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Pathway to the Boardroom – Sydney, September 2026
Michelle Gardiner • October 12, 2026
Senior executives gathered in Sydney last month for our Pathway to the Boardroom event, a programme now in its second decade of helping executives become board ready.
We were privileged to be joined by Jacqueline Chow and Sylvia Wiggins who discussed what the transition from executive life to the boardroom actually involves and what it demands once you're there. Six themes stood out.
The path looks different for everyone.
The journey to becoming a Non Executive Director is individual and varied. For some, it starts with the realisation that they can create more impact in the boardroom than as an executive leader. Often this comes with a preference for the breadth of a board role, over the narrower focus of life as an executive. For others, it follows an event that prompts a deliberate rethink of their career.
Not every board is going to be right for you.
One thing some directors wish they had known at the beginning of their journey is that not every board is the right fit for you personally. The pathway involves a lot of rejection, and it takes maturity to reflect on what you have to offer as well as personal interest. Boards appoint based on what the organisation needs, so a rejection reflects a decision made in the board's interest rather than a judgement on the individual.
It's also important to do due diligence on boards before joining. Non negotiables for joining a board include hygiene issues such as financials and legal but testing the people and culture of a board is imperative, this includes checking who among your own network has already worked with people on that board. Board culture reflects both an ability to vigorously debate ideas and a commitment to board solidarity to make a collective decision. A successful board is comfortable with both.
The skillset is different.
Skills that serve well in an executive career don't automatically transfer to the boardroom. Early on, a new director may be eager and want to ask lots of questions, but in a boardroom, what adds the most value is listening and adding a considered perspective. At a board meeting some of the most impactful directors can often sit quietly for most of a board meeting and make one well-judged contribution that makes a pivotal difference to the decisions made.
The mindset shift matters too, in the executive world, a role carries responsibility for a function, but board directors are accountable for the whole organisation, which includes identifying contradictions, such as a growth target that conflicts with the risk appetite.
Board composition expectations are shifting.
The skills matrix is evolving. Finance, legal, governance and industry expertise remain core, but emerging skills such as cyber, work health and safety, and AI, once viewed as a specialty sitting with one expert board member, are now shifting to an expectation that all board members must understand. Directors need to be diligent about upskilling, particularly in AI, which is changing how organisations do business.
Behavioural attributes matter just as much as technical capability: relentless curiosity to understand what is happening in the organisation, the confidence to change your mind and be challenged in your thinking, and a collaborative style comfortable with viewing the board as a collective that gains from the diversity of everyone in the room.
Succession planning must be continuous.
Boards need to discuss succession planning continuously to ensure it is orderly and timely, whether in response to volatility in the world, or externalities that require a transformational pivot. This includes carefully considering the timing of bringing on a new director.
Chief Executive Officer succession is a particular challenge, requiring a balance between people feeling safe in their roles and the reality that a CEO who is well regarded today may not continue to be the right person for the organisation in a fast changing environment.
The importance of building strong relationships can't be underestimated
Trust is the foundation of a well-functioning board. In a crisis, directors rely on colleagues who will commit time and energy to resolving the problem as a team, and who can be counted on to ask the hard questions. That confidence has to be built well before it is needed. Because board members typically meet once a month or less often, relationships need deliberate attention, such as volunteering for a committee together, suggesting a webinar or inviting a fellow director for a coffee.
_________________________________________________________________________
Our thanks to Michelle Gardiner, Managing Partner at Derwent, for hosting the morning, and to Jacqueline and Sylvia for such generous, practical insight into the realities of board life.
Continue the conversation
For further insights or to explore how Derwent can support your organisation's approach to board composition and succession, connect with our 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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By most measures, this is the fastest adoption of a transformative technology in human history, and the pace itself, more than the tools, is what's testing leaders right now. The question we explored at our AI & The People event in Perth last week wasn't whether to engage with AI, it was how quickly leaders could learn to work through the ambiguity it creates – adapting their leadership style and their team's dynamics on the move, without the luxury of mastering every technical detail first. A shift which asked a lot more of leaders than most changes they've led before. We were lucky to have both Peter Tonagh , Executive Chair at Quantium, and Jacky Connolly , Chief People Officer at CBH Group, join the conversation. Five key themes stood out. The energy is there. The paradox is what happens next. Most people aren't resistant to AI, they're cautious, and the caution has more to do with job security than the technology itself. Some roles changed materially enough to bring the challenge of redeployment. For most people though, roles simply changed shape, and the job for leaders is to harness that energy rather than manage it down. Underneath that sits a harder problem. The productivity paradox. Individuals are getting faster and better at their jobs with AI, but those personal gains rarely show up as enterprise level returns. Team members without proper support will find their own workaround – bringing in their own unsanctioned tools or leaving for an organisation who gives them a better one – so the case for organisations investing properly is not really a choice. Lead it from the top. Guard it just as fast. This is an organisational problem before it's a technology one. Business models are set by leaders, not technologists, and senior people being visibly comfortable using the tools is what gives everyone else permission to engage with them. The common myth is that graduate roles are most at risk, however the real risk sits with middle management – executives will become more productive and carry more direct reports, resulting in fewer layers in between. Guardrails need to be set fast rather than perfected in advance, particularly around the risk of losing intellectual property. Starting with a small set of approved tools, and expanding as trust builds, is better than waiting for a comprehensive policy before allowing any use at all. Boards need to be brought in early too, so they understand their own obligations from the start rather than being briefed after the fact. AI tools tend to agree too readily. Adjusting the settings to instruct the tool to push back and challenge assumptions, instead of defaulting to agreement, was raised as a small fix that can help improve decision quality. Bring the whole workforce. Not just the office. AI tools in organisations work when technology and people are treated as one problem. Leaders need to understand the tools well enough to drive change through them, rather than leaving it to IT alone. Frontline and operational team members matter just as much as corporate functions: practical wins like rostering and attendance carry real weight, and leaving teams behind undermines the case for AI everywhere else in the business. There is also a real shift reshaping recruitment. Hiring is moving away from purely skills-based selection towards attributes: curiosity, critical thinking, persistence, agility, and optimism. It's a genuine move back toward classical study, backed by heavier investment in structured training to bring people onto the same page. Claim the gain. Then change how you measure people. The strongest examples of AI delivering enterprise value tend to be simple and specific – one tool that is purposefully built and applied across the organisation, is better than everyone building their own individual version of the same thing. But individual productivity gains don’t redirect themselves. Organisations need to actively claim the time being freed up and decide what it's used for, rather than leaving the decision to individuals. That same discipline needs to extend to how performance is measured. Early adopters should be rewarded for bringing others along and sharing what they’ve learned, not just for their own output. A cost-out mentality, or pitting people against each other, will corrode culture quickly. Redesign the work. Don’t just hand out the toolkit. The most common mistake organisations make is retooling an existing process rather than redesigning the work itself. Give someone an AI tool without rethinking their role, and the result is usually chaos, not efficiency. The real gains come from pairing someone who understands the AI tools with someone who deeply understands the work, then letting them rebuild roles and workflows together from first principles. New competitors are already emerging built exactly this way – a key consideration for any organisations still only automating. One example was given of a leader building a personal "digital twin", an AI trained specifically on their tone, feedback style, and decision-making patterns. It was developed over approximately 200 hours, though the benefit was felt within the first couple of hours of use. Six leadership principles had already been documented; the AI was then used to interview and draw out roughly 30 more. The tool is now used for communications, coaching a wider team, and personally – including when weighing a difficult decision while tired. The organisations that get this right won't be the ones with the best AI. They'll be the ones whose leaders go first – closing the gap between individual and enterprise gains, setting guardrails fast, bringing the whole workforce with them, and redesigning the work rather than just the toolkit. _________________________________________________________________________ Our thanks to Lindsay Every , Group Managing Partner at Derwent, for hosting the morning, and to Peter and Jacky for such generous, on-the-ground insight into what AI adoption looks like. A special thanks to Julie Colvin , Managing Partner – Perth, and our Perth team for their support in bringing this event to life. Continue the conversation For further insights or to explore how Derwent can support your organisation's approach to AI and workforce transformation, connect with our team at perth@derwentsearch.com.au To register your interest in future Derwent events, please reach out to us at events@derwentsearch.com.au .
The boardroom has changed. Permanently. The issues filling board agendas today are not temporary disruptions. They are the operating environment. AI, cyber risk, geopolitical instability, regulation, climate exposure and cost volatility are reshaping how organisations compete, invest and make decisions. For boards, the expectations have changed. Directors are being asked to understand more, engage more deeply and bring increasingly relevant experience to the table. Regulators, investors and other stakeholders are also looking more closely at whether boards are equipped for what lies ahead. The question is no longer simply whether a board is well governed. It is whether the board has the right mix of capability, judgement and adaptability to lead the organisation into its next chapter. The capability conversation is changing Credentials and experience remain important, but they are no longer enough on their own. Curiosity, adaptability and a willingness to keep learning are becoming equally valuable. AI is a clear example. Directors do not need to become technologists, but they do need enough understanding to ask informed questions about risk, ethics, data, accountability and return on investment. Cyber security and data governance present a similar challenge. These issues now sit firmly within board accountability. Scenario planning, crisis preparedness and understanding where the organisation’s exposures lie are no longer occasional agenda items. They are part of the boards regular rhythm. Renewal cannot wait for a vacancy Strong board renewal starts with future strategy. What capabilities will be required over the next five to ten years? Which risks will become more material? Where does the board need deeper commercial, functional or sector experience? Which perspectives may be missing? These questions are more useful than simply asking whose term is ending next. The most effective boards are moving beyond static skills matrices and periodic succession discussions. They are treating board composition as a dynamic capability plan that evolves alongside the organisation. They are refreshing skills matrices against future strategy, building learning agendas across AI, cyber, ESG, risk and geopolitics, reviewing committee structures and linking succession to capability rather than tenure alone. They are also paying closer attention to board dynamics. A technically capable board can still underperform when trust is low, challenge is poorly handled or directors struggle to work together under pressure. Constructive challenge, sound judgement and the ability to listen, learn and adapt are central to effective governance. The briefs are changing Across Derwent’s Board practice, we are seeing more mandates where recent sector and functional experience is a primary driver of selection. Boards are seeking contemporary expertise in areas including technology and AI governance, audit and risk, renewables and infrastructure, capital allocation and mergers and acquisitions. The profile of who is considered “board-ready” is therefore broadening. Traditional governance experience remains valuable, but boards increasingly need directors who bring current knowledge, diverse perspectives and the ability to contribute to new and fast-moving conversations. Board search and succession planning are not simply about filling a vacant seat. They are about building a board that is ready for the future of the organisation. The strongest boards will be those that renew with intent – bringing together the experience, behaviours and perspectives required not only for today’s agenda, but for the decade ahead. ___________________________________________________________________________ If you're reviewing your board's composition, capability, or succession planning, reach out to Michelle Gardiner , Managing Partner – Board Practice, or contact us here . We'd welcome the conversation. Derwent brings together executive search, interim solutions, and board search, partnering with your organisation to find and connect the right high-impact talent to support your leadership needs, now and into the future.
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By most measures, this is the fastest adoption of a transformative technology in human history, and the pace itself, more than the tools, is what's testing leaders right now. The question we explored at our AI & The People event in Perth last week wasn't whether to engage with AI, it was how quickly leaders could learn to work through the ambiguity it creates – adapting their leadership style and their team's dynamics on the move, without the luxury of mastering every technical detail first. A shift which asked a lot more of leaders than most changes they've led before. We were lucky to have both Peter Tonagh , Executive Chair at Quantium, and Jacky Connolly , Chief People Officer at CBH Group, join the conversation. Five key themes stood out. The energy is there. The paradox is what happens next. Most people aren't resistant to AI, they're cautious, and the caution has more to do with job security than the technology itself. Some roles changed materially enough to bring the challenge of redeployment. For most people though, roles simply changed shape, and the job for leaders is to harness that energy rather than manage it down. Underneath that sits a harder problem. The productivity paradox. Individuals are getting faster and better at their jobs with AI, but those personal gains rarely show up as enterprise level returns. Team members without proper support will find their own workaround – bringing in their own unsanctioned tools or leaving for an organisation who gives them a better one – so the case for organisations investing properly is not really a choice. Lead it from the top. Guard it just as fast. This is an organisational problem before it's a technology one. Business models are set by leaders, not technologists, and senior people being visibly comfortable using the tools is what gives everyone else permission to engage with them. The common myth is that graduate roles are most at risk, however the real risk sits with middle management – executives will become more productive and carry more direct reports, resulting in fewer layers in between. Guardrails need to be set fast rather than perfected in advance, particularly around the risk of losing intellectual property. Starting with a small set of approved tools, and expanding as trust builds, is better than waiting for a comprehensive policy before allowing any use at all. Boards need to be brought in early too, so they understand their own obligations from the start rather than being briefed after the fact. AI tools tend to agree too readily. Adjusting the settings to instruct the tool to push back and challenge assumptions, instead of defaulting to agreement, was raised as a small fix that can help improve decision quality. Bring the whole workforce. Not just the office. AI tools in organisations work when technology and people are treated as one problem. Leaders need to understand the tools well enough to drive change through them, rather than leaving it to IT alone. Frontline and operational team members matter just as much as corporate functions: practical wins like rostering and attendance carry real weight, and leaving teams behind undermines the case for AI everywhere else in the business. There is also a real shift reshaping recruitment. Hiring is moving away from purely skills-based selection towards attributes: curiosity, critical thinking, persistence, agility, and optimism. It's a genuine move back toward classical study, backed by heavier investment in structured training to bring people onto the same page. Claim the gain. Then change how you measure people. The strongest examples of AI delivering enterprise value tend to be simple and specific – one tool that is purposefully built and applied across the organisation, is better than everyone building their own individual version of the same thing. But individual productivity gains don’t redirect themselves. Organisations need to actively claim the time being freed up and decide what it's used for, rather than leaving the decision to individuals. That same discipline needs to extend to how performance is measured. Early adopters should be rewarded for bringing others along and sharing what they’ve learned, not just for their own output. A cost-out mentality, or pitting people against each other, will corrode culture quickly. Redesign the work. Don’t just hand out the toolkit. The most common mistake organisations make is retooling an existing process rather than redesigning the work itself. Give someone an AI tool without rethinking their role, and the result is usually chaos, not efficiency. The real gains come from pairing someone who understands the AI tools with someone who deeply understands the work, then letting them rebuild roles and workflows together from first principles. New competitors are already emerging built exactly this way – a key consideration for any organisations still only automating. One example was given of a leader building a personal "digital twin", an AI trained specifically on their tone, feedback style, and decision-making patterns. It was developed over approximately 200 hours, though the benefit was felt within the first couple of hours of use. Six leadership principles had already been documented; the AI was then used to interview and draw out roughly 30 more. The tool is now used for communications, coaching a wider team, and personally – including when weighing a difficult decision while tired. The organisations that get this right won't be the ones with the best AI. They'll be the ones whose leaders go first – closing the gap between individual and enterprise gains, setting guardrails fast, bringing the whole workforce with them, and redesigning the work rather than just the toolkit. _________________________________________________________________________ Our thanks to Lindsay Every , Group Managing Partner at Derwent, for hosting the morning, and to Peter and Jacky for such generous, on-the-ground insight into what AI adoption looks like. A special thanks to Julie Colvin , Managing Partner – Perth, and our Perth team for their support in bringing this event to life. Continue the conversation For further insights or to explore how Derwent can support your organisation's approach to AI and workforce transformation, connect with our team at perth@derwentsearch.com.au To register your interest in future Derwent events, please reach out to us at events@derwentsearch.com.au .
The boardroom has changed. Permanently. The issues filling board agendas today are not temporary disruptions. They are the operating environment. AI, cyber risk, geopolitical instability, regulation, climate exposure and cost volatility are reshaping how organisations compete, invest and make decisions. For boards, the expectations have changed. Directors are being asked to understand more, engage more deeply and bring increasingly relevant experience to the table. Regulators, investors and other stakeholders are also looking more closely at whether boards are equipped for what lies ahead. The question is no longer simply whether a board is well governed. It is whether the board has the right mix of capability, judgement and adaptability to lead the organisation into its next chapter. The capability conversation is changing Credentials and experience remain important, but they are no longer enough on their own. Curiosity, adaptability and a willingness to keep learning are becoming equally valuable. AI is a clear example. Directors do not need to become technologists, but they do need enough understanding to ask informed questions about risk, ethics, data, accountability and return on investment. Cyber security and data governance present a similar challenge. These issues now sit firmly within board accountability. Scenario planning, crisis preparedness and understanding where the organisation’s exposures lie are no longer occasional agenda items. They are part of the boards regular rhythm. Renewal cannot wait for a vacancy Strong board renewal starts with future strategy. What capabilities will be required over the next five to ten years? Which risks will become more material? Where does the board need deeper commercial, functional or sector experience? Which perspectives may be missing? These questions are more useful than simply asking whose term is ending next. The most effective boards are moving beyond static skills matrices and periodic succession discussions. They are treating board composition as a dynamic capability plan that evolves alongside the organisation. They are refreshing skills matrices against future strategy, building learning agendas across AI, cyber, ESG, risk and geopolitics, reviewing committee structures and linking succession to capability rather than tenure alone. They are also paying closer attention to board dynamics. A technically capable board can still underperform when trust is low, challenge is poorly handled or directors struggle to work together under pressure. Constructive challenge, sound judgement and the ability to listen, learn and adapt are central to effective governance. The briefs are changing Across Derwent’s Board practice, we are seeing more mandates where recent sector and functional experience is a primary driver of selection. Boards are seeking contemporary expertise in areas including technology and AI governance, audit and risk, renewables and infrastructure, capital allocation and mergers and acquisitions. The profile of who is considered “board-ready” is therefore broadening. Traditional governance experience remains valuable, but boards increasingly need directors who bring current knowledge, diverse perspectives and the ability to contribute to new and fast-moving conversations. Board search and succession planning are not simply about filling a vacant seat. They are about building a board that is ready for the future of the organisation. The strongest boards will be those that renew with intent – bringing together the experience, behaviours and perspectives required not only for today’s agenda, but for the decade ahead. ___________________________________________________________________________ If you're reviewing your board's composition, capability, or succession planning, reach out to Michelle Gardiner , Managing Partner – Board Practice, or contact us here . We'd welcome the conversation. Derwent brings together executive search, interim solutions, and board search, partnering with your organisation to find and connect the right high-impact talent to support your leadership needs, now and into the future.
