Questions to Ask a Managed Service Provider
These are questions to ask a potential MSP before you sign, written for the owner, office manager or in-house IT person who has to choose the company that will run the business's computers, accounts and backups. They follow the order the decision usually takes: whether the provider suits a business like yours, what the monthly fee covers, how support works day to day, security and backups, the move across, then the contract and the way out. Fees, service levels and terms differ from one provider to the next, so treat every answer as something to get in writing.
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The questions
Each question, and why to ask it
Fit
What kinds of businesses make up most of your client list, and how many are close to our size?
Why ask it
A provider built around 200-seat firms tends to treat a 12-person office as a small account, and one that mostly serves five-person shops may not have the depth for you. Get the head count of their typical client and of their largest. The comfortable place to be is somewhere in the middle of that range.
Do you have clients in our industry, and which of its rules do you already work under?
Why ask it
Health care, finance, legal work and government contracting each bring their own requirements, and they differ by country and state. Don't take a general 'we do compliance' as the answer. Ask which requirement by name and what they do for that client each month, then check the rule itself with your own adviser.
How long have you been selling managed services, and how many clients are on a monthly plan today?
Why ask it
An IT firm can be twenty years old and have offered a monthly plan for two, having billed by the hour before that. The number of clients on a plan shows whether managed service is the main business or a sideline to repair work. A young firm is not a reason to walk away, but find out who covers when the owner is on vacation.
How many technicians do you employ, and how many end users does that team support?
Why ask it
Divide one number by the other and compare the result across the providers you meet. There is no correct ratio, but a firm with three technicians and a long client list is one resignation or one flu season away from slow tickets. Ask what happened the last time someone on the team left.
Can we speak to two or three clients like us, including one who joined in the past year?
Why ask it
Long-standing clients can describe day-to-day service, but only a recent one remembers the changeover. Three things to put to each: how long tickets really take, whether the invoices held surprises, and what they wish they had asked before signing.
Is there anything in an office like ours that you do not support?
Why ask it
Printers and copiers, the phone system, door entry and cameras, the website, an employee's own phone: providers draw this line in different places. For each item they exclude, find out whether they will at least deal with the other vendor for you. Whatever is left is yours to manage, so write it down while you are still comparing firms.
Which of the applications we rely on have you supported for another client?
Why ask it
Bring the names: the accounting package, the practice or job management system, anything your trade depends on. No provider knows them all, so what matters is what happens when they do not: whether they will call the software maker's support on your behalf and stay on the ticket until it is closed.
Which tools and standards do you require every client to adopt?
Why ask it
Many providers run one set of tools across all clients: a particular firewall, antivirus and backup product, sometimes a maximum age of computer. That standard is how they keep support fast, so it is a reasonable thing to insist on. The thing to learn is how firm it is: whether a product you already pay for and like could stay, and what happens to support for a machine that falls outside it.
We have someone in-house who handles some IT. How would you split the work with them?
Why ask it
Skip this one if nobody on staff touches IT. If someone does, three things need settling: who takes the first call, who holds administrator rights, and whether your person can see the provider's tickets and documentation. A shared arrangement is often priced differently from the whole job, and not every provider offers it.
Why did the last client who left you leave?
Why ask it
Every provider loses clients: some are bought, some outgrow the service, some were unhappy. A plain account of one departure, with what the provider did about it, is more reassuring than a claim that nobody ever goes. Note whether the blame lands entirely on the client.
Fees
What exactly does the monthly fee include, and what is billed on top of it?
Why ask it
Ask for the answer as two written lists, included and excluded, and read the second one first. Common extras are projects, on-site visits, after-hours work, new equipment setup and security add-ons, but every agreement draws the line somewhere different. Anything said in the meeting that is not on the list should be added before you sign.
Do you charge per user, per device or a flat rate, and what happens when our head count changes?
Why ask it
Each model moves differently. Per user follows staff, per device counts every laptop, server and sometimes printer, and a flat fee may be reviewed once a year. A business that shrinks in the off season should also learn how soon the bill drops after someone leaves, and whether there is a minimum to pay however small it gets.
Which kinds of work count as a project and get quoted separately?
Why ask it
A new server, an office move, a migration to cloud email or a second site often sits outside the monthly fee. Name what you can see coming in the next two years and have them say whether each is included. For the rest, ask for the hourly rate and whether clients on the plan get a lower one.
Are on-site visits included, and is there a travel charge or a minimum?
Why ask it
A lot of support is done over a remote connection, so a plan may count visits, bill each one or include them without limit. A useful number is how many times a technician went to a client your size last year. Two more things decide the cost: how far away their nearest person is, and who gets to say a visit is needed.
What does support outside business hours cost?
Why ask it
Round-the-clock help, a higher hourly rate after a set time and emergencies only are three different offers, and a proposal can call any of them after-hours support. Tell them when your people actually work, including early shifts, weekends and other time zones, and have the answer priced against that.
Do we have to buy hardware and software through you, and how do you set the price?
Why ask it
Reselling equipment and subscriptions at a margin is ordinary practice for an IT provider. Two details matter more than the markup: whether something bought elsewhere will still be supported, and whether your Microsoft or Google subscriptions would be billed through the provider's reseller account. That second one affects the day you leave, so raise it again when you reach the contract.
What would we have to fix or replace before you take us on, and who pays for that?
Why ask it
Providers often find aging computers, an unsupported server or a missing firewall in their first look and make fixing them a condition. Get that list with prices before you compare monthly fees, because a low fee with a large cleanup bill is not the cheaper offer. Then have them mark which items could wait six months.
Can you show us a sample invoice for a client about our size?
Why ask it
With the name blacked out, a real invoice shows what a proposal does not: how many lines there are, how extras are described and how much sits outside the plan in an ordinary month. If they would rather not share one, ask a reference how their bill compares with the original quote.
Support
When one of our staff has a problem, how do they reach you, and who picks up?
Why ask it
Phone, email, a portal, a chat window or an icon on the desktop: ask which gets the fastest answer. Then ask who is on the other end, a dispatcher logging the ticket or a technician who can start fixing it. Your least technical employee will use this every week, so picture them doing it.
Is the help desk staffed by your own employees or by a company you contract with?
Why ask it
Handing the first line or the night shift to an outside help desk that serves many IT firms is a common arrangement, and it can work well. If that is the setup here, you need three facts: where those people are, what they are allowed to touch, and how a ticket gets back to the provider's own technicians.
What response and resolution times do you commit to in the agreement, at each priority level?
Why ask it
Response means someone has acknowledged the ticket and resolution means it is fixed, and many agreements promise only the first. Ask to see the table in the service-level agreement itself, and find out what you receive if a target is missed: a credit, a right to leave, or nothing.
Who decides whether a ticket is urgent, and what puts it in the top tier?
Why ask it
The fast times in an agreement usually apply only to the highest priority, and the provider normally assigns it. Give them three cases of your own, such as one person locked out, the card terminal down and the whole office offline, and ask which level each would get.
What were your real response and resolution times over the past few months?
Why ask it
A provider that measures this can pull the report from its ticketing system in a minute, ideally for clients on the plan you are considering. Compare the figures with the times in the agreement. If nobody can produce them, the targets in the contract are probably not being tracked either.
How does a ticket move up when the first technician cannot solve it?
Why ask it
A good answer has a clock in it: after a set time the ticket goes to a senior technician with the notes attached, so your employee is not made to explain the problem a second time. Finish by getting the name and direct number of the person you call when a ticket has stalled.
How do you support people who work from home or on their own laptops and phones?
Why ask it
Describe your real mix first: how many people are remote, how far away, and on whose equipment. The answers worth having are how a dead laptop gets replaced for someone who cannot come to the office, and whether technicians will touch a personally owned device at all. Policies on personal devices vary by provider, and some decline them on security grounds.
How do you watch our systems, and what happens when an alert fires at two in the morning?
Why ask it
Installing monitoring software is the easy part, and nearly any proposal will mention it. What varies is whether a person acts on an alert overnight or it waits for the morning. Have them describe a recent problem they caught before the client noticed, and say which alerts wake someone up.
When we hire someone or someone leaves, what do you need from us, and how fast is it done?
Why ask it
Setting up a new hire and shutting off a leaver are requests you will send again and again, so the routine matters. Find out whether there is a form, how many days' notice a new laptop and account need, and how quickly access can be cut when a departure is sudden. Check too whether preparing a new machine is inside the fee.
Will we have a named account manager, and how often would we sit down together?
Why ask it
A regular review, often quarterly, is where ticket trends and repeat problems come up before they turn into emergencies. Ask what the last review for a client like you covered and whether you could see the report. If you suspect the meetings are mostly a pitch for add-ons, a reference will tell you.
Do you help us plan and budget for IT, or only fix what breaks?
Why ask it
What you are hoping for is a yearly plan on paper: which machines to replace, what is going out of support, what next year should cost. It may come with the monthly plan or be sold as a separate advisory service at its own price. If you have no one in-house to do this thinking, it can be worth more than a slightly lower monthly fee.
Security and backups
Which security protections are part of the base fee, and which are sold as add-ons?
Why ask it
Have them go item by item: antivirus or endpoint detection, email filtering, multi-factor sign-in, patching, staff training, around-the-clock threat monitoring. Proposals often show a security bundle as a separate line, and the cheapest quote may simply have left it out. Compare providers on the same list.
How do you secure your own business, given that your staff would hold the keys to ours?
Why ask it
A provider's remote access tools reach into every client at once, which makes the provider itself a target. Good signs are an individual login with multi-factor sign-in for each technician, a log of who connected to your systems and when, and an audit by an outside party. A request to see the audit summary is fair.
What gets backed up, how often, and where are the copies kept?
Why ask it
Pin down which machines and cloud accounts are covered, how many times a day, and whether one copy is held somewhere a break-in to your network could not reach. Ask who owns the backup account. If it sits in the provider's name, add it to your list for the exit conversation.
Is the data in our cloud email and file storage backed up as well?
Why ask it
Businesses often assume Microsoft 365 or Google Workspace keeps everything forever. What those services retain, and for how long, depends on the plan and its settings, so ask the provider to show you what applies to yours. Then ask whether their backup covers mailboxes and shared drives or only the machines in the office.
How often do you test restoring our data, and would we see the result?
Why ask it
A backup that has never been restored is an assumption. Ask for a scheduled test, at least of a few files and ideally of a whole machine, with a short report sent to you. The follow-up is how long the last full restore took, because that is your downtime.
If our server failed or the office was out of use, how long before we could work again, and how much work would we lose?
Why ask it
These are the two figures a disaster recovery plan rests on: the time to recover and how far back the last good copy is. Have them stated in hours for your own setup, not as a general capability. If the plan costs more than you expected, ask what a slower, cheaper version would look like.
If ransomware got in, what would you do in the first day, and is that work inside the fee?
Why ask it
Listen for an order of events: isolate machines, tell you, find how it got in, restore. Then ask the money question, since many agreements treat incident response as billable project work. Your cyber insurer may also have rules about who you call first, so read your policy before relying on the provider's plan.
How quickly are security updates applied, and who checks that they went in?
Why ask it
Computers and servers are usually on a schedule. The firewall, the switches and the Wi-Fi equipment are the group that gets forgotten, so name them. The useful follow-up is the report: can they show you, for a current client, which machines are up to date today and which are not?
Will you help us fill in a cyber insurance application or a customer's security questionnaire?
Why ask it
Insurers and larger customers send long forms about multi-factor sign-in, backups and staff training, and you will need the provider for the technical parts. Ask whether that help is included and how fast they turn one around. Their reaction to the form also shows which of those controls they already run for clients.
Onboarding
What happens between signing and the day you are fully supporting us, and how long does it take?
Why ask it
You are after the steps in order with rough dates: the audit of what you have, installing their tools, collecting passwords, introducing the help desk to your staff. A provider that does this often has a written plan it can send you. Check who runs it, and whether that person stays on your account afterwards.
What will you need from us and from our current provider or IT person?
Why ask it
Expect a list: administrator logins, network details, license records, vendor contacts, a floor plan of who sits where. Some of it only the outgoing provider has, and you are the one who has to request it. Check your current agreement for its notice period and handover terms before you set a start date.
How do you handle the changeover so there is no gap in support?
Why ask it
The awkward weeks are the ones where the old provider has been told and the new one is not fully in. Ask whether the two overlap, who staff should call during that time, and when the old provider's access is removed. A date for that removal should be on the plan.
What will our staff notice in the first week?
Why ask it
New software on each machine, a different number to call, perhaps a prompt to set up multi-factor sign-in or change a password. Ask what the provider sends employees beforehand, and whether someone comes in person on the first day. A short introduction saves a week of 'who are these people' tickets.
How will you document our setup, and can we see that documentation whenever we want?
Why ask it
Careful providers keep a record of every device, login, license and vendor in a documentation system. Ask whether you get your own access to it or an export on request, and in what format. It is the same material you would need if you ever changed provider, so settle it at the start.
What most often delays an onboarding, and what could we do now to avoid it?
Why ask it
Missing passwords, an uncooperative previous provider and equipment too old to take the new tools are the usual suspects. Whatever they name, ask what you can do this month to clear it, and whether the monthly fee starts on the signing date or once the work is done.
Contract and exit
How long is the initial term, and how does the agreement renew?
Why ask it
Terms run from month to month up to several years, and many renew automatically unless notice is given by a set date. Get that date and put it in a calendar. If the provider wants a long first term, ask whether a shorter one or a trial period is available at a slightly higher price.
How can the monthly fee change during the term and at renewal?
Why ask it
Look for the clause, not the reassurance: some agreements allow a yearly increase, some tie it to their suppliers' prices, some hold the fee fixed. Ask what existing clients saw at their last renewal. A cap written into the agreement is worth requesting.
If the service falls short, can we end the agreement early, and what would we owe?
Why ask it
Some contracts require the rest of the term to be paid whatever the reason. Others allow an exit after repeated missed service levels or after a written chance to put things right. Have the provider point to the wording, and have whoever reviews your contracts read it, since what such a clause means depends on where you are.
Who holds the administrator passwords to our systems, and will we have our own copy from day one?
Why ask it
Your business should be able to reach its own network, email account, domain registrar and firewall without asking permission. Ask for the credentials to be kept somewhere you control, such as a password manager with an owner-level account in your name, and updated whenever they change. A provider reluctant to agree is showing you how an exit might go.
Whose name would our domain, our cloud accounts and our software licenses be registered in?
Why ask it
Go through them one by one, and add any firewall or backup device the provider supplies on rental. Whatever is registered to the provider or bought through its reseller account needs a transfer or a replacement when you part. Have anything that can be in your company's name put there now.
If we leave, what do you hand over, how quickly, and is there a charge?
Why ask it
The list to ask for: all passwords, the network documentation, backup data in a usable form, and cooperation with whoever comes next. Ask whether that is written into the agreement with a time limit and whether the hours are billed. Then ask what they remove, since their monitoring and security tools usually come off, and you would need replacements ready that day.
What insurance do you carry, and how does the agreement limit what you owe us if your mistake causes a loss?
Why ask it
Ask for certificates for professional liability and cyber coverage, and find the limitation clause, which often caps the provider's liability at some multiple of fees. Whether that cap is acceptable is a question for your lawyer or insurance broker. The provider's part is to show you the documents without fuss.
What would change for us if your company were sold or merged?
Why ask it
Small IT firms do get bought by larger ones, and a sale can change your technicians, your tools and your price. Ask whether the agreement lets you leave if ownership changes. Nobody can give you a forecast, but you will learn whether the contract protects you.
How to interview a managed service provider
Practical guidance for the conversation itself
Before you meet any provider
Count what you have
Write one page: how many people, computers, servers and sites, which cloud services you pay for, and the applications your work depends on. Every provider will ask, and their quotes are only comparable if they are pricing the same list. If you cannot fill in a line, say so, because finding out is part of what you are buying.
List what went wrong last year
Note the outages, the slow fixes, the security scare, the invoice nobody expected. Those are your test cases. Under Support and Security and backups, ask each provider how that exact event would have gone with them.
Decide what you are handing over
Full outsourcing, help for an in-house person, and security and backups only are three different purchases. Say which one you want at the start of the meeting so the proposal matches. A provider that sells only one of them will tell you, which saves you both an hour.
Read your current agreement first
If another provider or contractor looks after you now, find the notice period and what the agreement says about returning passwords and documentation. That date sets your timetable, and the handover terms tell you which Onboarding questions matter most.
Running the conversations
Use the first call for Fit and Fees
Those two groups tell you whether a second meeting is worth having. Save Support and Security and backups for a longer session with someone technical from the provider in the room, and Contract and exit for when you have the agreement in front of you.
Meet a technician as well as the salesperson
The person who sells the service is often not the one who answers tickets. Ask for twenty minutes with a lead technician or the service manager and put the Support questions to them directly. How they explain things to you is how they will explain things to your staff.
Ask to be shown
A sample monthly report, the response-time figures, a blanked-out invoice, the onboarding plan, a page of another client's documentation with the details removed. Each takes a well-run provider a few minutes to produce. Collect the same items from every firm you are considering.
Bring three scenarios of your own
Pick three events from your list of what went wrong and describe each one the same way to every provider: who would be called, how soon, and whether it would cost extra. Answers to a concrete case are far easier to compare than answers about policy.
Comparing the proposals
Put every quote on the same scope
Reprice each proposal for the same number of users and devices, with the security items and backups included, plus the one-off work each provider says must happen first. Then total the first year and a normal year separately. The ranking often changes once the extras are in.
Lay the exclusions side by side
The list of what is not covered is the most informative page in a managed services agreement. Set the exclusions from each provider next to one another and ask about any item one firm excludes and another includes.
Keep the reference calls short and specific
Three things are enough: how long an ordinary ticket takes, whether the bill matches what was quoted, and what the changeover was like. Ask the reference how many staff they have, so you know whether their experience would resemble yours.
Get spoken promises into the agreement
If a salesperson said after-hours calls are included or that passwords will be shared from day one, ask for the sentence to be added to the agreement or for the proposal to be attached to it. Have someone qualified read the final contract before you sign, since nothing on this page is legal advice.
Where these deals go wrong
Choosing on the per-user price
The monthly figure is the easiest number to compare and the least complete. A lower price that leaves out security tools, on-site visits or after-hours help can cost more by the end of the year than a higher one that includes them.
Letting the provider be the only one with the keys
If every administrator password, the domain and the backup account sit with the provider alone, changing provider depends on its goodwill. Settle ownership and access under Contract and exit before the work starts, while everyone is still on good terms.
Signing a long term before you have seen the service
A multi-year agreement may bring a lower price, but you have not yet seen a single ticket handled. A shorter first term, or a clause allowing an exit after the first few months, gives you a way out if the service differs from the sales meeting.
Assuming outsourcing leaves you nothing to do
Someone on your side still has to approve purchases, tell the provider about new hires and departures, attend the reviews and read the reports. Name that person before onboarding starts and give them the time for it.