Outsourced IT Provider: Ask These 8 Questions If Your Business Is Questioning Your Current IT Vendor

As your business grows and you add workstations, connected devices, other network components it’s a slow fade to when IT issues become the norm as you start to experience performance issues with hardware or software. Let’s say you’re a small office and don’t have a million dollars for an IT budget or to hire full-time IT manager, so outsourcing it is your only option.
And let’s also assume you’ve hired someone that “moonlights” as an outsourced IT person, or the IT vendor you’ve been working with just isn’t cutting it.

With so many competing Hartford-based IT services firms, how do you choose the best one?

  • Should you choose based on price?
  • Do you need to pay for a monthly fee to handle all your IT needs, when you only seem to have problems every once in a while, despite your staff telling you that the performance of your hardware is nothing short of atrocious?
  • What things SHOULD you be paying for, versus what’s a luxury?
  • And how much security does a guy really need, anyway?

If and when you’re in this situation, don’t hire just any IT firm. Ask these eight questions to find the best long-term fit.


What IT services are included in your monthly agreement?

You don’t want to wait until an issue arises to realize it falls outside your IT services companies wheelhouse.

At the very least, the company should include:

  • Help desk support. PC issues spring up daily and your IT support team should have a defined process in place to quickly respond to these minor issues.
  • Cybersecurity. Security of your network, your business formation, customer data, and your office devices is absolutely critical to your business. But, not every IT services company is equipped for the job, which means you’ll need to ask about which threat management, firewall, and virtual private network technologies your potential IT company uses.
  • Risk management. Your IT services firm should prevent IT issues, not only respond to them. You want them to be proactive, as well as reactive by evaluating and managing risk and auditing your IT environment.
  • User training and education. It’s one thing to introduce new technologies, it’s another to ensure every department is using them properly. Understand the type of user training and education you’ll receive.
  • Backup and disaster recovery. You should uncover whether or not your IT firm monitors onsite and offsite backups, how often they restore your data, and if you can see a written plan for how you would recover my company data in the event of a disaster.

Why should I work with you over another IT support company?

The best IT support companies know their strengths and weaknesses. If this question catches the company off guard, it probably offers service and protection.

Can you provide client referrals for companies in similar industries to mine?

You should see proof of expertise in certain industries before signing a managed services contract. If the IT company you’re talking with can’t provide strong customer referrals, with specific knowledge related to your industry, it likely doesn’t provide standout services or excellent customer service.

What IT certifications does your team hold?

Technology is constantly changing, and your IT support company should commit to continuous education. Forward-thinking IT support companies invest in employee training to stay ahead of the curve. If your company relies on vendors like Microsoft, Amazon or Cisco, make sure your IT firm has a firm grasp those platforms and technologies.

Is the monthly cost for IT support services predictable? What are the costs?

Of course, you’ll want to know how much IT support services will set you back each month. But instead of price shopping alone, investigate what each service includes. The cost is in the value. If you expect end-to-end IT services but the company only offers basic network support, that base price will quickly go up each month in add-ons.

Get a clear understanding of the offering and compare that alongside price to determine the best option. Find out what you should expect to pay for IT services in Hartford or the greater Boston area.

How do you anticipate and plan for my future business needs?

You need an IT company that will be around for the long haul. You don’t want to discover the IT firm is unresponsive or inadequate after a few months and go back to the drawing board.

This question says a lot about your IT support company and separates the true IT partners from reactive service providers. A long-term IT partner will take time to understand your short- and long-term business goals upfront and recommend ways to prepare for growth. They’ll meet with you every few months to review what’s changed and realign priorities.

Do your homework, and evaluate how the MSP will go the extra mile for your business.

How long have you been offering cloud services?

The future of technology is cloud. On-premises solutions won’t die any time soon, but the cloud is an entirely different beast. Your IT services firm should be prepared for the cloud revolution.

It’s not enough to offer cloud services. Ask how long the IT firm has been deploying cloud solutions. If it’s less than five years, and the company doesn’t have many cloud customers, it might be stuck in the past.

Find a managed IT services company that has at least seven years of cloud experience under its belt. A longer cloud tenure means it’s likely worked out the kinks, so you won’t be a guinea pig.

Where does your internal team fall short and how do you fill those gaps?

No MSP can be everything to every customer. Each undoubtedly has some weak areas.
For instance, some IT firms outsource help desk services. If this is the case, ask: Where are they located? How do you ensure service quality?

Look for an IT firm that offers most core managed IT services in-house and only outsources specific projects to select, reputable companies. If they’re guarded around this question, there’s a good chance they rely heavily on outsourcing, and you should go elsewhere.


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