What are good questions to ask before agreeing to a sit?

[EmilyDickinson]

What is a good question to ask before agreeing to a sit?

One question we have started asking homeowners is:

‘What have you been unhappy about with previous sitters?’

Or, slightly softer:

‘What is something that did not work well for you in a previous sit?’

We have asked this a couple of times now, and both times the answer was really useful.

In both cases, it was about sitters not reporting something quickly enough. One time it was a strange sound in the swimming pool system. Another time it was something with a hot water tank on the roof. In both situations, the homeowner was worried that if something is not reported immediately, the repair can become much more expensive.

I found that very helpful to hear. We have been homeowners ourselves, so I understand very well that you want to know quickly if something is wrong. A leak, a strange noise, a machine that stops working, those things matter.

It also made me wonder why some sitters might not report things straight away. Maybe they are afraid they will be blamed or charged. I don’t know. Of course, if you do something careless yourself, that is different. But if something simply stops working, I think it is much better to say it immediately.

For us, this kind of question helps us understand whether we are a good match. It opens up a more honest conversation. We like homeowners to tell us what matters to them, what they worry about, and what they really need from sitters.

The same goes the other way around. As sitters, we also have things that are important to us. For example, we don’t accept sits where we cannot see clear photos of the home. For us, that is a no-go. If someone does not want to share them, that is fine, but then it is not the right match for us.

I’m curious how others approach this. Do you ask homeowners or sitters what they have been unhappy about in the past? And has that helped you decide whether a sit was a good match?

P.s. Photo is from ‘our’ doggies watching the Fiji sunset together. Looking now like angels and they can also be energetically in a power struggle for our attention

[Globetrotter]

As a sitter of eleven years and lots of great reviews, I don’t really ask any direct questions nor have I been asked many. I don’t want to feel like I’m conducting a job interview. I approach the homeowner in a very friendly and casual manner. I like to get a feel more for their personality and can usually tell if they are a rigid or easygoing person in a phone call. I worked in an industry where I interviewed people so I tend to “go with my gut”. I’m also a very easygoing person who tends to “go with the flow” on a sit. I won’t apply on sits where I see unmade beds or clutter in a listing as I’m an orderly person. It’s worked great for me so far.

[Cathie]

I think that’s a great question. I might steal it. I am very picky about what I apply for, even though I am heavily influenced by certain pets (looking at you Labradors). I always scan photos carefully and read all the details including past sitter reviews. I have learnt so much from being on the forum and was absolutely naive to all the things that could go wrong when I was fresh. So much better informed now. I am never desperate for a sit, it’s just bonus for me so that helps. Strangely all our hosts have been a similar age bracket to us, but I have been smartly declined by a couple of younger ones. Oh well I won’t hold it against them .

[WeRPAWsome]

Hi @EmilyDickinson

I think that’s a very good question because it encourages an honest conversation rather than putting either side on the defensive.

Over many years and hundreds of sits, we’ve found that the best discussions are the ones where both sides talk openly about what matters most to them. We don’t have a fixed list of questions, but there are a few things we always like to understand:

• Is there anything that surprised previous sitters?
• Is there anything you wish every sitter knew before arriving?
• What isn’t in the Welcome Guide that you’d nonetheless like us to know before we arrive?
• Is there anything that’s perfectly normal in your home that we might otherwise mistake for a problem? For example, a noisy appliance, a gate that sticks, or a pet with an unusual habit.
• If something in the house isn’t working quite right, how would you like us to handle it?
• If one of your pets became ill or had an emergency, how would you like us to handle that? For example, should we contact the vet first if it’s urgent, or contact you first?
• What’s the one thing that would make you come home and think, “That was a perfect sit”?

Those conversations often tell us far more than a checklist ever could. Like you, we’d always report anything unusual straight away, whether it’s a strange noise, a leak, or an appliance that suddenly stops working. Likewise, it’s reassuring to know in advance how homeowners would like us to deal with a pet emergency, rather than having to make assumptions in the moment.

We also think it’s just as important for homeowners to ask sitters questions. Those conversations often determine whether it’s a good match for everyone.

Like you, clear photos of the home are important to us. They help set realistic expectations and usually reflect the openness and transparency of the homeowner.

[Felinelover]

As a HO, I really like the ‘softer’ version of the question as the other version would make me feel like I’m talking badly about specific sitter(s) behind their backs, and that’s not my style personally. But a general ‘what didn’t work well in the past’ is a bit more general and leaves out the ‘with Sitters’ part. I’d be more open to sharing a couple of pet peeves that way.

Also as a HO I really like questions from sitters. I’m often surprised at some sitters that really don’t ask much on the video chat. I’m also starting to piece together that the sitters I’ve like best have asked some good questions during the video chat.

One reason I’ve started sharing my welcome guide with sitters ahead of the video chat and well before we confirm: those sitters that are shy with the questions can read and then decide if it’s a good match for them. I’ve had sitters back out for quirky reasons (one didn’t like that they could t use our community pool, but the HOA rules don’t allow guests unaccompanied by owners. I don’t list a pool as an amenity, or show a photo of it. It was in the welcome guide because when they get here they would see the community pool; another didn’t want to wake up early - I’ve since added my dogs 6:30 am wakeup time to the listing itself; a third was afraid of coyotes that are endemic in this area).

So, I applaud your question about questions and would really encourage sitters to ask these thoughtful types of questions upfront. It also (I would imagine) give you a better sense of who the HO is, and there style of hosting (hands-off? hospitality-minded? easily flustered/annoyed with questions? Etc).

[PV592]

I ask them to expand on what they stated on their post. Example: they stated the dog takes meds. So I ask, “what meds to they take and when?”

[EmilyDickinson]

@Cathie Hi Cathie,

That might actually be an interesting topic for a separate discussion.

Do homeowners tend to prefer sitters who are roughly in the same age bracket? And does the opposite happen too, with sitters feeling more comfortable with homeowners of a similar age?

Sometimes I get the same impression as you, although I’m not sure it’s actually true. It could also simply be that experience changes how you choose. People who are newer, and often younger, may be more willing to accept almost any sit because they’re excited to get one. Those with more experience may become more selective because they know what works well for them and what doesn’t.

I’m genuinely curious whether there’s any real pattern, or whether it’s just something our brains notice because it stands out.

[EmilyDickinson]

Hi @PV592,

That’s a great suggestion, thank you.

We do have quite a bit of experience giving medication, but there’s a huge difference between different types of medication and, just as importantly, how comfortable the pet is with receiving it.

For example, giving a tablet hidden in a tasty treat is usually very straightforward. But other treatments can be much more challenging. We’ve cared for a dog that needed medicated baths twice a week. One dog might happily enjoy a warm shower, while another finds the whole experience very stressful, no matter how calmly and patiently you approach it.

Another thing that makes a difference is whether it’s medication the pet is already used to, or something new. If it’s a new treatment, the pet is not only adjusting to a new sitter, but also to a new routine or an unpleasant experience. That can require extra time, patience and trust.

So I really like your suggestion to ask what medication it is and how it’s normally given. It gives a much better idea of what’s actually involved.

Thanks for the suggestion and for sharing your experience!

[EmilyDickinson]

@Globetrotter

I really like that approach too. A conversation often tells you much more than a list of questions ever could. You quickly get a feel for whether someone is easygoing or more rigid, and I can imagine that your years of interviewing people have made you very good at picking up those signals.

At the same time, I also find it interesting to be aware of cultural differences. I’m Dutch, but I also have a Swedish background, and your answer reminded me of that. Generally speaking, asking direct questions is very normal in the Netherlands, whereas the Swedish approach is often closer to yours, getting to know each other first and letting the conversation unfold naturally. Of course, these are just general tendencies, not fixed rules.

Growing up with both cultures has probably made me a bit more aware of different communication styles. That doesn’t mean I always get it right. I still make the occasional wrong judgement, just like everyone else.

In the end, I think my biggest criterion is simply enjoying being around people who accept that none of us is perfect. You could call that being flexible, or perhaps just not being too rigid.

[EmilyDickinson]

@Felinelover

Thank you for your thoughtful reply. I really appreciate that you don’t want to feel as though you’re talking about previous sitters behind their backs. I think that’s a very respectful attitude, and I can completely understand why you prefer the softer wording.

At the same time, I really appreciated the examples you shared. They don’t criticise anyone, but they do help other homeowners and sitters think about things they may never have considered before.

That’s one of the things I enjoy most about this community. We all come from different countries, cultures and backgrounds, so we notice different things and learn from one another. I also found your preference for the softer approach interesting. It made me think about how the wording of a question can change the whole tone of a conversation.

One thing your post made me wonder: have you noticed whether sitters who ask thoughtful questions beforehand also tend to communicate more during the sit? I’d be curious to know if you’ve seen that pattern.

Thanks again for your contribution. Your post also made me think of another possible topic: things we’ve learned over the years from house sitting and pet sitting. Maybe that topic already exists somewhere, but I think it could be a really useful one.

[EmilyDickinson]

@WeRPAWsome

Thank you for taking the time to write such a thoughtful reply. I can see why your approach works well after so many sits.

I have to admit I smiled a little when I read the list. I recognise several of those questions because I asked ChatGPT to help me think of possible questions. It’s a great brainstorming partner, but I’m curious how it works in real life.

Do you actually ask all of these questions during a video call?

For me, that would feel a little overwhelming. I usually rely much more on my gut feeling, the conversation itself, the listing, the reviews and the available Welcome Guide. Often, after talking for half an hour, all people already have a pretty good sense of whether we’re a good match.

Some of your questions, like asking what a ‘perfect sit’ looks like, are interesting, but for me they would start to feel a bit like a job interview. Of course, if that approach works well for you, that’s great. We all have different communication styles, and that’s one of the things I enjoy about this community. Maybe you have a friendly tone of voice

I’m genuinely curious how you use your list in practice. Do you ask every question, or is it more of a checklist in your own mind that you only use when the conversation naturally leads there?

Thanks again for sharing your experience. It’s always interesting to see how people arrive at the same goal in different ways.

[WeRPAWsome]

Hi @EmilyDickinson

Thank you.

That made me smile because, although ChatGPT helped me organise my thoughts for the forum post, the approach itself comes from our own experience over many years and hundreds of sits.

No, we certainly don’t run through that list as though we’re reading from a script. Most of those questions are simply prompts in the back of our minds. A relaxed conversation usually answers many of them naturally without us needing to ask directly.

If there are any gaps by the end of the call, we might ask one or two questions that seem most relevant to that particular sit. Every sit is different, so the conversation is too.

Like you, we rely a lot on the overall feel of the conversation, the listing, the reviews and our instincts. The questions are there to fill in any blanks, not to turn the call into an interview.

I think we’re actually aiming for exactly the same thing… finding out whether it’s a good fit for both sides before anyone makes a commitment.

[BonnyinBrighton]

Our particular questions outside of all the normal ones:
*If your cat goes missing where are their favourite hiding spots?
*Are there any dogs in the area that your dog treats as an ‘enemy’?
*Are your neighbours weird, or to be avoided etc
*Can we take the dog to visit my 90 year old uncle nearby?
*If something needs fixing is it ok for my husband to just do normal domestic DIY (he’s a retired engineer)….. taps, door latches, smoke alarms, etc

[andrealovesanimals]

@BonnyinBrighton “Are your neighbours weird, or are you the weird ones?”

[BonnyinBrighton]

Well I’d say in our block of 7 flats I’ve been described by others as ‘obviously an ex headteacher’ as I give out reminders when required on our WhatsApp group of the leasehold policies eg no wet washing hanging on balconies and no items ‘parked’ in the stairwell….also more recently ‘do not park across the electric entrance gate’…..

[EmilyDickinson]

@BonnyinBrighton Sooo many questions after reading your post, but I’ll save them for a cup of tea if we ever happen to bump into each other.

[BonnyinBrighton]

Please come visit me in Brighton! There’s dozens of nice sits locally.

[Silversitters]

We always ask the following because they are deal breakers for us .

For Dogs - where are they walked ? If the sitter is required to transport them daily our car to get to that location it’s a decline from us

Where do the pets sleep ?

Are all the pets registered with a vet and is an account set up for payment ? Read this thread for the reasoning behind this question Sitter has to pay veterinary expenses up front!

What are the date and time you are leaving / returning ?

This has frequently led to surprising answers - very often hosts are leaving or returning a day later or earlier than the listing . So this question helps avoid any last minute surprises. There was also a 12 day listing where the hosts built in overlap either end so they were only away for 7 days - we withdrew our application after that call ..

[Prissie]

I’ve been asked about any issues we’ve had with prior sitters so that past mistakes will be avoided. I appreciate that question and have an ever growing list ready to go. I cover it in the Welcome Guide but for most of the items (unless asked), I don’t say “this is where prior sitters messed up”, I just make sure to emphasize what needs to be done, the right way to do it, and potential problems that may occur if the instructions aren’t followed.

[GotYourBack]

@EmilyDickinson, we don’t ask this question. We often glean such information, to some extent, from prior reviews. But it seems a perfectly fair question to ask.

But we have evolved our video call mindset a great deal since early housesits. At first, we were selling ourselves. Given experience, we seek to have a direct peer-peer conversation.

We balance some exploratory open questions (e.g. tell us about your pet) with closed questions (e.g. date/time of travel plans).

We also learn. Through housesitting we have come to better understand our own subjective preferences for pets, pet care, people, properties, locations. As we learn, we evolve our questions (e.g. where does pet sleep?).

For us, the video call is about assessing two-way fit.