Curious Playful and Provocative

The leadership capabilities we need now | Executive Private Brief October 2026

When leaders are expected to navigate uncertainty, the pressure to have an answer can be intense. AI is reshaping work, familiar approaches are being challenged and many decisions must be made before the picture is complete.

In my coaching work, I see how easily that pressure can narrow our thinking. We move quickly, take control or solve the problem ourselves. The question is whether these familiar responses still serve the situation in front of us.

The University of Sydney’s 2027 Skills Horizon places play among the capabilities leaders need and encourages productive, provocative leadership. Maximus International’s Brent Duffy offers a complementary perspective in Leadership in the AI Era: organisations need to develop human judgement, learning agility and the capacity to ask good questions, while creating room to test, fail and learn.

For me, these ideas point to a practical leadership task: stay curious, make space for experimentation and ask the questions that improve the thinking around you.

Begin with curiosity

Expertise and decisiveness matter. So does recognising when our first interpretation may be incomplete.

Under pressure, we may overanalyse, avoid a difficult issue, try to keep everyone happy or immediately offer a solution. These responses often come from strengths that have helped us succeed. They can also limit what we hear and prevent others from contributing.

Curiosity begins with a pause. What am I assuming? Whose perspective have we not heard? Am I helping people think, or doing the thinking for them?

That pause gives us a chance to choose a more useful response. It can also reveal whether the problem needs our expertise, a better question or someone else’s contribution.

Make room for play and experimentation

I see purposeful play as a way to explore uncertainty: to test, imagine and try something without needing the answer in advance. Creativity often begins with that permission.

This is part of why I use immersive experiences in The Level Up Program™. An unfamiliar VR challenge gives participants something concrete to reflect on: who asks questions, who takes control, how information is shared and what happens when the plan stops working.

A misunderstanding or unsuccessful attempt can become a learning opportunity in a controlled setting, without involving a live client project. Participants can examine their response and practise another approach.

The learning depends on skilled facilitation and a deliberate progression: Experience → Reflect → Understand → Practise → Apply. We connect what happened in the activity with a real workplace situation and identify something to do differently.

An experience may be memorable. Reflection, practice and follow-through are what give it a route into everyday work.

Ask questions that create productive discomfort

Being provocative means respectfully surfacing what a team may be avoiding. A useful question challenges familiar thinking while preserving trust.

· Are we solving the right problem?

· Where are we using AI to speed up work that needs redesigning?

· What are people reluctant to tell us?

Then comes the harder part: listening without immediately defending, explaining or fixing. The quality of that response shapes whether people will offer an honest perspective next time.

Create the conditions for people to contribute

Inviting experimentation has little value if an unsuccessful attempt is punished or a question is treated as incompetence. People need clear expectations, sensible guardrails and confidence that they can raise concerns or ask for help.

Duffy’s distinction between performance and perfection is useful here. Leaders can maintain high standards while recognising that learning requires some attempts that do not work. They need to make clear where experimentation is appropriate, what risks require approval and how the team will learn from the result.

AI adds urgency to this work. Decisions about what to automate, redesign or retain require judgement and input from people who understand the work. Leaders need to invite that knowledge into the conversation and remain accountable for the choices made.

Our own behaviour is a starting point. How we respond to uncertainty, challenge and mistakes helps establish what others believe is possible.

A reflection for this week

Choose one current leadership challenge and ask:

· What assumption needs testing?

· What small experiment could we try within clear boundaries?

· What question would help us see this differently?

Bring those questions to your next team conversation. Notice what becomes possible when you make room for other people’s thinking before offering your own answer.

Experience Level Up

Curious about what immersive learning could offer your team? I offer a complimentary introductory Level Up VR demo for leaders exploring team and leadership development. Experience the approach and discuss how it could support your people and business priorities.

​Explore Level Up and enquire about a complimentary VR demo.​

Kelly Magowan is an executive coach, leadership program designer and creator of The Level Up Program™. She helps executives and teams strengthen self-awareness, communication and leadership effectiveness through coaching and experiential learning.

Further reading

Peter, S., Riemer, K. and Norman, P. (2026). The 2027 Skills Horizon. Sydney Executive Plus, The University of Sydney. Read the report​

Duffy, B. (2026). Leadership in the AI Era: What the fastest transformation in history really demands of leaders. Maximus International. Expert insights, particularly sections 1, 2 and 4.

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