Session Recap: Bringing Ease to Managing a Legal Team

The average cost of losing an associate who joined as an articling student is somewhere between $300,000 and $500,000. They tend to leave right around year four or five, exactly when they start becoming profitable. A significant driver of that turnover is management behavior that many firms have not figured out how to measure or reward.

That was the thread running through the session Sandra Bekhor of Bekhor Management and I hosted on June 25. See the recording here. Sandra has spent more than 20 years coaching lawyers on leadership and team management, with a particular focus on delegation and feedback. I came at it from the profitability side. What kept coming back is how directly management habits shape firm economics, and how rarely firms treat the two as connected.

Why Managing a Legal Team Is So Hard

We started with what most managing partners already know but rarely name directly: lawyers are not trained to manage people. Law school trains the critical, analytical mind. It rewards the lawyer who finds the flaw in an argument and who assesses risk before anyone else in the room does. Those skills are essential for legal work. In a management conversation, the instinct to find the flaw is usually the thing that gets in the way.

Sandra made the point that good management requires a different part of the mind: empathy and the ability to listen without immediately judging. Lawyers have those capacities. They are just not the ones that get reinforced in legal training or firm culture.

So when lawyers move into senior roles, they are expected to lead and develop their people, without much preparation for either. And without strong role models in the firm to learn from, most are expected to figure it out on their own, which usually means they do not.

The Cost of Withheld Feedback

One of the patterns Sandra sees consistently: litigators who will argue fearlessly in court will not give a direct piece of critical feedback to an associate.

Her explanation made sense to me. In court, everything is rule-bound. The norms for how to behave are clear, and following them is not seen as aggressive. In a feedback conversation, there is no rulebook. The associate is someone you work beside every day. So the conversation gets deferred.

The cost compounds. An associate who makes a mistake in January and does not hear about it will repeat it in February, March, and April. By year-end review, the associate is hearing critical feedback for the first time, on twelve months of work. That is not just a development failure. It is a profitability problem. You have a person billing on your behalf all year at a fraction of what they could be producing.

One point Sandra raised that I do not think gets enough attention: your strongest performers want feedback just as much as anyone who is struggling, if not more. High performers are driven to grow. If your firm is not part of that growth, they will find one that is. They tend to leave right around year four or five. That is exactly when your investment in them starts to pay off.

Why Delegation Does Not Happen

This is where the financial case becomes very direct. Work that goes to a $350 associate should not be sitting with a partner billing at $800 or $900 an hour. The billing math here is clear, even if the behavior rarely reflects it.

Sandra identified fear of losing control as the primary obstacle. That fear is legitimate and takes different forms. Some partners worry about their reputation if a file goes wrong. Some fear client complaints. Some are simply convinced the work will come back needing to be redone anyway.

I added the structural piece. In many firms, partner compensation is tied primarily to billable hours. A partner who delegates aggressively is reducing her own hours. Her compensation reflects that. So she keeps the work. That is a rational response to the system in front of her, but it works directly against your firm’s long-term profitability.

Sandra’s reframe on this: partners who invest in training their team lose some billable hours in the short term. But if the team develops and stays, profitability rises over time. In my experience, the partners who invest in their people tend to build the more profitable practices.

What to Do About It

The practical suggestions we landed on were straightforward.

At the start of each year, each associate identifies two or three personal goals in conversation with the supervising partner. Specific goals tied to that person’s career trajectory, not pulled from a firm-wide checklist. Then a check-in every 90 days. This gives the partner a natural framework for feedback that does not feel adversarial, and it signals to the associate that someone is paying attention. That signal matters more than most firms realize.

Sandra and I both referenced the Balanced Scorecard as a structural tool worth considering. The idea is to measure partner performance beyond billing metrics. Financial results matter, but so does how well partners are developing their teams and building capacity for the long term. For a managing partner compensated partly against a balanced scorecard, the non-billable work of developing people gets counted. That changes behavior.

The harder question, which an audience member put directly, is how you make management changes stick when partners are still paid primarily on billable hours. The honest answer is that you probably cannot, not at scale and not over time. Some portion of partner compensation needs to reflect how well partners are managing and delegating. Even five or ten percent signals that the firm takes it seriously. Setting those goals at the start of the year and reviewing them at the 90-day mark gives it structure.

The AI Question

Near the end of the session, an audience member raised a specific question about AI and delegation: if junior work is being replaced by AI, what do you do with your junior associates and paralegals?

One view: you retrain them as validators. Have AI take the first pass. Have the junior associate review the output and produce a corrected version, then send that to a senior associate or partner for a final pass. The skills shift from producing the work to interrogating it. That is a legitimate developmental path, and some firms are already building it into how they count billable hours.

Sandra’s point: whatever structure you build around AI tools, the management principles for developing your people hold.

None of what Sandra and I described is complicated. What makes it hard is that many small and midsize firm partner compensation systems actively reward the opposite behavior. If you want to think through what changing that looks like in your firm, reach out.

Rethinking the COO Role in Law Firms

Law firms have always been led by lawyers. The senior partner was often both rainmaker and chief administrator, managing everything from finances to facilities. That model worked when the business of law was simpler and the competition was local. It no longer fits the complexity of today’s legal market.

It is time to rethink what this role should entail and who is best suited for it.

The Role of the COO

The main role of a COO in a law firm is to run the firm’s business operations. Partners’ time is best spent practicing law and building client relationships. Someone must ensure that the business runs efficiently behind the scenes.

The COO position includes creating the systems and discipline that enable partners to focus on client work. A strong COO connects the dots between finance, operations, people, and strategy. This relieves partners of this task and helps execute the firm’s goals.

The New Skills Required

The skill set for today’s COO has changed. Now legal COOs must be fluent in both management skills and technology. They must understand automation and AI applications that can streamline workflows and improve decision-making.

Strong COOs now act as translators between business strategy and operational execution. They can analyze profitability at the matter and client level. They can interpret financial and operational data to guide strategic investments. And they can communicate these insights to lawyers in ways that lead to action.

The most effective COOs combine four abilities:

  • Operational discipline to ensure the firm’s core systems run smoothly.
  • Financial literacy to create budgets and new pricing models.
  • Technology fluency to identify where automation and AI create leverage.
  • Leadership credibility to influence senior lawyers without authority based on title.

These abilities rarely come from the traditional legal path. That is why many of the most successful COOs in professional services come from finance, consulting, or technology backgrounds.

Why Some Firms Struggle to Empower the COO

Even when firms hire a capable COO, many fail to use the role effectively. In some partnerships, operations managers are limited to managing facilities, HR, or IT. This limits the COO’s ability to execute. Without clear authority, the role becomes reactive rather than strategic.

Empowering a COO requires the managing partner and the executive committee to treat the role as part of firm leadership, not support staff. The COO should sit at the table where strategic and financial decisions are made, with access to the same data and accountability.

The COO and Change Management

Law firms face rising cost pressures and technology-driven disruption. These challenges cannot be solved through individual effort or incremental change. They require systemic thinking, the kind that a professional COO brings.

A forward-looking COO can lead firmwide initiatives in areas such as:

  • Redesigning work allocation models that improve leverage and profitability.
  • Introducing firm-level KPIs and dashboards to measure performance in real time.
  • Managing AI adoption projects across practice groups.
  • Building training programs that develop “business of law” concepts among lawyers.

The goal is to help the Managing Partner execute on the firm’s strategic plan. The COO becomes the connection that links strategy with day-to-day execution. COOs can also take on many of the regular duties of the Managing Partner so that they can focus on higher-level firm strategy and leadership objectives.

What Law Firms Should Do Next

Every firm should begin by asking a simple question: What is our COO actually accountable for? If the answer sounds administrative rather than strategic, the firm may be missing an opportunity.

The next step is to align the COO’s role with measurable outcomes. Examples include improvement in profit per partner or percentage of work automated. These are results that move the firm forward and justify the investment in senior operational leadership.

Closing Thoughts

The modern law firm operates more like a business than a traditional partnership. Rethinking the COO role involves giving COOs more authority and accountability to give the firm a strategic advantage. This can also lead to non-lawyer COOs becoming CEOs or recruiting non-lawyer CEOs from other industries. Given the immense changes happening in the legal industry today, high-end professional management in law firms is becoming a must-have in order to succeed.

Can a Small or Mid-sized Firm Lead the Legal Transformation?

How Smaller Firms Can Adapt the Four-Pillar Blueprint to Win

The legal industry stands at a crossroads. While Big Law firms grapple with their transformation challenges, smaller and mid-sized firms possess a hidden advantage that could reshape the competitive landscape entirely.

A compelling strategic framework, introduced by Ted Theodoropoulos in his article “Big Law 2.0: A Radical Transformation Blueprint” (May 2025), outlines a powerful approach. Theodoropoulos proposes that firms revisit their foundational strategies around structure, funding, talent, and delivery.

Although his blueprint targets large firms and assumes eventual regulatory reform, the core concepts are highly relevant to firms with fewer than 100 lawyers. With some adjustments, smaller firms can use this approach to create meaningful differentiation and future-proof their practices.

Pillar 1: Create a “NewLaw” Division Inside the Firm

Rather than splitting the firm into two separate entities, a smaller firm can carve out a focused internal division dedicated to innovation. This unit can run pilot programs that test new service models, such as fixed-fee offerings, AI-assisted research, or client subscription packages.

Even a small team, e.g. one or two lawyers supported by a tech-savvy coordinator, can progress if given the space to operate outside traditional billable-hour metrics.

Why this matters for smaller firms:
Mid-sized firms are typically more agile than large national or international firms. This agility allows them to pilot new approaches without being delayed by layers of internal approval. Small, targeted projects launched today can generate a lasting competitive advantage.

Pillar 2: Fund Innovation with Purpose (No Outside Capital Required)

Theodoropoulos advocates for private equity or IPO capital in the original blueprint to drive innovation. While this may be viable in jurisdictions with alternative business structures, most Canadian and U.S. firms are still bound by rules prohibiting non-lawyer ownership.

Even without external funding, a smaller firm can designate a portion of annual profits, perhaps between 1 and 3 percent, to fund a strategic innovation budget. These funds can be used to:

  • Develop internal legal tools
  • Invest in legal technology or AI pilots
  • Hire external consultants or specialists to guide delivery reform

Why this matters:
The goal is not to build a large innovation fund but to consistently invest in ideas that improve client service and internal efficiency. Smaller firms benefit from having fewer stakeholders in funding decisions. Where a large firm might need extensive partner approval for innovation spending, a smaller firm can move quickly on promising opportunities.

Pillar 3: Expand the Definition of “Top Talent”

The third pillar addresses the changing nature of legal talent. Winning firms will compete for the best lawyers and professionals in technology, operations, design, and data analysis.

Smaller firms can:

  • Establish innovation or legal tech roles outside the partner track
  • Introduce bonuses or phantom equity programs tied to firmwide goals
  • Empower business services professionals with real leadership responsibility

Why this matters:
Modern legal services require interdisciplinary thinking. A smaller firm that values and promotes non-legal expertise will be more equipped to innovate and deliver differentiated value to clients.

Pillar 4: Reinvent How Legal Work is Delivered

This pillar focuses on evolving beyond the traditional billable-hour model. Rather than handling each matter as a one-time engagement, firms can develop repeatable service models that deliver continuous client value.

Examples include:

  • Creating subscription-based legal advisory offerings
  • Using automation to streamline document production
  • Building client-facing knowledge portals powered by AI
  • Packaging compliance and regulatory advice into productized services

Why this matters:
Clients want predictable, transparent, and outcomes-focused solutions. A smaller firm offering scalable legal services can grow revenue without relying solely on increasing lawyer hours.

Getting Started Without Overhauling the Entire Firm

You do not need to adopt the entire blueprint all at once. Many firms begin with one or two pilot projects and build from there. For example:

  • Test a subscription pricing model in a specific practice group
  • Allocate a small portion of profits to innovation experiments
  • Appoint a part-time innovation lead to coordinate internal ideas
  • Initiate partner-level conversations about long-term strategy and capital allocation

Each of these actions builds capability and leadership alignment over time.

Final Thought: Small Firms Are Well-Positioned to Lead

As Ted Theodoropoulos observed, “The market doesn’t wait for consensus. It rewards those prepared to lead the change.” Smaller firms don’t need Big Law’s resources to capitalize on current market dynamics. They need strategic clarity, committed leadership, and the confidence to act while competitors hesitate.

The legal industry’s transformation creates unprecedented opportunities for firms willing to embrace change. Smaller firms that move decisively today may find themselves leading the profession tomorrow.


Attribution:
This article is inspired by and references the Four-Pillar Transformation Framework presented in:

Ted Theodoropoulos, “Big Law 2.0: A Radical Transformation Blueprint,” published May 15, 2025. Ted is a Legal Tech Innovator and 2024 ILTA Innovative Leader of the Year.