Hybrid Work and Digital Legal Training: Emerging Risks for Law Firms
Hybrid work has permanently altered how junior lawyers learn their craft. For decades, legal training relied heavily on observation-based learning: sitting in on meetings, overhearing partner discussions, and learning through proximity and osmosis. In hybrid environments, much of this knowledge transfer can be reduced or lost. Informal supervision – through quick desk-side questions, ad-hoc feedback, and real-time course correction – now happens less frequently or is replaced by scheduled digital check-ins.1
How hybrid work is changing legal training models
As firms adapt to these changes in how learning happens, technology has become both an enabler and a complicating factor. Digital platforms, remote collaboration tools, and increasingly, AI-enabled research and drafting systems, are changing how legal work is managed – and how judgment, risk awareness, and professional standards are learned. New risks are surfacing, but there are also opportunities: when used thoughtfully, technology can help firms more effectively share expertise across their organisation and demonstrate the quality and accuracy of their work.
We’re in genuinely new territory, where both action and inaction carry risk.
Paul Howse, AVP, Bond & Specialty Claims for Travelers Europe
"Moving too fast with untested technology can expose firms to client and regulatory harm, but refusing to engage at all could leave lawyers unprepared to deliver the service enhancements their clients need and train their next generation of partners. Through careful, controlled experimentation, firms can build understanding without putting clients or the firm at risk," said Howse.
Where professional indemnity risk can increase for new legal hires
In the evolving legal workplace, risks are most clearly felt in the area of professional indemnity (PI). Increasingly, technology is making it possible for lawyers to make decisions with limited oversight and corroboration. Remote work can obscure when a junior lawyer is struggling or overreaching, particularly if AI tools produce work that appears polished but masks gaps in understanding. Studies on legal AI use have already highlighted risks of overreliance, including hallucinated citations and flawed reasoning if outputs are not carefully reviewed.2
Reduced supervision and experience gaps
In practice, risks can appear in subtle but significant ways. For example, AI is making it easier for lawyers to dabble in areas of the law or in jurisdictions where they don’t have the training to provide advice. While advising a client on setting up a trust, an insurance lawyer could encounter a seemingly minor tax question and, in an effort to provide responsive service, plug a tax question into an AI tool. If they weave the answer into the guidance they provide to the client and don’t verify the information, they create a risk that the client will act on misinformation.
Inconsistent training and quality control
A tech-supported, hybrid working model may also lead to uneven training experiences if risks aren’t carefully managed. Junior lawyers embedded in teams with strong digital supervision practices may progress well, while others receive minimal guidance. Senior lawyers who haven’t fully embraced new tools and ways of working – or simply are less familiar with them because they didn’t exist during their own training – can create gaps in oversight. These variables increase the possibility of inconsistent advice, procedural errors, and ultimately PI exposure.
Law firms can best support their lawyers in this area if they treat training consistency as a risk management issue, not just a people issue.
Sharon Glynn, Managing Director at Travelers Europe
“It’s important to have a risk management framework that embeds clear supervision standards, escalation pathways, and review protocols across all teams and staff," said Glynn.
Cybersecurity implications of tech-dependent lawyer training
Alongside judgment and supervision risks, technology-dependent training introduces a parallel set of cyber risks. Lawyers routinely use cloud-based document systems, collaboration platforms, and AI tools that process sensitive client data. Each system expands the firm’s attack surface.
Training environments themselves can become vulnerabilities. Shared sandbox systems, weaker access controls for new hires, or insufficient awareness of phishing and social engineering risks for all staff can introduce new threats.
Regulators and cyber authorities have repeatedly warned that human error remains a leading cause of breaches, particularly among less experienced staff.
Sharon Glynn, Managing Director at Travelers Europe
"Inadequate training in secure technology use can therefore translate directly into data protection failures and downstream liability. To manage these risks, it’s critical for lawyers and staff at all levels across a firm to remain up to date,”3 said Glynn.
But risk is only one side of the equation.
Case study: Kennedys uses AI to scale expertise, not replace it
Alongside the risks, AI presents significant opportunities to rebalance what has been lost in hybrid legal training by making a firm’s best expertise more accessible to junior lawyers. This is something that Catherine Goodman, Chief Knowledge Offer and AI Lead at Kennedys, is aiming to capture in her work with junior lawyers at the firm.
Goodman is leading an initiative to help junior lawyers build practical skills in an era when traditional entry-level tasks are increasingly affected by automation. Under her direction, Kennedys has formed a strategic partnership with the generative AI platform Spellbook to create a training programme that uses simulated scenarios and AI-assisted drafting exercises to replicate real-world legal work that might otherwise disappear due to automation. This approach aims to combine legal expertise from across the firm with advanced AI technology to ensure junior lawyers develop both legal reasoning and AI fluency. The programme, which Kennedys is piloting in its UK and US offices, offers structured feedback designed to mirror the valuable coaching aspects of traditional mentorship provided by senior lawyers. It is among the first large-scale efforts in the legal sector to directly address AI’s impact on early-career legal training.4
Goodman has emphasised that the initiative is about using AI to nurture learning rather than replace it - and to experiment with it in controlled, non-client-facing contexts where risks can be managed.
Whenever new technology appears, there can be an instinctive resistance to change.
Catherine Goodman, Chief Knowledge Offer and AI Lead at Kennedys
“I saw it years ago when I was lecturing at a London law school and online lectures were introduced, yet students embraced them because they could learn at their own pace and convenience. The lesson is to keep the learner at the centre: if you do that, you can use the tools and expertise inside the firm to enhance learning rather than dilute it. With AI, that means safely harnessing collective experience through simulations and training environments, so junior lawyers benefit from the best of everyone while risks to clients and the firm remain contained,” said Goodman.
When technology becomes a defensive asset in PI claims
Notably, many of the same technologies that support training have the potential to strengthen a firm’s position if something goes wrong. Digital training platforms, document management systems, and workflow tools create audit trails that did not exist in traditional models. Training logs, version histories, tracked feedback, and documented approvals can all help demonstrate that work was appropriately supervised - and if something goes wrong, to quickly identify where it happened. In professional indemnity claims, firms are often judged on whether they exercised “reasonable care”. Well-designed digital systems can provide objective evidence of oversight and review, and also help ensure firms carry out those steps.
What this means for law firms and their advisers
Hybrid work and AI are reshaping not just how junior lawyers work, but also how future partners are developed. As training approaches evolve, so should the risk conversations about them. Firms that proactively integrate supervision, cyber security awareness, and documented oversight into digital training can manage their evolving PI risk while still capturing the productivity and talent benefits of modern legal technology.
For firms navigating these changes, the challenge is finding that balance in practice.
Law firms don’t need to choose between caution and innovation.
David Hawkins, Solicitor & Claim Relationship Specialist at Travelers Europe
“They are finding ways to safely test new tools in ways that protect clients, support junior lawyers, and facilitate learning – all while building the capabilities and confidence that will help them compete,” said Hawkins.
Travelers partners closely with brokers and their clients in the legal sector to help them monitor and manage their emerging risks. Learn more here.
Sources
1 https://www.travelers.co.uk/insights/legal-sector/improving-hybrid-workplace-culture-for-law-firms
2 https://www.americanbar.org/groups/journal/articles/2024/will-generative-ai-ever-fix-its-hallucination-problem/
3 https://www.gov.uk/government/statistics/cyber-security-breaches-survey-2024/cyber-security-breaches-survey-2024
4 https://www.kennedyslaw.com/en/news/2025/kennedys-partners-with-spellbook-to-launch-groundbreaking-legal-training-programme-for-the-ai-era/
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