Author: Nolan Witkowski

You’ve got a legal assistant who’s been with the firm for years. Sometimes you wonder what you’d do without her: she knows where to find any file, she’s on a first-name basis with your top clients, and she keeps the lawyers’ calendars clean and organized.

Then one day she hands in her notice.

In her exit interview, she says she's exhausted. Too many dropped calls with IT support, too much time waiting for systems to load, too many mornings wrestling with a VPN that only sometimes works. She doesn't say the technology drove her out. But it did.

As a law office manager, your employee retention tools are normally compensation, culture, and a balanced workload. While those are important, there’s one contributor to staff burnout and departure that rarely makes it onto the HR agenda: bad IT.

The Numbers Behind the Frustration

The numbers behind this assertion are hard to ignore. Microsoft's 2025 Work Trend Index, which surveyed 31,000 workers across 31 countries, found that nearly half of them (46%) are experiencing burnout due to issues like poor VPN connection, ignored help desk tickets, and document management systems that crash when a deadline looms.

North American law firms are feeling it too. Thomson Reuters' 2025 Report on the State of the Legal Market found that the law offices who invest in newer and better technology are more successful at retaining top talent. Those that resist technological change, on the other hand, experience higher turnover. It’s 2026, and unstable systems can make it impossible for people to do their jobs.

Be warned: your staff likely won’t complain about this in performance reviews. They'll initially try to adapt or come up with workarounds - at least for a while. But they’ll eventually decide that they don't want to do it anymore.

Why Are Law Firms Especially Vulnerable to a ‘Tech Exodus’?

Law firms run on tight deadlines. When technology fails, the fallout can be far-reaching. A document management system that crashes during a filing deadline isn't a minor inconvenience: it can impact the timeline of the case. Similarly, a remote access tool that won't connect when a lawyer is working from home can lead to frustrating delays.

Your legal support staff tend to feel this most acutely. They're the ones triaging the day-to-day responsibilities, managing client calls, and keeping the firm running while lawyers are in court or client meetings. When their tools don't work, disorganization and frustration set in.

A 2025 survey by Workspace 365 found that 86% of legal professionals surveyed would consider leaving their jobs due to poor workplace technology - a higher rate of dissatisfaction than any other industry group in the study. While this data reflects the UK legal market, the pattern it describes is consistent with what firms on this side of the Atlantic are reporting as well.

The Retention Angle You Might Be Missing

Replacing a staff member costs anywhere from a third to twice their annual salary when you account for recruiting, onboarding, and the lost productivity during the transition. For a legal assistant earning $55,000 a year, that can add up to a lot of money. For a firm that loses two or three people in the same year, the combined cost is a pretty heavy line item.

The problem is that most of those departing employees may not give you their real reason for leaving. People don't usually write "slow computers and a help desk that takes three days to respond" in their resignation letters. They say they found an opportunity that's a better fit. They say they're looking for something new. But the daily hassle of bad technology is part of why they started looking in the first place.

While system breakdowns are frustrating for anyone, younger staff members, who now make up a growing portion of law firm support teams, have little patience for technology that can't keep pace with their day. They've grown up with fast, reliable tools in their personal lives. When the systems at work are slower and clunkier than what they use at home, it says something to them about how much the firm values their time.

What You Can Do as a Law Office Manager or Administrator

Unstable tech has to be addressed if you want to stay competitive and maintain client trust. But while you locate a trusted Ontario IT service and support provider, here are same steps you can take to treat IT as a retention issue: 

• Ask your staff directly. A short, anonymous survey asking about technology frustrations can surface problems you didn't know existed. You might find that half your team has a workaround for a system that should have been fixed two years ago. You can't fix what you don't know about.
• Track IT complaints alongside HR data. If you're seeing turnover in a particular team or role, look at what their daily technology experience is like. Is their software outdated? Are their support requests taking too long? The correlation may not be obvious at first, but it's worth looking for.
• Set a response time standard with your IT provider. If your team is waiting days for help desk tickets to be resolved, that's a morale issue, not just a technical one. A 20-minute average response time, for instance, is achievable and makes a measurable difference in how supported staff feel day to day.
• Make technology part of onboarding conversations. When new staff start, ask them about the tools they're comfortable with and flag early when something isn't working for them. Building that feedback loop from the beginning makes it easier to catch problems before they become a reason to leave.

The Bigger Picture

Retention strategies in law firms have traditionally centred on compensation, mentorship, and flexibility. Those things still count. But they work best when the basics are already in place, and for a lot of firms, reliable technology is still a basic that hasn't been sorted out.

Staff who trust that their systems will work (and that help is available when they don’t) are the staff who stay. That's not a complicated conclusion. It's just one that tends to get overlooked until someone hands in their notice.

The cost of good IT support is predictable. The cost of losing good people isn't.

Nolan is an expert in IT for law firms. In 2024 he became CEO of IT support company Inderly, local to Hamilton and Toronto and serving law firms across Ontario.  

When not leading the Inderly team, Nolan can usually be found writing and shooting independent films, playing D&D, or enjoying Toronto’s best theatre productions and concerts.