Start with what you actually need
Before the questions, write down three things: what breaks most often, what would hurt most if it broke, and what you are paying for today. A provider who cannot speak to those three in the first meeting is selling a package, not a service.
Then decide the model. Our outsourced IT support guide explains break-fix versus managed support versus managed support with strategy. Most 10 to 250-person businesses need the middle one, with security built in.
The twenty questions
Onboarding
- What does your onboarding involve, and how long does it take? Good: a documented process with an audit, ownership checks and a handover plan. Bad: "we just take over the passwords".
- What will you need from our current provider, and what if they will not cooperate? Good: a list, and experience of difficult handovers.
- Who owns our domain, tenant and licences at the end of onboarding? The only acceptable answer is you.
Proactive management
- What do you do when nothing is broken? Good: patching cadence, monitoring, backup checks, security reviews, with reports. Bad: silence, or "monitoring" that means an inbox.
- How do you patch, and how do you prove it? Good: named tooling and a report you can see.
- How often will we hear from you without raising a ticket? Good: a named person and a review rhythm.
Security responsibilities
- What security is included as standard, and what is extra? Good: named products and a clear line.
- Who is responsible if we are breached because a setting was wrong? Listen for whether they take ownership of configuration.
- What is monitored out of hours, and who responds? See our 24/7 SOC guide for what a real answer contains.
- Will you help us with Cyber Essentials, and do you hold it yourselves? [TO CONFIRM: our certifications.]
- How do you handle a leaver on the day they leave? A process, or a shrug.
Support scope
- What are your hours, response targets and actual performance last quarter? Real numbers, not contractual ones.
- Is on-site included, chargeable or capped?
- Do you support Macs, phones, our line-of-business software, and our printers? Watch for the things quietly excluded.
- Who will we talk to? A queue, or people who know your business.
Contracts and exit
- What is the term, and what is the exit process? Good: no lock-in, or a short term with a clear handover on exit.
- What happens to our documentation, admin credentials and monitoring tooling if we leave? They come with you.
- How are licences billed, and can we see the Microsoft price alongside yours?
- What is not included that we are likely to need? An honest provider has a list.
- Can we speak to a client of our size in a similar sector? And then actually do it.
Not sure which of these applies to your business? Ask an engineer.
Book a Discovery CallSignals beyond the answers
Good signs: an engineer, not just a salesperson, on the first call. Questions about your business before a quote. A written proposal that itemises what is included. Willingness to say "you do not need that". Evidence: reports from real clients (anonymised), a documented onboarding process, certifications you can verify.
Bad signs: a quote on the first call. "Enterprise-grade" without a product name. Contracts with automatic renewal and long notice periods. Reluctance to put your tenant in your name. Vague answers about out-of-hours. A helpdesk you cannot phone.
How Black Sheep Support answers these
We wrote the list from the questions we wish every prospect asked, so here are our answers in brief: a documented onboarding with an audit and ownership fixes first; proactive management with monitoring, patching and backup checks reported monthly [TO CONFIRM cadence]; security built in as the baseline, with 24/7/365 SOC monitoring available [TO CONFIRM scope]; Cyber Essentials preparation as standard [TO CONFIRM our own certification]; support for Windows, Mac and mobile; no lock-in contracts; your tenant, domain and licences in your name from day one; engineers on the discovery call.
The rest is evidence, which is what the discovery call is for. If you would like to see how we think first, the IT support in Brighton page and our guides are a fair sample.
Want a second opinion before you buy licences?
We will look at your tenant, tell you who would actually benefit, and what needs fixing first. An engineer, not a salesperson.
Frequently asked questions
What is the most important question to ask an IT support company?
Who owns our domain, tenant, licences and admin credentials? If the answer is not 'you', everything else is negotiable in their favour.
Should we choose a local IT company?
Most support is remote, so location matters less than it did. Local still matters for on-site work, hardware and the occasional office move, and it usually means the provider knows businesses like yours.
How many quotes should we get?
Two or three, itemised the same way. More than that and you are comparing marketing, not services.
What accreditations should an IT provider have?
Cyber Essentials (ideally Plus) is the minimum credible security signal; Microsoft partner status shows competence on the platform you use. Ask to verify them rather than taking a logo on a website.
Is a long contract a bad sign?
Long automatic-renewal contracts with punitive exit terms are. Some providers use twelve-month terms reasonably. Read the exit clause before anything else.
How long should choosing take?
A few weeks: discovery calls, itemised proposals, a reference call, then a decision. A good provider will not rush you, and a rushed decision is usually the wrong one.
Meet Black Sheep Support
Ask us the twenty questions. A discovery call with an engineer is the fastest way to find out whether we are the right fit for your business, and we will tell you if we are not.
- Our answers to the questions above, with evidence.
- What onboarding would look like for you.
- What is included, what is extra, and what it costs.
- A clear next step, whether or not that involves us.
What has changed on this page
- 10 September 2026Page published.
