Daniel Yim
Founder | Sideline
Coaching and mentoring in the age of AI
Supporting those who supervise, coach and mentor tomorrow's lawyers.
99.00
Online / On-demand
2 CPD hours: professional development and solicitor wellbeing | eLearning
On-Demand Webinar
About this course
Coaching and mentoring has always been at the heart of how good lawyers are made, but AI is changing the shape of that relationship. In this candid, practice-based conversation, Daniel Yim (lawyer, software developer and founder of Sideline) and Gareth Thomas (former Head of Commercial Litigation at Herbert Smith Freehills Kramer) draw on more than 40 years of combined experience training junior lawyers.
Together they trace how supervision has evolved, from the "learning by doing" culture of the 1990s to today's hybrid, always-on working environment and confront the questions every legal supervisor is now asking: How do you know when a junior's work can be trusted? What makes a good supervisor? Can AI ever replace human mentorship, or does it simply raise the stakes for getting supervision right?
This webinar is essential viewing for partners, senior associates and anyone with responsibility for developing junior legal talent.
Why choose this course
A frank, experience-led conversation that gives legal supervisors practical frameworks for coaching, trusting and developing junior lawyers as AI reshapes how legal work gets done.
Build trust, not guesswork:
Practical markers for judging when a junior’s work – and understanding – can genuinely be relied on.
Cross-jurisdictional insight:
How cultural context shapes feedback, trust and supervision styles across teams.
The apprenticeship model reframed:
Why personalised mentorship remains essential even as the nature of junior work changes.
Course syllabus
Key learning points
By completing this webinar, you will:
- Understand how the traditional “learning by doing” model of legal training is being tested – and reshaped – by AI
- Identify the fundamentals that build genuine trust in a junior’s work, beyond simply whether a task has been done before
- Recognise the four qualities of effective supervision – time, consistency, empathy and cultural awareness – and why each still matters
- Understand the real cost and ethical weight of training junior lawyers, and why supervision should be treated as a firm-wide priority, not an optional extra
- Evaluate the risks of an AI “supervisor digital twin” and why human mentorship remains the gold standard
- Understand the current legal position on AI and privilege following United States v Heppner and Warner v Gilbarco Inc, and the practical steps firms should take to protect confidentiality when using AI tools
