How to choose an IT support company in NYC: 12 questions to ask
Choosing an IT company is mostly about one thing: who is actually going to pick up when something breaks, and what they've promised to do about it. Prices matter, but a cheap plan with vague scope costs more the first time you have a real problem. These are the questions we'd ask if we were hiring someone.
The short answer
Ask for response times, what's included, contract terms, and how they handle your passwords and backups, in writing. Then ask who your technician is and talk to them. A good provider answers all of it plainly.
12 questions to ask before you sign
1. Who answers when we call?
A person who knows your setup, a helpdesk, or a voicemail? Ask what happens at 9 AM on a Monday when three people can't log in.
2. What are your response times, and are they in writing?
Look for separate numbers for "we acknowledged you," "someone is working on it," and "a tech is on-site." Be wary of "we respond fast" with nothing defined.
3. Where do you go on-site, and is travel extra?
In New York this matters. Ask which boroughs and counties get same-day visits and which are scheduled, and whether travel time is billed.
4. What exactly is included in the monthly fee?
Get the list: helpdesk, updates, monitoring, Microsoft 365 or Google Workspace admin, backups, security tools, on-site visits. Then ask what's not included.
5. How long is the contract, and how do we cancel?
Twelve-month terms and five-seat minimums are common. Month-to-month is better for you while you find out if it works.
6. How do you handle our passwords and access?
You want named accounts for each technician, multi-factor sign-in, an encrypted password vault, and a record of who accessed what. "We keep a spreadsheet" is a red flag.
7. Are backups included, and when did you last test a restore?
A backup nobody has ever restored is a hope, not a backup. Ask how often they test, and what gets backed up: computers, Microsoft 365 or Google Workspace data, servers.
8. What security basics do you set up on day one?
At minimum: multi-factor sign-in on email, updates on every computer, endpoint protection, and email filtering. If you're in a regulated field, ask how they help with that (for New York businesses, the SHIELD Act applies to anyone holding New Yorkers' private information).
9. Will we get documentation, and what happens if we leave?
You should own a record of your accounts, devices, and network, and get every admin password back if you switch providers. Ask how long handover takes.
10. Who are the technicians?
Ask who'll actually work on your account, and who covers when that person is out. Smaller teams can be great if the backup plan is clear.
11. Have you supported offices like ours?
Ask about the software you use (QuickBooks, Clio, dental imaging, POS systems) and offices your size. Ask for a reference or reviews you can check yourself.
12. What does the first month look like?
A good onboarding inventories your users and devices, fixes the obvious risks, and gives you a written summary. Ask if that's included or a one-time fee.
Red flags
- No written scope or response times
- Long contracts with automatic renewal and no exit
- Pressure to replace all your hardware before they've looked at it
- They want your passwords by text or email
- Nobody can tell you who your technician is
Quick answers
Should I pick the cheapest quote? Only if the scope is the same. Compare on-site visits, backups, security, and contract terms, not just the per-user price.
Is a small local IT company riskier than a big one? Not if coverage is defined. A local team that knows your office can be faster and more accountable; just get the backup plan in writing.
How long should switching providers take? A few weeks for a small office, mostly to collect passwords and documentation and get monitoring in place.
Talk it through with us
Ask us all twelve. We'll answer in writing, look at your setup, and give you a flat monthly price with no long contract. Book a business IT review, see what our plans include, or browse IT support by industry.
Still stuck? A tech can fix it today.
Remote in minutes, on-site same day across NYC and Long Island. Flat quote before any work.
We do this for a living: Small business IT support (Plans from $89/user/mo · month-to-month) · Cybersecurity checkup & SHIELD Act (Flat-quoted · on-site $129/hr)