10 Questions to Ask Before Hiring a Dog Sitter

You've found a potential dog sitter. Maybe you're planning a week-long vacation and don't want to board your anxious senior. Maybe your work trip overlaps with your usual walker's availability. Maybe you want someone in your home while you're gone—not just for your dog, but for the peace of mind that comes with an occupied house.

Here's what makes dog sitting different from walking: duration creates compounding consequences. A dog walker spends 30-60 minutes with your dog; mistakes are limited in scope. A dog sitter controls your dog's environment for days or weeks. A missed medication dose becomes three missed doses. A failure to recognize early illness symptoms becomes a veterinary emergency that could have been prevented. A mismatch in energy management creates a dog who destroys furniture out of boredom or anxiety.

The questions you ask must reflect this extended responsibility. You're not just evaluating someone's ability to clip a leash and walk around the block—you're evaluating their judgment, their home environment (if boarding), their ability to handle medical needs without supervision, and their crisis response when you're in a different time zone and unreachable.

Below are the 10 questions that separate professional dog sitters from people who "love dogs and have a flexible schedule."

The 10 Essential Questions

1. "Describe your home environment—other pets, hazards, yard security, and who else lives there."

Why it matters: Your dog will live in this space unsupervised. Unlike drop-in visits to your own dog-proofed home, boarding exposes your dog to unknown hazards, unfamiliar animals, and people you've never met. A "friendly" resident cat that swats at dogs can cause corneal scratches requiring emergency care. An unfenced yard—or a fence with gaps—creates escape opportunities you cannot control remotely. A roommate who leaves chocolate on the counter or props doors open introduces risks the sitter may not even recognize. In Chicago specifically, older buildings often have lead paint, radiators that burn curious noses, and gaps between vintage baseboards where small dogs get stuck.

What to listen for:

• Detailed inventory, not reassurances ("I have one cat who's dog-tested—she ignores dogs completely. No other pets. My backyard is fully fenced, 6-foot wooden privacy fence, no gaps. I've walked the perimeter.")
• Hazard awareness ("I keep cleaning supplies locked. No houseplants—I removed my pothos and philodendron because they're toxic. Trash cans have locking lids.")
• Household transparency ("I live alone. My sister visits on weekends but knows to keep doors closed and not feed the dog. I'll let you know if anyone else will be there.")
• Sleeping area specifics ("Dogs stay in my bedroom with me—door closed, no access to the rest of the house unsupervised at night")
• Climate control ("I have central air and heat. In summer I keep it at 72°F; I know brachycephalic breeds need cooler temperatures.")

Red flag: "My place is totally safe" or "don't worry, I've done this before" without specifics. If they cannot inventory hazards, they haven't assessed them. Also concerning: hesitation about other household members or roommates who "come and go."

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2. "What's your overnight routine? Where will my dog sleep, and how do you handle nighttime needs?"

Why it matters: Nighttime is when anxiety peaks and supervision disappears. Approximately 40% of dogs show increased anxiety behaviors their first night in an unfamiliar environment—pacing, whining, inability to settle. A dog who seems fine during the daytime meet-and-greet may panic at 2am when the house goes dark and quiet. Senior dogs often need midnight bathroom breaks; puppies need them every 3-4 hours. A sitter who sleeps through whining or ignores scratching at the door creates situations where dogs soil their sleeping area (causing shame spirals and house-training regression) or injure themselves trying to escape.

What to listen for:

• Specific sleeping arrangements ("Dogs sleep in my bedroom. I have a crate set up if they're crate-trained, or a dog bed next to my bed. Door stays closed so they can't wander.")
• Nighttime awareness ("I'm a light sleeper—I wake up if a dog whines or paces. For senior dogs or puppies, I set an alarm for a 2am bathroom break the first few nights.")
• Anxiety protocols ("If a dog can't settle the first night, I sleep on the couch near them. I use a white noise machine and keep a nightlight on. For severe anxiety, I'd discuss short-term calming aids like Adaptil spray with you beforehand.")
• Emergency access ("I keep a flashlight by the bed in case we need a sudden middle-of-the-night vet trip. My car keys are always in the same spot.")

Red flag: "They'll figure it out" or "dogs sleep in the living room." Leaving an anxious dog alone in an unfamiliar room overnight is how you get destruction, self-injury, and noise complaints. Also concerning: "I've never had a dog have trouble sleeping"—that means they've either been lucky or don't notice distress.

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3. "What's your experience with extended stays—more than 3 days? Tell me about your longest booking."

Why it matters: Day two and day seven require completely different skills. The first 48 hours test a sitter's ability to establish routine and manage transition anxiety. Days 3-5 test consistency—can they maintain medication schedules, exercise patterns, and feeding routines without drift? Days 7+ test their ability to handle behavioral changes that emerge over time: dogs who become territorial about "their" new space, dogs who develop guarding behaviors with the sitter, dogs whose initial politeness fades into their real personality. A sitter who's only done weekend stays has never navigated these phases.

What to listen for:

• Specific duration experience ("My longest stay was 3 weeks with a senior Lab while her owners were in Europe. Most of my bookings are 5-10 days.")
• Phase awareness ("The first two days are adjustment. By day three or four, most dogs settle into a routine. Around day seven, some dogs start testing boundaries or showing behaviors they suppressed initially—that's when I maintain consistent structure.")
• Long-stay observations ("Extended stays taught me that dogs need increasing mental stimulation as novelty wears off. By week two, I add puzzle feeders and new walking routes to prevent boredom.")
• Owner communication patterns ("For stays over a week, I send daily photo updates but also do a video call mid-stay so you can see your dog and they can hear your voice")

Red flag: "I've mostly done drop-in visits and a few overnights." Drop-in experience doesn't translate to multi-day care—it's a completely different job. Also concerning: no stories about how extended stays differ from short ones.

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4. "If I'm unreachable during an emergency, what decisions are you authorized to make?"

Why it matters: Emergencies don't wait for callbacks. GDV (gastric dilatation-volvulus) kills dogs within hours; waiting for owner approval while a dog's stomach twists is not caution—it's negligence. Severe allergic reactions cause airway closure within minutes. A sitter who "always calls you first" will freeze when you're on a 14-hour flight to Tokyo, and frozen minutes become permanent damage. This question reveals whether someone has thought through decision-making authority—and whether you're comfortable granting it.

What to listen for:

• Clear decision framework ("For life-threatening emergencies—GDV symptoms (bloating, retching without producing anything, restlessness), severe bleeding, seizures, collapse, difficulty breathing—I act immediately and contact you on the way to the vet. I don't wait for permission to save a dog's life.")
• Financial authorization understanding ("I'll need pre-authorization in writing for emergency vet care up to a certain amount—typically $2,000-$5,000—so the vet can treat immediately without waiting for you to answer.")
• Specific emergency vet locations ("I know MedVet Chicago in Lincoln Park is 24/7. For the South Loop, I'd use Chicago Veterinary Emergency Services. I have these addresses saved with one-tap navigation.")
• ASPCA Poison Control awareness ("If your dog ingests something toxic, I call 888-426-4435 immediately for guidance—they'll tell me whether to induce vomiting or rush to the vet")
• Backup contact clarity ("If I can't reach you within 15 minutes during an emergency, who's my secondary contact? Do they have the same decision-making authority?")

Red flag: "I'd never do anything without your approval." That sounds respectful, but it's actually dangerous—it means they'll hesitate when hesitation costs lives. Also concerning: no awareness of emergency vet locations or poison control resources.

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5. "Does my dog have medical needs? Walk me through how you'd handle medications, dietary restrictions, or health monitoring."

Why it matters: Medication errors during extended stays can be fatal. Insulin timing for diabetic dogs must be precise—a dose given 4 hours late or early causes blood sugar crashes or spikes that lead to seizures, coma, or death. Phenobarbital for epileptic dogs requires consistent timing; missed doses lower seizure thresholds. Apoquel for allergies seems low-stakes until a dog scratches themselves bloody overnight. And unlike a quick drop-in where you verify the medication was given, multi-day stays require trusting that every dose happens correctly for days without your observation.

What to listen for:

• Specific experience ("I've administered insulin injections for diabetic dogs—I know the pinch-and-inject technique and how to rotate injection sites. I've given oral medications, ear drops, and eye ointments.")
• Documentation approach ("I keep a medication log with timestamps. I'll send you a photo of each dose being given so you have verification.")
• Understanding of consequences ("I know that timing matters for medications like insulin and thyroid supplements. I set phone alarms and don't rely on memory.")
• Dietary restriction competence ("If your dog has food allergies, I won't give any treats without your approval. I keep their food completely separate from my own pets' food.")
• Health monitoring awareness ("I know to watch for changes in appetite, water intake, energy level, and bathroom habits. A dog who stops eating on day two isn't 'just adjusting'—that's a symptom worth reporting.")
• Demonstration willingness ("If you want, we can do a practice medication session during our meet-and-greet so you can see my technique")

Red flag: "I'll figure it out" or inability to describe medication administration experience. Also concerning: overconfidence about complex medical needs without asking questions about your specific dog's protocol.

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6. "What's your daily routine and exercise plan for my dog?"

Why it matters: Dogs thrive on predictable structure, and extended stays without routine create anxiety, behavioral regression, and destructive boredom. A dog who normally walks at 7am, 12pm, and 6pm will pace and whine if those walks happen at 10am and 4pm instead. A high-energy Border Collie who normally gets 2 hours of exercise will destroy furniture by day three if they're getting 30-minute walks. A senior dog who normally rests most of the day will be exhausted and sore if a sitter thinks "more exercise is always better." The routine question reveals whether someone will maintain your dog's life or impose their own schedule.

What to listen for:

• Schedule flexibility ("Tell me your dog's current routine, and I'll match it as closely as possible. I'm an early riser, so 6am walks are no problem. If they normally eat at 7am and 5pm, that's what we'll do.")
• Exercise customization ("What does your dog need daily? A 15-minute senior stroll, or a 45-minute high-energy adventure with off-leash time? I adjust based on the dog, not my own preferences.")
• Mental stimulation awareness ("Physical exercise isn't enough for most dogs. I use puzzle feeders, snuffle mats, and training sessions to tire them mentally—especially for smart breeds like Poodles, Border Collies, and Australian Shepherds.")
• Breed-appropriate planning ("I know brachycephalic breeds like Bulldogs and Pugs can't do long walks in heat. I know sighthounds need chances to run but shouldn't be off-leash near traffic. I'll plan activities that fit your dog's breed and age.")
• Indoor alternatives ("On days when it's too hot, too cold, or storming, I do indoor play sessions, training games, and food puzzles instead of skipping exercise entirely")

Red flag: "I'll walk them when I can" or no questions about your dog's current routine. A sitter who doesn't ask about your dog's schedule doesn't intend to follow it. Also concerning: one-size-fits-all approaches ("all dogs get two 20-minute walks").

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7. "How often will you communicate with me, and what updates should I expect?"

Why it matters: Without communication, small problems become big surprises. A dog who "seemed a little off" on day two but wasn't reported is a dog whose illness progressed for five days before you knew. A sitter who mentions "a little diarrhea" on day five neglected to tell you about the three days of GI upset that preceded it. And for your own peace of mind: you're trusting someone with a family member while you're away. Radio silence creates anxiety that ruins your trip; constant updates let you actually relax knowing your dog is thriving.

What to listen for:

• Specific cadence ("I send a morning update with a photo after the first walk, and an evening summary. If anything notable happens—a weird bowel movement, a limp, unusual behavior—I message immediately.")
• Communication platform ("I use Time to Pet for scheduling and updates, which includes GPS walk tracking. You can see exactly where we went and when.")
• Proactive reporting ("I report the small stuff: if your dog didn't finish breakfast, if they seemed less playful than usual, if they had soft stool. These details help you notice patterns I might miss.")
• Your preference accommodation ("Some owners want multiple daily updates; some want one evening summary. Tell me your preference and I'll match it.")
• Video calls for long stays ("For stays over a week, I offer video calls so you can see your dog and they can hear your voice—some dogs really perk up hearing their owner")

Red flag: "I'll let you know if there's a problem" or "no news is good news." That's passive communication that conceals developing issues. Also concerning: inability to commit to a specific update schedule.

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8. "Do you have a backup sitter if something happens to you?"

Why it matters: Sitters get sick. They have family emergencies. They get in car accidents. A professional sitter has thought through what happens if they cannot continue your booking—an amateur hasn't, and you'll discover this gap at 11pm when they call to say they're in the ER and your dog is alone in their house. This question reveals operational maturity: does this person run a professional service, or are they winging it?

What to listen for:

• Named backup ("My backup is Sarah, who's also a professional sitter. She knows my clients' dogs, has copies of their care instructions, and can take over within 2 hours if I'm incapacitated.")
• Backup vetting ("My backup has the same insurance coverage and has met several of my regular client dogs. She's not just 'someone who can help'—she's a qualified sitter.")
• Handoff protocol ("If I need to transfer care, I'd call you first to get approval, then do an in-person handoff with written care instructions. I wouldn't just leave your dog with someone you haven't authorized.")
• Emergency contact sharing ("I'll give you my backup's contact information before the stay starts, so you can reach her directly if you can't reach me")

Red flag: "I've never needed a backup" or "I'd figure something out." Everyone needs a contingency plan. Also concerning: "my roommate/partner would take over"—are they qualified? Have you met them? Do they have the same insurance?

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9. "How will you handle home access and security while I'm away?"

Why it matters: For in-home sitting, you're giving a stranger keys to your home while you're not there to monitor. Package theft, unauthorized visitors, and security lapses create problems beyond pet care. For boarding at the sitter's home, you need to know your dog won't escape through a door left open or slip out when someone enters. This question addresses the logistics everyone forgets until something goes wrong.

What to listen for:

• Key management ("I treat client keys like my own house keys—on a dedicated keyring, never labeled with your address, returned immediately after the stay. I don't make copies unless you authorize it.")
• Home security awareness ("I'll follow your alarm system instructions exactly. I won't let anyone into your home without your explicit permission—not delivery people, not neighbors, not my friends.")
• Package and mail handling ("I'll bring in packages and mail daily to avoid advertising that you're away. I'll water plants if you want. I'll keep lights on timers or manually vary them.")
• Boarding security ("At my home, dogs are never outside unsupervised. I have a double-gate system—the yard gate stays closed when the house door opens. I verify collars and ID tags are secure before every outdoor moment.")
• Visitor protocols ("I don't have guests over during client stays. If I need a plumber or maintenance person, dogs go in a secured room first.")

Red flag: "I'm pretty careful" without specifics. Also concerning: no mention of how they prevent door-dashing when entering or exiting.

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10. "Can you provide references from multi-day stays specifically—not just drop-in visits?"

Why it matters: References validate claims. But generic references from 30-minute drop-ins don't tell you anything about overnight competence, medication management, or extended-stay experience. You need to talk to people who've trusted this person with their dog for multiple consecutive days—ideally a week or more. Their experiences predict yours: did the sitter communicate well? Did the dog come home happy or stressed? Were there any issues, and how were they handled?

What to listen for:

• Willingness to provide contacts ("Absolutely. I'll give you three references from stays of 5+ days. One is a senior dog with medical needs, one is a high-energy young dog, one is an anxious rescue.")
• Specific reference details ("Sarah used me for 10 days last summer while she was in Europe. Her number is... Michael's dog has diabetes and I did his insulin for two weeks—he can speak to my medical care.")
• Variety of scenarios ("I can provide references from first-time clients and repeat clients, from simple healthy dogs and dogs with complex needs")
• Online review presence ("I'm also on Rover with 40+ reviews, most from overnight stays. You can read those as a starting point before calling individual references.")

Red flag: "I don't give out client information" or only offering references from family/friends. Also concerning: references only from drop-in visits or dog walking—different skill set entirely.

The Answers You Should Actually Receive

Here's a quick reference for what solid answers sound like versus what should give you pause:

Question	Strong Answer Signals	Weak Answer Signals
Home environment	Detailed hazard inventory, fence inspection, other pet details, household members named	"My place is safe"
Overnight routine	Specific sleeping location, nighttime protocols, anxiety management plan	"They'll figure it out"
Extended stay experience	Multi-week booking history, phase awareness, long-stay observations	"I've done a few overnights"
Emergency authority	Clear decision framework, financial pre-auth understanding, vet locations memorized	"I'd never act without your permission"
Medical needs	Specific medication experience, documentation approach, demonstration willingness	"I'll figure it out"
Daily routine	Schedule matching, exercise customization, mental stimulation awareness	"I'll walk them when I can"
Communication	Specific cadence, proactive reporting, platform named	"No news is good news"
Backup sitter	Named backup, vetting confirmation, handoff protocol	"I've never needed one"
Home security	Key management protocol, alarm competence, visitor policies	"I'm pretty careful"
References	Multi-day stay references, variety of dog types, specific names and durations	"I don't share client info"

What If You Don't Want to Do All This?

We understand. You're hiring a dog sitter precisely because you're busy enough to need one—adding "conduct thorough interviews with multiple candidates" to your pre-vacation checklist feels impossible.

And you're right to feel that way. The pet care industry has no licensing requirements. Anyone can call themselves a dog sitter tomorrow. The burden of verification falls entirely on you, and most people don't have the expertise to evaluate answers even if they ask the right questions.

This is exactly why we built Tails.

Every sitter on our platform has already answered these questions—and proven their answers through verified experience. We check home environments for boarding sitters. We verify insurance coverage and backup plans. We confirm medication competence and emergency protocols. We collect references specifically from extended stays, not just quick visits.

When you book through Tails, you're not starting the vetting process from scratch. You're choosing between pre-qualified professionals who've already demonstrated they can handle multi-day care. The meet-and-greet becomes about chemistry and fit—not interrogation and evaluation.

You still ask questions. You still trust your gut. But you ask knowing the fundamentals are already verified.

Your Pre-Meeting Checklist

Before meeting a potential sitter, prepare:

Information to share:

• Your dog's complete daily routine (walk times, feeding schedule, medication timing)
• Behavioral profile: fears, triggers, quirks ("terrified of thunderstorms," "resource guards food bowls," "counter-surfs when bored")
• Medical needs with written instructions and vet contact
• Emergency vet pre-authorization in writing with spending limit
• Your travel itinerary with time zones and reachability windows
• Secondary emergency contact with decision-making authority

Documents to request:

• Proof of liability insurance (certificate with coverage amount)
• Business license if applicable
• 2-3 references from multi-day stays (not family/friends)
• Backup sitter contact information

Questions to ask yourself:

• Does their schedule actually work for your dog's routine?
• If boarding: have you seen their home in person?
• Are you comfortable with their emergency decision-making authority?
• Do their communication preferences match yours?

Observations during the meeting:

• How does the sitter interact with your dog? (Forcing interaction vs. letting dog approach)
• Does your dog's body language relax over 15+ minutes?
• Does the sitter ask good questions about your dog's specific needs?
• Do they take notes, or just nod along?

Making Your Decision

After meeting potential sitters, trust your gut—but verify with your notes. A sitter who answered every question with specifics, asked thoughtful follow-up questions about your dog's needs, and connected naturally with your dog has demonstrated the competence that matters.

A sitter who was vague about their experience, defensive about your questions, couldn't provide multi-day references, or didn't engage with your dog's specific needs? Keep looking. Extended care is too high-stakes for "probably fine."

The right sitter is out there. The difference between finding them and settling for "good enough" is whether you ask the right questions and listen for the right answers. Your dog will live with this person for days—that responsibility is worth taking seriously.

Ready to skip the interview marathon? Find a pre-vetted sitter on Tails and meet sitters who've already passed the test.

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Frequently Asked Questions

How is hiring a dog sitter different from hiring a dog walker? Duration creates compounding consequences. A dog walker spends 30-60 minutes with your dog; mistakes are limited in scope. A dog sitter controls your dog's entire environment for days or weeks—their feeding, their sleep, their medication, their safety. Errors compound: one missed medication dose becomes several missed doses; one failure to recognize illness symptoms becomes a preventable emergency. Sitters need overnight competence, extended-stay experience, emergency decision-making authority, and either a safe boarding environment or the judgment to maintain your home responsibly. Walkers need leash skills and route planning. The overlap is smaller than most people assume.

Should I choose in-home sitting or boarding at the sitter's home? Both have advantages depending on your dog's personality. In-home sitting keeps your dog in familiar surroundings, which reduces anxiety for dogs who stress in new environments, senior dogs with mobility limitations, and dogs with territorial tendencies. Your dog maintains their routine in their own space. Boarding at the sitter's home provides more supervision (the sitter is always there rather than visiting), often costs less, and works better for social dogs who enjoy novel environments. For highly anxious dogs, dogs with escape tendencies, or dogs with complex medical needs, in-home sitting is usually safer. For healthy, social dogs who adapt easily, boarding often provides more enrichment and companionship.

How far in advance should I book a dog sitter? For popular travel periods—Thanksgiving, Christmas, spring break, summer vacation—book 4-8 weeks in advance. Quality sitters fill their calendars early because repeat clients rebook the same weeks annually. For regular weekends or off-peak times, 1-2 weeks is usually sufficient. For emergency or last-minute needs, expect limited options and potentially higher rates. Building a relationship with a regular sitter means you get priority booking—another argument for finding someone great and sticking with them.

What should I do if my dog has never stayed with a sitter before? Start with a trial overnight before committing to your full trip. This reveals whether your dog adjusts well to the new environment and whether the sitter's updates match your dog's actual needs. Some dogs who seem confident develop separation anxiety overnight; some anxious dogs surprise their owners by settling quickly. You cannot know until you test. For the trial, stay local and available so you can retrieve your dog if needed. If the trial goes well, book your full stay with confidence. If problems emerge, you've learned this while you can still find alternatives—not while you're boarding a plane.

What's a reasonable price range for dog sitting? In Chicago, expect $50-85 per night for professional in-home sitting and $40-70 per night for boarding at the sitter's home. Rates vary based on the sitter's experience, your dog's needs (medical care and multiple dogs cost more), and time of year (holiday premiums are standard). Significantly lower rates—under $30/night—often indicate missing insurance, lack of experience, or someone treating pet sitting as casual side income rather than a professional service. For extended stays of two weeks or more, many sitters offer discounted weekly rates. Remember: you're paying for someone's time, expertise, insurance, and the peace of mind that your dog is genuinely cared for—not just fed and watered.

What if something goes wrong during the stay? This is why the emergency protocol question matters so much. Before you leave, establish: What decisions is the sitter authorized to make without your approval? What's the spending limit for emergency vet care? Who's the backup contact if you're unreachable? Get these agreements in writing. If something does go wrong, a professional sitter will have documented everything—timestamps, symptoms, actions taken, vet communications. This documentation protects everyone and helps your vet provide better care. If a sitter handles an emergency well, consider them a permanent part of your pet care team. If they handled it poorly—delayed action, poor communication, inadequate documentation—don't use them again, regardless of how the emergency resolved.

How do I know if my dog had a good stay? Your dog's behavior in the 24-48 hours after returning home tells you more than any update during the stay. Signs of a good experience: normal appetite, normal energy, happy to see the sitter again when you mention their name or return for future bookings. Signs of a stressful experience: lethargy, GI upset (stress-induced), reluctance to eat, clinginess, regression in house training. Some mild adjustment upon returning home is normal—dogs need time to readjust to any transition. But significant behavioral changes warrant conversation with the sitter and potentially finding a different caregiver for future stays. Trust your knowledge of your own dog: you know their baseline better than anyone.

Should I leave detailed written instructions? Absolutely—and professional sitters expect them. Write down feeding amounts and times, medication protocols with exact dosing, walking schedule, behavioral notes ("he barks at the mailman but it's fine," "she's scared of men in hats"), emergency contacts, and your vet's information. Include quirks that might not seem important ("she won't drink from a metal bowl," "he needs his blanket to sleep"). More information is always better than less. Professional sitters will read everything, ask clarifying questions, and refer back to your instructions throughout the stay. If a sitter seems annoyed by detailed instructions, they're the wrong sitter.