Hiring a Managed Service Provider is not an IT decision.

It is a business risk decision.   If you get it right, your technology supports growth, protects your data, and saves time.  If you get it wrong, you inherit outages, security gaps, and finger-pointing.

You need a clear way to evaluate MSPs before you sign anything.

Start With Your Business, Not Their Tools

Many MSPs lead with software lists.
That’s a red flag.

Before you talk to vendors, clarify your needs.

Ask yourself:

• How much downtime can your business tolerate?
• Are you regulated, insured, or contractually required to meet security standards?
• Do you need 24/7 support or only during business hours?
• Are you growing, acquiring, or adding remote staff?

A good MSP will ask these questions first.
A bad one will jump straight to pricing.

If they don’t want to understand your business, they won’t protect it.

Look for Security-First Thinking

In Canada, small businesses are a prime target for cyberattacks.
Ransomware, email compromise, and credential theft don’t discriminate by company size.

Ask direct questions:

• Do you include cybersecurity by default or sell it as an add-on?
• Is monitoring proactive or reactive?
• Who responds when there’s a security incident?
• How fast is response, measured in minutes not days?

If security feels optional in their offering, walk away.

A modern MSP should treat security like electricity.
Always on. Always monitored. Never optional.

Demand Clear Accountability

You should never wonder who owns a problem.

Ask:

• Who is accountable for outages?
• Who manages vendors like Microsoft, ISPs, and security platforms?
• Who escalates issues when things break badly?
• Do you assign a dedicated point of contact or a rotating queue?

Look for defined roles like Client Success, vCIO, or Technical Alignment.
These roles show structure and maturity.

If everything funnels through a generic help desk, you’ll feel it later.

Pricing Should Be Predictable

Surprise IT bills destroy trust.

In Canada, many small businesses still get trapped in hourly models that punish growth.
More users, more devices, more chaos, more cost.

Ask for:

• Flat, predictable monthly pricing
• Clear inclusions and exclusions
• Minimum commitments explained upfront
• Transparent onboarding fees

If pricing feels vague now, it will feel worse six months in.

Check How They Handle After-Hours Support

This matters more than you think.

Ask:

• Who answers at 2 a.m.?
• Is after-hours outsourced or in-house?
• Are emergencies triaged by trained technicians or call centers?
• Is response time guaranteed or “best effort”?

Downtime doesn’t care about office hours.
Neither should your MSP.

Validate Experience With Businesses Like Yours

Generic experience is not enough.

Ask for examples:

• Clients in your industry
• Similar size and complexity
• Comparable compliance or security needs
• Multi-site or remote environments if applicable

Then ask what went wrong in those environments.
You learn more from failures than success stories.

A strong MSP can explain how they adapted, fixed issues, and improved processes.

Watch How They Communicate

This is often overlooked.

Pay attention to:

• How clearly they explain technical topics
• Whether they speak in outcomes or jargon
• How fast they follow up
• Whether documentation is provided without being asked

You don’t want an MSP that makes you feel uninformed.
You want one that makes you feel confident.

Ask About Strategic Guidance

Support keeps the lights on.
Strategy moves the business forward.

Ask:

• Do you provide IT roadmaps?
• Do you review risks, budgets, and lifecycle planning?
• Will someone challenge bad decisions, even if it means less short-term revenue?

An MSP should act like an advisor, not just a fixer.

If they never push back, they’re not thinking long term.

Don’t Ignore Culture Fit

You’ll work with this team every week.
Sometimes every day.

Ask yourself:

• Do they take ownership or deflect blame?
• Do they listen or talk over you?
• Do they treat small issues seriously?
• Do they respect your staff?

Technology problems are stressful.
Your MSP should reduce stress, not add to it.

Final Question You Should Always Ask

“If something goes seriously wrong, what happens next?”

Listen carefully to the answer.

You’re not just hiring an MSP.
You’re choosing how problems are handled when the pressure is on.

That moment defines the relationship.

If you’re evaluating MSPs and want a second opinion, ask hard questions now.
It’s much cheaper than fixing a bad decision later.