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How do I evaluate a Sitter or Dog Walker

Updated 6/10/2025
Winniepaws Team

How do I know if the Pet Sitter is right for my pet? Start looking in plenty of time. The best Pet Sitters and Dog Walkers can get booked up quickly, esp

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Winnie Paws Before Booking

How do I know if the Pet Sitter is right for my pet?

Start looking in plenty of time.

The best Pet Sitters and Dog Walkers can get booked up quickly, especially during the holiday seasons. Start your search early to be fully aware of your options. Winnie Paws is a good place to look for Pet Sitters in your area. You can check how they meet your needs well in advance.

We recommend contacting two to three sitters or dog walkers when beginning your search. That way you'll have lots of options when you're ready to book your first service.

It takes time to find the right sitter, and a planned approach benefits everyone involved - especially your pet. Rushing the process can often lead to stress and increase the risk of either you, your pet or both of you having a poor experience.

If you're requesting care for multiple pets, then each of your pets must have a completed profile and be added to the booking. Learn how to add a pet profile to your account. [LINK] to correct page needed


Research Sitter Profiles

Take the time to carefully review sitter profiles. Look for:

  • Experience with dogs (or cats) of a similar size, breed and temperament to your own dog (or cat).
  • The type of service offered (overnight boarding, extended stays, daycare etc.).
  • The sitters availability during your travel dates.
  • Reviews from other pet owners who have used this sitter for their pets.
  • Photos of their home environment to ensure it's safe and suitable for your furry family member.

The Winnie Paws Guarantee offers coverage for all services booked and paid for through the Winnie Paws website or app. This gives you peace of mind for anything unexpected.

When you find a suitable sitter you like, you can send them an enquiry for more information. Arranging a Meet and Greet at this stage is a good idea.


Winnie Paws Before Booking - trial stay

Arrange to have a Meet & Greet

Once you contact a sitter or dog walker, make sure you arrange a Meet & Greet with them. This allows you to get to know them in person and make sure they're the right fit for you and your dog. Since your pet will be staying in their home, visiting it is essential to ensure it's a good fit. This is also a necessary step to activate the Winnie Paws's Guarantee. During the Meet & Greet:

  • Observe how the sitter interacts with your dog and other pets in the home.
  • Discuss your pet's routine, dietary needs, and special requirements.
  • Check that their home is clean, secure, and pet-friendly.
  • Ask about their experience with dog behaviour, training, and emergencies.
  • Ensure they understand dog safety protocols and have an emergency plan in place.
  • If your dog has anxieties, such as fear of children or crowds, inform the sitter so they can avoid stressful situations.

For your convenience we have made a
Meet & Greet Checklist, which you can download here.
(Opens in a new tab)

Pet Handover forms, which you can download here.
(Opens in a new tab)

We should also make available "Pet Handover Forms" filled out by the owner for the sitters information for every booking. Whether they actually use or fill out any forms isn't our biz but I think it'd be good to include them for download. Makes us look even more helpful..


Compare Home Boarding Facilities

Since Winnie Paws pet sitters offer boarding in their own homes, evaluating their setup is crucial. What is wonderful for one pet may be completely unsuitable for another. Consider factors such as:

  • How many pets are being boarded at the same time for the space available.
  • If other animals are present, do they get along with your pet? - and your pet with them?
  • The level of supervision and interaction provided by the pet sitter.
  • The safety and cleanliness of the home and yard environment.
  • Availability of comfortable, secure sleeping spaces and quiet areas for rest.
  • Access to fresh water and a well-maintained yard or play area.
  • Secure fencing and gates, especially for jumpy, "escape artist" dogs.

After a successful Meet & Greet, either you or the sitter can select "Book Now" [LINK] to chat page. from your conversation on Winnie Paws. Once both you and the service provider have confirmed the booking, the service is booked.


Winnie Paws Before Booking - trial stay

Do a Trial Stay

If at all possible, arrange a short trial stay before your trip. You could initially try a stay for an afternoon, then an overnight perhaps. This helps your dog get to know the sitter and the new place. It makes things easier when you leave for your holiday. A trial stay can also highlight any potential issues, such as separation anxiety.

Having a trial helps you see if your dog can settle. If there are any issues, you can fix the problem while you are still close by. This way, you won't have to deal with it from far away during your trip.

To protect your privacy, we don't display your personal contact information until a service is booked. However, if you request your sitter to pick up and drop off your pet at the beginning and end of a stay, then your home address will be viewable to the sitter in your pending request.

All services must be paid for through Winnie Paws. This is outlined in our Terms of Service. Booking on Winnie Paws also gives you the Winnie Paws Guarantee and an easy, secure and convenient way to pay.


Book Your Sitter Through Winnie Paws and Get Your Booking ID

Once your booking is confirmed and you have your booking ID and the booking commences, Winnie Paws's Guarantee Coverage starts - to give you peace of mind.


Winnie Paws Before Booking - trial stay

Provide Detailed Care Instructions to your Pet Sitter

Once you've chosen and booked your sitter, ensure they have all the information they need to care for your dog properly. Use Winnie Paws's Pet Handover forms as a guide. Provide details on:

  • Your dog's daily routine, feeding schedule and exercise needs.
  • Any medical conditions, medications, and emergency vet contact information.
  • Any behavioural quirks or anxieties.
  • Important items not to forget, such as their blanket or bed, favourite toys and food.
  • Specific instructions for dog safety, such as leash rules or dietary restrictions.

Ensure a stress free drop-off of your pet

When it's time to leave for your holiday, keep the drop-off calm and low-key. Avoid making a big fuss, as this can increase your pet's anxiety. Trust the sitter's experience in creating a welcoming environment.

Your sitter may also offer an add-on service for pick-up and drop-off. You can refine your search using Winnie Paws's 'Advanced Filters' to find sitters who provide this service.


Keep in Touch

A great pet sitter will keep you updated with messages and photos throughout your trip. This reassurance lets you enjoy your holiday knowing your dog is happy and well cared for. Make sure to share how often you want to be contacted. Do you want regular updates or just occasional check-ins?


Winnie Paws Before Booking - keep in touch

Leave a Review for the sitter

Once your booking is completed and your pet is safely back home, leave a review to help future pet owners make informed decisions. Your feedback also supports great sitters and helps them improve their services.

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