Foreword
The group of senior female leaders convened by Oxana Brookes identify a number of key capabilities for the next generation of CEOs. They get behind the cliches and rhetoric to focus on the realities of making important decisions. These include incomplete information, balancing incompatible stakeholder expectations and maintaining confidence when the path forward is far from clear.
One of the capabilities they identify to meet these challenges is judgement. In my recent book, Judgement at Work: Making Better Choices, I suggest that it is one of the defining capabilities of effective leadership. It means combining relevant knowledge, experience, awareness and context to determine the right course of action, particularly when the answers are far from obvious. AI will further increase the need to apply it.
Not only does good judgement matter but having a leader with bad judgement is, frankly, a bit of a nightmare. Boards need confidence that the leaders they appoint possess not only the expertise to run complex organisations, but also the ability to apply it. As this paper sets out, capabilities including judgement need to be central when identifying, developing and appointing the next generation of CEOs.
Sir Andrew Likierman
Professor of Management Practice and former Dean London Business School
Contributors:
Suleman Alli
UK Power Networks, Director of Customer Service, Strategy, Regulation & Technology
Louisa Bell
P&O Ferries, Chief Commercial Officer / Managing Director – Passenger
Nicola Bell MBE
National Highways, Chief Capital Delivery Officer
Ruth Dunphy
Mace Group, Chief Transformation Officer
Emma Gilthorpe
Turner & Townsend, Chief AI Transformation Officer
Shiona Rolfe
CrossCountry Trains, Managing Director
Caroline Sheridan
NATS, Capital Programmes and Transformation Director
Katy Taylor
Chief Executive Officer, Wightlink Ferries
I recently hosted a breakfast with a group of senior female leaders, where I asked them:
What is the biggest crisis you’ve had to lead through?
The answers were wide-ranging. Public scrutiny. Board tension. Operational failures. Transformation programmes that lost momentum. Stakeholder conflict. Reputational issues that lingered far longer than anyone expected.
The discussion reinforced what I’ve been hearing in many conversations with CEOs and Boards across infrastructure, transport, energy and utilities. While every organisation faces different challenges, few leaders describe operating in a period of prolonged stability.
Over the past decade, they have navigated Brexit, Covid, supply chain disruption, the energy crisis, geopolitical instability and rapidly changing public expectations. For many, disruption has become part of the operating environment rather than an interruption to it.
As Katy Taylor put it:
Instability and disruption aren’t something that sit on top of the job anymore. In many sectors they are the job.
– Katy Taylor
The environment in which CEOs operate has become markedly more complex. As a result, judgement, stakeholder management and the ability to lead through uncertainty have become increasingly important aspects of the CEO role.
Drawing on conversations with senior female leaders across infrastructure, transport, energy and utilities, this paper explores how the CEO role is evolving and the implications for CEO succession, leadership development and Board decision-making.
Crisis Leadership to Mitigate Public Scrutiny?
In infrastructure, a crisis rarely remains contained.
A service failure quickly becomes a regulatory issue. A stakeholder concern becomes a media story. A transformation programme becomes a Board discussion. A commercial decision becomes a question of public trust.
Managing the immediate issue is only part of the job. The greater challenge is often navigating the period that follows, when regulators, government, employees, communities and the media continue to judge every decision through the lens of what has already happened.
Caroline Sheridan reflected on one of the most difficult aspects of leading through uncertainty: making decisions without ever knowing how events will unfold.
People often ask afterwards whether it was the right decision. The honest answer is that, from where I was sitting, with the information available at the time, it felt like the right decision. Senior leadership often means making difficult choices without knowing how events will unfold. Judgement is having the confidence to make that decision and stand behind it.
– Caroline Sheridan
For Boards, this reinforces the importance of understanding how prospective CEOs respond when organisations come under sustained external scrutiny. Crisis preparation is not only communications plans or operational response. It also requires stakeholder alignment, clear governance and leaders who can maintain trust when confidence is under pressure.
That becomes even more challenging when you consider the number of stakeholders CEOs are expected to balance.
Government. Regulators. Environmental bodies. Communities. Employees. Unions. Investors. Customers. The media. Boards.
Each has different priorities, different expectations and, often, a different definition of what success looks like.
Nicola Bell spoke about this challenge:
You can have the technically right answer, but that does not mean you can easily deliver it. The challenge is understanding the different stakeholders, finding a way to be heard, and bringing people with you without losing credibility in the process.
– Nicola Bell
It becomes far more about building trust across multiple stakeholder groups, balancing competing expectations and maintaining confidence even when there is no solution that satisfies everyone.
Why infrastructure needs more T-shaped leaders
One of the most interesting discussions centred on the type of leader today’s environment demands.
Infrastructure has traditionally valued deep technical expertise, and rightly so. These are complex, highly regulated businesses where operational credibility matters. Many CEOs have built their careers by becoming exceptional functional leaders, whether in engineering, operations, finance or programme delivery.
The question is whether that is enough today.
Nicola Bell spoke of a useful distinction between “I-shaped” and “T-shaped” leaders.
The I-shaped leader develops deep expertise in a single discipline. The T-shaped leader combines that depth with broader commercial awareness, stakeholder management, communication skills and the ability to lead through ambiguity.
-Katy Taylor
As organisations become more complex, those broader capabilities become increasingly important.
Today’s CEOs are expected to move seamlessly between operational performance, Board discussions, regulatory engagement, political scrutiny and organisational leadership. They need to understand the technical challenge, but also the wider context in which decisions are being made.
Louisa Bell described why that breadth of perspective matters, particularly when leading transformation:
Transformations rarely succeed or fail because of any single part of an organisation. They succeed or fail based on how well the parts work together. Leaders need to understand how a change in one area ripples through outcomes elsewhere to ensure they land on the optimum solution. That breadth of experience and understanding is often what turns strategy into results. Without that breadth of experience, even good strategy can stall in the gaps between teams.
– Louisa Bell
When organisations are performing well, the difference between an I-shaped and T-shaped leader may not always be obvious. When the environment becomes more uncertain, it often is.
This has important implications for leadership development. Technical expertise remains fundamental to leadership in infrastructure, but Boards need to ensure it is complemented by the broader capabilities the modern CEO role demands.
That means exposing future leaders to regulators, government, investors and enterprise-wide decision-making much earlier in their careers, rather than expecting those capabilities to emerge naturally once they reach executive level.
Without that deliberate breadth of experience, organisations risk developing leaders who are exceptionally capable within their discipline but less prepared for the realities of the modern CEO role.
Why Experience Builds Executive Judgement
Whether leaders are dealing with a crisis, transformation or stakeholder management, the underlying capability is often executive judgement.
Not judgement in the sense of choosing between different options, but knowing when to move quickly, when to pause, when to challenge, when to hold the line and, perhaps most difficult of all, when to step away.
Ruth Dunphy spoke about the judgement required to recognise when continuing is no longer the right course of action.
If the agenda of the business has changed, walking away may be the right decision. Continuing regardless is not always resilience. Sometimes it’s simply refusing to acknowledge reality. Having the judgement to know, often with limited context, is critical. Experience builds perspective.
– Ruth Dunphy
Persistence is often celebrated. We admire leaders who push through adversity and refuse to give up. But in complex organisations, there are times when changing course is the stronger leadership decision. Recognising that moment requires judgement rather than determination alone.
Judgement is shaped by perspective.
Emma Gilthorpe illustrated this with a story about her youngest daughter sitting a difficult GCSE maths paper. Emma offered reassurance, recognising how stressful it must have been. Her daughter simply replied: “Mum, this is just exams”.
It was a light-hearted anecdote, but it carried an important lesson: perspective changes how we see a challenge. What feels overwhelming in one moment can look very different when viewed in a broader context.
Over time, experience teaches leaders what is genuinely existential, what requires immediate action and what simply needs calm, measured leadership.
Shiona Rolfe echoed a similar point when reflecting on moving from one senior leadership role to another.
I thought I understood crisis leadership from previous executive roles. Then I found myself leading through a completely different level of scrutiny and realised just how much more there was to learn. Experiences like that fundamentally change your perspective.
– Shiona Rolfe
Perspective isn’t taught in a classroom. It is built through exposure to situations where there is no playbook, decisions carry significant consequences, and leaders must balance operational priorities with the expectations of regulators, government, Boards, employees and the public.
Perhaps that’s also why peer networks matter. Whatever challenge a leader is facing, someone else has almost certainly navigated something similar. Those conversations rarely provide the answer, but they often provide perspective. And it is perspective that turns experience into judgement.
What Should Boards Look for in Future CEOs?
Is the next generation of leaders prepared for a world where disruption is no longer the exception, but part of the role?
If the environment has changed, succession planning needs to change with it.
Boards need to look beyond who has delivered the strongest results. They also need to consider who is most likely to lead effectively when the context changes overnight, stakeholders disagree and there is no obvious right answer.
01
Stop promoting functional excellence as a proxy for CEO readiness
Operational expertise and technical credibility remain essential, particularly in complex, regulated sectors. But they aren’t enough on their own. Future CEOs also need commercial judgement, stakeholder influence and the ability to lead across organisational boundaries.
02
Assess judgement, not just experience
A strong track record explains what a leader has achieved. It tells you less about how they will respond when information is incomplete, pressure is mounting and every option carries risk. Boards should spend as much time assessing judgement as they do performance.
03
Develop T-shaped leaders earlier
The capabilities required of modern CEOs are built over years, not during the final stages of a succession process. Future leaders need earlier exposure to Boards, regulators, investors, public scrutiny and enterprise-wide decision-making if they are to develop the breadth today’s CEO role demands.
04
Look for leaders who create confidence
During periods of uncertainty, people rarely expect CEOs to have every answer. They do expect them to provide clarity, maintain trust and create confidence across employees, Boards, regulators and external stakeholders. Those qualities increasingly differentiate the most effective leaders.
05
Redefine what CEO readiness looks like
The capabilities required of CEOs continue to evolve. Boards should regularly ask whether their definition of CEO readiness has evolved with them, ensuring future leaders are prepared not only to deliver strategy, but to lead through uncertainty.
These capabilities become particularly important as the operating environment continues to change. As Suleman Alli explains:
Decarbonisation-driven investment growth, rapid advances in technology and AI, and increasing customer and regulatory expectations are creating a more complex and dynamic operating environment. In this context, major strategic challenges rarely sit neatly within one function.
Strong leadership requires the ability to bring together different expertise, perspectives, and judgement around a coherent vision; to understand enough about technology and data to ask the right questions; and to remain curious about what other sectors can teach us.
Ultimately, it is this breadth of thinking that enables leaders to cut through complexity, make clearer decisions, improve performance, and deliver better outcomes for customers, stakeholders, and shareholders
– Suleman Alli
Final thought
The CEOs who shared their stories all faced very different challenges. Some managed operational crises. Others navigated public scrutiny, Board tension or organisational change. And they all emphasised that leadership isn’t defined by having all the answers.
It is defined by the judgement to make difficult decisions, the perspective to keep them in context and the ability to bring people with you along the way.
Perhaps that’s why one quote resonated so strongly throughout our discussion:
People will forget what you said, people will forget what you did, but people will never forget how you made them feel.
– Maya Angelou
The demands placed on CEOs continue to evolve. Identifying leaders with the judgement, breadth of experience and stakeholder capability to succeed in increasingly complex environments has never been more important.
If you’re reviewing your CEO succession plans, assessing leadership potential or considering the capabilities your organisation will need in the years ahead, we’d be pleased to share our perspective.
Get in touch to discuss how Redgrave supports organisations with CEO succession, executive search and leadership advisory.
About the author
Oxana Brookes is Partner and Head of Energy & Infrastructure at Redgrave, advising Boards and executive teams on senior leadership appointments across infrastructure, transport, energy, utilities and industrial businesses.
She works with listed companies, private businesses, investors and public sector organisations to appoint CEOs, executive directors and non-executive directors, while advising Boards on leadership succession, organisational capability and executive assessment.
Oxana is passionate about the future of leadership within infrastructure and regularly brings together senior industry leaders to discuss the challenges shaping the sector and the evolving capabilities required to lead through change.
