Rethinking How Legal Leaders Are Built

AI is changing the work through which lawyers develop judgment. General Counsel now need to rethink how that judgment is built, assessed and sustained.

LEADERSHIP BRIEFINGS

Cassandra Lim

8/11/20266 min read

a robot standing next to a wall covered in stickers
a robot standing next to a wall covered in stickers

The mandate of the modern General Counsel is being reshaped by digitalisation, automation and the integration of AI into the legal function. As these technologies change how legal work is delivered, they also raise two more fundamental questions about how future legal leaders will be developed:

As AI removes more junior legal work, what else disappears with it?

Where will the next generation build the judgment that used to come through the work?

That question is becoming more pressing as AI moves further into mainstream legal work. Research, first-pass drafting, contract review, and initial analysis are all becoming faster and easier to automate or augment.

At the same time, the talent agenda inside legal functions is changing. GCs are placing greater emphasis on technology fluency, commercial judgment, adaptability and the ability to operate across legal, data, process and business issues. Many are being asked to increase the capacity of their teams without corresponding increases in headcount.

There is a less obvious consequence underneath all of this. AI is changing some of the experiences through which lawyers historically developed those capabilities. It is also making some of them harder to assess.

That has implications for talent development, hiring and succession.

How judgment has traditionally been built

Much of the work AI can now accelerate has historically sat early in a lawyer's development.

It was often repetitive, but repetition created pattern recognition. Initial analyses were reviewed and challenged. Junior lawyers encountered similar issues in different contexts and gradually learned which facts, risks and commercial considerations mattered. None of this was particularly systematic. It simply happened alongside the work.

As AI increasingly provides the research base, first draft or initial issue set, lawyers start further into the process. The immediate work product improves, but there may be fewer opportunities to frame the problem from the beginning, wrestle with incomplete facts or discover the limitations of an initial view.

Used well, AI can accelerate learning. But development can no longer be assumed to occur simply because the work is being done.

AI is changing how capability is assessed

The quality of a lawyer's work has traditionally provided useful evidence of capability. Strong drafting, rigorous analysis and careful issue spotting required much of the underlying thinking to be done by the lawyer.

Today, a relatively inexperienced lawyer can now produce technically strong work with substantial assistance from AI. The finished product may reveal much less about how well the lawyer understands the problem, where the analysis is weak or how confidently they can adapt when the facts change. Managers therefore need better evidence of the reasoning behind the output.

The same applies to hiring. Employer pedigree, years of experience and transaction lists remain relevant, but they do not necessarily show how much responsibility the lawyer personally carried, how often their judgment was tested or whether the complexity of their decisions increased over time.

Those distinctions have always mattered in senior legal assessment. AI makes them important much earlier.

5 Ways GCs Can Build Judgment and Develop Future Legal Leaders in the Age of AI

If legal functions want the productivity benefits of AI without weakening the future leadership pipeline, development will need to become more deliberate. These five areas matter most:

1. Preserve independent reasoning at selected points

Junior lawyers need to learn how to use AI well. They should not be expected to work without it as a matter of principle.

There should, however, be selected assignments where the lawyer first frames the issue, forms a view and explains the reasoning before turning to AI. The comparison then becomes part of the development process.

A supervisor can see what the lawyer identified, what was missed, which assumptions were weak and how the final view changed. This provides visibility into the lawyer's thinking that may otherwise be hidden by the quality of the finished product.

2. Allocate experience as deliberately as work

Legal departments are generally disciplined about distributing workload. They are less systematic about distributing the experiences that build future leaders.

This matters because learning agility, which is the ability to take lessons from one experience and apply them effectively in a new or unfamiliar situation, does not develop simply through tenure. It develops when people are repeatedly placed in situations that stretch how they think, relate to others, adapt and make decisions.

A GC can shape this quite deliberately.

A lawyer who is technically strong but uncomfortable with ambiguity may need responsibility for a matter where precedent provides only part of the answer. Someone who needs greater commercial judgment may benefit from working directly with a business leader whose priorities conflict with the legally safest position. A future people leader may need to manage a difficult team situation rather than another technically complex transaction.

The important point is the variety and increasing difficulty of the experience, followed by reflection and feedback.

Over time, these assignments develop intellectual flexibility, comfort with unfamiliar problems, the ability to deliver under pressure, awareness of one's own impact on others and the capacity to adapt when an established approach stops working.

For high-potential lawyers, succession planning should therefore include an explicit view of the experiences still missing from their careers. Current performance shows how well someone handles today's job. The pattern of experiences they are being given says much more about whether they are being prepared for a larger one.

3. Recalibrate assessment and hiring

Technical quality and legal expertise remain fundamental. But assessing future legal leaders requires a deeper examination of what the individual has actually been responsible for, how they exercise judgment and how their capability has developed over time.

Rather than simply establishing that a candidate worked on a major transaction, investigation or regulatory matter, a rigorous assessment should examine what they personally owned: the ambiguity they faced, the recommendation they made, how they handled challenge and what happened as a result. Across a career, these examples reveal the trajectory of the lawyer's judgment.

Has the individual moved from solving defined legal problems to framing ambiguous ones? Has their scope shifted from giving advice to influencing senior decision-makers? Has the complexity and consequence of the decisions they personally carry increased?

This is where in-depth executive search assessment becomes particularly valuable. The objective is not simply to verify experience, but to identify patterns, distinguish participation from ownership and test whether the candidate's judgment has developed across progressively more demanding situations.

References can then be used to test those hypotheses rather than simply confirm that the candidate performed well.

4. Make senior reasoning more visible

Most legal functions capture outcomes far better than they capture how those outcomes were reached. Little is preserved about why a particular risk was accepted, why another was escalated, which commercial consideration changed the legal position or how uncertainty was handled.

As AI makes legal information easier to retrieve, this reasoning becomes more valuable.

Senior lawyers need to make more of their thinking visible through matter reviews, supervision and knowledge-sharing. That does not require another large process. It requires greater discipline in explaining the judgment behind important decisions.

5. Keep developing lawyers close to consequential work

As support work reduces, junior lawyers may have fewer natural reasons to be present in the discussions where difficult legal judgment is exercised.

Their exposure therefore needs to be more intentional.

Developing lawyers should see how experienced counsel handles uncertain regulatory positions, difficult investigations, commercial resistance to legal advice and management decisions where there is no clean answer. They do not need premature ownership of those decisions. They do need enough proximity to understand how experienced lawyers make them.

The succession consequence

For in-house legal functions, there is another dependency.

A significant part of early legal development still takes place in private practice. Companies routinely hire lawyers several years after qualification and benefit from the training, repetition and responsibility accumulated elsewhere. Changes to junior staffing, leverage and work allocation in law firms will therefore eventually reach the in-house market as well.

The lawyers moving towards Head of Legal, Regional GC and ultimately Group GC roles over the next decade are developing their judgment now. Their depth will depend partly on the work they are given, the decisions they are allowed to carry, the feedback they receive and the senior lawyers they are able to observe.

AI is changing each of those conditions.

The opportunity for GCs is to treat talent development as part of the design of an AI-enabled legal function, rather than as a separate people agenda running alongside it. That means building experience deliberately, assessing judgment more carefully and making sure efficiency does not quietly narrow the range of situations through which future leaders develop.

The capacity gains from AI will become visible quickly.

The quality of the next legal leadership bench will take much longer to reveal itself. By the time the gap becomes obvious, much of the development window may already have passed.