You have two or three quotes open in different tabs. They all say “updates, backups, security, support”. The prices differ, the wording does not, and you have a fifteen-minute call booked with one of them tomorrow. What should you actually say on that call?
This post is a working list of questions to ask before hiring a website maintenance company, grouped by the part of the relationship they test. For each one there is a note on what a straight answer sounds like and what an evasive one sounds like. You do not need to ask all of them. Pick the ones that matter for your site, write them down, and ask every provider the same set so the answers are comparable.
Before the call: write down three things about your own site
Good questions come from knowing what you are protecting. Spend ten minutes on this first, because a provider can only answer well if you can describe what you have.
- What the site does for the business. Is it a brochure people glance at, a lead form that feeds your sales team, or a shop that takes money? The answer changes which questions matter most.
- What has gone wrong before. A form that stopped, a slow month, a hack, an update that broke the layout. Past trouble is the best predictor of future trouble.
- What you can and cannot access today. Hosting login, domain account, WordPress admin, email. If you cannot get into one of these, say so on the call. A decent provider will help you sort it out rather than quietly work around it.
Questions about how they will get to know your site
The first month tells you a lot. Someone who starts updating plugins on day one without looking around first is guessing.
“What do you check in the first week, before changing anything?”
A good answer mentions a full backup taken and stored somewhere other than your server, a list of installed plugins and themes with their status, the PHP version, and a note of anything already broken. A weak answer is “we’ll run all the updates and let you know”.
“Will you tell me what is already wrong before you start?”
Most sites arrive with a few existing problems: an abandoned plugin, an expired licence, a contact form sending to a mailbox nobody reads. You want those named in writing at the start, so nobody argues later about whether the provider caused them.
“Do you need anything from me, and in what order?”
The answer should be a short, specific list. Admin access, hosting access, perhaps registrar access, and a contact person. If the provider asks you to transfer the domain or hosting into their name as a condition of the service, slow down. That is covered in our post on warning signs in a maintenance provider.
Questions about the monthly routine
Updates, backups and scans are the everyday work of any website maintenance company, so every proposal lists them. These questions get at how the work is actually done, which is where providers differ.
“Where are updates tested before they reach the live site?”
Some providers run updates on a staging copy first. Others update the live site directly and check it immediately afterwards, with a backup ready to roll back. Both can be reasonable for a simple site. What you do not want is no answer at all, or “updates are automatic”.
“What do you do when an update is risky?”
Major version jumps in a page builder, WooCommerce or a membership plugin can change how things work. Ask whether they hold those back, read the changelog, and schedule them at a quiet time. A provider who treats every update the same has not been burned yet.
“How long do you keep backups, and can I have a copy?”
Retention matters more than frequency. A hack or a quiet data problem can go unnoticed for weeks, and if the provider only keeps the last few days, every copy may contain the problem. Ask how far back you could restore, and whether you can download a full backup whenever you want one.
“What will the monthly report actually contain?”
Ask to see a real one with the client’s details removed. What a useful report should cover is set out in the guide to reading a maintenance report, and a sample tells you more than any feature list.
Questions about the day something breaks
This is the part you are really paying for, and it is the part sales calls skip.
“How do I report a problem, and who reads it?”
Email, WhatsApp, a ticket form? More important is who is on the other end. A shared inbox watched by one person in a different time zone is a different service from a small team that checks messages during your working day. Neither is wrong, but you should know which one you are buying.
“What happens if your update breaks my site?”
The answer should be simple: they restore or fix it at no extra charge, because it was their change. Be wary of any provider who hesitates here.
“What happens if I break my own site?”
This is the more revealing question. You or a staff member will eventually install a plugin, paste code into a page, or delete something by accident. Some plans include fixing self-inflicted problems. Others bill them separately. Either way, you want it stated before it happens.
“What do you not fix?”
A provider who says they fix everything is either very expensive or not being careful with their words. Honest answers include things like “we do not fix your email if it is hosted with a third party” or “we do not rebuild features that a plugin vendor has discontinued”. Listen for specifics.
Questions about money
Price is easy to compare. The terms around the price are not.
- “Is the monthly fee the whole cost, or are premium plugin licences extra?” Many sites depend on paid plugins that need renewing. Find out who pays and who remembers.
- “How many content changes are included, and how do you count them?” One provider counts a request, another counts minutes. Ask for an example of something that would fall outside the allowance. Bring one real recent change to the call and ask how it would be counted.
- “How do you quote work that is not maintenance?” You want a written quote before work starts, not a surprise line at the end of the month.
- “Is the price fixed for a period, and how much notice do you give before it changes?”
Questions about leaving
Asking about the exit before you have started feels awkward. Ask anyway. The way a provider answers tells you whether they expect to keep you by doing good work or by making it hard to go.
- “What notice do I need to give?”
- “On the last day, what do I get?” The answer should include a recent full backup, every login returned or changed back to yours, and a list of what plugins and licences are in use.
- “Are any of my accounts registered in your name?” If yes, ask how they will be moved to you.
The written side of this, notice periods and handover terms, belongs in the agreement itself, and the post on what a maintenance contract should cover goes through it clause by clause.
Website maintenance provider questions that people forget
A few questions rarely come up, yet they often decide whether the arrangement works:
- “Who exactly will work on my site?” One person or several? If one person is unavailable, does someone else have access and notes?
- “Do you keep notes about my site?” Things like which plugin must not be updated without checking the booking form, or why a certain redirect exists. Notes are what stop the same problem being solved twice.
- “What do you need from me each month?” Some providers expect you to approve risky updates or confirm the site looks right. Better to know you have a small job too.
- “What time zone do you work in?” Not a deal-breaker, just something to plan around. A provider in India serving a UK business will be working while you sleep, which can be useful for scheduled updates and less useful for a live emergency at your lunchtime.
How to judge the answers
When you put these questions to a few providers, you are not looking for the most impressive answer. You are looking for the most specific one. “We take daily backups, keep them off the server, and you can download any of them from a link” beats “we use enterprise-grade backup solutions”. Specific answers can be checked. Vague ones cannot.
Write the answers down in a simple table, one column per provider, while the call is happening. Afterwards, look for the gaps. The provider who said “I’d need to check” and then followed up in writing the same week is often a better bet than the one with a polished answer to everything.
Pay attention to the questions they ask you, too. A careful provider wants to know what your site does, what has broken before and who else touches it. If they quote a price without asking anything about your site, the price is for a generic site, and yours is not one.
Finally, compare like with like. If one quote is from a single freelancer and another from a team, the questions about cover and continuity carry more weight. The comparison of a freelancer against a maintenance firm covers that trade-off in its own right.
A short list of questions to ask before hiring a website maintenance company
If you only have time for a handful, these five do the most work:
- What do you check before changing anything on my site?
- How far back could you restore my site, and can I download a backup?
- What happens if your update breaks something? And if I break something?
- What is not included, with an example?
- What do I get on the day I leave?
Ask them in the same order on every call, and note the answer word for word where you can. Comparing the exact wording later is easier than comparing your memory of three conversations.
Asking us the same questions
Put every one of these to us too, and ask for the answers in writing before you decide anything. If you want them alongside a look at where your site stands today, the free website health check is the easiest place to begin, and it comes with no obligation to sign up for anything.
Next in this series: Website Maintenance Company Red Flags to Watch For
