When you meet a potential pet sitter, it is natural to arrive with your own list of questions.
Are they insured? How will visits be documented? Who provides care if the regular sitter becomes unavailable? How much experience do they have with dogs, cats, or pets with medical needs?
Those are all important. But the questions coming from the sitter can tell you just as much.
A professional pet sitter should be curious about more than feeding times and where you keep the leash. They should want to understand what a normal day looks like for your pet, how they communicate, what makes them nervous, and what would signal that something is not quite right.
Great care starts with good information. Here are the questions a thoughtful pet sitter should be asking before you leave home.
What Does Your Pet’s Normal Routine Look Like?
A sitter should begin by learning how your pet’s day usually works.
What time do they eat? When do they normally go outside? When are they most playful? Do they disappear for an afternoon nap and reappear precisely three minutes before dinner?
Routine provides valuable context. It also gives the sitter a baseline for recognizing changes.
For a dog, this might include:
- Typical walk times
- Usual bathroom habits
- Normal energy level
- Feeding and treat routines
- Where they rest after a walk
For a cat, it may include:
- Meal times and portion sizes
- Favorite hiding or sleeping spots
- Normal litter box habits
- Preferred types of attention
- Times when they are usually active
Small animals may have their own detailed routines involving fresh food, enclosure care, temperature, or handling preferences.
The more closely care follows the pet’s normal rhythm, the easier it is for them to feel comfortable while their person is away.
What Does Normal Behavior Look Like for Your Pet?
“Normal” looks different for every animal.
One cat may greet every visitor at the door. Another may spend the entire visit under the bed and consider that a perfectly successful social interaction. One dog may bounce around the moment the leash appears, while another waits quietly by the door.
A sitter should ask what they can reasonably expect.
This helps prevent harmless personality traits from being mistaken for problems. More importantly, it helps the sitter recognize when a behavior truly is unusual.
Questions might include:
- Is your pet usually social or reserved?
- Do they normally finish every meal?
- Where do they tend to hide?
- How vocal are they?
- What does their usual bathroom behavior look like?
- Do they sleep through most visits or stay close to the caregiver?
A sitter who knows your pet’s baseline is better prepared to notice subtle changes in appetite, movement, mood, or behavior.
Are There Any Fears, Triggers, or Handling Preferences?
A good pet sitter should never assume that friendliness in one situation means comfort in every situation.
Some pets dislike being picked up. Others are sensitive around their paws, ears, food bowls, or medication. A dog may react to skateboards, buses, unfamiliar dogs, or sudden construction noise. A cat may become nervous during storms or when neighborhood sounds drift through an open window.
Chicago adds its own collection of possible surprises. A quiet walking route can suddenly fill with street festival activity. A Cubs home game can change the feel of Wrigleyville for hours. Fireworks may begin well before July 4th and continue well after everyone agrees they should have stopped.
A sitter should ask:
- What tends to frighten or overwhelm your pet?
- How do they show discomfort?
- What usually helps them feel calmer?
- Are there situations, routes, people, or animals they should avoid?
- How do they prefer to be approached or handled?
For shy or sensitive pets, a respectful approach matters enormously. Our article Why Familiar Caregivers Matter for Anxious or Shy Pets explores how consistency and patient relationship building can make everyday care feel safer.
How Does Your Pet Interact With Other Animals and People?
Your sitter should understand how your pet handles the world outside the home.
Does your dog enjoy passing other dogs, or do they need extra space? Are they comfortable with children? Do they pull toward squirrels, pigeons, or rabbits? Is there a particular dog on the block whose appearance turns an ordinary walk into neighborhood theater?
The goal is not to label a pet as “good” or “bad.” It is to give the sitter enough information to make thoughtful decisions.
For cats in multi-pet homes, the sitter should also understand the relationships within the household. Who eats together? Who steals food? Does one cat block another from a litter box? Which pets play comfortably, and which prefer separate spaces?
Our guide to How to Keep the Peace in a Multi-Cat Household covers why these details matter when several cats share one home.
What Are the Exact Feeding Instructions?
“Feed them dinner” leaves quite a bit open to interpretation.
A professional sitter should ask for specific instructions, including:
- Food type and brand
- Portion amounts
- Meal times
- Treat limits
- Supplements
- Food allergies or sensitivities
- Whether pets must eat separately
- What to do if a meal is refused
If one cat receives a prescription food while another is committed to stealing it, that matters. If a dog needs a slow feeder, water added to kibble, or medication hidden in a very specific amount of cheese, that matters too.
The sitter should also know what is normal. A pet skipping one meal may be unusual for one animal and fairly common for another.
Clear instructions help the sitter maintain routine and respond appropriately if something changes.
Does Your Pet Take Medication or Have Medical Needs?
Medication questions should be detailed and direct.
A sitter should ask:
- What medication is given?
- What is the correct dose?
- When and how should it be administered?
- Does it need to be given with food?
- What happens if the pet refuses it?
- Are there side effects or changes the sitter should watch for?
- Who should be contacted with questions?
The same applies to ongoing health concerns, mobility limitations, recent procedures, or age-related changes.
A pet sitter is not a substitute for veterinary care, but they should understand the care plan, follow it accurately, and recognize when veterinary guidance may be needed.
For pets with medical needs, it is especially important to choose a professional who is comfortable with the required routine and honest about their experience.
What Should Happen in an Emergency?
No one expects an emergency, but every care plan should include one.
A sitter should ask for:
- Your preferred veterinary clinic
- The nearest emergency veterinary hospital
- Authorization for emergency care
- A local emergency contact
- The best way to reach you
- Any financial or treatment preferences that should be documented
- The location of carriers, leashes, and medical records
The local contact is especially important when you are traveling. They may be able to assist if a key stops working, a building issue occurs, or the sitter needs support reaching a veterinarian.
Good emergency planning is not alarmist. It simply removes guesswork in situations when clear decisions matter.
How Should We Enter and Secure Your Home?
Home access deserves more attention than “the key is under the mat.”
Chicago homes come with all kinds of entry routines. There may be lockboxes, front desks, call boxes, shared gates, side entrances, alarm systems, or doors that require a very particular combination of patience and shoulder pressure.
A sitter should confirm:
- Where keys or access devices are located
- Which entrance should be used
- How alarms work
- Whether doors lock automatically
- Which windows or doors must remain closed
- Whether anyone else will enter the home
- What to do if access fails
They should also ask about household safety concerns. Are there rooms pets should not enter? Does a cat rush the door? Is there a loose screen, unreliable gate, or closet that must stay closed?
Clear access instructions help visits begin smoothly and end with the home properly secured.
Where Are the Supplies We May Need?
Food and leashes are only the beginning.
A well-prepared sitter should know where to find:
- Litter and waste bags
- Cleaning products
- Towels
- Medications
- Extra food
- Carriers
- Harnesses and walking equipment
- Paper towels
- Enclosure supplies for small animals
- Flashlights and basic household emergency items
This is especially useful when something unexpected happens. A water bowl gets knocked over. A cat produces a hairball worthy of its own ZIP code. A dog returns from a rainy walk looking like they personally discovered mud.
Your sitter should not have to search the entire home while trying to care for your pet.
What Kind of Updates Would Be Helpful?
Communication preferences vary.
Some pet parents love detailed visit notes and several photos. Others want a concise confirmation that everyone ate, used the bathroom, and remains in good spirits.
A sitter should ask what information helps you feel connected and reassured while you are away.
At a minimum, updates should confirm that the visit happened and mention anything notable about behavior, meals, medication, bathroom habits, or the home.
At Chicago Pet Sitters, care updates and instructions are managed through Time To Pet. Keeping feeding, medication, access, and behavior details current in the portal helps caregivers work from the latest information. Printed notes left inside the home may not be seen until after the sitter has already arrived, and they can create confusion if they conflict with the existing care plan.
If you are preparing for cat sitting, How to Prepare Your Cat for Vacation Pet Sitting includes a more detailed checklist for organizing instructions and supplies before a trip.
Who Will Be Providing the Care?
The questions should not flow in only one direction. The sitter or service should also explain how care is assigned.
Will your pet see the same caregiver regularly? Is there a small team? What happens if the assigned sitter becomes unavailable? How are backup caregivers introduced to the pet’s instructions?
Familiarity can be especially important for pets who need time to trust new people. At the same time, professional backup systems help ensure that care continues when illness, emergencies, or schedule changes occur.
The best arrangement combines personal relationships with reliable support.
That same principle applies to dog walking. In What Makes a Great Dog Walker?, we discuss why consistency, communication, judgment, and company support all matter when choosing ongoing care.
Good Pet Sitters Ask Because the Details Matter
A professional pet sitter should be curious.
They should want to know why your cat eats in one room but not another, which block your dog refuses to walk down, how your rabbit prefers their greens arranged, and what “normal” looks like in your home.
These questions are not excessive. They are evidence that the sitter understands how personal pet care really is.
Anyone can refill a bowl. Thoughtful care requires listening, documenting, observing, and adjusting to the pet in front of you.
When you are choosing a pet sitter, pay attention not only to how they answer your questions, but to what they ask in return. The right questions show that they are preparing to care for your pet as an individual, not simply complete a list of tasks.
Chicago Pet Sitters provides professional in-home care built around clear communication, familiar caregivers, and the routines that help pets feel most comfortable. If you are looking for reliable pet sitting in Chicago, a thoughtful consultation is a good place to begin.
