Avoiding Awkward Situations with Your Sitter

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Avoiding Awkward Situations with Your Sitter


In early 2020 (a lifetime ago!), we wrote about the often-awkward conversations that arise when working with babysitters. Discussing issues of privacy and finance, for instance, is important, but it can also be uncomfortable. In addition to encouraging families to cover their bases with in-person interviews and trial sittings to ensure they hire the sitter or sitters who will best fit their families, we provided tips for heading off some of the most awkward circumstances in advance.

Three years later, some additional awkward conversations may have presented themselves in light of COVID-19 and the many considerations around healthcare, cancellations, and expectations for sitters. Keep reading for more insights from CareFinder!


Health is a highly personal subject. Whether your child has a chronic medical condition, an acute illness, or is currently healthy, their wellbeing is of course a top priority. But just as you wouldn't erect a billboard to your kid's recent runny nose, you also recognize that your sitter may not be enthusiastic about discussing their own health.

COVID-19 has heightened awareness of and attention to healthcare practices, standards, and expectations. As Japan begins to loosen its requirements, such as mandatory mask-wearing, it is now the individual's responsibility to determine precautionary measures and risk-tolerance.

You know your family best. One of the easiest ways to avoid issues with a sitter who does not understand your healthcare-related requests is to be very clear about them in your job post! If you require vaccination, prefer sitters to remain masked during the job, or otherwise have specific standards, provide those details in advance. We ask all of our sitters to ensure they can meet expectations before applying, so as long as you are straightforward in your post, you can expect to have a sitter who meets your family's needs.

We also ask all sitters — and families — to monitor their health and cancel jobs if they, or someone they've had close interaction with, is unwell.


Speaking of which: sometimes jobs are cancelled. Whether you no longer plan to enjoy a romantic night out or no longer need an extra hand on vacation, job cancellations are inevitable. And as mentioned above, sometimes it's for the best; we all know how important it is to stop the spread of illness whenever possible!

But in those instances when sickness is not to blame, CareFinder has recently made conversations around cancellation policies much easier to have: We now have a community-wide policy! For all sitters who wish to implement fees in the event of cancellation, there is a standard schedule. This means there are no surprises or awkward negotiations if your dinner plans change last minute, or your appointment was rescheduled.

Sitters who do not wish to charge a cancellation fee will include this information in their profile. So it is, again, important to be thorough in the interview process to ensure you are familiar with the sitter's policies before choosing to work with them.

Expectations for Sitters

To reiterate: One of the easiest ways to avoid uncomfortable conversations and situations with babysitters is to ensure that the sitter you choose to work with is suited to your family's needs!

Be clear in your job posts about the specific expectations you have — whether they're language-related, additional requirements like meal preparation or light housekeeping, age-related skills like diaper changing or infant CPR, or practical details like job-length, location, or recurrence. All sitters are required to accurately represent their competencies, certifications, and other experience; the CareFinder team works diligently to ensure only high-quality, trustworthy sitters are approved to join the community. But identifying the sitter who is best for your family is personal.

On the occasion that an issue arises between family and sitter, more often than not it is because wires were crossed in job expectations. Review applicants' profiles to ensure that they are a match on paper and coordinate a trial sitting to ensure that the sitter is a match in practice!

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