Do Chicago Law Firms Really Need an IT Company?

The Real Cost of “We’ll Deal With It Later” 

When we speak with attorneys candidly, we often see this question come up:

Do we actually need an IT company? Or is this something we can handle when problems come up?

It’s a fair question. IT services can be expensive, and when everything appears to be working, ongoing support can feel unnecessary. Many law firms operate for years without a major incident and assume they’re doing something right.

The problem is that this decision is often misunderstood. Not hiring an IT company isn’t a cost-saving strategy – it’s a risk decision.

We don’t believe in fear-based marketing, but it’s important to take a realistic look at what law firms are actually trading off when they choose to “deal with IT later,” based on what we consistently see with Chicago-area law firms.

Why This Question Comes Up So Often in Chicago Law Firms

Chicago law firms face a unique mix of pressures that make this decision more complex than it first appears.

Many firms operate with:

• Hybrid or remote staff across the metro area 
• Cloud-based practice management, document management, and billing systems 
• Strict confidentiality expectations from clients 
• Court deadlines that don’t pause for technical failures 

At the same time, Chicago has a large number of small and mid-sized firms that grew quickly – often without a long-term IT strategy in place. Technology decisions were made reactively: one tool here, another fix there, and eventually a patchwork system that “mostly works.”

That’s usually when the question surfaces… 

The Truth? IT Without a Provider Is a Gamble, Not a Strategy

One experienced MSP put it bluntly in a law firm discussion we came across on reddit:

“Not having IT is like not having insurance. It’s great until it isn’t.”

If nothing ever goes wrong, you save money. If something does go wrong, the cost isn’t linear – it multiplies.

What most firms underestimate isn’t just the technical risk, but the financial and operational exposure that comes with it.

What Actually Happens When There’s No Chicago IT Company Supporting Your Law Firm

Everything Becomes Emergency Work

Without an IT provider:

• There’s no contract pricing 
• No guaranteed response times 
• No one who already knows your environment

Every issue becomes time and materials work.

Emergency IT rates commonly start at a few hundred dollars per hour, and serious incidents usually require more than one engineer. Costs escalate quickly, and none of it was planned for.

Ransomware Isn’t Always the Biggest Cost… Downtime Is

When firms think about cyber incidents, they focus on ransom demands. The real damage often comes from what happens while systems are down:

• Attorneys unable to access files 
• Staff unable to work 
• Missed or delayed filings 
• Clients waiting for answers

Best-case scenario: a day of downtime. Worst-case scenario: several days or longer. 

Courts don’t care why your systems are unavailable.

There’s No Guarantee You Get Your Data Back

Even if a firm decides to pay a ransom:

• There is no guarantee that files will be restored 
• There is no guarantee that systems will be usable 
• There is no guarantee the same thing won’t happen again

Without monitored backups and a recovery plan, outcomes are uncertain at best.

Break-Fix Gets More Expensive Over Time

Many firms rely on break-fix IT because it feels flexible and cheaper.

In reality:

• Problems become more frequent 
• Systems age without oversight 
• Security gaps grow quietly 
• Each incident costs more than the last

Eventually, firms spend far more recovering than they would have spent preventing the issue.

Why Managed IT Services for Chicago Law Firms Feel Expensive (Until They Aren’t)

Managed IT services typically include:

• Continuous monitoring 
• Security tools and updates 
• Backup and recovery planning 
• Vendor coordination 
• Predictable monthly costs

When nothing is wrong, it can feel unnecessary.

When something breaks, the value becomes very clear:

• Faster response 
• Lower recovery costs 
• Someone accountable for the outcome

Having worked with Chicago-based law firms on both sides of this decision, the difference isn’t technical sophistication… It’s preparedness.

Is This Just Fear-Based Marketing?

That criticism comes up often, and sure, sometimes it’s warranted.

But there’s a difference between fear marketing and risk math.

Every law firm has to decide:

• What data they’re willing to lose 
• How much downtime they can afford 
• Who absorbs the cost when something goes wrong

Choosing not to hire an IT company isn’t “free.” It’s choosing to self-insure without a cap on liability.

When “We’ll Deal With It Later” Actually Works

To be fair, some law firms can get by without managed IT services – at least temporarily.

This usually applies to:

• Very small firms 
• Minimal data exposure 
• Low operational complexity 
• A clear tolerance for risk

The challenge is that risk grows quietly as firms grow. What worked completely fine with two staff members often fails with ten staff members. 

So Does Your Chicago Law Firm Actually Need an IT Company? 

The honest answer is that not every law firm needs the same level of IT support, but every firm makes a choice when it comes to risk, whether they realize it or not.

Choosing not to work with an IT company isn’t a neutral decision. It means accepting:

• Uncapped recovery costs 
• Unplanned downtime 
• Emergency-only support 
• Uncertainty when something breaks

Some firms are comfortable with that tradeoff. Others aren’t — and that’s where managed IT becomes less about technology and more about continuity, accountability, and protecting the business you’ve built.

For Chicago law firms, where deadlines are fixed and client trust is non-negotiable, the real question isn’t if something will eventually go wrong – it’s whether you’ll be prepared when it does.