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Leadership Unfiltered – Sydney & Canberra, March 2026

Katharine Whittaker • April 21, 2026

 

Advancing women in technology has been a priority for most organisations for years. The gap between intention and outcome has barely moved. At our recent Leadership Unfiltered breakfast in Sydney, senior tech executives gathered to move beyond awareness into the kind of candid, practical conversation that rarely happens in public.


We heard from Brendon Riley, Former Chief Executive at Telstra Infraco, and Duncan Hewett, Former Senior Vice President and General Manager Asia Pacific and Japan at VMware – two of Australia's most respected technology leaders – who drew on their careers to share the specific actions, missteps, and sponsorship moments that helped women on their teams break through to senior roles. Sheryl Carroll, Integrative Health Practitioner and Women's Health Coach, brought a complementary and often overlooked perspective: how women's health and wellbeing intersects with career advancement at every stage – and what organisations are missing by not accounting for it. 


The dimension organisations aren't accounting for

Sheryl opened a conversation that is largely absent from leadership forums: the physical and hormonal arc of a woman's working life. From significant health challenges that can affect energy, focus, and confidence at any career stage, to pregnancy and parental leave, to the cumulative weight of the invisible load – the domestic and emotional labour that disproportionately falls on women – the biological reality of the working experience is rarely factored into how organisations are designed or how leaders are prepared.


The response doesn't require a complex program. It starts with genuine awareness and leaders who ask how someone is really doing – and mean it.

From directing to unlocking

Both Brendon and Duncan were candid about getting it wrong first. Early in their careers, both led through instruction — pushing harder, assuming effort and direction from the top was what drove performance. 


The shift that changed how they led was moving from directing to removing the barriers that prevented people from performing at their best. The insight, when it came, was the same: the potential was already there. The role of the leader was to surface it, not manufacture it. For both, that realisation didn't come from a leadership program – it came from paying closer attention to what was actually happening around them.

 

The relationship gap that costs you talent

One of the harder themes of the morning: the cost of leader relationships that don't go deep enough. When leaders don't know what's really happening in someone's life – their ambitions, their constraints, the pressures they're managing alongside their role – they can't support them effectively.


Women, both speakers observed, tend to manage the whole picture. They are often highly capable of compartmentalising and getting on with it, even when significant things are happening beneath the surface. That places a real responsibility on leaders to ask the second question – and to build enough trust that the real answer feels safe to give.


Confidence is the barrier – and it's addressable

What most often holds women back isn't capability. The women in these conversations weren't lacking skills – they were navigating environments where visibility was inconsistent, sponsorship was patchy, and the path forward was unclear.


The response that works isn't more training. It's active, deliberate sponsorship – advocating in rooms where the person isn't present, creating visibility, and building the conditions for women to see themselves in the role ahead rather than just knowing it exists in theory.


This isn't theoretical. Leaders in the room had tested it at scale – running programs designed to address the skills gap in women returning to technology, only to find the skills gap wasn't the issue. Confidence was, every time.


The double burden of emotional intelligence

A question that surfaced in discussion: if the qualities that make women effective leaders – holding the whole picture, asking the deeper question, attending to the wellbeing of the team – are also the qualities that can quietly add to their load, how do women embrace them without being typecast by them?


The answer that emerged wasn't to dial those qualities back. It was for organisations and leaders to recognise them for what they are – a strategic asset – and to stop treating them as an informal tax. When emotional intelligence is expected but unacknowledged, it becomes invisible labour. When it's recognised and valued in how people are assessed, promoted, and supported, it becomes a genuine differentiator.


The responsibility sits with the organisation as much as the individual


Design it in – don't bolt it on

Brendon spoke to the difference between retrofitting diversity into an existing culture and designing it in from the start. When the opportunity exists to build something new, the early decisions about who is in the room and what behaviours are rewarded shape everything that follows.


Brendon referenced research on representation suggesting that when a minority group reaches around 25% a tipping point the dynamic in the room shifts. The culture changes. Interactions change. Getting there requires deliberate choices made early, not after the habits have already formed.


The role male leaders play

What made this conversation distinctive was its framing. This wasn't a discussion about what women need to do differently. It was two senior male leaders reflecting honestly on the specific decisions and the specific failures that shaped the women on their teams.


The consistent thread: they weren't giving women an advantage. They were removing disadvantages that had always been there. Sponsoring people into rooms they weren't in. Creating space for contribution before it felt warranted. Backing someone before they felt ready, because the leader could see what the person couldn't yet see in themselves.


For male leaders in technology, the ask is clear: the question isn't whether to be involved in this work. It's whether the decisions being made every day are advancing it or quietly undermining it.


The conversation didn't stop in Sydney. The following week in Canberra, Claudine Beltrami, Former ANZ Head of Public Sector at Verizon Business, and Lucy Poole, Deputy Chief Executive Officer – Digital Strategy, Policy and Performance at the Digital Transformation Agency, brought their own experience of senior leadership in technology to a roundtable of women in the industry.


Our thanks to Katharine Whittaker for facilitating both conversations with the honesty and depth they deserved, and to Brendon, Duncan, Sheryl, Claudine, and Lucy for their honesty and generosity.

 

Continue the conversation

For further insights or to explore how Derwent can support your organisation's approach to women in technology leadership, connect with our Digital & Technology Practice team at sydney@derwentsearch.com.au

 

To register your interest in future Derwent events, please reach out to us at events@derwentsearch.com.au.

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