acclimate. Platforms like My Tails encourage meet & greets as a standard step before any booking.

What information should I leave with the sitter? A complete care card covering: your regular vet's name and number, any allergies or medications, your dog's daily routine (feeding times, walk schedule, sleep habits), specific behavioural notes, and an emergency contact beyond your own.

How many reviews should a good sitter have? There's no magic number, but five or more detailed, specific reviews give you enough to identify patterns. Quality matters more than quantity — look for reviews that describe real situations, not just generic praise.

Should I choose boarding or a sitter at my home? It depends entirely on your dog's temperament. Our comparison of boarding vs an in-home pet sitter walks through which dogs do better with each.

How much should a good sitter cost? On My Tails, boarding starts at €14/night (recommended €22) and house sitting from €15 (recommended €20). See the full service-by-service breakdown in our Madrid dog sitter cost guide.

My Tails connects pet owners with verified sitters in Madrid, Barcelona, and Valencia. Every profile is reviewed before going live. Learn more at mytails.eu.