An open day at a boarding school can feel like an overwhelming experience. The grounds are immaculate. The pupils are warm and rehearsed. The headteacher gives a confident speech. You are handed a glossy brochure and shown around facilities that look considerably better than your kitchen.
And then you come home and realise you don't know any more than you did before.
Most boarding school visits are designed to impress, not to inform. The questions families ask on tours tend to be the obvious ones, about results, about uniform, about the swimming pool, and the answers tend to be polished.
These 20 questions are the ones that cut through the polish. They are not trick questions. But they are the questions that reveal whether the boarding house is what the prospectus suggests and whether this school is the right environment for your specific child.
About the boarding house and staff
1. Who actually lives in the boarding house? You are looking for a resident houseparent, someone who sleeps in the building. Not just a duty rota of day staff who pop in for the evening. Ask whether the houseparent has a family, and whether they live on site. The answer tells you a great deal about the pastoral culture.
2. What does a houseparent do all day? At the best schools, houseparents know every child individually, as pupils and as people. At weaker schools, they manage logistics. Ask this question and listen for specific examples, not generalities.
3. What is the staff-to-boarder ratio in the evenings? You want a number, not a description. A ratio of 1:8 or better is what good pastoral care looks like in practice. Higher than 1:15 and the individual attention starts to thin.
4. Who is on duty overnight, and where do they sleep? Some schools have a resident adult in the building; others rely on staff in nearby accommodation who can be called. Ask specifically. The answer matters for your peace of mind.
5. How long have the current houseparents been in post? High turnover of boarding staff is a warning sign. Continuity of care matters enormously for children who are away from home. If the houseparents have been in place for several years, that tells you something about the culture.
About the boarding routine
6. What does a typical Tuesday evening look like? Not an Open Day evening. A Tuesday. What time is supper? Who supervises prep? What activities are on offer? What time are lights out for different year groups? The specificity of the answer tells you how seriously the school has thought about its boarding programme.
7. How are devices and screens managed? Ask for the policy and ask how it is enforced in practice, these are often different things. Ask specifically what happens at bedtime with phones for younger boarders.
8. What do children do if they are not interested in the organised evening activities? This is a useful question because it reveals whether the programme is mandatory or genuinely optional, and what the boarding house culture is around downtime.
9. What are the weekend arrangements? Can children go home every weekend, or only on designated weekends? Is there Saturday school? What happens to children who stay on campus at the weekend, is there a meaningful programme, or are they largely left to manage themselves?
About pastoral support and pastoral challenges
10. What happens when a child is unhappy at 10pm on a Wednesday? This is the most important question on this list. The answer should describe a specific, human process, not a policy document. You want to hear about a named person who is available and how they would be approached.
11. How do you handle homesickness, and how long does it typically take to resolve? Every boarding school has homesick children. The question is not whether it happens, but how it is managed. Ask whether there is a pattern to when it tends to resolve, and what the school does in the interim.
12. Can you give me an example of a time a boarding arrangement wasn't working, and what you did? Schools that have genuinely pastoral cultures will answer this question with a real (anonymised) example. Schools that have not had to deal with it, or who deflect, are telling you something.
13. How do you support children whose parents are deployed, working abroad, or not easily reachable? This is particularly relevant for military families, international families, or parents with demanding travel commitments. Ask specifically, not generally.
14. What is your approach to bullying in the boarding house? Ask this directly. A good school will tell you clearly how it is defined, how it is reported, and what the consequences are, without being defensive.
About academic support
15. What support is available during evening prep if a child is struggling with work? Is there a member of academic staff available during prep, or just a boarding supervisor? What happens if a child has fallen behind in a particular subject?
16. How do boarding staff communicate with academic staff about a child's progress? This is a question about integration between the pastoral and academic sides of the school. In a good school, these are not separate worlds.
About practicalities and the package
17. What is included in the boarding fee, and what is billed additionally? Ask for a written list. Common extras: EAL, music lessons, LAMDA, sports kits, equestrian, trips, laundry. The more that is included in the fee, the easier the budget planning.
18. What is the nightly rate for additional overnight stays beyond a standard package? A school that publishes this transparently is signalling something about its culture. A school that is vague about it is also signalling something.
19. What happens if the boarding arrangement isn't working after a term? Is there a graduated reduction, from full boarding to flexi, for example, or is the commitment all-or-nothing? Ask specifically what the options are, and how that conversation would happen.
The one question to ask yourself when you leave
20. Did the children look happy?
Not the children who were assigned to show you round. The ones you passed in the corridor who didn't know you were there. The ones at supper who weren't performing for a prospective family. The ones who were arguing over something and forgot to be on show.
That is the answer that matters most, and it is the one no brochure can give you.
At Leweston
We welcome the difficult questions. When families visit Leweston's boarding house — not on a polished Open Day but on a quieter afternoon or early evening — we will answer all of the above. We would rather you made the right decision for your child than the one that fills a place.
Call 01963 211015 or visit leweston.co.uk to book a visit or speak to the team.
Leweston School is a co-educational independent day and boarding school in Sherborne, Dorset, for pupils aged 3 months to 18, offering Nursery, Pre-Prep, Prep, Senior and Sixth Form on a single campus.