The Ambidextrous Lawyer: Integrating Law, Technology, and Risk in the Age of AI

As AI accelerates the pace of business, the role of in-house legal is shifting from a reactive control function to a more embedded, strategic partner. The challenge is no longer just managing risk, but ensuring it is integrated directly into decision-making.

Michele Giordano Mensitieri, Senior Legal Counsel at Generali Global Corporate & Commercial, shares his perspective on how the legal profession is evolving in response to this shift, and why the modern lawyer must combine legal expertise with technological understanding.

In this Q&A, Michele reflects on AI adoption, cultural barriers to innovation, and the rise of the “ambidextrous lawyer” who can balance governance, risk, and speed in a changing environment.

Enjoy the interview below.

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1. How has the nature of your role as an in-house legal counsel changed over the past decade, and what skills do you find yourself relying on today that weren't part of your training when you first entered the profession?

There is one thing I always like to keep in mind when we talk about the evolution of the role of the lawyer, because it helps to put everything into perspective. 

If you look at it without indulgence, the profession of the lawyer does not change. The context changes, the speed changes, the lexicon changes. But the function remains the same: to govern risk when the business pursues opportunity.

Already in classical Athens, there were logographers - experts who sat next to the defendant and wrote the defense speeches that he would later deliver himself. It was a primitive, but already sophisticated, form of legal assistance: someone who transformed the complexity of law into usable arguments.

Since then, everything has been stratified: Roman law, continental codifications, and Common Law. But the thread remains unique: risk control, interpretation, defense of the interest whether it is of the organisation or of the law firm's client.

The discontinuity has come in recent years with the irruption of AI that does not change the perimeter of law, but the posture of the legal within the organization.

In my experience, the passive function of the lawyer - that is, the one who intervenes downstream of the finalization of the project - simply no longer holds. 

The time of business has contracted to such an extent that the law, if it is not incorporated into the process, is circumvented.

And when this happens, the risk does not disappear: it simply shifts, often amplifying itself.

For this reason, a new figure emerges that I like to call "ambidextrous lawyer", a jurist who integrates law and technology in the same decision-making gesture.

In 2026, the lawyer can no longer stand on the sidelines.

I like to quote the incipit of a famous book by Glenn O'Brien: "Don't stand there. Rise up and evolve!"

2. What does “legal innovation” mean to you personally, and how has that definition shifted over time?

I believe that legal innovation is, first of all, a matter of mentality rather than tools.

The real shift is from "it can't be done" to "how can it be done without losing control of risk".

It is a question that the ambidextrous lawyer is able to ask himself before others, precisely because he understands both the legal risk and the functioning of technology, without being blocked by either.

At the beginning of my career, innovation was often synonymous with digitisation: automation of repetitive tasks and operational efficiency. 

Although this remains an important element, today it is no longer sufficient.

Over time, my vision has evolved: today innovation is no longer just technical, but becomes directional because it orients the organization.

In concrete terms, innovating means aligning three dimensions: governance, risk and speed. In the absence of this alignment, the organization either slows down or loses control.

In the world of In-House, AI has made one aspect particularly evident: it is not only used to do better, but to free up cognitive space. And that freed time must be reinvested where the lawyer creates value: in the study of law in a strategic key and in the relationship with stakeholders. 

Today, then, a new responsibility also emerges: to spread AI expertise within the organization. 

And this responsibility is no longer an individual issue, but a systemic one.

In short, legal innovation does not coincide with productivity, but with the ability to achieve better results with the same or a reduction of risk. This is the real distinction.

3. How do you foster a culture of experimentation within a function traditionally associated with risk aversion?

Today, the legal function helps the organization to contain risk, but, in the current context, the caution in risk management by the lawyer can become a factor of instability; not because it is wrong, being a structural feature of the legal profession, but because it is off the charts.

I therefore believe that caution should not be eliminated, but reinterpreted.

In my experience, and with the irruption of today's technology, what works is the transition from a control function to a responsible orientation function. It is no longer a question of blocking the use of technology, but of enabling it within clear perimeters.

This is where a fundamental principle comes into play: controls must be incorporated into the organization's processes, not be external to them.

If control is perceived as an obstacle, it will be circumvented; if it's integrated into the process, it becomes a natural part of the workflow.

The European Regulator is also moving in this direction: experimentation, yes, but within governed perimeters.

In my opinion, therefore, the message is clear: risk is not eliminated, it is administered.

Obviously, alongside the processes, there is a crucial cultural dimension: people must feel empowered, not replaced. When they understand that their judgment remains central - and that technology amplifies it - they naturally become more open to experimentation.

The lawyer, therefore, remains fully responsible and central to the decision-making process, but in a logic of empowerment.

4. Contract lifecycle management, e-discovery platforms, and AI-powered legal research tools have been around in various forms for years, yet adoption remains uneven. What do you think are the real barriers preventing in-house teams from embracing technology more fully?

The main barriers to adoption are not technical, but cultural and organisational, such as inertia, mistrust and misalignment.

The jurist is structurally prone to doubt: it is a defensive quality, which becomes a limit when the context requires speed.

However, the distrust of us lawyers towards AI is understandable. In particular, the phenomenon of hallucinations represents a real risk: linguistic models can generate incorrect content, with possible reputational and professional consequences. The cases of non-existent jurisprudential citations inserted in judicial documents clearly demonstrate this.

For this reason, using AI always requires human supervision.

This is not a limitation, but a structural condition: AI remains a professional-driven tool.

But the most critical point is another: the lack of a narrative. 

If an organization doesn't understand why it needs to adopt a tool, it won't. Or it will do it badly.

Added to this is fragmentation: isolated initiatives, without governance, which increase risk instead of reducing it.

And finally, the unresolved knot of responsibility: who is driving? Legal, IT, Compliance? When no one decides, the system crashes.

Last but not least, the economic issue: the value of risk prevention is difficult to measure, and what is not measured is difficult to finance.

5. In your experience, what types of legal tasks are well-suited to AI assistance right now, and where do you still believe human legal judgment is not just preferable but irreplaceable, and why?

In my daily work, I have directly observed the value of AI, but also its limitations.

It is important to avoid polarization: it is neither a universal solution nor an absolute risk.

AI, in fact, excels where the work is repetitive and scalable: classification, synthesis, and first analysis. It is also useful as a guidance tool in non-family legal territories: it reduces information asymmetry, allowing a more efficient use of external consultants.

But here ends its superiority.

Law is not just a norm: it is context, relationship and reputation. Anything that is not formalized remains, by definition, out of the reach of the machine.

Furthermore, a piece that I consider fundamental is institutional memory, indeed that informal heritage that guides the decisions of the lawyer and that no model can replicate.

Last but not least, the decisive dimension: The relationship. 

Convincing, negotiating, building trust: this is where the value of the legal is measured, and it is here that technology simply stops.

6. Insurance law sits at a unique intersection of heavy regulation, complex financial risk, and direct consumer impact - how did you learn to work effectively across those disciplines, and how long before you felt you truly understood the business?

Insurance law is a particularly complex area because it sits at the intersection of stringent regulation, financial risk management and direct customer impact.

In this context, solid legal expertise is not enough: a deep understanding of the business is required, which develops over time through operational experience.

In my case, this awareness has matured progressively, thanks to the continuous comparison with the various company functions.

Today, complexity has increased even further with the introduction of AI.

The AI Act classifies systems used for risk assessment and pricing, for example, in life and health insurance, among other things, as high-risk.

This leads to stringent compliance requirements and adds an extra layer of complexity that requires soft skills.

Insurance law, therefore, becomes a privileged terrain for the lawyer I call "ambidextrous" (a jurist who integrates law and technology in the same decision-making gesture): a professional capable of integrating the regulatory dimension, risk, economic sustainability, impact on the client and conscious use of AI.

It is a balance that is built over time, and that remains, by its nature, dynamic.

7. How do you stay on top of emerging legal trends and turn new insights into practical improvements in your work?

Staying up to date is not just about gaining information, it's about operationalising it.

This translation ability is, in my opinion, one of the key skills of the modern lawyer.

In my approach, this translates into a mindset of continuous exploration: I follow the evolution of legal tech and, when possible, I directly test the tools in my workflows.

Comparison with other In-House Counsels — often in informal contexts — is particularly useful, because it allows you to distinguish between theoretical solutions and truly effective applications.

On a technological level, the ecosystem is evolving rapidly: AI platforms integrated into legal databases, RAG models that combine information generation and retrieval, GraphRAG systems based on knowledge graphs and multi-agent architectures.

Those who merely observe change remain irrelevant: those who test, adapt and scale it, gain an advantage.

The real competence of today's lawyer is to know how to use these technologies and understand them enough not to suffer them. 

Between uncritical enthusiasm and a priori rejection, there is only one sustainable position: a conscious supervision. 

And it is here, in my opinion, that the lawyer who will remain relevant is located.

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Michele’s insights highlight a key shift for in-house legal teams: success lies not in replacing traditional legal skills, but in integrating them with technology and embedding risk management into business processes.

Michele will be joining Future Lawyer Europe - Italy Day 2 for the panel “The Future Business Partner: Redefining In-House Legal in the Age of AI”, exploring how legal teams can operate more strategically, enable innovation, and contribute to business growth in a technology-driven environment

Register now to join the discussion at Future Lawyer Europe - Italy.