A confidential sounding board for the person carrying the weight of the organisation.
The CEO role is different. The decisions are bigger, the scrutiny is higher and there are fewer people you can speak to with complete freedom.
Kylie Hammond’s CEO Mentoring Program provides experienced, confidential one-to-one support for Chief Executives navigating the realities of leading an organisation: board relationships, executive team performance, stakeholder expectations, strategy, transformation, difficult people decisions, succession, career risk and the constant pressure to perform.
This is not generic leadership coaching. It is practical CEO mentoring grounded in executive search, board search, governance, human capital, leadership assessment and more than two decades of working with senior executives and boards.
The work is tailored to the CEO, the organisation and the situation. Some clients need a regular strategic sounding board. Others need intensive support around a board relationship, a 360-degree assessment, a leadership transition, a major organisational issue or a period where performance expectations have shifted.
The objective is to help the CEO think more clearly, lead more effectively and handle the issues that matter before they become bigger problems.
CEOs can self-engage. Chairs, boards and HR Directors can commission the work as a confidential, board-supported development program.
A capable CEO will usually have plenty of people around them. That does not mean they have many people they can speak to openly.
The Chair has a governance role. The board is assessing performance. Direct reports have their own priorities. Internal HR may be part of the issue, or may not be the right place for a completely candid conversation. Investors, owners and other stakeholders bring another layer of expectation.
A strong CEO mentor sits outside those dynamics.
The value is not simply advice. It is having a commercially experienced person who can challenge your thinking, identify blind spots, help you prepare for difficult conversations and bring an external perspective when you are too close to the issue.
At times that means pushing back. At other times it means helping the CEO slow down, separate the real problem from the noise and decide what needs to happen next.
“The CEO role comes with plenty of advice. What it often lacks is a genuinely confidential place to think.”
Every engagement is different, but CEO mentoring commonly includes work across the following areas.
Working effectively with the Chair and board is one of the most important parts of the CEO role. We can work on board communication, board papers and reporting, meeting preparation, managing expectations, constructive challenge, rebuilding trust, handling difficult feedback and improving the quality of the CEO-board relationship.
We focus on the real leadership issues in front of you: decision quality, prioritisation, delegation, executive presence, communication, accountability, leadership style, organisational influence and the behaviours that either strengthen or undermine confidence in the CEO.
Where appropriate, the program can incorporate a structured 360-degree assessment. This may involve feedback from the Chair, directors, direct reports and other key stakeholders, with the board’s support. The goal is not a scorecard for its own sake. It is to identify patterns, strengths, blind spots and practical priorities for the CEO’s development.
Receiving board feedback is one thing. Working out what it means and what to do with it is another. Kylie can help the CEO interpret feedback, separate signal from noise, prepare a constructive response and translate it into visible changes in leadership behaviour or communication.
CEO mentoring can include the leadership and structure of the executive team: capability gaps, succession, difficult executives, performance management, role clarity, team dynamics, recruitment decisions and how to lift the collective performance of the ELT.
Major change puts pressure on the CEO personally as well as operationally. Mentoring can support the CEO through restructures, mergers, turnarounds, growth, digital or AI transformation, operating model change and other periods where the organisation needs strong, consistent leadership.
CEOs often need to manage a complex stakeholder environment including owners, investors, regulators, customers, partners, employees, media and community stakeholders. We work on stakeholder strategy, communication and the judgement required when interests do not neatly align.
There are decisions a CEO cannot delegate. Senior appointments and exits. Performance concerns. Conflict with the Chair. A director who is overstepping. A key executive who is not working. A strategy that is failing. A crisis. Mentoring gives the CEO somewhere to test the approach before entering the room.
The CEO’s own career still needs active management. Support can include contract renewal, remuneration positioning, succession, tenure decisions, external opportunities, reputation, Board Portfolio® development and planning for life after the CEO role. Related support: Executive Career Mentoring and, where an appointment process is live, Interview Coaching.
Working effectively with the Chair and board is one of the most important parts of the CEO role, and one of the easiest to underestimate.
The relationship is rarely only about the quality of the last board paper. It is about expectation, communication, trust, judgement and whether directors feel they understand what is happening in the organisation.
We work on board communication, board papers and reporting, meeting preparation, managing expectations, constructive challenge, rebuilding trust, handling difficult feedback and improving the quality of the CEO-board relationship.
CEOs can raise this work privately. Chairs and boards can also commission structured support when the relationship needs closer attention, with confidentiality agreed from the outset.
“A board relationship rarely deteriorates because of one meeting. It deteriorates when expectations, communication and trust stop lining up.”
One of the most valuable applications of CEO mentoring is a structured development program supported by the board.
This can be particularly effective where the board wants to invest in the CEO, strengthen the relationship between governance and management, give the CEO clearer feedback or create a more disciplined development plan without turning the process into a formal performance-management exercise.
A typical process may include:
The credibility of a CEO 360 depends on clear confidentiality, scope and reporting arrangements from the outset. The purpose is to create useful information the CEO can act on, not to turn a development process into a covert assessment process.
“The best 360 feedback is useful enough to act on and safe enough for people to tell the truth.”
Anonymised case study
A senior CEO engaged Kylie Hammond during a period where the relationship with the board, leadership expectations and the CEO’s own performance priorities required closer attention.
With the support of the board, Kylie conducted a comprehensive 360-degree assessment to gather structured feedback and identify where the CEO was performing strongly and where changes would have the greatest impact. The work then moved into ongoing one-to-one coaching and mentoring.
A significant part of the engagement focused on helping the CEO deal more effectively with the board: understanding what directors needed, preparing for key conversations, improving communication and responding constructively to feedback rather than allowing tension or ambiguity to build.
The program gave the CEO a confidential external adviser who understood both sides of the table. It also gave the board confidence that the CEO had structured support around the issues that mattered.
The value of the work was not a generic leadership-development exercise. It was targeted intervention around real decisions, real relationships and real organisational consequences.
The transition into the CEO role is one of the biggest jumps in an executive career. Many highly capable executives discover that the skills that made them successful as a functional leader do not automatically prepare them for enterprise leadership.
The first-time CEO has to establish a relationship with the Chair, understand how the board wants to work, set the tone with the executive team, make early people decisions, communicate with confidence and resist the temptation to stay too close to the function they know best.
Mentoring during the first six to twelve months can help a new CEO establish the right operating rhythm early rather than learning everything through avoidable mistakes.
Experienced CEOs do not necessarily need more theory. They often need a high-quality external conversation.
The issues may involve growth, board dynamics, investor expectations, a difficult executive, succession, fatigue, reputation, a potential exit or the simple reality that the organisation has changed and the leadership approach needs to change with it.
The mentoring relationship gives the CEO a place to work through those issues without internal politics and without needing to perform for the person sitting opposite them.
CEO mentoring can be initiated by the CEO directly or commissioned by the organisation.
Where the Chair, board, HR Director or Chief People Officer is sponsoring the engagement, the program should begin with a clear agreement about objectives, confidentiality and what, if anything, will be reported back to the organisation.
That clarity matters. The CEO needs enough privacy for the mentoring relationship to be useful, while the sponsoring organisation needs confidence that the work is addressing the agreed development priorities.
Kylie can work with both parties to establish a sensible framework that protects the integrity of the mentoring relationship and keeps the work connected to the organisation’s objectives.
The value of the program sits in the combination of perspectives. That is what distinguishes this work from generic executive coaching for CEOs.
Understanding how CEOs are assessed, appointed, retained and replaced.
Understanding what Chairs and directors expect from the CEO and how board dynamics work in practice, including through Tiger Boards and board search.
Experience with performance, talent, executive teams and 360-degree feedback.
The ability to support the CEO as an individual, including career risk, market positioning, succession and future options.
Mentoring that stays connected to business outcomes, stakeholder confidence and what the CEO is actually accountable for.
For CEOs, that breadth matters. Leadership issues are rarely isolated. A board relationship can become a performance issue. A weak executive appointment can become a strategy issue. A transformation problem can become a reputation issue. A succession discussion can become a career decision overnight.
“Good CEO mentoring is not about giving the CEO another framework. It is about helping them handle the real issue in front of them.”
The program is designed around the individual CEO and can be structured as a focused intervention or an ongoing mentoring relationship. Mentoring can be delivered privately by video or another agreed format.
The engagement can include:
The program is not sold as a rigid curriculum. Its strength is that it can follow the issues that are live for the CEO while still maintaining clear goals, accountability and momentum.
CEO mentoring only works when the conversation can be candid.
Confidentiality arrangements are established at the beginning of the engagement, particularly where the organisation is funding the program. The CEO should understand what stays in the room, what may be reported at a high level and how any stakeholder feedback will be handled.
This allows the CEO to discuss difficult issues properly rather than editing the conversation because they are unsure where it may end up.
Kylie Hammond is an executive and board search consultant, CEO mentor, executive career adviser, board adviser and founder of Tiger Boards.
For more than 20 years, Kylie has worked with CEOs, C-suite executives, senior leaders, Chairs and directors across executive search, board search, executive coaching, talent management, career transition and governance-related assignments.
She holds a Master of Laws in Enterprise Governance and brings deep experience across human capital management, leadership assessment, executive recruitment and 360-degree feedback. She has completed more than 20,000 hours of executive coaching and mentoring and has worked with senior executives across major organisations and complex career and leadership situations.
Her perspective is practical and unusually broad: she understands what the CEO is dealing with, and she also understands what the board, Chair, HR Director and executive market are looking at.
Related work includes Tiger Boards, Board Portfolio® and board search.
CEO mentoring is confidential one-to-one support for a Chief Executive focused on the practical realities of the role. It can cover board relationships, leadership effectiveness, decision-making, executive team performance, stakeholder management, strategy, succession, career risk and other issues where an experienced external perspective is valuable.
There is overlap, but CEO mentoring can be broader and more advisory. The work is not limited to coaching technique or a predetermined leadership curriculum. It can draw on lived experience across executive search, governance, boards, talent, career strategy and organisational leadership to help the CEO deal with the issue in front of them.
Yes. CEO mentoring can be initiated by the CEO or commissioned by the Chair, board, HR Director or Chief People Officer. Where the organisation sponsors the program, objectives, confidentiality and reporting arrangements should be agreed at the outset.
Yes. A structured 360-degree assessment can be incorporated where appropriate and may include feedback from the Chair, directors, direct reports and other agreed stakeholders. The findings are used to identify practical leadership priorities and guide the mentoring program.
Yes. Confidentiality is fundamental to the relationship. Where a third party is funding the engagement, the boundaries around confidentiality and any reporting back are agreed before the program begins.
Yes. The first year in a CEO role is an ideal time for mentoring because the executive is learning a new relationship with the Chair and board while establishing authority with the executive team and organisation.
Yes. CEO-board effectiveness is a core area of the program. The work can include preparing for board meetings and Chair conversations, interpreting board feedback, improving communication, clarifying expectations and helping the CEO respond constructively to tension or changing expectations.
The program can be delivered virtually, allowing CEOs and senior executives to work with Kylie regardless of location, subject to scheduling and engagement requirements.
The structure depends on the need. Some assignments are focused around a specific issue or transition, while others run for six or twelve months with regular mentoring and periodic review.
The first step is a confidential discussion with Kylie Hammond to understand the context, who is commissioning the work, what the CEO needs and whether a mentoring, 360 assessment or broader CEO advisory engagement is the right fit.
They need the right conversation, with the right person, at the right time.
Whether you are a CEO looking for a trusted external adviser, a Chair seeking to strengthen the CEO-board relationship, or an HR Director designing support around a critical leader, Kylie Hammond can develop a confidential CEO mentoring program around the situation in front of you.
Start with a private discussion about the CEO, the organisation and the outcomes you need.
