House Sitting – The Arrangements

B&W drawing of a castle

Hello and Goodbye!

It seems to us that the key to house sitting successfully is working well with homeowners. It’s funny, though, we don’t spend much time with the owners, of course, as they’re gone.

A few emails, usually a phone conversation, maybe FaceTime or Skype and, where possible an hour or so on a home visit. There is usually some time together when we arrive, and then they leave. 

Here are some of the things we’ve learned about working with owners and setting up good house sitting arrangements. We hope it will be helpful to others.  

B&W drawing of an old church

Listings and More Listings 

Most homeowners post listings a month or two before their travel dates. Others plan way in advance, up to a year. There are also those that post only a few days in advance. We’re learning to flow with it and keep things open enough to accommodate a variety of opportunities.

Some house sitters leave things open so they can respond quickly to appealing listings – like for this weekend. Others book a full year in advance.

We tend to fall more into the second group. However, there are times when a last-minute stay works just right for us too, filling a gap between other stays. There’s something for everyone. That’s the best part of the websites: great variety.

B&W drawing of a small ocean town

There are pros and cons to early scheduling. On the positive side, it makes travel planning easier and reduces the urgency in looking for and securing houses. However, it’s a challenge scheduling around firm dates months in the future as our calendar is not wide open.

Also, a perfect opportunity might get posted, but we’re usually already committed and have to pass on it as we do not want to back out of agreements we’ve made. 

That means that we are always looking for new house sits and in various stages of conversation with at least a couple of homeowners. We keep logs for all of them: it’s who, what, where and when as well as what’s next in the process. It helps keep things straight.

What happens from then on, and what we do to arrange a house sit, depends on many factors. 

B&W drawing of a stately castle

Responding to New Listings 

Early on we simply needed to book house sits close to my work, period. The challenge was convincing homeowners we could help them out. With postings for homeowners we’ve never met, we all have to go through the sandbox portal.

What’s that? That’s finding out if we want to play in the sandbox with each other: references, profiles, and the details of their needs. Getting that question answered happens in many ways and typically it happens quickly.

The next step is can we play in the sandbox: for that, practical elements take over. For repeat house sits and referrals, we know we want to play together, and all we need to do is check our calendar for open dates.

B&W drawing of an old town

Some homeowners like to have a phone conversation right away; some are comfortable with an email thread and then personal contact. Others like to have a Skype or FaceTime conversation right away, especially if we won’t be able to visit.

It seems to depend on how comfortable the owner is with house sitting. If they have done it before, it’s easier for them; they don’t have anxiety about the process and don’t need a lot of conversation. Homeowners who are new to house sitting may require more time and contact to make a decision. 

B&W drawing of an Asian building

Items to Cover in Conversations

Contracts, Deposits, Utilities – Initially, these came up a few times for us one way or another. We’ve now completed over 70 house sits and only had a handful of homeowners ask for a signed contract. We have only been asked once for a deposit and payment of some utilities (same homeowner).

Most homeowners mention in their listing if they are asking for a deposit or some utility payments, but it’s good to check. No one wants that kind of surprise at the last minute. Each house sitter needs to decide what they are and are not willing to do to get a house sit. 

B&W drawing of an old English manor house

The Hand-Offs – Homeowners may ask you to arrive a couple of hours early or even a day or two early. They may invite you for a meal, and they may or may not have flexibility about their exact departure and return time. Some homeowners are specific about their requirements, others less so.

We’ve found it incredibly important to confirm repeatedly the exact starting and ending dates and times in writing, and how the handoffs will work at both ends of the stay. We’ve been surprised a few times and have learned this is a must.

Whenever people are planning trips, there is a lot to do before leaving and sometimes even obvious things can fall through the cracks. This part should be explicit.

B&W drawing of an old English manor house

Interviews and Home Visits

Home visits are crucial to us, and worth the time and cost involved. It’s the absolute best way to help homeowners decide if they can trust us, and for us, to see if we want to do the house sit. Not every match is made in heaven and sometimes you don’t know until you have real face-time with each other.

Within five minutes we usually know if it’s a match. Jim looks at me, and the reality is right there on my face: very intuitive, very decisive. A couple of times our visits included a walk with the dog and even a visit to the local dog park. When dogs come with a house sit, there is no better way to see what you’re getting yourself into.

B&W drawing of an old English house

During the interviews, we are our most polite selves, ask lots of questions, notice all we can, and show interest in the pets. We do not do it for show or sales purposes, though it might help make our case. The questions we ask will help us do the house sit. We’re pretty practical people that way.

We ask a lot of questions about the pets either through email or during our visit: their daily routine, habits, personality, we certainly ask about their ages, health condition, and medications. We also like to know how the pets came to be with the host family.

Many that we’ve met are rescue animals, a few came from breeders, others found on the streets, abandoned. But whatever the source, they have this in common: they are loved by their owners.

B&W drawing of an old harbor

Reaching a Decision

In the beginning, most of our house sits resulted from home visits. During the second and third years, we haven’t been able to do as many home visits since we move around quite a bit. At this point, we get quite a few house sits as a result of a referral from other homeowners. Most have been agreed to after phone or Skype conversations. We’ve also had a few owners choose us simply from reading our profile on a house-sitting website.

Of course, it is a mutual decision and sometimes what looks good on paper – well, you know. No one wants creeps in their house or careless folks in charge of their pets. And, we don’t want to be stuck in some strange place with sick or hostile animals or a dirty house in general disrepair.

B&W drawing of an old house

The profile, photos, and references on the house-sitting websites play a big part in the decision-making process for the homeowner. You might resemble a relative of theirs and get the job (that happened to us), or you might look like a relative and no way you’ll get it. 

When it comes down to it, it seems it’s a matter of personal connection (it’s there, or it isn’t) trust on both sides and timing. The formalities of any screening process will never trump a decision made from the gut.

B&W drawing of a castle far off in the distance

Communication During our Stay

We learned quickly if you want to be good house sitters you need to communicate with the owners regularly, intelligently and often.

For the most part, homeowners have at least some anxiety about leaving their pets and want to know how they are doing. That includes finding out if their pets are pulling the wool over the eyes of the substitute teachers, wandering around the neighborhood and eating all the canned pet food the first day!

We ask right away what form of communication the hosts prefer; calls, texts or emails, and would they prefer daily, weekly, or only if the house burns down! We usually send one or two messages during the first 24 hours and then follow their preference.

B&W drawing of a house and lake

So far, working with homeowners has gone well for us. We enjoy meeting them, taking care of their homes and pets and thereby helping them enjoy their trips all the more. Whether from care or luck, doesn’t matter to us, but everyone we’ve dealt with has been honest, fair and accommodating.

Maybe the whole house sitting world is that way! We hope so.

What’s Next Three short house sits 

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