Uncertainty is no longer an occasional disruption to leadership. It is part of the operating environment.

Artificial intelligence is reshaping how work is performed. Expectations of leaders are changing. Trust is increasingly fragile, and organisations are being asked to respond to issues that do not have simple or established answers.

In this environment, leaders cannot wait for perfect information or rely solely on what has worked before.

The 2027 Skills Horizon | Sydney Executive Plus describes the years ahead as a “decade of disorientation”. Among the capabilities it highlights are the ability to accept uncertainty, embrace play, redesign work and be provocative.

These ideas strongly resonate with what I have observed through more than 25 years of executive coaching, leadership development and, more recently, the design of the Level Up Programs.

The leaders and teams most able to navigate uncertainty are not necessarily those with the fastest answers. They are often those who remain curious for longer, experiment before overcommitting and are prepared to challenge familiar thinking.

But these capabilities cannot be developed through information alone.We need to experience them.Begin with curiosity rather than certainty

Executives are frequently rewarded for expertise, judgement and decisiveness. These are valuable capabilities, but they can also create pressure to appear certain when the environment is anything but certain.

Under pressure, many of us revert to familiar patterns.

We may take control, move too quickly, overanalyse, avoid the difficult issue, try to keep everyone happy or immediately solve the problem for other people.

These responses are understandable. They are often the behaviours that have helped us succeed. But they can also limit curiosity, silence alternative perspectives and prevent others from contributing.

Curious leadership begins by noticing the response before acting on it.

• What is happening in me right now?
• What am I assuming?
• What might I be missing?
• Whose perspective have we not heard?
• Am I helping people think, or am I solving the problem for them?
• What could we explore before reaching a conclusion?

In Level Up Leader, this is part of the movement from automatic reaction to intentional leadership. The Saboteur reacts to protect. The Sage responds to lead. Curiosity creates the pause between the two. It does not prevent decisive action. It improves the quality of the thinking that precedes it.

Play is not the opposite of serious work Play is sometimes dismissed as something light, recreational or unrelated to executive performance. I see it differently. Play is one of the ways human beings explore uncertainty. It creates permission to test, imagine, take a risk and engage with a situation without needing to know the answer in advance.

That makes play a serious leadership capability.

In the Level Up Experience, participants move through a cycle of:

Play → Explore → Create → Connect → Reflect

The objective is not simply to have fun. It is to create a temporary interruption to the usual patterns of work.

When people step into an unfamiliar experience, their habitual responses often become visible. We can observe who takes control, who waits, who asks questions, who includes others, who becomes frustrated, who creates clarity and how the group responds when the plan stops working.

These moments provide rich material for learning because people are not discussing teamwork or leadership in the abstract. They are experiencing it in real time.

Using VR to interrupt familiar thinking

Virtual reality can be particularly powerful in creating this interruption.

A leader or team can enter an unfamiliar environment, face a shared challenge or be asked to collaborate with incomplete information. Familiar titles and hierarchies can temporarily recede as people focus on navigating the experience.

This creates an opportunity to notice:

• How do I respond when I am not immediately competent?
• Do I become more curious—or more controlling?
• Do we listen to one another under pressure?
• How quickly do we make assumptions?
• Who speaks, and who is overlooked?
• Are we experimenting, or trying to avoid getting it wrong?
• Can we retain humour and connection while solving a serious problem?

VR is not valuable simply because it is novel or technologically impressive.

Its value lies in its ability to make invisible human dynamics visible. It can help people encounter ambiguity, emotion, communication and collaboration rather than merely talking about them.

The technology serves the learning. From experience to insight

An immersive experience alone is not enough. Without reflection and application, it may be memorable but have little lasting impact.

The Level Up methodology follows a deliberate progression:

Experience → Reflect → Understand → Practise → Apply

First, people encounter an unfamiliar situation.

Then they reflect before judging themselves or others. They examine what happened, how they responded and what effect their behaviour had on the wider group.

They connect that experience to relevant leadership and behavioural insights, practise a different response and identify how they will apply it in the workplace.

This is also where coaching becomes important.

Coaching invites people to move beyond “What happened?” and consider:

• What does this reveal about how I lead?
• What pattern may be helping me in one context but limiting me in another?
• What conversation am I avoiding?
• What would I do differently if curiosity replaced judgement?
• What condition do I need to create for others to contribute and thrive?

The experience creates the opening. Reflection creates awareness. Practice and coaching create transfer.

Curiosity needs psychological safety

Telling employees to experiment will achieve little if mistakes are punished, questions are interpreted as incompetence or challenging a senior leader carries personal risk.

Play, curiosity and provocation all depend on psychological safety.

Psychological safety does not mean lowering standards or removing accountability. It means creating conditions in which people can speak honestly, ask for help, test an idea, admit uncertainty and challenge thinking without fear of humiliation or retaliation.

This is particularly important when teams are working under pressure.

Level Up TEAM uses shared experiences to explore the invisible network that sits beneath performance: trust, communication, inclusion, empathy, relationships and the willingness to raise what needs to be said.

These relational conditions produce visible organisational outcomes. When they are strong, teams can disagree more constructively, respond more quickly and make better use of their collective intelligence.

Be provocative without becoming combative

Future-focused leadership also requires a willingness to ask questions that create productive discomfort.

Provocative leadership is not about being confrontational for effect. It is about respectfully surfacing what a team may be avoiding.

• Are we solving the right problem?
• What are we pretending not to know?
• Is this process still serving us, or is it simply familiar?
• Where are we using AI to accelerate work that should be redesigned?
• What work should we stop doing?
• What would someone outside our organisation find strange about how we operate?
• What are people reluctant to tell us?
• If we designed this role or service today, would it look the same?

These are Conversations That Matter.

The leader’s task is to ask, listen, challenge and coach—not immediately tell, fix, rescue or direct.

A useful provocation challenges the thinking rather than attacking the person. It combines candour with curiosity and accountability with respect.

AI requires human and relational capability

AI makes these leadership capabilities more important, not less.

The transformation ahead is not solely a technical implementation challenge. It is a human and organisational redesign challenge.

Leaders and teams will need to explore which tasks should be automated, augmented, redesigned or removed. They will need to decide where human judgement must remain central, how accountability will operate and how people will continue developing expertise rather than simply offloading their thinking.

These decisions cannot be made effectively by a few executives working in isolation.

They require people close to the work to question, experiment, learn and contribute. They require psychological safety, thoughtful challenge and a shared willingness to enter territory where nobody has the complete answer.

Creating the conditions for people to thrive

Leadership is not simply what we know or personally deliver. It is also the environment we create around us.

Every interaction creates conditions. It can increase trust, clarity, curiosity and accountability—or reinforce silence, dependency and avoidance.

The challenge for leaders is therefore not to eliminate uncertainty. It is to create the conditions in which people can move through it together.

This means setting a clear direction without over-controlling the route. It means making room for play and experimentation while maintaining purpose and accountability. It means asking difficult questions while preserving trust. And it means being willing to learn alongside the people we lead.

A practical leadership rhythm might be:

Experience. Notice. Pause. Ask. Explore. Challenge. Practise. Apply.

The leaders who thrive in the years ahead may not be those who project the greatest certainty. They may be those who are grounded enough to say, “We do not know yet,” curious enough to explore what might be possible, playful enough to experiment and courageous enough to ask the question that changes the conversation.

A Level Up reflection

Consider one current leadership or business challenge:

• What assumptions are you bringing to it?
• Which of your habitual responses appears under pressure?
• What question have you not yet asked?
• What could you safely experiment with?
• Who else needs to be part of the thinking?
• What condition—trust, clarity, curiosity or accountability—do you need to strengthen?
• What will you apply differently over the next 30 days?

Leadership development is not about becoming someone entirely different. It is about becoming more aware, more intentional and more fully able to access the leader you can be.

Kelly Magowan is a strategic executive coach, leadership program designer and creator of The Level Up Program. She works with executives and teams to strengthen self-awareness, communication, decision-making, psychological safety and leadership effectiveness through coaching and experiential learning.