Conference As a Mirror: When AI Certainty and Uncertainty Collide

May 6, 2026 | AI and technology

By KDVI Affiliate, Andrea Foot

As I walked into Legal Innovation and Tech Fest 2026 in Sydney last week, I could feel my usual anticipatory rush at joining my community in person. I love a group, meeting new contacts and longstanding friends, and watching how people have moved around employers and between ecosystem players. And that’s before we even get to the speakers and panels.

Almost immediately I noticed that the number of exhibitors seemed to have significantly expanded and the majority of them were AI-something-something. I was very struck by the one-note confidence being projected by the vendors about AI. Because, of course, the purveyors of technology have always needed to be certain about the benefit of the solutions they offer. Certainty is the product, as much as the software. Trust us. Buy Your Trust Here.

Listening to speaker sessions there were a wider range of perspectives, from examples of successful AI use, to how to bring lawyers into the AI journey, to the future of legal work and a wide range of largely AI-centric topics in between. The tone of these sessions was more diverse, some very assured, others more questioning, or having more questions than answers. This felt more aligned with the emotional tone of the delegates, who were seeking information and answers to the plethora of questions they hold about AI.

Thinking psychodynamically, this presents an interesting Petrie dish of group behaviours and what those responses tell us about the uncertainty of AI’s impact on the legal sector, on work, and on the people living through it.

A Spectrum of (Un)Certainty

What I was observing across those two days was not simply a diversity of views. I saw a system organising itself around systemic anxiety, and doing so in a very particular way. Confidence about AI showed up in a spectrum across the three groups present. The vendors occupied one end, publicly projecting maximum certainty not least because their commercial survival depends on it. The speakers occupied the middle, ranging across the spectrum from the highly assured to the deeply questioning. And the delegates occupied the other end, holding the most uncertainty, arriving with questions they could not always fully articulate and leaving with answers that felt helpful but with questions about whether they could apply them to their actual situations.

This spectrum is not accidental. It’s the system unconsciously finding its way through something very unsettling. Certainty congregates where it is most commercially and professionally required. Uncertainty settles where it is most personally felt. And the most open voices in the room, the speakers with more questions than answers, the delegates who did not yet know quite what they were asking, tend to be the ones least structurally positioned to shape the conversation. Uncertainty bubbles under the surface of all the groups, coming to the surface in private discussions between people who know each other well. A clue about who holds uncertainty often lies with those projecting the most confident certainty.

What this means is that the conference, for all its genuine value, was organised in a way that kept the anxiety about AI contained rather than examined. The vendor hall offered definite solutions, the word Trust featuring on many a booth. The speaker programme offered helpful frameworks. The delegate experience offered the feeling of being addressed. But the deeper questions, about what AI means for professional identity, for the nature of expertise, for what it will mean to be a lawyer or someone who supports lawyers in the next year or in ten years, were present in the room without quite having anywhere to land.

The Law Firm – Mirrored

Here’s what struck me, walking between sessions and exhibition stands, to give you a hypothesis to mull over. The dynamic I was observing at the conference is not unique to the conference. It is a reproduction of what is happening inside law firms right now.

In the firm, the technology function or innovation team occupies the vendor position. They are the carriers of certainty, the people whose role requires them to project confidence about what AI can do and where the firm should go. Their credibility depends on it. Leadership occupies the speaker position, ranging from the highly committed to the openly sceptical, delivering strategy and direction with the authority their role requires. And the practitioners, the business services teams and the lawyers doing the daily work, occupy the delegate position. They hold the most unresolved uncertainty. They are receiving confident answers to questions they have not yet fully formed, from people who are themselves managing their own anxiety through the performance of certainty.

The certainty spectrum runs through firms in the same direction as it ran through the conference. Certainty at the top and at the edges, where it is institutionally required. Uncertainty in the middle, where it is most personally felt and least safely expressible.

And just as the conference format has no particular mechanism for closing the gap between the confident deliverer and the uncertain receiver, most firms have no particular mechanism for it either. The technology roadmap flows downward. The training programme is delivered. The policy is written and circulated. What does not flow, in either direction, is the honest exploration of what people are actually experiencing. The practitioner who does not know what AI means for their role. The innovation lead who feels less certain than they appear. The managing partner who is watching competitors and feeling the pressure to have a position they do not yet fully hold.

What We See in the Mirror

What the conference made visible, by gathering all three groups in the same space for two days, is that the boundaries between certainty and uncertainty are considerably more porous than the roles people occupy would suggest. The vendor who speaks with total confidence about AI’s transformative potential is also, privately, navigating a market that is changing faster than any roadmap can accommodate. The speaker delivering assured answers is also, in many cases, working from a position that is more provisional than the stage allows them to admit. The delegate receiving the content is also, in many conversations I had in corridors and over coffee, more thoughtful and more perceptive about what is actually happening than the format gave them room to express.

The convergence is the story. The groups are not as separate as a conference structure implies. They are all, in different ways and from different positions, navigating the same genuinely uncertain territory. What the conference format does is organise them into roles that manage that shared anxiety rather than acknowledge it. And what most law firms do, in their approach to AI, is exactly the same thing.

What Would It Take Instead?

The firms that will navigate this well are not the ones whose technology function projects the most confidence or whose managing partner plants the most decisive flag. They are the ones that find a way to close the gap between the spectrum’s two ends, to create conditions in which the practitioner’s unresolved questions become visible to the people setting the strategy, and in which the genuine uncertainty of the people projecting certainty becomes speakable without cost.

That is not a structural fix. It is a cultural one. It requires leaders who are willing to inhabit the middle of the spectrum rather than one of it’s ends, who can hold their own uncertainty alongside their people’s rather than managing it through the performance of having already worked it out.

The conference gave me a great deal to think about. It also gave me, as it usually does, a very clear picture of the work that remains to be done. Not on the technology. On the conditions inside which the technology is being received, and the gap between what is being confidently delivered and what is actually being felt.

That gap is not a conference problem. It is the central organisational challenge of this moment. And it was sitting in plain view, across two days in Sydney, for anyone curious enough about uncertainty to notice it.

Oriane Kets de Vries:

Oriane Kets de Vries is CEO and owner of the Kets de Vries Institute. She leads a global team of coaches, consultants and educators dedicated to developing reflective, emotionally intelligent leaders and cultivating workplaces where people can thrive. In her faculty role, she draws on extensive experience designing and directing leadership programmes for senior executives, contributing her expertise in psychodynamic coaching, organisational culture, and transformational leadership development.

Oriane has served as consultant, coach, and programme director for clients including Pictet, Deutsche Bank, Merck, UBS, Mishcon de Reya, and Engie, and she has taught on open-enrolment programmes with leading institutions such as Cambridge Judge Business School, Oxford Saïd, INSEAD, ESCP, ESMT and CEDEP. Her interests centre on the human side of leadership, particularly identity, creativity, entrepreneurship and gender dynamics. She holds an MBA and Executive MA in Coaching and Consulting for Change from INSEAD, has trained at the Harvard Kennedy School, and brings more than a decade of professional experience in creative and entrepreneurial industries into her work with leaders.

Manfred Kets de Vries:

Manfred Kets de Vries is a pioneering authority in leadership development, coaching, and organisational change. He is a founder and director of the Kets de Vries Institute (KDVI) and served as Distinguished Clinical Professor of Leadership Development and Organisational Change at INSEAD. With academic credentials in economics (University of Amsterdam), management (MBA and DBA, Harvard Business School), and psychoanalysis (trained in Canada), he brings a uniquely interdisciplinary perspective to leadership. His work bridges management theory and clinical insight, establishing him as a global thought leader in executive coaching and transformation. At INSEAD, he founded the Global Leadership Centre and led the flagship programme The Challenge of Leadership for 31 years. He also served as scientific director of Coaching and Consulting for Change, an 18-month Executive Master’s programme that has shaped over 3,000 senior leaders and executive coaches worldwide. He has advised and coached senior executives at global firms including Goldman Sachs, BP, Shell, Unilever, McKinsey, and Volvo. A prolific author of over 60 books and 400 articles, his work appears regularly in The Financial Times, The Economist, and Harvard Business Review. Recognised by Le Capital, Wirtschaftswoche, and The Financial Times as one of the world’s top 50 management thinkers, he is widely regarded for advancing more human-centred approaches to leadership.

Yulia Chupina:

Senior Adviser (Luminary) at Accenture and executive coach with over 12 years of board experience. Formerly a banker and McKinsey consultant, Yulia has led banking transformations in digital, agile, organisational change, and talent development. Her coaching spans the finance, tech, and consumer goods sectors, blending technological insight with emotional intelligence to guide leaders through transformation. Recently, she advised BBVA on agile methodologies and senior talent development. Influenced by thought leaders such as Manfred Kets de Vries and Gabor Maté, Yulia brings an analytical, reflective approach to leadership. She has lived and worked across the UK, Spain, the US, and Russia.

Elizabeth Florent:

Elizabeth has worked closely with Manfred Kets de Vries for many years and has served as a Senior Lecturer and Research Fellow at INSEAD. Her extensive background in leadership development spans organisational consulting, executive coaching, and academic research. She holds advanced degrees in Organisational Development and Clinical Organisational Psychology and is a certified Coaching Supervisor through the Tavistock Institute. Her doctoral research explored experiential domains in executive education, and she has authored or co-authored numerous academic articles, case studies, and books on leadership and organisational dynamics. Elizabeth led the development teams behind KDVI’s diagnostic instruments, including the GELM, OCA™, and ITI. Drawing on her diverse training and global experience, she brings deep cross-cultural insight to her work with leaders worldwide. Originally from California, Elizabeth has made France her home for over 30 years.