Out of the box – revisiting the art of great conversation

The Marlene Bar at the Hotel Intercontinental is the beating heart of learning for those attending OEB. It always has been for the past 30 years. It’s here that we engage freely with fresh thinking, new people and old friends. Testing hypotheses, exchanging ideas and debating the debate!

For many years, I had the privilege of working alongside Jay Cross and Charles Jennings at OEB and whilst many of our conversations took place in the beloved Marlene Bar. Jay was a visionary and wonderful raconteur. He was a radical and his lifetime he continuously challenged the way that we think about learning and how we support it. He was the first to use the term e-learning online back in 1999 – I worked with him then and believe me, it meant something completely different than today!  it was Jay that drew our attention to the fact that most of our learning occurs informally, yet most of our budget is allocated to formal interventions Jay’s vision that we create more space within the conference itself for connection and conversation. Together we explored and experimented with unconference formats that allowed us to learn together without agenda.




Jay’s box of stories


In one of these sessions Jay shared a single screen – a grid of 9 numbered boxes, pictures and captions. He wasn’t just presenting but he was orchestrating serendipity. The box contained 9 possibilities, each concealing a story or a conversation starter. The captions were obscure and photo’s intriguing. The idea was that the audience not only chose the order in which the stories unfolded, but to co-create meaning from them as they did.

It was classic Jay, pure rebellion against linear thinking and an experience of learning as Jay envisioned it: organic, social and delightfully unpredictable.


Stories as Learning Currency

With his mysterious box of conversation starters, Jay demonstrated what he preached – that stories are how we make sense of the world. The box wasn’t just a collection of topics; it was a treasure chest of narratives waiting to spark connections. “Stories are the original viral learning tool,” Jay would say. “They spread understanding and meaning in a way PowerPoint never will.”


The Power of Conversation

“All learning is social. Even when you’re reading a book, you’re having a conversation with the author.” This core belief shaped Jay’s approach to the box format. When an audience member called out their choice, they weren’t just selecting a topic – they were initiating a dialogue. One story would spark another, connections would emerge unexpectedly, and collective wisdom would build.


Learning is Working, Working is Learning

“Learning is not something that requires time out from being engaged in productive work. Learning is the essence of productive work.” The unpredictable order of these box-inspired conversations mirrors Jay’s observations about workplace learning – not through carefully structured curricula, but through meandering paths of discovery, driven by curiosity and immediate relevance.


Beyond the Formal: Embracing the unexpected

“The folks who create formal training and development programs have their hearts in the right place, but they’re trying to force-feed knowledge to people who are too busy to be interrupted.” Ouch!  Jay’s wasn’t afraid to share his revolutionary understanding that most valuable learning happens outside formal structures. When a story about jazz improvisation unexpectedly resonates with a discussion about organizational change, we’re experiencing what Jay championed – the rich, multilayered learning that happens in the informal spaces. His box of stories created seeds of serendipity.


The Trust Factor

What made Jay’s box format so powerful was its trust in the audience. Trust to find their own path. Trust in the power of conversation. Trust in the unexpected connections that emerge when we create space for them. As Jay noted, “Learning is more effective when it’s pulled by the learner than when it’s pushed by the teacher.”


The Innovation Challenge

“In times of change, learners inherit the earth, while the learned find themselves beautifully equipped to deal with a world that no longer exists.” The box format challenges us to move beyond traditional approaches to learning. It’s about being open to surprise, comfortable with ambiguity, and ready to learn from every conversation.


Carrying Forward Jay’s Legacy

Whilst Jay Cross may no longer be with us, we still celebrate and remember the ageless lessons that he shared. At the end of every OEB we still honour Jay’s box of stories in our Closing conversation session at 4.30pm on the Friday.  As we look back on the conference them ‘The courage to redefine learning’ we’ll draw on each other’s stories, reflect, make serendipitous chance encounters and have fun. 

Those joining this session get to experience a litte of what Jay called  “working smarter” – learning through conversation, story, and shared discovery. Because in the end, as Jay showed us, the most powerful learning moments often come not from following a preset path, but from being open to the wisdom that emerges when we explore together. It’s a fun way to close out the conference and of course, the conversations almost always flow over into the Marlene Bar before we head home.

“Learning is that which enables you to participate successfully in life, at work, and in the groups that matter to you.”

Let’s keep participating, keep sharing, and keep learning together.

Look out for the unexpected at the other unconference sessions at OEB this year:



Written for OEB Global 2024 by Laura Overton.

Leave a Reply

Your email address will not be published.