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May, 2026
Golden Ticket - Facility Plus - Office Moves - November 1/23 - December 31 /25 Leaderboard
May, 2026 | Presidents Message

President's Message

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Issacson, Ava
Author Ava Isaacson

Welcome back Team TLOMA!

Sending a big thank you to all who organized and attended TLOMA events in April. What an exciting month! Despite the battle between spring and old man winter – our members came out on top!

April Event Debrief


The 2026 Compensation Survey launched on April 8, 2026. If you wish to participate and/or purchase the survey but have not yet registered, make sure to do so by June19, 2026.

Our first Networking Event of the year was held at The Joneses on April 15. Special shoutout to our event sponsors PaayaTech, Dexco & iCompli. Another big thank you to our undercover mole played expertly by James MacInnis and our super sleuth winner - Michelle Bilboe!


Sandra Bekhor led an excellent SIG on April 21 re Feedback that Works: Coaching Managers for Real Impact. If you missed it, or would like to watch it again, be sure to login to Member365 to watch the recording.

May is for Mental Health

As members of management, our roles can be isolating and all-consuming. Without having proper support systems in place (and even with support systems), the toll on one’s mental health can be extreme. Benefits service providers in recent years have amped up their EAP offerings to keep up with the demand but burnout and the stigma around it are still prevalent.

This year, consider participating in and promoting mental health awareness during Mental Health Week. Every year the Canadian Mental Health Association (CMHA) dedicates a week towards educating and providing resources to those in need. Mental Health Week will take place from May 4-10, 2026 with the timely theme, "Come Together" which aims to foster belonging and reduce loneliness.

I also encourage those who are feeling burnt out or need to vent to reach out to your fellow TLOMA members. I say it every month but I mean it! For those participating in the Mentor Match program, consider discussing with your mentor/mentee. For those feeling a little shy, reach out to a colleague in your Human Resources department (if you have one),  your EAP provider or visit our Wellness Resource landing page on the TLOMA website.

Nominating Committee

Beginning the first week of May, TLOMA will be sending out information requesting TLOMA members to volunteer to be part of the Nominating Committee. By participating on the Board or volunteering for one of our other roles, you'll gain valuable insight into how a Not-For-Profit Association operates. Want to Make an Impact and Help Fill Key Roles! Please watch your inbox for details.

Upcoming Events

We have a Technology SIG on May 13 and an Operations SIG on May 27 – both topics TBA. Be sure to register so you don’t miss out on great speakers and all of the current law firm changes.

Last but not least, on behalf of the Board of Directors, we are pleased to announce on June 24, 2026 we will be holding a virtual “Meet the Board” session where we will provide updates on what the Board is working on, answer your Q&A’s, canvas member suggestions and some networking. Stay tuned for further information on how to sign up!

‘til we meet again!

Ava

Ava Isaacson is the Director of Team Development at Sherrard Kuzz LLP, one of Canada’s leading employment and labour law firms, representing employers. Her responsibilities include recruiting, training, managing, supervising, coaching and motivating the support team firm wide.  Ava has been in the legal industry for more than 10 years, in both the public and private sectors, with a focus on employment and labour relations.

Ava has a Bachelor of Arts degree in communications with a specialization in creative writing and journalism from University of Windsor, and an Ontario College Graduate Certificate in human resources management from Seneca College. She is a licensed paralegal and has obtained her CHRP certification. 

Ava is honoured to be selected as a member of the Board of Directors and is looking forward to tackling the exciting new challenges ahead.

May, 2026 | Article

TLOMA 2026 Annual Conference and Trade Show

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Hinsperger, Amanda
Author Amanda Hinsperger

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!

The end of this month marks the end of Early Bird Pricing – so be sure to Register soon and cash in on this discount! 

This year’s Conference will be 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 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 22nd 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 has been the trending topic in law office management for the last several years so this year we’re asking the question: what levels up law firms Beyond the Billable? Wednesday, Sept 23rd kicks off our programming 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. In addition to workshops by three of our Elite Sponsors, Jelly Marketing LawStream by Streamline IT and Thorpe Benefits, Wednesday will also see 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 Partner’s vetted providers of every service you can imagine, but they are also industry leaders who love to share the inside scoop on what they are seeing in our industry.

Wednesday will close with a networking reception and dinner where we can mix and mingle with our new connections and Business Partners alike! Enjoy an extra opportunity for more conversation 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.

Keep an eye out for emails coming your way, announcing more sessions, or peek at the Agenda to see what has already been announced! We are sure this year’s event will bring you new solutions and new ways of thinking about how you can build value in your firm Beyond the Billable.

I look forward to sharing more details about this exciting event and cannot wait to see you in September!

Sincerely,

Amanda Hinsperger
Conference Chair

Having built a career in Operations and HR, I ventured into the wild and wonderful world of legal management in 2022 when I joined my current firm, Evans, Philp LLP, an insurance defence firm in Hamilton, where I am now Director of Operations. 

As so many of us TLOMA members do, I manages my firm’s day to day operations, client compliance, HR and (the seemingly never ending) more. I may have built my career in operations and HR, but boy was there a lot to learn about the nuance of law office management! TLOMA has been an incredible resource for not only reliable, applicable information, but also helping me build a network of peers I never would have met otherwise. 

I joined the Conference Committee in 2024 as a way to contribute to the community, jumpstart that networking and push myself out of my comfort zone. Now I am proud to be Chair for our 2026 Conference in Hamilton! I am so grateful to be the Board representative for the incredible committee we have built. The committee has been hard at work to bring a packed agenda, and we hope to see you in September!

May, 2026 | Article

Feedback that Works: A Simple System HR Can Share with Firm Leaders

Feedback that Works
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Bekhor, Sandra
Author Sandra Bekhor, MBA, CPQC,

Giving feedback is stressful for everyone – avoiders to straight shooters. Does any of this look familiar?

  • Sara was just promoted and is now managing her old law school friend. But Lisa is missing the big picture on her files. Sara needs to say something, but she’s afraid of damaging the friendship.
  • Luke knows he’s very direct. He’s fast and efficient. He says exactly what he thinks in the moment. So why don’t they get better, even when he tells them exactly what to do?
  • Tom assigns what he needs to, and when it comes back with errors (the same ones, again and again), he just fixes them. That’s his job as the senior lawyer, isn’t it? Besides, he gets along with everyone and he likes it that way.

 

So, what’s this aversion really about? Managers worry they’ll appear unfair or trigger a negative reaction, so they delay, delegate, or dilute their feedback. Meanwhile, issues quietly fester, underperformance gets entrenched, and high performers get ignored because “they’re fine”—until they leave for somewhere they can really grow.

At some firms there’s an expectation that HR can “handle” performance‑management conversations on behalf of lawyers and that this checks the box. But associates want to hear from the people who assign them work, see their day‑to‑day performance, and understand as lawyers what “good” looks like. When HR is asked to step in, it weakens the sense of being known and supported by the person whose opinion matters most about their future.

Underneath much of this discomfort is social uncertainty: it’s not clear what “appropriate” looks like in this kind of conversation, especially when you’d really like to avoid creating tension with someone you work with every day.

Here’s where HR can help. Instead of asking managers to “be braver” or “just do it,” you can give them a simple, shared structure to lean on. It’s not unlike having court rules. Even very polite lawyers can shift into fierce, focused advocacy in the courtroom because there’s a structure that makes that behaviour permissible, expected even.

Giving feedback in 3 stages

Before: getting ready

  • Get clear on goals: what success looks like in this role, for this person’s career, and for the firm.
  • Choose 1–3 priorities for this conversation rather than “everything at once.”
  • Gather concrete examples (good or bad) so you’re talking about real data, not impressions.
  • Check assumptions and biases, including any recent events that might colour your view.


During: the conversation itself

  • Manage yourself immediately before and throughout the meeting. Notice any signs of discomfort – sweaty palms, fidgeting, shallow breathing. Take a few mindful breaths to come back to your calm, grounded self.
  • Make it a two‑way conversation. Ask questions, stay curious, and resist the pull to assume you already know the whole story.
  • When appropriate, share a story from your own experience to show you recognise the hurdles they’re facing. This helps build trust and makes it more likely they’ll respond and your conversation will have real impact.


After: turning it into a rhythm

  • Agree on 1–2 concrete next steps to establish accountability.
  • Set a schedule for ongoing feedback conversations, so you’re not waiting for a crisis or an annual review.
  • Ask for feedback on your feedback, and make it easy for them to be honest by sharing how their input will help you support them better.

 

Hybrid work amplifies all of this discomfort. Thank‑yous get shortened or forgotten. Small issues are harder to see until they’re big. And because people aren’t chatting casually, giving feedback feels even more socially awkward.

To get comfortable with this process, we need to take a closer look at what it means to be “kind.” Avoiding hard truths or just “being nice” can feel kinder in the moment. But it’s not kinder to let someone believe they’re performing at a higher level than they are, only to be deeply disappointed when a promotion doesn’t come through.

We also need to look at what it means to lead. Hierarchy isn’t always helpful. The team needs to know that you’ve been there yourself and can still relate to what’s going on for them—as an ally, rather than a distant superior. Being willing to be a bit vulnerable and share something relatable from your own journey helps people see that they’re not being judged for talking about current limitations or struggles.

I can’t count the number of times I’ve coached smart, young professionals who share a real struggle and, when I ask if they’ve told their supervisor, the answer is no. Every time. Why? Because they worry it will make them look bad and be held against them later. It doesn’t occur to them that by asking for help they could get the support they need and possibly accelerate their growth as a result.

At the end of the day, this process is about building trust. Being honest isn’t always easy. Adjusting your communication style so you can be heard—and so you can really understand—isn’t easy either. But if you trust someone enough to be genuinely honest with them about how they’re doing and what they need to do to get better, they may trust you enough to be honest about what they really need.

You can be that manager who makes your team feel safe enough to open up—and model the way for your leadership group to follow.

That’s what will make your keepers want to stay.

Sandra Bekhor, MBA, CPQC, is a practice management coach and Certified Positive Intelligence Coach at Bekhor Management. For 20 years, she has supported lawyers and other professionals in building practices that align with their real goals. Sandra presents extensively for professional bodies, including for TLOMA, the Toronto Lawyers Association, and the Canadian Bar Association, and hosts the ‘Get in the Driver’s Seat’ podcast on leadership in professional practice.

To learn more:

https://www.bekhor.ca/
https://www.youtube.com/@BekhorManagementToronto
https://www.linkedin.com/in/torontomarketingconsultant/
https://GetInTheDriversSeat.buzzsprout.com

May, 2026 | Article

Mastering information governance

Mastering information governance - 1
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Peter Lamb
Author Peter Lamb

Information governance as an enabler: Why strong governance supports innovation, not constraint

If article 1 established that information governance is broader than records management, the next hurdle is perception.

Even when leadership understands that governance extends across systems and lifecycle stages, there is often a lingering concern — particularly at partner level — that governance introduces restriction. More rules. More oversight. More administrative friction.

In Canadian firms that value professional autonomy and efficiency, that perception can quietly stall progress.

But the firms that have advanced their governance maturity tend to reach a different conclusion.

Weak governance creates friction.

Strong governance removes it.

Where the friction really comes from

When governance is underdeveloped, operational inefficiencies multiply quietly.

Lawyers search across expanding repositories where inactive matters sit alongside current ones. Collaboration workspaces remain accessible long after work concludes. Email archives grow without clear lifecycle boundaries. IT teams manage infrastructure expansion without corresponding data reduction. Risk teams respond to increasingly complex client audits without centralized visibility into lifecycle enforcement.

None of these issues are dramatic on their own. But together, they create drag.

Time is lost searching through outdated content. Storage costs rise steadily. Audit responses become more complex. Innovation initiatives — particularly those involving AI — raise concerns about data quality and exposure.

In these situations, governance is not the obstacle.

Its absence is.

Governance as infrastructure for efficiency

Strong governance reduces noise.

When matters are classified correctly at intake, retention expectations are clear from the outset. When closure, for example, triggers structured review, dormant content does not accumulate indefinitely. When retention rules are enforced consistently across systems, repositories remain proportionate and manageable. This discipline does not restrict lawyers. It supports them.

A cleaner information environment improves search results. Defined access controls reduce unnecessary exposure. Structured lifecycle management reduces the burden of periodic clean-up campaigns.

Governance becomes invisible infrastructure — operating in the background while improving operational clarity.

For Canadian firms operating with lean teams, that efficiency is not theoretical. It reduces manual workload and prevents reactive projects.

Supporting client confidence

Client expectations are evolving and Canadian firms increasingly receive security and governance questionnaires that go beyond perimeter controls. Clients want to understand lifecycle management, retention enforcement, and access review practices. They want evidence of structured oversight.

When governance is informal, responding to these requests requires explanation. When governance is structured, firms respond with data.

That difference strengthens client confidence, and it also shifts the internal narrative. Governance is no longer something imposed externally. It becomes part of how the firm demonstrates professionalism and control.

Enabling responsible innovation

Perhaps the clearest example of governance as an enabler lies in innovation.

Many firms are exploring AI-assisted research, document automation, analytics, and knowledge management platforms. These initiatives depend on high-quality, well-classified, appropriately retained information.

If data is duplicated, inconsistently classified, or retained indefinitely without lifecycle discipline, AI tools introduce risk. Sensitive information may surface unintentionally. Outdated content may distort analysis. Access exposure may widen.

Strong governance mitigates these risks before innovation begins.

When retention is enforced and classification is consistent, data sets become more reliable. When access is reviewed systematically, exposure narrows. When lifecycle discipline is embedded, firms can adopt new technologies with greater confidence.

Governance does not slow innovation - it creates the conditions under which innovation is sustainable.

The cultural shift

In many firms, governance hesitancy stems from culture rather than policy. Partners value autonomy. Practice groups operate independently. Change initiatives must demonstrate practical benefit to gain traction.

Reframing governance as infrastructure rather than restriction helps overcome resistance.

Instead of focusing on deletion or compliance, firms can position governance around:

  • Operational clarity
  • Risk reduction
  • Client assurance
  • Technology readiness

 

When governance is tied to these objectives, it aligns with leadership priorities and it becomes easier to articulate why lifecycle control matters — not as a regulatory obligation, but as a foundation for firm performance.

Reducing strategic risk

Canadian firms operate in an environment of increasing complexity. Cross-border matters introduce data residency considerations. Provincial privacy frameworks evolve. Cyber threats remain persistent. Clients in regulated industries expect demonstrable controls.

Weak governance amplifies exposure in each of these areas. But strong governance reduces uncertainty. It ensures the firm can identify what information it holds, where it resides, and how long it is retained. It provides defensibility if questioned. It narrows the gap between policy and operational reality and strategically, that control supports stability.

Firms that can demonstrate lifecycle discipline are better positioned during mergers, lateral integration, and system upgrades. Governance provides structure during change.

Addressing the “constraint” argument directly

It is worth addressing the concern directly: does governance introduce additional steps?

Sometimes, yes. Structured closure reviews. Documented disposition approvals. Periodic access validation. But these steps are not administrative overhead. They replace larger, more disruptive interventions later.

Without embedded governance, firms conduct periodic clean-up initiatives that consume significant time. They respond reactively to audit findings. They undertake urgent remediation after incidents.

Structured governance distributes effort consistently over time rather than concentrating it during crises. So, in that sense, governance reduces disruption rather than creating it!

From perception to practicality

Once governance is recognized as enabling infrastructure, the conversation shifts. The question is no longer whether governance is necessary. It becomes how to implement it in a way that reflects the firm’s size, structure, and resources.

Firms often don’t have dedicated governance departments. They must align existing teams. They must prioritize incremental progress. But that reality does not prevent maturity. It shapes the approach.

In the next article, we will move from mindset to design — exploring how firms can build a practical, phased information governance strategy that fits their operational landscape and delivers measurable progress without requiring large-scale transformation.

Because once governance is understood as an enabler, the logical next step is structured implementation.

You are welcome to register for the second session in our ‘Mastering information governance’ webinar series. On June 25th, (11am EST), Peter Lamb, will discuss that whilst firms understand the importance of information governance many can struggle to move from intention to action. Limited resources, competing priorities, and unclear ownership often cause governance initiatives to stall before they deliver value. 

This webinar will focus on how firms can build an information governance strategy that fits their size and structure, and how that strategy can be delivered in practice without a dedicated governance team. We will also explore why a phased approach is more effective than trying to do everything at once, and how shared ownership across teams enables progress.

Designed for firms at an early to mid-stage of maturity, this educational session will provide practical guidance on shaping a realistic strategy, defining responsibility, and turning governance principles into day-to-day action.  Click here to register. 

Peter Lamb brings over three decades of experience in legal technology, having served as CIO for two of Canada’s largest law firms where he advanced the use of technology to improve practice management and operational efficiency. He has also worked as a senior account manager helping firms navigate complex technology landscapes and deliver practical solutions to operational challenges. Throughout his career, Peter has successfully led large-scale change management initiatives and has been an active contributor to the legal technology community, including serving on ILTA’s Board of Directors and as Conference Co-Chair.
May, 2026 | Article

Cognitive Decline Frequently an Under Addressed Aspect of Mental Health

Cognitive Decline
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Mabey, Stephen
Author Stephen Mabey

It goes without saying that a firm has a duty to protect clients, ensure competent representation, and take reasonable steps when a partner shows signs of cognitive decline. That includes internal action (adjusting duties, supervising, or transitioning the partner) and, if necessary, reporting to the law society when the risk to clients becomes material.

The often-delayed internal handling and reporting of cognitive decline to the bar society highlight the emotional complexity: loyalty, respect, and the partner’s identity tied to their work. These dynamics often delay action, despite compassionate intervention protecting everyone—clients, the firm, and the partner’s legacy.

Law societies expect firms to report when a lawyer’s conduct may constitute a serious breach of professional obligations. Reporting when the issue is cognitive decline is not automatic!

Technically, reporting is necessary when:

  • The partner’s impairment creates a real risk of client harm;
  • The partner refuses to step back, accept supervision, or adjust duties;
  • The firm cannot mitigate the risk internally, and
  • There is evidence of actual harm, such as missed deadlines, client complaints, or compromised judgment.

 

The third bullet is the most frequent obstacle to firms reporting cognitive decline to law societies.

While the goal of the law society is protection, not punishment, the following typical steps that law societies may undertake in cases of reported cognitive decline are often not seen that way by either the professional identified or the firm:

  • Capacity assessments;
  • Practice restrictions or supervision orders;
  • Mandatory medical evaluations;
  • Temporary suspension if the risk is high; and
  • Support for structured retirement or practice wind‑down.

 

As a result, reporting is tardy if at all.

Cognitive decline is frequently very visible and, unless being ignored because management does not want to deal with it (frequently there but by grace of god go I mentality), can be found normally in the following four key aspects of a lawyer’s practice:

1.  Performance:

  • Increasing errors in routine tasks;
  • Difficulty managing multi-step matters;
  • Overly risk-averse;
  • Reduced ability to integrate facts.


2.  Behavioural:

  • Memory lapses (names in particular).
  • Losing the thread of a conversation mid-sentence;
  • Taking longer to review documents;
  • Becoming overwhelmed by new information or changes, and
  • They get stuck in their own viewpoint when faced with new information.


3.  Interpersonal:

  • Avoidance of complex matters;
  • Heightened irritability or defensiveness;
  • Second-guessing all decisions that previously were routine, and
  • Change in professional persona (from meticulous to disorganized).


4.  Practice Management:

  • Billing issues – drop-in billable hours; inconsistent time entries;
  • Client complaints (responsiveness, clarity, accuracy).
  • Missed compliance obligations; and
  • Technology – difficulty operating systems that they previously navigated easily.

 

At the risk of a penetrating glimpse into the obvious, cognitive decline is a very sensitive issue that should receive more focus from firms because of its direct impact on:

  • Ethical duties (competence, diligence, communication).
  • Client risk;
  • Professional liability exposure;
  • Reputational risk; and
  • The lawyer’s dignity and career identity.

 

This absence of timely action by firms results in many adopting a crisis-driven response.

Stephen has been advising law firms for over 15 years on a wide range of issues, including - strategic action planning, leadership, understudy (succession) planning, compensation (Partner and Associate), organizational/governance structures, partnership arrangements, business development, capitalization of partnerships, partnership agreements, lawyer &staff engagement, marketing, key performance indicators, competitive intelligence, finance, mergers, and practice transitions.

Applied Strategies Inc.'s website contains references from clients describing the value of the services rendered https://www.appliedstrategies.ca/references.php.

Stephen can be reached by email - smabey@appliedstrategies.ca or by phone at 902.499.3895.

May, 2026 | Article

The Lawyers Who Never Have to Sell

The Lawyers Who Never Have to Sell
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Southren, Jane 6oct20
Author Jane Southren

The Lawyers Who Never Have to Sell

On leading clients, serving deeply, and building a practice without a sales pitch in sight

“They don’t just ask clients and contacts what keeps them up at night. They tell them what should be keeping them up at night.”

A Word Most Lawyers Would Rather Avoid

 

Most lawyers are deeply uncomfortable with applying the word “selling” to themselves. That discomfort is not something to be criticized. It is a rational response to what the word has come to mean in the popular imagination: persuading people to buy things they do not need, using charm where substance is absent, and prioritizing your own interests over the person sitting across from you. Lawyers are trained to do the exact opposite, so it is no surprise the concept sits badly with them.

That version of selling has almost nothing to do with how excellent lawyers actually build and sustain a practice. In law, the most effective business development does not look like sales at all. It looks like the kind of generous, courageous, deeply engaged work the best lawyers already bring to every conversation, whether that conversation is with a longstanding client, a new contact, or someone they have just met who may never instruct them directly but might one day send someone who does. Leading clients and serving them well are not in tension. Leading is the highest form of serving, and it is also, as it turns out, the most powerful form of practice development.

Two Things That Are Actually One Thing

 

When lawyers think about business development, they tend to imagine it as a separate activity from the work of being a good lawyer. Something you do after the real work is done, or instead of it. A necessary awkwardness layered on top of the professional identity they actually value. That framing is the source of most of the discomfort, and it is also, in my experience, almost entirely wrong.

The Challenger mindset, which I will describe in a moment, is simply a way of showing up in every professional interaction: genuinely curious, actively listening, applying experience and judgment to what you are hearing, and offering insight and foresight rather than waiting to be asked. You do not need a deep relationship to do this. You can do it from the very first conversation with someone, and doing it well is precisely how the relationship deepens over time. The mindset and the relationship-building are not sequential. They are the same activity, viewed from two different angles.

What that mindset builds, applied consistently across clients, contacts, and connections at every stage of every relationship, is a practice. Not through a deliberate sales process, but as a natural consequence of being genuinely useful to everyone you engage with. Clients come because they have heard you are exceptional. They stay because they feel genuinely looked after. They refer because working with you is an experience they want people they care about to have. Contacts who never become clients become referral sources for the same reason: you were the person who gave them something real, even when you had no particular obligation to.

This dissolves the frame that makes business development feel uncomfortable. There is no moment in this model where you are pitching or persuading. There are only interactions where you choose to bring your full expertise and genuine interest to whoever is in front of you, or interactions where you hold back. The question is never whether to sell. It is whether to serve or lead.

The Challenger: A Different Kind of Professional

 

Research on high performance in complex, relationship-based professional services identified five distinct professional profiles: the Relationship Builder, the Reactive Problem Solver, the Hard Worker, the Lone Wolf, and the Challenger. Each of the first four has genuine strengths. Relationship Builders create warmth and loyalty. Problem Solvers deliver under pressure. Hard Workers inspire confidence through diligence. Lone Wolves bring bold, independent thinking. But each also has a characteristic blind spot, whether that is prioritizing client comfort over honest counsel, reacting to fires rather than preventing them, generating effort without strategic direction, or working in ways that are difficult to translate into client action.

The Challenger is the profile that synthesizes the best of all of them and adds the one quality that makes those strengths truly land: the courage to lead. In complex, relationship-based contexts like law, Challengers account for more than 50% of top performers. They do not just ask clients and contacts what keeps them up at night. They tell them what should be.

Notice what this is not. A manipulative advisor tells you what you want to hear because that serves them. A Challenger tells you what you need to hear because they are genuinely invested in your long-term success, even when that creates short-term discomfort. This is not something you deploy after trust has been established. It is, in many cases, how trust gets established in the first place. A contact who walks away from a first conversation thinking “that person gave me something I did not expect and that they did not have to give me” is a contact who will remember you.

What This Looks Like in Practice

 

Becoming a Challenger is a mindset shift before it is anything else. But there are concrete habits that make it real. These apply whether you are sitting across from a longstanding client, meeting a prospective client for the first time, or having coffee with a contact who may never instruct you directly but whose goodwill matters to you or who you just can and want to help.

1. Invest seriously in understanding their world. Read your clients’ and contacts’ industry publications. Understand their business pressures and sector dynamics. If you work in more personal areas of law, immerse yourself in the experience that brings people to need your help. The more fluently you speak someone’s world, the more credibly you can offer perspective that goes beyond the question they brought you, or that they did not yet know to ask.

2. Deploy genuine curiosity and real listening. Do not let familiarity breed assumption. Ask questions. Bring fresh eyes to every interaction, even with people you know well. Understand the perspective the person in front of you actually holds right now, in this situation. Then do your own thinking from that foundation rather than simply reflecting their view back at them. 

3. Share your insight and foresight. Whether you are advising on a matter or responding to a question from a contact, form a clear view on the best path and say it. Do not hide behind a menu of options and leave the person to choose. Many lawyers produce thorough analyses of the legal landscape and then stop short of the one thing the person actually needed: a recommendation, stated with conviction and backed by reasoning. That is the step that distinguishes a strategic partner from a technician, and it is also the step that people remember and talk about. 

4. Get comfortable holding your position. The ability to maintain a well-reasoned view in the face of pushback, calmly and without becoming defensive, is one of the most valuable things a lawyer can develop. It is also one of the most practisable. Role-play difficult conversations before they happen. Work through the likely objections in advance. AI tools can be genuinely useful for this kind of preparation.

5. Find ways to bring more value than they expected. A risk assessment framework, a short sector briefing, a decision matrix tailored to their situation: these things signal that you have been thinking about them beyond the scope of what was asked. They are memorable precisely because they are unexpected and demonstrate the kind of genuine investment in someone’s success that builds the loyalty and goodwill that a practice runs on over the long term. If you are not sure what that looks like in your specific area of practice, it is worth exploring. The answer is almost always closer than you think.

The Lawyers Clients Call First

 

Some lawyers worry that challenging clients and contacts will damage the relationship. In my experience, the opposite is consistently true, provided the challenge comes from the right place. Challengers do not oppose the objectives of the person they are talking to. They elevate them by deeply understanding the context and offering better ideas for reaching those objectives. Delivered with genuine care for the other person’s long-term success, that kind of engagement deepens trust rather than eroding it, whether the relationship is ten years old or ten minutes old. And if leading feels like too large a step right now, start with just focusing on being of real service in the conversations you are having. That is already most of the way there.

As AI takes on more of the routine work and clients face increasingly complex decisions under pressure, the value of a lawyer lies more and more in the ability to guide, challenge, synthesize, and lead. The lawyers who will thrive are the ones who show up to every interaction with genuine curiosity about the person in front of them, the willingness to say the difficult thing when it needs to be said, and a deep investment in outcomes that go beyond the scope of what they were asked.

Imagine being the lawyer your clients think of at two in the morning when something important is happening. The one they call before they call anyone else, not because you are the most available, but because you are the one they trust most completely to tell them what they actually need to hear. That is what this approach builds, over time and one interaction at a time.

The question is not whether you can afford to practise this way. It is whether you can afford to keep practising without it.

Jane Southren is a former litigator and the founder, chief consultant, coach and trainer at Southren Group. She is passionate about helping professional services providers to achieve greater success and have broader influence. Jane passionately guides her clients by applying a continuum of better thinking and better action for  better results.

“Supporting clients — seeing them not only find success, but emerge stronger, more confident and more skilled at creating meaningful, mutually rewarding professional relationships — is incredibly gratifying.”.

May, 2026 | Business Partner Spotlight

Business Partner Spotlight: Executive Furniture Rentals

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Lade, Chris
Author Chris Lade

How Executive Furniture Rentals Serves the Legal Industry 

Tell us a bit about your company.

With over 65 years of serving our customers, Executive Furniture Rentals delivers temporary furniture instantly for homes, offices, and special events. Nearly half of our business provides temporary furniture solutions for commercial offices spaces, including many law firms. We specialize in delivering high-quality, stylish, and functional furnishings that help firms stay agile and professional. Whether you are opening a new office, renovating, or need short-term solutions, we deliver a seamless solution from start to finish.

What makes your product or services a good fit for the legal sector?

Law firms value professionalism, discretion, and adaptability—so do we. Our furniture is designed to reflect the prestige of your practice, and our rental model gives you the flexibility to scale as your needs change. We offer white-glove service, quick turnaround, and a deep understanding of the legal industry’s standards and timelines. We do not just rent furniture—we help create environments that inspire confidence and productivity.

What’s one success story or project you’re especially proud of?

We’ve partnered with many law firms over the years of various sizes and scale. As one example, we created a swing space for 15 months for a national Bay Street law firm. We delivered temporary offices and boardrooms while they renovated their existing offices. We furnished a total of 20,000 square feet of space. The result? A polished and consistent furniture solution with zero disruption to their operations and staff.

What are some common challenges you help law firms solve?

We help law firms solve space uncertainty, budget control, and especially tight timelines. We can deliver furniture within 48 hours. Whether it’s a surprise lease, a merger, or a renovation project, we provide turnkey solutions that eliminate the stress of purchasing, storing, and managing furniture.

Why did you choose to partner with TLOMA?

TLOMA connects us with a community of legal professionals who value excellence and integrity—values we share. We’re excited to support our members with solutions that make their workspaces work harder for them.

What advice would you offer legal professionals navigating today’s evolving workplace?

Stay flexible, design-forward and future-focused. The workplace is evolving, and your space should evolve with it. Consider solutions that give you the freedom to adapt without long-term risk. And don’t underestimate the impact of a well-designed space on your team and your clients.

What’s something most people wouldn’t guess about you or your company?

We’re a small-but-mighty team that’s a tad obsessed with the details—like perfectly aligned chairs and flawless finishes.

If your company had a theme song, what would it be?

“Don’t Stop Me Now” by Queen. It’s upbeat, bold, and all about seizing the moment—just like we do for our clients every day.

When you’re not working, where would we find you?

You’ll likely find us outdoors—hiking, biking, or exploring the many exciting neighborhoods in Toronto and beyond. exploring new coffee shops. We also are strong advocates of our community, most notably with our long-term commitment for our Victory Garden and partnership with the Vita organization that provides services to help adults with developmental disabilities and chronic mental illness.

How can TLOMA members connect with you?

We’d love to connect!
Website:
www.FurnitureRental.ca
LinkedIn: executive-furniture-rentals
Email: info@executivefurniturerentals.com
Phone: 416-785-0932

May, 2026 | Movers and Shakers
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