TLOMA Today

Welcome back Team TLOMA!

May was certainly a whirlwind! Experiencing 3 seasons the week of Victoria Day was certainly not on my bingo card, but very happy we are here in sunny June because we have lots of great things in store!

Before we get to that though, I would like to share a quick recap for the fantastic SIGs we had last month.

May Event Debrief

On May 13, Christian Calabrese & Nick Di Paola from HUB Technology Group Inc. led a SIG on Public vs. Private AI: What Every Legal Professional Needs to Know. A very timely lesson to help us make smarter choices when selecting the right AI for our firms. If you have any questions for Christian or Nick – please free to connect with them directly.

Miguel Ribeiro from VBS IT Services led a SIG on May 27 on Workflow Debt: Why Most Legal AI Initiatives Fail, and What to Do About It. Miguel’s honest 4 step-framework will certainly come in handy when implementing or adjusting any AI adaptation. To connect with Miguel, please see the links in his bio. 

Now to the part you’ve all been waiting for!

Upcoming Events

SIGs

A couple of SIGs coming up before we break for summer:

• June 10 - Finance SIG - Tools of the Trade: A Vendor Showcase of Legal Management & Accounting Software
• July 8 - Marketing SIG

Both sessions promise to be informative and engaging.

Summer Networking

On June 16 join us for our Summer Networking Event at the Cactus Club sponsored by iCompli, MSP Corp, and IT Solutions – can’t wait to share a bubbly beverage with you!

Be sure to purchase your ticket early to ensure your spot! As always, if you have a colleague or acquaintance who would be a great fit for TLOMA, please reach out to Karen & Courtenay to secure a complimentary pass for them to attend so they can get a taste of TLOMA!*

*Limited number of complimentary passes, so act fast!

2026 TLOMA Conference Preview/Info Webinar

If you have not yet signed up for conference and would like more information – please join your 2026 Conference Chair and Conference Vice Chairs Amanda Hinsperger and Brad Keenan respectively for all of the conference details and more!

Virtual Town Hall

We have our inaugural Virtual Town Hall on June 24! Don’t miss your chance to “Meet The Board”. We look forward to seeing you all there and answering your questions!

As I said earlier – June is action packed! If you haven’t been as active in your membership recently and are looking to get back into it – this month is a perfect opportunity to reconnect with your fellow members and make some new connections.

Stay cool TLOMA!

Every Autumn TLOMA hosts our Annual Conference and Tradeshow, after what has felt like a nearly unending winter, I am the last person to rush summer’s end, nonetheless the days fly by and September will be here before we know it so I am excited to share a little bit about what you can look forward to this year!

Register anytime!   

Never been to Conference? Join us on June 17^th for a 30-minute virtual session where we share everything you can look forward to, as well as insider tips and tricks to maximize your experience! Register Here!

This year’s Conference is being held at the Hamilton Convention Center. Hot off the heels of the Junos last month, the HCC has seen a number of upgrades, and we’re excited to host our event at this venue for the first time ever! Do you work or live in the GTA and have struggled to attend past events that are farther outside Toronto? This is your year!! Hamilton is accessible by train, bus, even plane – and we are so excited to host this year’s Conference in a location that is more accessible to those in the GTA.

The Conference Committee is hard at work making sure this will be another jam-packed event you won’t want to miss. Event registration kicks off the afternoon of Tuesday September 22^nd followed by our Welcome dinner at the beautiful Art Gallery of Hamilton (conveniently located right across the street from the Conference venue and hotel)! Will this be your first year at Conference? Be sure to join us for the exclusive First-Time Attendee Cocktail Reception where you can connect with other first-timers as well as get to know some long-time members, excited to help you maximize your first Conference experience!

Technology continues to be a trending topic in law office management so this year we’re turning the spotlight back onto the people behind the tools we use, asking what levels up law firms Beyond the Billable? Wednesday, Sept 23^rd kicks off with a high-energy Opening Keynote by Daniel Lewis, who will inspire us to build environments where people and performance flourish, because the future of law isn’t just more efficient – it’s more intentional. Choose a workshop that best suits your interest and needs, then we are excited to bring everyone together for our second annual Expertise Exchange! After receiving overwhelmingly positive feedback on this session last year, we are bringing back the Expertise Exchange and making it even better, with longer sessions on the hot topics we all want to know more about – this event is sure to bring you a ton of knowledge and peer connections!

The Tradeshow kicks off immediately following lunch on Wednesday and is one of the most exciting parts of our event – be sure to wear your comfortable shoes and walk the aisles to meet your favourite (and new!) Business Partners, who are here to talk with you about the latest and greatest in their fields. Pick up swag and connections alike – and be sure to get your badge scanned to be entered into a draw for great prizes later that night! Not only are our Business Partners vetted providers of every service you might imagine, but they are also experts and leaders who love to share the inside scoop on what they are seeing in our industry.

Wednesday will close out with a bang at our networking reception and dinner where we can mix and mingle with friends and Business Partners alike! Enjoy an extra opportunity for more conversation during a beautiful meal or kick back and have some fun with your new friends! While the annual Conference and Tradeshow are about soaking up as much information as possible – equally important are the connections we build at this event. Connect with like-minded people, who are trying to solve the same problems you are and build a network of reliable peers for life.

We’re right back at it Thursday, Sept 24^th with a full day of education! The Agenda is live – so take a look to see all the sessions we’ve got planned! We are sure this year’s event will bring you new solutions and more ways to build value in your firm Beyond the Billable.

If you’ve never been to Conference before, be sure to register for our exclusive webinar, where we’ll share details and insider tips on what you can expect from this year’s event!

Remember to Register, we cannot wait to see you in September!

Sincerely,

Amanda Hinsperger
Conference Chair

“Do you know what went into it?” 

The integration of artificial intelligence across Canadian law firms is no longer a futuristic concept. It is a daily reality. According to a March 2026 Thomson Reuters survey of the Canadian legal market, 89% of firms have now adopted AI tools, with no firms reporting that they are avoiding the technology entirely. Most firms are using it in some way, whether for legal research, document review, admin support, or hiring. At this point, the conversation is not really about whether firms should use AI. It is about how to use it properly without losing the human judgment that still matters so much in legal recruitment.

Nobody is denying the efficiency of AI tools. They can help sort resumes, organize candidate information, automate scheduling, and reduce administrative churn. For busy firms and hiring managers, that can be a real advantage.

But as we know, legal hiring is rarely straightforward.

A resume can tell you where someone has worked, what software they have used, and how many years of experience they have. What it cannot always tell you is how that person handles pressure, how they communicate with a demanding partner, or whether they have the right temperament for a fast-paced litigation desk or to support multiple partners.

This is where I find human connection still makes a difference.

Take a senior legal assistant with a gap on their resume or a couple of shorter stays at smaller firms. An automated system may see that as instability and auto-reject them. But when you sit down with the candidate, the context changes entirely. Maybe they stepped away to handle a family matter. Maybe the short stint had more to do with firm culture than performance. Those details completely reframe a candidate, and you won’t find them in a keyword scan.

In legal support roles, technical skill is important, but fit is often what determines whether someone succeeds long term. Law clerks, legal assistants, billing coordinators, and support staff are the people keeping the firm moving behind the scenes. They need to be organized, reliable, professional, and able to work with different personalities. You can't measure that through an automated filter.

Many of the strongest legal professionals are not actively applying to jobs. They are already employed, busy, and often cautious about making a move. Connecting with those candidates takes trust, timing, and a real conversation. A well crafted job posting might open the door, but it takes genuine relationship-building to convince them to walk through it.

Firms that ignore technology are going to lose out on speed, but the ones that rely entirely on it are going to lose out on talent. Efficiency is great, but a bad hire costs far more time than an algorithm will ever save you. When selecting the talent that will actually elevate your practice, real conversations remain irreplaceable. Software might identify the candidate, but it still takes human connection to build the team.

Geoff Silva is a Partner at Kent Legal in Toronto. Since 1972, Kent Legal has been a cornerstone of the GTA’s legal community, utilizing decades of experience and strong industry ties to effectively match professionals with even the most demanding positions.

You can reach Geoff at gsilva@kentlegal.com for any market information or recruitment needs.

Once a firm understands what information governance truly is - and accepts that it enables rather than restricts progress - the next question is immediate:

Where do we begin?

For many firms, this is the moment where momentum slows. Governance feels expansive. It touches every system, every practice group, and multiple operational teams. There is concern that “doing governance properly” requires a dedicated department, a major technology overhaul, or a multi-year transformation programme. That assumption is often what prevents action.

In reality, the most effective governance strategies are not comprehensive from day one. They are phased. They are pragmatic. And they are designed around the firm’s operational maturity rather than an idealised future state.

A governance strategy that fits is not the one that looks most ambitious. It is the one that can be sustained.

Why one-size-fits-all governance fails

Large international firms may have formal governance offices and global compliance frameworks. Smaller regional firms may operate with simpler system environments and informal oversight. Mid-sized firms sit in a more complex position. They often:

• Operate across multiple offices or provinces
• Serve sophisticated clients in regulated industries
• Manage growing digital repositories
• Work with lean operational teams
• Lack dedicated governance headcount

Adopting a framework designed for a global firm can overwhelm resources. Attempting to manage governance informally can leave structural gaps. Your strategy must reflect reality.

It must consider how matters actually open and close in your firm. How classification decisions are made. How financial systems interact with document repositories. How access is granted in practice, not just in policy.

Governance design that ignores operational culture will stall.

Phase one: Establishing visibility before change

The first stage of a practical governance strategy is not reform. It is visibility.

Before implementing new workflows or introducing system adjustments, firms need a clear picture of their current lifecycle landscape. This often involves answering questions such as:

• How many matters are technically open but operationally dormant?
• How consistently is retention classification applied at matter intake?
• What percentage of stored data is associated with inactive matters?
• Are collaboration workspaces aligned with document management retention rules?
• How is disposition currently approved and documented?

In many firms, the answers reveal predictable patterns. Closure may depend on manual reminders. Retention categories may not always be validated. Access permissions may remain static long after activity ends.

This stage is not about identifying fault. It is about identifying misalignment. Without visibility, strategy becomes speculative. With visibility, it becomes targeted.

Phase two: Clarifying governance structure and ownership

Once the firm understands its operational landscape, the next phase involves defining responsibility. Some firms do not have an information governance team. Instead, governance responsibilities are distributed across:

• IT
• Records
• Risk or Compliance
• Finance
• Operations

A strategy that fits does not attempt to centralize everything immediately. It clarifies roles.

Who is responsible for maintaining retention policy integrity?
Who ensures system rules reflect policy updates?
Who approves disposition?
Who reports governance metrics to leadership?

Shared ownership works when it is structured. Without clarity, important decisions stall. Retention enforcement hesitates because no one wants to authorize deletion. Closure reviews become inconsistent and access validation is postponed.

Defining governance structure does not require new titles. It requires defined decision rights.

Phase three: Prioritising high-impact controls

A practical strategy does not attempt to address every governance issue simultaneously.

Instead, it prioritises areas that:

• Reduce measurable risk
• Improve operational clarity
• Support client expectations
• Demonstrate early progress

For many Canadian mid-sized firms, this often means focusing first on:

• Matter closure discipline
• Retention enforcement consistency
• Visibility into dormant data
• Structured disposition workflows

These areas typically deliver measurable impact without significant disruption.

For example, aligning financial matter status with document repository lifecycle can immediately surface inactive content. Validating retention classification at intake reduces downstream ambiguity and introducing structured disposition approvals improves defensibility.

Early wins build internal confidence.

Phase four: Embedding governance into workflow

Governance strategies fail when they remain project-based. Periodic clean-up campaigns may temporarily reduce data volumes, but without embedded workflow controls, accumulation resumes.

A strategy that fits must integrate governance into routine operations:

• Matter intake should require validated classification.
• Closure should confirm lifecycle status and trigger retention timelines.
• Dormant matters should surface automatically for review.
• Disposition should follow documented approval workflows.

When governance becomes part of existing processes, it stops feeling like an initiative and starts functioning as infrastructure. For mid-sized firms, this is critical. Limited headcount means governance must operate efficiently within established workflows.

Phase five: Executive oversight without bureaucracy

A practical governance strategy also includes executive visibility. This does not require complex dashboards at the outset. It requires consistent reporting of a small number of meaningful indicators:

• Volume of open versus closed matters beyond expected thresholds
• Retention enforcement activity
• Disposition volumes
• Data growth trends

When leadership reviews governance metrics alongside operational performance metrics, it reinforces importance. This leads to governance becoming part of firm management - not an isolated compliance activity.

Avoiding the perfection trap

One of the most common reasons governance strategies stall is the pursuit of completeness before action. Firms attempt to design a fully mature governance framework before implementing initial controls which can delay progress.

A phased strategy recognizes that maturity evolves. Incremental alignment — improving closure discipline, clarifying ownership, validating classification, embedding retention enforcement — creates cumulative improvement.

Perfection is not required at launch. Direction and consistency are.

Designing for sustainability

The most important test of a governance strategy is sustainability.

Can the firm maintain it with existing resources?
Can workflows support it without constant oversight?
Can leadership monitor it without excessive reporting burden?

If the answer to these questions is no, the strategy is misaligned.

Firms benefit from governance strategies that respect operational bandwidth while improving control and a measured, phased approach is more durable than ambitious transformation.

The strategic outcome

A strategy that fits achieves more than compliance.

It provides leadership with clarity.
It reduces operational friction.
It strengthens defensibility.
It builds readiness for innovation.

It allows the firm to demonstrate structured lifecycle control - internally and externally.

And importantly, it creates a stable foundation for the next stage of maturity because once strategy is defined and phased implementation is underway, the next challenge becomes execution at scale — ensuring governance operates consistently across systems.

In the next article, we will explore the role of technology in making information governance work in practice, and why system alignment is essential for sustainable enforcement.

Here's a confession: I spent years trying to be the kind of person who blocks time for business development and actually follows through.

You know the drill. Tuesday afternoon, it’s on the calendar: 2-4pm: “BD time." You sit down with your carefully curated list of people to call, emails to send, ideas to nurture. You open LinkedIn. You stare at your screen. You think about how you should phrase that follow-up. You wonder if it's weird to reach out after three months. It probably is, so you check your email. You refill your coffee. You tell yourself you'll come back to it.

And somehow, two hours evaporate.

For the longest time, I thought this was a discipline problem – a character flaw, even. I envied – and still do, frankly – people who took to time-blocking like fish to water.

As it turns out, I can embrace time-blocking for focused BD time – just not alone. When it becomes collaborative work, I can adhere to time-blocking with panache… if I do say so myself.

What if we've been thinking about BD wrong?

Business development is inherently relational. It's about connecting with people, building trust, and creating opportunities for collaboration. So why do we treat it like a solo sport?

So often, advice on this sounds something like: "Block your calendar and make it a priority. Just do it."

Which is... fine. Except it doesn't account for the fact that some of us have brains that don't naturally stay on task when left to our own devices. Why hello, fellow ADHD’rs! Do you relate to me when I tell you that my brain is excellent at many things. Staying focused on a single task without external structure… that is not one of them.

Business development is particularly vulnerable to this. It's important – but it’s rarely urgent. It's open-ended. There's no hard deadline, no client waiting, no fire to put out… which means it's exactly the kind of work that gets endlessly postponed in favour of literally anything else that pings, beeps, or appears in my inbox.

My brain runs on deadlines and dopamine. Give me a crisis or a clear deliverable, and I'll hyperfocus my way through it. But BD doesn't work like that. There's no due date. No obvious finish line. Just this vague instruction to 'stay visible' and 'build relationships,' which my ADHD brain interprets as 'do this never’.

Enter: body doubling

This concept comes from the ADHD community, but it turns out to be useful for everyone – like so many ADHD strategies – because distraction is a pretty universal experience.

The idea is beautifully simple: you do your thing while someone else does their thing, at the same time, in the same space. That's it.

Sometimes it's over Zoom. Sometimes it's side-by-side at a coffee shop. It can even be in a boardroom at the office, if your partner in this is a colleague. Sometimes you announce what you're working on. Sometimes you just nod hello and get to work. But you show up together, and yes, things actually get done.

It works because it creates external accountability and shared focus. When someone else is there – also working, also resisting the urge to check their phone or fall down a research rabbit hole – you stay on task. Not through willpower. Through presence.

What this looks like in practice

Last month, I had a colleague over to my place for two hours. She needed to draft a lengthy proposal and I had about fifteen email reach-outs that I needed to send. That is exactly the kind of outreach that's easy for me to start and then abandon halfway through when something shinier catches my attention.

We set a timer. We worked in parallel. We barely spoke.

Imagine legal operations like a series of conveyor belts in a factory. If you want the final product faster, does simply speeding up the belts actually help? Not if there’s already a bottleneck slowing things down. And what if one belt is supposed to feed into another—but they’re slightly misaligned?

Why Technology Alone Can’t Fix a Broken Process

The same dynamic shows up in law offices every day. As legal operations become more digital, technology and AI promise greater efficiency and productivity. But when workflows have gaps, bottlenecks or hidden errors, those tools don’t solve the problem—they expose it. Automating a broken process doesn’t reduce chaos; it accelerates it. Work moves faster between steps that don’t quite connect. Errors spread more quickly. Small misunderstandings turn into recurring operational headaches.

This becomes even more apparent as a firm grows. Processes that once lived in one person’s head are suddenly repeated by multiple team members, each interpreting them a little differently. To compensate, firms often layer on more technology to “coordinate” the work. Over time, though, that technology can magnify the original process issues. Staff end up distracted by constant troubleshooting and workarounds. Before you know it, digital friction has quietly embedded itself into your day-to-day operations.

The Office Manager’s Reality: Keeping The Firm Running

As a law office manager, you sit at the intersection of people, process, and technology. When there are operational deficiencies, the complexity without structure can be exhausting. Especially if you become the human glue holding everything together. There simply may not be time to think about how the work ‘flows’.

You don’t need more tools. You need clarity. Clarity about how work starts, how it moves through the firm, who is responsible at each stage and what “done” really looks like. When that clarity exists, technology becomes a powerful ally instead of another source of friction.

Before Speeding Up, Slow Down

The current digital movement favors increasing productivity and efficiency with automation and AI. This has obvious appeal and benefits because it reduces costs and allows the law office to meet the pace demands of our modern business environment.

However, to truly benefit from these tools it is imperative to implement business process re-engineering before automation. Without a long-term strategy, technology improvement efforts can end up being fragmented and eventually require a lot of reworking.

This doesn’t require a monumental operational shift. Change can be incremental, starting with tasks and projects that are best suited for automation. High-volume, repeatable processes deliver the clearest returns. Contract review and approval, NDA processing, compliance sign-offs, budget approval requests and matter triage are great places to start. Processes with clear decision points, defined stakeholders and consistent steps are particularly effective candidates.

A Thoughtful, Guided Path from Friction to Flow

Once the processes to be improved have been identified, consider a thoughtful 3-step approach.

Step 1: Define the Workflow Before you Improve it

Before automating any process, define it clearly from initiation to completion.

This doesn’t need to be overly technical. At a minimum, you want to understand:

• Where the process starts and what triggers it
• Who is involved at each stage
• What inputs are required and what outputs are produced
• Where decisions are made and who makes them
• How success is measured

This exercise alone often surfaces hidden assumptions and inconsistencies. Two people may believe they are following the same process—only to discover they’ve been doing it differently for years.

For office managers, this clarity reduces dependency on individual “workarounds” and creates shared understanding across the firm.

Step 2: Identify Bottlenecks and Redundancies

Once the workflow is defined, patterns start to emerge. Are any of the following noticeable?

• Unnecessary approvals
• Duplicate data entry
• Outdated procedures
• Disconnected systems

You may notice steps that exist purely because “that’s how it’s always been done”, handoffs that introduce delays because ownership isn’t clear, or manual checks that duplicate work already happening elsewhere.

By identifying and correcting bottlenecks, redundancies and common errors, you can simplify the process before layering on technology. This is where real efficiency gains are made—not by doing more, but by doing less more intentionally.

Step 3: Improve and Automate with Purpose

Only after a workflow is mature and well-understood does technology truly shine.

At this stage, automation supports the process instead of dictating it. Tools are chosen to reinforce good habits, reduce risk, and make work easier for everyone involved.

When evaluating new software or technology tools, it helps to step back and assess each option through five practical metrics:

• Integration capabilities matter because tools should fit naturally into the systems your team already relies on, not create more manual work or silos.
• Scalability ensures the platform can grow with your firm, whether you’re adding staff, opening a new practice area, or adapting to new client demands.
• Security compliance is non‑negotiable in the legal environment, where protecting client data and meeting regulatory obligations is an inherent responsibility.
• Development flexibility speaks to how well a tool can adapt over time, allowing for updates, customization, or new features without forcing a full replacement.
• A strong vendor ecosystem provides reassurance that you’re not relying on a single, fragile solution, but rather a supported platform with partners, integrations, and guidance available when you need it.

From Chaos to Confidence

When workflows are streamlined, aligned and then supercharged with the right technology, the positive impact can be felt firmwide. The firm doesn’t just move faster—it moves more predictably. This unlocks a road to smooth operations and successful scaling.

The right workflow turns digital friction into flow. It replaces constant troubleshooting with steady progress. And it allows office managers to be strategic leaders shaping how the firm operates.

You don’t need to fix everything at once. You just need to start in the right place.

Law firms, as part of their normal evolutionary path, have historically moved from small practices to full-service mid-sized firms.

Their reasoning for expansion made sense. Markets have historically punished service gaps more than they have punished firms that overreached, and midmarket-sized clients have sought firms that could handle all or most of their legal affairs.

Further, lateral hires and a lack of succession planning resulted in the addition of practice areas and industry alliances – national, global, and specialty-focused - that have allowed firms to "punch above their weight" by reinforcing the ability to offer full-service locally.

Current market conditions, however, are making the traditional evolution less financially prudent than in the past. Several developments are contributing to this:

• Client consolidation and paneling are resulting in reduced demand for outside counsel.
• Talent wars with big firms and specialized boutiques, recruiting senior partners and practice groups from midsize firms.
• Scale economics and cross-border reach.
• Price/fee pressure and alternative arrangements.
• The ability of boutiques with clear niche expertise (e.g., securities, competition, FinTech, life sciences) to attract premium mandates.
• Technology and process investment and efficiency variations
• Declining revenue streams for mid-sized firms due to clients shifting routine work to alternative legal service providers or in-house legal ops teams.
• In‑house counsel sophistication.
• Marketing and international networks that midsize firms cannot belong to or capture.

So, what are the simple indicators that big law firms and specialized boutiques are squeezing your mid-sized firm out? They include:

• Fewer mid- to large-sized mandates and more commoditized work.
• Competing on price without the scale or tech to reduce costs.
• Losing rainmakers or senior lawyers (talent drain) undermines client retention and the capacity to handle bigger matters.
• Being perceived as lacking specialization or bench strength for top-tier work.

A full-service "focused" model, while not the only solution, has the greatest chance of responding effectively to their squeeze play.

A key criterion for evolving into a "focused" full-service firm is the discipline to stick to the necessary strategy. The strategy involved in such a transition should include:

1.  Choose 3–5 "anchor specializations" and dominate them. These are practice areas where the firm can realistically rank in the top 3 in the region.
2.  Maintain "supporting" practice areas – but only those that protect client retention, are profitable, and do not require expensive, large infrastructure.
3.  Increasing your complement through alliances, referrals, and co-counsel, not adding bodies.
4.  Dedicated investment in operational excellence - speed of service, responsiveness, AI-enabled delivery, workflow efficiency, etc.
5.  Redesigning your service pricing to match mid-market client expectations, including various alternative arrangements.
6.  Building your brand on specificity, not generalist (we specialize in X, Y, and Z and support your legal needs across the rest).
7.  Embracing succession planning as a recruitment tool, a client retention strategy, and a growth opportunity.

In pursuing this strategy, Steve Woodruff's comment comes to mind, where he pointed out, "Not all business is good business, and not every customer is a good customer." ― Clarity Wins: Get Heard. Get Referred.

Moving to a "focused" full-service firm is not the only long-term solution, nor will it guarantee a leveling of the playing field with big law and specialty boutiques, but doing nothing will result in an increased squeeze on mid-sized firms at multiple levels.

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.