At a recent roundtable hosted by The Preston Associates in Hong Kong, a diverse group of senior leaders explored a shared challenge: developing and exercising sound judgment individually and across their organisations.
How do leaders decide the right thing to do when information is incomplete, priorities compete and conditions keep changing?
Then one word brought an unexpected note to the conversation: fun. I t sparked a different energy in the room and opened up a distinctly human way of looking at leadership and judgment.
What’s behind “fun” at work? Collaboration that pays off.
Think of a time when you enjoyed working through a difficult problem with others. Someone offered a fresh perspective. You questioned an assumption. Someone built on your idea. Through discussion and perhaps disagreement, you weighed the options and consequences, finding a way forward none of you would have reached alone.
There is something deeply satisfying about that experience. You feel seen and heard. Your expertise counts. Connections with others bring out your best thinking and help you reach a considered judgment, with greater clarity and conviction about what to do next. Together, you can tackle something bigger and make a greater impact. And you know you are not on your own.
The conditions that make collaboration fulfilling – worthwhile purpose, meaningful contribution, thoughtful challenge and shared responsibility – also support sound judgment.
Clarity creates the freedom to play
Too often, we jump straight to how to get things done before clarifying why they matter or what we are trying to achieve. For contribution to feel meaningful, people need both. Purpose and a clear picture of collective success provide anchors for judgment. For a team launching a service, for example, success might mean customers can use it confidently, not simply that it launches on time. That clarity helps people weigh priorities and make choices.
Leaders are accountable for articulating this direction clearly and consistently. As we discussed at the roundtable, that direction is the chorus: you have to keep repeating it. People need to understand what they are working towards and see how their contribution helps make it happen. Once that clarity is in place, creativity, innovation, and even fun have room to thrive. In those moments of out of the box thinking, strong judgment is even more critical.
A greater need for human judgment
AI is changing how we work and the information available to us. Geopolitical shifts unsettle plans and assumptions. Leaders face pressure to act while making sense of unfamiliar situations, and that pressure can leave little room to step back and think.
One takeaway from the executive roundtable was the openness with which leaders agree that no one has all the answers. Bringing focus and clarity means drawing on people across the organisation who understand customers, know how the work happens and bring different expertise. Harnessing this collective intelligence means seeking out their perspectives and examining them together, including those that challenge the prevailing view.
Thinking together helps us see more. We still have to weigh what we see, make a choice and take responsibility.
AI can help us explore possibilities and work faster. But deciding what is right to do – whose interests to consider, which consequences to accept and what commitments to uphold – remains a human responsibility. That makes developing people’s judgment across the organisation a leadership priority we cannot delegate to technology.
Leaders create the conditions for strong judgment and good fun
Someone questions a plan. A colleague asks for help with a difficult call. A team member spots something the rest of the room has missed.
How leaders respond in those everyday moments shows people how they are expected to think and work together, and shapes what people bring to the next conversation. Alongside keeping the direction clear, leaders need to invite thinking, welcome challenge, and give people room to decide within clear boundaries. Acknowledging uncertainty and reconsidering their own views sets the tone.
If every difficult call returns to the same few leaders, judgment remains concentrated. People need opportunities to practice it where the action happens. Working through decisions and reflecting on outcomes helps leaders and their teams sharpen their judgment together. These everyday interactions shape the working environment and, over time, the organisation’s culture.
The power of the leader as a coach
A key insight from the roundtable was the need to move beyond seeing coaching as a remedy for performance gaps. Leaders can proactively and intentionally use a coaching mindset and skill set to improve performance: drawing out others’ thinking, harnessing collective intelligence, and developing sound judgment in themselves and their teams. This makes coaching part of everyday leadership.
For example, when someone brings a difficult decision, it can be tempting to supply the answer. Sometimes that is exactly what the situation requires. At other times, a few questions can do more.
“What do you recommend?”
“What are you weighing up?”
“Where would another perspective help?”
Working through these questions helps people practice judgment and gives leaders access to thinking they might otherwise miss. Both get to see more clearly. The skill is knowing when to give direction, when to help someone think, and who will make the decision. Participants’ reflections brought us back to curiosity and humility, alongside the skills to listen, question and challenge thoughtfully. Organisations can cultivate these capabilities through everyday conversations where decisions take shape and judgment develops. It becomes fun when ego and posturing are replaced with openness and willingness to try new ideas.
These qualities also help leaders draw on different cultural perspectives, a point raised at the roundtable. Cultural norms can shape how people think and communicate. A coaching mindset encourages leaders to question their own assumptions and adapt how they invite contributions, helping bring out people’s best thinking across cultures.
So, what’s fun got to do with it?
Perhaps this is what makes work feel like fun: doing something worthwhile, knowing our contribution matters, and having others to think it through with. We can disagree, learn and shape what happens without having to know everything or tackle it alone.
In an age of powerful technology, there is good reason to dial up our humanity. Curiosity, connection and shared responsibility help us put our collective intelligence to work. Leaders help make this possible by providing direction and creating room for people to contribute, strengthening their own judgment while helping others develop theirs. Along the way, work may become deeply fulfilling – and, yes, fun.
Fun is, after all, one of The Preston Associates’ key values. And there are good reasons to take fun seriously.
Maria Sit, with nearly 30 years of leadership experience across Asia and Europe, including senior roles at Sun Life, AIA Group and AXA Investment Managers, is an Executive Coach at TPA Asia, helping senior leaders and teams navigate complexity, strengthen judgment and translate strategy into sustained performance.
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