Strategic Career Management for CEOs, C-Suite Executives and Senior Leaders
A senior career rarely moves in a straight line.
There are promotions to negotiate, difficult bosses and boards to manage, restructures, succession decisions, opportunities that appear unexpectedly and periods when an executive knows something needs to change but is not yet sure what the next move should be.
Executive Career Mentoring gives senior leaders a confidential, experienced adviser outside their organisation.
Kylie Hammond works one-to-one with executives to help them make better career decisions, position themselves for future opportunities and actively manage the next stage of their professional life.
This is not career coaching in the conventional sense. It is strategic career management, informed by more than two decades working across executive search, board search, talent management and senior executive careers.
“Your career should be managed as deliberately as your business.”
A confidential conversation directly with Kylie about where you are now, where you want to go and what may be getting in the way.
Executives do not necessarily seek mentoring because something is wrong. Often the opposite is true. They are performing well, increasingly visible and reaching a point where the decisions they make over the next three to five years will have a disproportionate impact on the rest of their career.
You are operating above the level of your current title and need to determine how to position yourself for a larger executive role, including the C-suite.
At senior levels there are fewer people inside an organisation with whom you can speak completely openly. An external adviser provides an independent perspective. CEOs who need a sounding board for the role itself may be better served by CEO Mentoring.
A promotion, CEO succession process, restructure or leadership change may require careful positioning. Or the role is still comfortable, but progression has slowed and it is time to determine whether the next move should happen internally or externally.
Before resigning, an executive should understand their market position, financial runway, realistic time to market and the alternatives available. An attractive title or larger salary does not automatically make an opportunity the right career move. If you have already been released, executive outplacement may be the more appropriate service.
Senior executives increasingly need an external professional profile rather than relying entirely on their current employer’s brand.
Executive roles, non-executive directorships, advisory positions and other commercial interests can sit alongside one another. The move from full-time executive leadership into board, advisory, consulting or portfolio work should ideally begin years before leaving corporate life.
There is no useful one-size-fits-all executive career plan. Someone positioning for their first CEO appointment needs something very different from a CEO contemplating a portfolio career. The work follows the issues that actually matter.
Long-term executive career planning, CEO career strategy, C-suite progression, promotion strategy, succession planning and executive leadership development.
Navigating organisational politics, managing relationships with a CEO, Chair or Board, stepping into a newly expanded role, deciding whether to stay or leave, and repositioning transferable experience across a career or industry transition.
Salary and contract discussions, preparing for executive search processes, senior interview preparation, headhunter engagement and accessing the unadvertised employment market. Related support includes interview coaching where an appointment process is live.
Executive résumé development, LinkedIn positioning, professional biography, executive value proposition, networking strategy, reputation, market visibility and thought leadership. Dedicated executive résumé writing is available where a defined piece of work is needed.
Board Portfolio® development, non-executive director pathways, advisory board opportunities, portfolio career development and preparing for semi-retirement. See Board Portfolio® and Tiger Boards.
Difficult career situations that cannot be discussed internally. The relationship is personal and one-to-one with Kylie, not a junior coach allocated after you sign.
One of the mistakes executives make is waiting until there is a problem before becoming active in the market.
A redundancy occurs. A CEO changes. A restructure removes the next promotion. A new Chair arrives. The executive suddenly realises they have not spoken to a headhunter for five years, their résumé is outdated, their LinkedIn profile does not reflect their current level and most of their professional network sits inside one organisation or sector.
That is career reaction. Career management is different.
An executive should know what their next two or three potential moves could be, what experience they still need, what they are worth in the market, which organisations could realistically employ them, which search consultants, CEOs, Chairs and industry leaders know them, how they are perceived externally, whether their digital footprint supports their ambitions, what risks exist in their current role, and how their board strategy fits with their executive career.
The objective is not to have an executive constantly looking for another job. The objective is to make sure they have options.
“Do not wait until you need a job to manage your career.”
Retain, develop and support the executives you cannot afford to lose.
CEOs, Boards, HR Directors and Chief People Officers engage Kylie to work confidentially with a senior executive as a retention and development investment, not as remedial coaching.
The most valuable executives are not always the people who need “fixing”. Often they are the people the organisation most wants to retain.
Executives being prepared for promotion, moving into the C-suite, taking on significantly greater responsibility, or being considered as part of a succession plan.
Executives transitioning into a CEO role, onboarding into a senior position, returning after an extended absence, or requiring greater external perspective as the brief expands.
Senior leaders dealing with a difficult leadership environment, navigating organisational change, or needing somewhere confidential to test decisions without creating unnecessary internal politics.
Providing a confidential external mentor can give a high-performing executive somewhere to work through career issues and gain perspective. Kylie can work alongside the executive, CEO and HR Director where appropriate while maintaining the confidentiality required for a productive mentoring relationship.
Replacing a high-performing senior executive is expensive. The financial cost is only part of the issue. There is also lost organisational knowledge, disruption to teams, succession risk and the time required for a new executive to become fully effective.
Executive career mentoring is particularly valuable when an organisation wants to demonstrate that it is genuinely investing in an executive’s future: executive development, high-potential leadership programs, CEO succession, retention, promotion preparation, onboarding into senior positions, confidential CEO or executive mentoring, and preparing executives for greater board exposure.
Most executives receive career advice from people who never actually appoint executives. Kylie works in the market.
Through her executive search and board search work she has spent more than two decades assessing senior executives, advising organisations, interviewing candidates and understanding why one person is appointed while another equally capable executive is not.
She understands what happens on the other side of the table. That means conversations can go beyond “What do you want to do?” They can include:
This is a different conversation from traditional coaching. Kylie can challenge the executive while also giving them a realistic view of how the employment market will interpret their experience, reputation, value proposition and ambitions.
Your next opportunity may never be advertised.
Senior appointments do not operate like conventional job searching. Executive opportunities can emerge through retained executive search, succession discussions, direct approaches, CEOs, Chairs, board directors, investors, professional networks, former colleagues, advisers and private conversations.
Career mentoring therefore includes developing the executive’s market ecosystem: making sure you are visible, credible and connected before an opportunity arises. That is not a promise of introductions or a job. It is the discipline of being ready when the conversation happens.
Selected executives also work with Kylie in a talent agent capacity where ongoing market representation is the better fit.
Your reputation enters the room before you do. Senior executives need a coherent market position, not a collection of outdated documents and an employer brand they do not own.
Not a historical job description. It should communicate scale, commercial impact, leadership scope and the problems the executive is capable of solving.
Senior decision-makers, search firms and potential employers will review LinkedIn. The profile should position the individual at the level they want the market to consider them.
A strong professional biography becomes increasingly valuable as executives develop board, speaking, advisory and industry opportunities.
What you do, what you are known for, the scale at which you operate, the problems you solve, and why an organisation should appoint you. Executives cannot rely solely on the brand of their current employer.
Related resources are also available through the online shop.
For many senior executives, the next phase is no longer simply job, then job, then retirement.
It may look more like an executive role alongside a non-executive directorship, an advisory position, investment activity, mentoring, consulting and industry contribution.
Kylie works with executives to determine when and how these elements should begin. Board development should not necessarily wait until retirement. Carefully selected board and advisory exposure can strengthen an executive career while also preparing the foundations for the next chapter.
Kylie Hammond is an Executive Search Consultant, Corporate Headhunter, Executive Career Mentor, Board Search specialist and Founder and CEO of Tiger Boards.
She has spent more than two decades advising CEOs, C-suite executives, board directors and senior professionals on executive careers, leadership and market positioning. She has delivered more than 20,000 hours of executive coaching and mentoring.
Her work sits at the intersection of executive search, career strategy, board search, personal branding and market intelligence.
Kylie has held senior positions with organisations including Gartner, Cisco Systems, PeopleSoft and Deloitte and has extensive experience in executive recruitment, human capital and talent management. She holds a Master of Laws in Enterprise Governance from Bond University and has professional affiliations across executive recruitment, HR, career development and governance.
Clients work directly with Kylie. This is not a large coaching practice where the executive is allocated to a junior consultant after signing. The relationship is personal and one-to-one.
Kylie Hammond is an executive and board search consultant, career mentor, board adviser and founder of Tiger Boards.
For more than 20 years she 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 understands how senior executives are assessed, how CEOs and boards make appointment decisions, how executive search firms operate, how remuneration is benchmarked, why careers stall and how the unadvertised executive market actually works.
That is what makes the conversation different. You are not being coached in the abstract. You are working with someone who still sits on the other side of the table.
Senior leadership can be isolating. There are conversations an executive cannot always have with their boss, board, colleagues, direct reports or internal HR team.
A confidential place to think properly about your career. Sometimes the executive simply needs somebody experienced enough to say:
A good mentor should not simply agree with the executive. They should challenge their thinking. That is part of the value of having someone genuinely independent.
Built around the executive, not a coaching template.
The engagement begins by understanding:
From there, Kylie works with the executive on the issues that actually matter. Mentoring can be delivered privately by video or another agreed format, including for executives across Australia and internationally.
You do not need to know which service you need before speaking with Kylie. Book a complimentary confidential career assessment.
Use the conversation to discuss where your career currently sits, your immediate priorities, possible next moves, current résumé and LinkedIn positioning, salary and market positioning, promotion opportunities, executive search strategy, potential industry change, board ambitions, career risks and longer-term career strategy.
Kylie can then recommend whether mentoring, career coaching or another service is appropriate. There is no obligation to proceed.
Executive career mentoring is confidential, one-to-one strategic career management for CEOs, C-suite executives and senior leaders. It is an advisory relationship covering career strategy, positioning, leadership challenges, internal politics, remuneration, succession, external opportunities, personal branding, market visibility, board appointments and longer-term portfolio career planning. It is not generic life coaching.
There is overlap. Executive career coaching is often more practical and program-based. Executive career mentoring is broader and more advisory: a confidential external adviser who can help you think several moves ahead. Kylie will recommend the better fit after a career assessment.
Executives who are performing well and reaching a point where the next three to five years will have a disproportionate impact on the rest of their career. That includes people positioning for a larger role, navigating succession or politics, considering a move, building market visibility, or planning a Board Portfolio®. Organisations also engage a mentor to retain, develop or support a senior executive.
Yes. At CEO and C-suite level there are fewer people inside the organisation with whom you can speak completely openly. Some CEOs need career mentoring around tenure, succession, market options and board work. Others need CEO Mentoring focused on the role itself: board relationships, executive team performance and the practical realities of leading the organisation.
Yes. CEOs, boards, HR Directors and Chief People Officers often sponsor mentoring as a retention and development investment. Confidentiality and any reporting arrangements are agreed at the outset.
Yes. Confidentiality is fundamental. Where an organisation funds the engagement, the boundaries around what stays in the room and what, if anything, is reported back are established before the work begins.
Yes. Mentoring can include how you are perceived internally, what experience you still need, how to position yourself for a larger brief, and whether the promotion in front of you is actually good for your career.
Mentoring can help you understand the gap between your current experience and what boards and search firms expect at that level, and then work on the positioning, visibility, experience and conversations required. It does not guarantee an appointment.
Yes, and it is often the right time to get advice before you resign. The conversation should cover market position, financial runway, realistic time to market and alternatives. If you have already been released, executive outplacement may be the more appropriate service.
Yes. Remuneration and contract discussions can form part of the mentoring work. The advice is informed by how senior packages are actually benchmarked and negotiated, not by generic salary surveys alone.
Yes. Personal branding is part of senior career management. That can include the executive résumé, LinkedIn positioning, professional biography and value proposition. Dedicated résumé writing is also available where a defined piece of work is needed.
Mentoring includes how executive search actually works and how to be known to the right consultants. Introductions are not guaranteed. The objective is to make sure you are visible, credible and properly positioned before an opportunity arises.
Senior roles often emerge through retained search, succession discussions, direct approaches and private conversations rather than advertised vacancies. Mentoring focuses on developing your market ecosystem. It does not guarantee a role or an introduction.
Yes, where the experience is transferable and the positioning is honest. The work includes how the market will interpret your background and what would need to change for a credible industry move.
Yes. Board and advisory work should not necessarily wait until retirement. Mentoring can include when and how to begin, and how board exposure sits alongside the executive career.
A Board Portfolio® is a planned combination of paid non-executive, advisory and related board appointments developed as a career in its own right, often alongside or after executive leadership. See Board Portfolio® services and Tiger Boards.
Yes. The work is delivered nationally, including Melbourne, Perth, Adelaide, the Gold Coast and internationally by video where appropriate. It is not geographically restricted.
You do not need to know before speaking with Kylie. A complimentary career assessment is the starting point. From there she can recommend mentoring, career coaching, interview coaching, outplacement, résumé work, talent management or Board Portfolio® support, or a combination. There is no obligation to proceed.
You may have spent twenty or thirty years building your career. The next move should not be left to chance.
Whether you are positioning for promotion, contemplating a change, moving towards CEO, developing a Board Portfolio® or simply wanting an experienced independent perspective, start with a confidential conversation.
