First Time Using a Dog Sitter? Here's What to Expect (And How to Prepare)

You've decided to hire a dog sitter. Maybe you're planning your first real vacation since getting your dog. Maybe boarding facilities feel too impersonal or stressful for your pup. Maybe you just want your dog to stay in a calm, home environment while you're away.

Whatever brought you here, you're facing questions that keep first-timers up at night:

What if my dog doesn't like them? What if something goes wrong while I'm gone? How do I know if my dog is actually okay—or just surviving? Is my home going to be safe with a stranger coming and going?

The short answer: with the right preparation, using a dog sitter is far less stressful than you're imagining. The longer answer is this guide.

We'll walk you through everything: how to prepare your home and your dog, what the meet-and-greet should accomplish, what information your sitter actually needs, and how to recognize when everything is working—or when it's not.

What Dog Sitting Actually Means

Before we get into preparation, let's clarify what you're booking—because "dog sitting" covers several different arrangements, and understanding the differences matters.

Types of Dog Sitting

Type	What It Means	Best For
In-home sitting	Sitter stays at YOUR home overnight with your dog	Dogs who are anxious in new environments; dogs with complex routines; when you want your home occupied
Host-home boarding	Your dog stays at the SITTER'S home	Social dogs who adapt to new environments; when your home isn't suitable for a sitter
Drop-in visits	Sitter visits your home 1-3 times per day but doesn't stay overnight	Dogs who are comfortable alone; shorter trips; combined with other care

This guide focuses primarily on in-home sitting (where the sitter comes to you) and host-home boarding (where your dog goes to them)—the two options that involve extended, continuous care.

Why Dog Sitting Works for Many Dogs

Unlike boarding facilities with 20-50+ dogs, noise, and rotating staff, dog sitting provides:

• One consistent caregiver who learns your dog's personality
• A home environment (yours or theirs) rather than a kennel
• Individual attention rather than crowd management
• Your dog's routine maintained as closely as possible
• Lower stress from reduced noise, fewer dogs, and personalized care

For dogs who get overwhelmed in busy environments, seniors who need calm, anxious dogs who need predictability, or dogs with medical needs requiring monitoring—sitting is often dramatically better than facility boarding. The difference shows in your dog's behavior: dogs who come home from sitting are typically relaxed and happy, not exhausted and needing days to recover.

Step 1: Finding the Right Sitter

What to Look For

The right sitter isn't just someone who's available—it's someone whose experience matches your dog's needs.

Factor	Why It Matters	What Happens If You Skip This
Experience with your dog type	A sitter great with calm seniors may struggle with high-energy adolescents	Mismatched care: your dog's needs aren't met, behaviors worsen
Verified background and insurance	Protects you from liability; ensures accountability	If something goes wrong, you have no recourse and absorb all risk
Clear communication style	You need updates to relax during your trip	Anxiety from silence; problems go unreported until they're emergencies
Professional protocols	How they handle emergencies, medications, routines	Improvisation during crises; inconsistent care quality
References from similar stays	Past performance predicts future performance	You're gambling instead of choosing

Questions to Ask Before Booking

Don't wait for the meet-and-greet to ask the important questions. Before you even schedule that meeting:

About their experience:

• How long have you been pet sitting professionally?
• Have you cared for dogs similar to mine? (Same energy level, age, behavioral needs)
• What's the longest stay you've done? Tell me about it.

About their setup (if your dog is going to their home):

• How many dogs do you care for at once?
• What other animals live in your household?
• Is your yard securely fenced? How do you prevent escapes?

About emergencies:

• What's your emergency protocol if something happens?
• Where would you take my dog for emergency vet care?
• What decisions are you comfortable making if you can't reach me?

About communication:

• How often will you send updates?
• What platform do you use for photos and messages?
• What should I expect to hear about?

A professional sitter will have clear, confident answers. Vague responses—"I've done this a lot" or "I'd figure it out"—indicate someone who hasn't thought through the details.

The Directory Problem vs. The Matchmaker Approach

Most pet care apps work like Craigslist: here are 500 profiles, you do the vetting. You scroll, read reviews that may not apply to your dog, compare prices, and hope for the best.

That's not finding a sitter. That's gambling on one.

Tails works differently. We interview every sitter, verify their experience and insurance, inspect their homes (for boarding), and track what each person excels at. When you tell us about your dog—anxious rescue, diabetic senior, high-energy puppy—we match you with sitters whose verified skills fit those specific needs.

You're not scrolling 200 profiles hoping for the best. You're meeting people pre-selected to succeed with your specific dog.

Find Your Sitter Match on Tails

Step 2: The Meet-and-Greet (This Is Non-Negotiable)

Never book sitting without meeting the sitter first—preferably in your home if they'll be doing in-home sitting, or at their home if your dog will be staying there.

This isn't optional politeness. Dogs form trust with individual humans, not profiles. Your dog needs to meet this person in a context where they feel safe (their own territory, with you present) before being left alone with them.

What the Meet-and-Greet Accomplishes

For you:

• See how the sitter interacts with your dog
• Assess their comfort level and genuine interest
• Walk through your home setup, routines, and expectations
• Share your dog's quirks, fears, and needs
• Ask remaining questions in person

For your dog:

• Meet this person while you're present and calm
• Form initial associations in familiar territory
• Begin building trust before the actual stay
• Show you their honest reaction to this person

For the sitter:

• Learn your dog's personality firsthand
• See the environment they'll be managing
• Ask questions about routines, preferences, behaviors
• Assess whether this is a good fit from their side too

What to Watch During the Meeting

Green flags:

• Gets down to your dog's level rather than looming
• Lets your dog approach on their own terms
• Asks detailed questions about behavior, routine, preferences
• Notices and comments on your dog's body language
• Seems genuinely interested in your dog, not just the booking
• Takes notes or asks to photograph your care instructions

Red flags:

• Rushes through the meeting
• Forces interaction your dog isn't offering
• Shows no curiosity about your dog's specific needs
• Makes promises that seem too good ("all dogs love me")
• Dismisses your concerns about anxiety or behavior
• Your dog remains uncomfortable after 15-20 minutes of calm interaction

Trust Your Dog's Reaction

Dogs read people through body language cues we often miss. If your normally friendly dog seems unusually anxious, avoidant, or won't approach the sitter after reasonable time, pay attention.

That doesn't automatically mean the sitter is bad—it might be an off day, or simply a personality mismatch. But it does mean you should either try another meeting or find a different sitter. Dogs who never warm up to their sitter during the meet-and-greet rarely do better when you're gone.

Step 3: Preparing Your Home

Whether the sitter is coming to your home or you're visiting theirs, preparation prevents problems.

For In-Home Sitting (Sitter Comes to You)

Physical preparation:

Area	What to Do	Why It Matters
Dog supplies	Organize food, treats, medications, leashes in one clear location	Sitter doesn't waste your dog's walk time hunting through closets
Cleaning supplies	Leave enzymatic cleaner, paper towels, and waste bags accessible	Accidents happen; quick cleanup prevents stains and repeat marking
Secure valuables	Lock away jewelry, cash, important documents	Not because sitters steal—but because you don't need to wonder
Remove hazards	Secure trash cans, remove toxic plants, put away chocolate/medications	Your dog may behave differently when you're not there
Off-limits areas	Close doors or use baby gates to restrict access	Prevents sitter or dog from entering spaces you want untouched

Access preparation:

Method	Best Practice	What Can Go Wrong
Smart lock	Create a temporary code for the stay; delete after	Dead battery = sitter can't enter; set battery alerts
Lockbox	Use combination-based; change code after each sitter	Combination gets shared; change code between bookings
Physical key	Never leave it in an obvious hiding spot	Hidden keys get found; you lose security control
Building access	Register sitter with doorman/management 24-48 hours ahead	Unregistered sitter denied entry while your dog waits

Chicago-specific considerations:

• High-rise buildings (River North, Streeterville, South Loop): Confirm elevator access, guest parking, and dog relief area protocols with your building.
• Walk-ups (Wicker Park, Logan Square, Pilsen): Walk your sitter through all locks—front door, vestibule, apartment door.
• Alarm systems: Write down the code AND demonstrate the keypad. Explain what happens if they trigger it accidentally.

For Host-Home Boarding (Your Dog Goes to the Sitter)

Visit the sitter's home during your meet-and-greet. Look for:

Safety checks:

• Securely fenced yard with no gaps (walk the perimeter if possible)
• No toxic plants accessible (lilies, sago palms, azaleas are common dangers)
• Secure doors that prevent door-dashing
• Safe sleeping area for your dog

Environment assessment:

• How many other dogs will be present?
• What's the noise level like?
• Is there a quiet space for your dog to decompress?
• Where will your dog sleep?

What to bring:

• Enough food for the stay plus 2 extra days (flights get delayed)
• Medications with clear written instructions
• Your dog's bed or a blanket that smells like home
• Familiar toys (but nothing they resource guard aggressively)
• Vaccination records (the sitter should require these)

Step 4: The Information Your Sitter Actually Needs

Verbal instructions get forgotten. Written instructions prevent disasters.

Create a care document that covers everything your sitter needs to know. This isn't paranoid—it's professional. Good sitters appreciate detailed guidance because it helps them provide better care.

Essential Information to Provide

Daily routine:

Topic	What to Include
Feeding	What food, how much, what time, any supplements or medications mixed in, feeding location, food allergies
Walks	How many per day, what times, how long, on-leash or off-leash areas, where they prefer to potty
Sleep	Where they sleep, bedtime routine, whether they're crated overnight, nighttime bathroom needs
Play	Favorite toys, games they enjoy, how much activity they need to settle

Behavioral information:

Topic	What to Include
Anxiety triggers	Thunderstorms, fireworks, strangers, other dogs, specific sounds
Reactivity	Leash reactivity, barrier frustration, resource guarding—and how you manage these
Commands	What commands they know and respond to; hand signals if used
Quirks	Things that seem strange but are normal for your dog ("he always barks twice before going outside")
Warning signs	How you know when they're stressed, uncomfortable, or about to react

Medical information:

Topic	What to Include
Medications	Exact name, dosage, timing, administration method, what happens if a dose is missed
Allergies	Food allergies, environmental allergies, known medication reactions
Health conditions	Ongoing conditions the sitter should monitor (joint issues, heart conditions, seizure history)
Veterinarian	Name, address, phone number, your account information
Emergency vet	Nearest 24/7 emergency clinic address and phone (in Chicago: MedVet, Chicago Veterinary Emergency Services)

Emergency authorization:

Provide written authorization for emergency veterinary care, including:

• A spending limit the sitter can authorize without reaching you
• Your secondary emergency contact (with their decision-making authority)
• Your vet's authorization to treat (call ahead to confirm this is on file)

Your contact information:

• Where you'll be and your time zone
• When you're reachable vs. when you'll be unavailable
• Who to contact if they can't reach you

Sample Care Sheet Structure

DOG CARE GUIDE FOR [DOG NAME]
Owner: [Your name] | Phone: [Your number]
Trip dates: [Start] to [End]

DAILY ROUTINE
- Morning: [walk time, length, feeding details]
- Midday: [any needed walks or check-ins]
- Evening: [walk time, feeding, bedtime routine]

FEEDING
- Food: [brand, type, dry/wet]
- Amount: [measurement per meal]
- Times: [specific times]
- Notes: [allergies, preferences, picky eating tips]

MEDICATIONS
- [Medication name]: [dose], [timing], [method]
  If missed: [what to do]

BEHAVIOR NOTES
- Triggers: [list what causes stress]
- Management: [how you handle triggers]
- Signs of stress: [what to watch for]
- Commands: [what they respond to]

VETERINARY INFORMATION
- Regular vet: [name, address, phone]
- Emergency vet: [name, address, phone]
- Authorization: [spending limit for emergencies]

EMERGENCY CONTACTS
1. [Your name]: [phone]
2. [Backup contact name]: [phone, relationship, authority level]

Step 5: The First Day and What to Expect

Before You Leave

On your departure day:

1. Do a final walkthrough with your sitter—point out supplies, demonstrate any tricky locks or alarm codes, answer last questions
2. Keep your goodbye brief. Dogs read your energy. If you're anxious and linger, you're telling your dog something's wrong. Quick handoff, confident tone, leave.
3. Give yourself buffer time. Don't schedule your departure so tightly that you're stressed during handoff—your dog will absorb that stress.

What Your Sitter Should Do

A good sitter will:

1. Follow your dog's cues on day one. Some dogs want immediate interaction; others need space to decompress.
2. Maintain your routine. Feeding at the same times, walks at the same times, sleep in the same place.
3. Send an update within the first few hours. You should know how the transition went before you get on your plane.
4. Watch for stress signals. Panting, pacing, whining, refusal to eat—and report these to you.

What Your Dog May Experience

Behavior	What It Means	When to Worry
Sniffing everything	Investigating the new person/situation; totally normal	Only if accompanied by constant panting or pacing
Following the sitter around	Seeking reassurance; normal first-day behavior	If it's frantic rather than curious
Decreased appetite	Mild stress suppresses hunger temporarily	If they refuse ALL food for 24+ hours
More sleep than usual	Adjusting is mentally tiring	Only if combined with lethargy, refusal to engage
Some whining or restlessness	Missing you; processing the change	If it escalates rather than decreases over 24-48 hours

Most dogs settle within 24-48 hours with a good sitter. By day two or three, they should be eating normally, engaging in walks, and showing their regular personality—even if they still seem to miss you.

How to Know If It's Working

Signs Everything Is Going Well

From your sitter's updates:

• Regular photos and messages as agreed
• Reports of normal eating, drinking, and bathroom habits
• Descriptions of walks, play, and settling periods
• Notes about your dog's personality (they're learning your dog)

From your dog's behavior (visible in photos/videos):

• Relaxed body language—soft eyes, loose posture
• Willingness to engage with the sitter
• Normal appetite and energy
• Comfortable in their sleep space

Signs Something May Be Off

Communication red flags:

• Radio silence for longer than agreed
• Vague updates ("everything's fine") without specifics
• Defensiveness when you ask questions
• Can't answer basic questions about what your dog did today

Behavioral red flags (if you can see or hear from updates):

• Persistent refusal to eat beyond 24-36 hours
• Constant pacing, panting, or vocalizing that doesn't resolve
• Avoidance of the sitter after initial adjustment period
• Any signs of injury or illness not promptly reported

If something seems wrong, trust your gut. A good sitter will welcome your questions and provide reassurance. A sitter who gets defensive about your concerns is showing you how they'll handle future problems.

After the Stay: What to Expect

Normal Post-Stay Behavior

When you return, expect:

• Excitement overload. Your dog missed you. They may be clingy, hyper, or overstimulated for a few hours.
• Tiredness. Adjusting to new situations is mentally exhausting. Don't be surprised if they sleep heavily.
• Some confusion. "Wait, you're back? Is my routine changing again?" They'll resettle quickly.

Concerning Post-Stay Behavior

Watch for signs that the stay was stressful:

Sign	What It May Mean	Action
Exhaustion lasting 2+ days	Stay was more stressful than enriching	Consider different care next time
Digestive upset	Stress-induced; diet change; possible illness exposure	Monitor; vet visit if persists
Behavior regression	House training accidents, increased anxiety, new fears	The stay environment wasn't right for your dog
Avoidance of reminders	Won't go near their leash, crate, or areas associated with the sitter	Something negative happened; investigate

If your dog seems "off" for more than 48 hours after returning, the stay likely caused stress—even if reports were positive. Some dogs tolerate care without thriving in it, and the recovery period tells the true story.

Building a Long-Term Relationship

Once you find a sitter who works for your dog, invest in that relationship.

The Value of Consistency

For your dog:

• Builds genuine trust over multiple stays
• Knows what to expect when the sitter arrives
• Adjustment period shortens with each booking

For you:

• Sitter learns your dog's quirks and needs
• Less preparation required for repeat bookings
• Peace of mind from proven success

For the sitter:

• Knows your dog intimately
• Can notice changes in behavior or health
• Invested in your dog's wellbeing, not just the paycheck

How to Maintain the Relationship

• Book early for holidays and peak times. Good sitters fill up weeks in advance.
• Communicate between bookings. A quick update when your dog has vet visits, behavioral changes, or medication adjustments keeps your sitter informed.
• Tip appropriately. 15-20% for regular stays; holiday bonus equivalent to one stay's fee is standard for regular sitters.
• Leave honest reviews. Helps the sitter build their business; helps other dog owners find them.

When to Find Someone New

Sometimes the fit isn't right, and that's okay:

• Your dog never warms up despite multiple stays
• Communication breaks down despite addressing it
• Your dog returns consistently stressed or exhausted
• Your needs change (new medical requirements, different schedule)

End professionally: "This isn't the right fit for us, but I appreciate your time." Then find someone whose skills match what your dog now needs.

The Tails Difference for First-Timers

Starting with a dog sitter is easier when someone has your back.

What makes Tails different:

Feature	How It Helps
Verified sitters	Background checks, interviews, insurance verification—done before you see a profile
Matched to your dog	Not random availability; sitters selected based on your dog's specific needs
Free meet-and-greets	Built into every booking; non-negotiable first step
In-app communication	Everything documented; easy to reference during and after the stay
Photo updates	See your dog every day; know they're thriving, not just surviving
Support if issues arise	We help resolve problems; rematch if needed

The discomfort you feel right now—trusting your dog to someone new—is exactly what good preparation addresses. With the right sitter and the right system, that discomfort fades into routine relief.

Get Started with Tails

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Frequently Asked Questions

How do I know if my dog is happy with their sitter? Dogs communicate through behavior, not words. Positive signs: relaxed body language in photos (soft eyes, loose posture, wagging tail), normal eating and drinking, willingness to engage with the sitter, settled sleeping. During the meet-and-greet: approaching the sitter voluntarily, relaxing over the visit, showing curiosity rather than avoidance. After the stay: normal energy, no prolonged exhaustion or clinginess, willingness to see the sitter again. Trust what you observe in photos and videos, and trust your dog's post-stay behavior—it tells you more than any report.

What if my dog has separation anxiety? Dogs with separation anxiety often do better with sitting than boarding because the home environment and individual attention reduce overall stress. But preparation matters more: do a longer meet-and-greet, consider a trial overnight, ensure the sitter understands anxiety management (not forcing interaction, providing safe spaces, maintaining strict routine). Discuss calming aids like Adaptil diffusers or Thundershirts with your vet before the stay. For severe anxiety, your vet may recommend situational medication. The key is matching with a sitter experienced in anxiety—someone who recognizes stress signals and knows how to respond.

How often should I get updates? Establish this before the stay based on your preferences and the sitter's communication style. Most pet parents want daily updates with photos—one morning check-in and one evening summary works well. For the first stay, more frequent updates provide peace of mind while you build trust. For longer stays with an established sitter, you may be comfortable with less. What matters: the sitter should proactively report notable events (soft stool, decreased appetite, anything unusual) regardless of your agreed schedule. "No news is good news" is not acceptable—you should know how your dog is doing, not just that nothing went wrong.

What should I do if I'm worried something is wrong during the stay? Trust your instincts, but gather information before panicking. Ask direct questions: "I noticed [concern] in the photo—can you tell me more about how [dog] is doing?" A good sitter will respond with specific observations, not defensiveness. If you're genuinely concerned about your dog's safety or health, you have every right to ask for a video call or additional photos. If the sitter is unresponsive or dismissive, that's valuable information about their reliability. For genuine emergencies (illness, injury, concerning symptoms), your sitter should be acting immediately—and you should have backup contacts and emergency protocols already in place.

Should I do a trial stay before my actual trip? Yes, especially for first-time sitting or dogs who are anxious, reactive, or have medical needs. A trial stay (one overnight or even a few hours of drop-in care) reveals how your dog actually adjusts—information you cannot get from a 30-minute meet-and-greet. It also tests the sitter's communication and reliability. If the trial goes well, you book your real trip with confidence. If problems emerge, you've learned this while you can still find alternatives—not while you're boarding a plane. The cost of one trial stay is minimal compared to the cost of a failed stay during an important trip.

How far in advance should I book? For regular dates, 1-2 weeks ahead usually works. For holidays and peak travel seasons (Thanksgiving, Christmas, summer vacation), book 3-4 weeks in advance—quality sitters fill up fast, and last-minute searches force you to compromise on fit. If you find a sitter you love, ask about recurring bookings to secure your preferred dates before they're gone. Building a relationship with a regular sitter means you get priority booking—another reason to find someone great and stick with them.

What if the sitter needs to cancel? This is why you should ask about backup plans during your vetting process. Professional sitters have named backups who can step in for emergencies—and you should have that backup's contact information before your stay begins. On Tails, if your sitter has an emergency, we coordinate replacement care so you're not stranded. For independent sitters, ask specifically: "What happens if you get sick or have a family emergency?" Vague answers mean no plan exists, and you'll be scrambling if something goes wrong.

Can my dog sitter handle medical needs? Depends on the sitter's experience. On Tails, you can filter for sitters experienced with specific medical needs—insulin injections, subcutaneous fluids, seizure management, prescription medications. During your meet-and-greet, have them demonstrate medication administration and discuss your dog's specific protocols. Ask what they would do if they noticed concerning symptoms. A sitter who's confident with medical care will have specific answers; one who's winging it will be vague. For complex medical needs, choose experience over convenience—your dog's health depends on competent care.