Before paying someone to cover care for a Shetland pony, ask about pony-specific experience, laminitis understanding, exact visit times and tasks, emergency and backup arrangements, references and insurance, and the full written price. A Shetland is not a small horse in care terms, and the wrong sitter usually fails on diet discipline rather than kindness.
Ask about Shetland and laminitis experience first
Ask first whether the sitter has actually handled Shetland ponies and understands why their grazing is restricted, because this answer predicts everything else. A good candidate explains without prompting that Shetlands are thrifty natives prone to laminitis on rich grass, that treats and extra feed are a genuine risk, and that a grazing muzzle or bare paddock is management, not cruelty. Ask how they would spot early trouble: reluctance to turn, a short stride on hard ground, heat in the feet, or a pony lying down more than usual. Follow with handling questions, since a Shetland can be strong, low, and entirely unbothered by an adult's dignity; ask how they lead a bargy pony and catch one who has decided the far corner is preferable. Anyone who describes Shetlands as simply easy because they are small has not yet met yours properly.
Pin down visits, times, and the exact task list
Pin down the service itself before money is discussed, because pony cover varies from a single daily glance to full yard care. Ask how many visits each day are included, at what times, and how long each visit lasts, then walk the task list together: grazing or muzzle routine exactly as you run it, measured hay, water trough checked and refreshed, feet picked out, shelter and bedding state, and a hands-on coat check. Ask whether mucking out, poo picking, fence checks, and rug changes are included or extras, and get that in writing rather than discovered mid-holiday. For a Shetland specifically, confirm the sitter will not move the pony onto better grass for convenience, will not accept treats from neighbouring liveries, and will send you the daily log or photos you agree on. Ask what happens to visit times on the days you leave and return, when handovers most often go wrong.
Ask about emergencies, backup people, and authority
Ask who steps in if the sitter is ill, injured, or their car fails, because a Shetland's grazing and feet routine cannot simply skip two days. The backup should be a named person the pony can meet beforehand, not a vague assurance that someone will be found. Then cover emergencies in detail: will the sitter call your vet first and you second if the pony shows laminitis signs or is injured, are they authorised by you in writing to agree urgent treatment, and how are vet fees handled until you return. Ask whether they hold insurance for care of other people's animals, whether they have references from pony owners you can actually contact, and whether they are comfortable administering any routine care your pony already receives, described precisely rather than assumed. A professional answers these questions easily; hesitation here is information.
Agree price, payment terms, and the written brief
Agree the money last and in full, because price disputes with a pony sitter are almost always scope disputes wearing a costume. Ask for the total for the whole period, what counts as an extra visit or extra task, mileage or call-out charges if any, when payment is due, and what cancellation terms apply on both sides. Put the agreed tasks, times, contacts, and price into a written brief you both keep, and do a paid trial visit or a supervised handover round before the holiday so the sitter has seen your muzzle fitting, hay soaking, gate clips, and where everything lives. Leave the vet, farrier, and your own contact order in that brief. When you are comparing local pony sitters through KinsLe in the Pet Services Directory, those answers are what separate a safe pair of hands from a cheap problem.