Top 5 Executive Coaches in Sydney for CEOs and Senior Leaders

1. Caroline Kennedy

Leading as the organisation becomes more complex

Caroline Kennedy is a former CEO who has led organisations generating up to $250 million in annual revenue and national teams of more than 500 people. Her executive coaching combines that operational experience with a focus on the leader’s behaviour and the way the organisation works around them.

Her published approach begins with psychology. She examines patterns in the leader’s behaviour alongside team dynamics and strategic alignment. The subsequent coaching and advisory work addresses issues such as decisions remaining with the CEO, difficult conversations being delayed or an executive team struggling to turn strategy into action.

That perspective may appeal to a senior executive who wants to examine their own contribution to an organisational problem while working through the practical decisions it creates. The conversation can connect personal development with questions about responsibility, team capability and how the business is being led.

For example, a useful starting point for a prospective client could be an executive team that refers too many decisions back to the CEO. Bring a recent decision and discuss who should own it, what support the team needs and how your own responses affect their willingness to take responsibility. That gives the coaching a specific connection to the way the organisation operates.

A useful fit when: Your role calls for both leadership development and an experienced sounding board for significant organisational decisions.

A useful question to ask: How would we connect the leadership behaviours I need to change with the decisions and responsibilities my executive team needs to own?

Learn more about executive coaching in Sydney with Caroline Kennedy.

 

2. James Skinner

Stepping into a larger leadership role

James Skinner is an organisational psychologist and executive coach whose Sydney-based practice works with CEOs and senior leaders. His background includes executive development at EY in the UK and Australia, culminating in coaching senior partners and executive directors. His services cover leadership performance, role transitions and sustainable performance.

His transition coaching addresses the demands of entering a new leadership position, including the expectations and risks associated with the role. His broader approach examines behaviour, self-awareness and how leaders respond to competing demands. For someone moving into partnership or taking on a wider executive remit, this creates a practical starting point for discussing what needs to change.

His transition work includes understanding the organisation’s systems, identifying key decision-makers and clarifying the expectations attached to the new role. It also considers the team’s strengths and challenges, giving the executive a clearer basis for deciding which relationships and changes need early attention.

James describes an initial conversation to assess fit, followed by a personalised coaching plan and regular sessions to set goals and review progress. His performance-coaching service also includes trying new skills and approaches, so development can be connected to situations arising in the role.

A useful fit when: A promotion or appointment has increased your responsibilities and you want to establish how to lead effectively in the new role.

A useful question to ask: How would we identify the people and expectations most important to my success in this new role?

 

3. Beth O’Leary

Leading people through organisational change

Beth O’Leary of iThrive Coaching is a Sydney-based executive coach and former HR Director. Her background spans leadership, People and Culture, and coaching across corporate, public and purpose-led organisations. Her individual executive-coaching offer addresses leadership transitions, stakeholder challenges and the demands of organisational change.

Her approach considers the leader’s organisational context, including the relationships and team dynamics influencing their work. That gives a prospective client a way to explore how their own decisions, communication and expectations contribute to what is happening around them. iThrive also offers team coaching, so it’s useful to clarify whether the engagement is for you individually or involves the wider leadership team.

Beth describes a collaborative approach that builds on the leader’s strengths. Her published background also includes supporting neurodiverse leaders and adapting to different communication styles and thinking preferences.

That gives a prospective client something specific to discuss. You might bring an example of a message that was clear to you but interpreted differently by colleagues, or a change initiative where agreement in meetings has not translated into action. Ask how the coaching would examine your contribution and help you work more effectively with the people involved.

A useful fit when: You are leading through change and need to strengthen the way you work with your team, peers or other stakeholders.

A useful question to ask: How would you help me adapt my communication to different stakeholders while building on my strengths?

 

4. Tom Loncar

Developing influence and adaptability

Tom Loncar is a Sydney executive coach whose practice focuses on helping leaders work through complexity and improve their effectiveness. He established his coaching practice in 2014, following experience across corporate, public-sector and smaller-business settings. His work includes communication, recognising unhelpful patterns and gaining clarity about priorities.

His published approach draws on psychological flexibility: being able to adapt your response to the situation while staying connected to what matters to you. He also uses strengths-based coaching and, where relevant, assessments. This provides a useful angle for an executive who wants to understand why familiar responses keep appearing under pressure and explore different ways of handling demanding conversations.

His available tools include the Leadership Circle Profile, a 360-degree assessment drawing on feedback from managers, peers and direct reports. It provides a way to compare your view of your leadership with how colleagues experience it, helping identify areas for further discussion.

He also uses Strengths Profile, which examines strengths through performance, energy and frequency of use. Assessments are used where relevant; his service description makes clear that the structure and duration of coaching are tailored to the engagement.

A useful fit when: You want to respond more thoughtfully to pressure and strengthen how you communicate, influence others and act on your priorities.

A useful question to ask: Would feedback from colleagues or a strengths assessment add value to my goals, and how would we use the findings?

 

5. Kylie Young

Turning technical expertise into stronger people leadership

Kylie Young offers executive coaching informed by her experience in psychology and corporate settings, with services available across Sydney. Her published approach specifically addresses managers and leaders who deliver strong technical results but receive feedback that their communication, interpersonal skills or ability to engage their direct reports needs attention.

Her coaching explores how personality and thinking styles affect leadership behaviour, alongside the organisational conditions the person is working within. Self-awareness and wellbeing are also part of her stated focus. For an executive whose expertise has been central to their career, this offers a way to examine how they now achieve results through other people.

Her wider practice includes psychological assessment. A prospective coaching client can ask whether assessment would clarify a recurring issue, such as why an approach that feels efficient to them is creating friction with colleagues. Discuss how any findings would be translated into practical changes and whether assessment is included in the proposed engagement.

Kylie offers a complimentary compatibility conversation before an engagement. Her published delivery options include face-to-face services across Sydney, often at the client’s workplace, as well as telephone and video sessions.

A useful fit when: Your technical capability is well established and you want to become more effective at communicating, developing others and leading a team.

A useful question to ask: Would an assessment help us understand the feedback I am receiving, and how would that inform the coaching?

 

Which approach fits your next leadership move

A coach’s biography becomes more useful when you connect it to an actual change in your responsibilities. Before arranging introductory conversations, identify the situation you want the coaching to address.

You are taking on a broader role

A move from functional leadership into an executive position can change who relies on your judgement and what you need to understand. You may need to contribute to decisions beyond your expertise, establish relationships with a board or work more closely with regional colleagues.

Ask a prospective coach how they would help you understand the expectations of the role. Discuss whose feedback would be useful, where you need to build credibility and what you should stop carrying over from your previous position.

Your organisation is growing around you

If the business has added people, products or markets, your leadership habits may need a similar review. A decision that once belonged with you may now sit more effectively with another executive. A team that waits for your approval may need clearer responsibility and better information.

Coaching can give you a structured place to examine your part in that pattern. Bring a specific example: a recurring escalation, a responsibility you keep taking back or an executive meeting that produces discussion without a decision. Ask how the coach would approach it.

Your results depend on people you do not directly manage

Broader leadership roles can involve competing priorities across functions, locations or business units. Progress may depend on your ability to understand another person’s concerns and develop an agreement they can support.

In an introductory conversation, describe one relationship where progress is difficult. Listen for questions that examine the circumstances and your own approach. That will tell you more about the working relationship than a broad promise to improve your influence.