Leadership – especially senior leadership can be isolating.
The more senior the position, the fewer people there may be who can provide independent, candid, and appropriately challenging feedback. Colleagues may hesitate to question decisions, direct reports may filter what they say, and Boards often have a different relationship with the executive than the people working alongside them every day.
A strong leadership coach can create a valuable space for reflection, challenge and development. They can help an executive recognise patterns, test assumptions, navigate complexity and make more deliberate choices about how they lead.
However, not every coach will be right for every executive or leader.
Choosing a leadership coach should involve more than reviewing a profile, checking credentials or deciding whether there is good personal chemistry. The right coach should understand the leadership challenge, work within clear professional boundaries and be capable of respectfully challenging the executive – not simply affirming what they already believe.
So, what should leaders look for?
Start with the outcome, not the coach
Before approaching a coach, it is worth becoming clear about what you are trying to achieve.
Are you:
- stepping into your first executive or CEO position?
- preparing for a broader portfolio or future leadership role?
- navigating organisational change or transformation?
- working through tension within an executive team?
- seeking to strengthen your relationship with the Board?
- experiencing difficulty delegating or letting go of operational detail?
- trying to improve your influence, communication or decision-making?
- leading through a period of sustained pressure or uncertainty?
The clearer you are about the leadership challenge, the easier it becomes to identify the type of coach, experience and approach that may be most useful.
An executive seeking support with Board relationships may need something different from a leader working on confidence, interpersonal impact or team dynamics.
Coaching should not begin with a generic promise of transformation. It should begin with a clear understanding of what needs to change and why that change matters.
Be clear about the type of support you need
The terms coach, mentor and adviser are often used interchangeably, but they describe different forms of support.
A coach will generally help you explore your thinking, behaviours, assumptions and choices. They should support you to arrive at clearer insights and actions rather than simply telling you what to do.
A mentor usually draws on their own experience and may offer guidance based on situations they have encountered.
An adviser is more likely to provide recommendations, subject-matter expertise or a specific course of action.
A psychologist may be appropriate where the work requires deeper expertise in behaviour, psychological assessment, mental health or personal wellbeing.
Some practitioners combine elements of these approaches. That is not necessarily a concern, provided they are clear about how they work, where their expertise sits and the boundaries of the engagement.
Executives should understand what service they are engaging and whether that service matches the issue they are trying to address.
Look beyond chemistry
Personal chemistry matters. An executive needs to feel able to speak openly and trust that the coach will handle sensitive information appropriately.
However, feeling comfortable should not be the only selection criterion.
The most valuable coaching relationships are not always the easiest ones. A strong coach should create psychological safety while also being prepared to question assumptions, challenge avoidance and identify behaviour that may be contributing to the problem.
A coach who agrees with every interpretation may feel supportive, but may not be particularly useful.
A worthwhile question to ask a prospective coach is:
“How would you approach the conversation if you believed my behaviour was contributing to the issue?”
The answer should provide some indication of whether the coach can balance respect, trust and appropriate challenge.
Executives do not need someone who is confrontational for the sake of it. They do, however, need someone who is willing to say what others may not.
Consider their experience and professional credibility
Credentials can provide useful evidence of formal training, ethical commitments and professional development. However, credentials alone do not determine whether someone will be an effective coach for a particular executive.
It is equally important to understand:
- the level of leaders they have worked with;
- the types of challenges they regularly support;
- the sectors and organisational environments they understand;
- their coaching methodology;
- whether they participate in ongoing professional development or supervision;
- how they recognise the limits of their expertise; and
- when they would refer a client to another professional.
Executives should be cautious of practitioners who claim to be able to coach every leader, across every issue, in every context.
Relevant experience does not necessarily mean the coach must have held the same role as the executive. In some cases, too much emphasis on having “been there before” can lead the coach to impose their own experiences or solutions.
The more important question is whether the coach understands senior leadership, organisational complexity and the context in which the executive is operating.
Look for organisational and systems awareness
Leadership challenges rarely exist in isolation.
An executive’s behaviour is shaped by and influences the broader organisational system. This may include the Board, the executive team, funding pressures, regulatory requirements, workforce capability, organisational culture, stakeholder expectations and the needs of the communities being served.
This is especially important in community services, health, government and purpose-led organisations, where leaders are often balancing commercial sustainability, service quality, workforce wellbeing, compliance and community impact.
A coach who views every challenge solely as a personal mindset issue may miss the broader context.
For example, difficulty delegating may be linked to the executive’s leadership style, but it may also reflect limited capability within the team, unclear accountability or previous failures in the organisation’s systems.
Strong coaching should help an executive distinguish between:
- what sits within their own behaviour and choices;
- what requires a team or structural response; and
- what is being driven by the wider operating environment.
The coach should be able to work with the individual while remaining alert to the system around them.
Understand how confidentiality will work
Confidentiality should be discussed clearly before the coaching engagement begins.
This is particularly important when the organisation, CEO or Board is funding the coaching.
The executive, coach and organisational sponsor should agree on:
- what information will remain confidential;
- whether progress updates will be provided;
- what information may be shared with the sponsor;
- who will have access to assessments or reports;
- how conflicts of interest will be managed;
- what happens if a serious risk or concern emerges; and
- how the engagement will be concluded.
Without clarity, the executive may be uncertain about how openly they can speak, while the organisation may have different expectations about what it will receive in return for its investment.
A good coach should be able to explain these boundaries confidently and transparently.
Ask how progress will be assessed
Coaching should be reflective, but it should also have purpose.
The executive and coach should agree on what meaningful progress might look like. Depending on the engagement, this could include:
- greater clarity and confidence in decision-making;
- improved communication with the Board;
- stronger executive-team relationships;
- more effective delegation;
- improved ability to manage conflict;
- clearer boundaries and priorities;
- greater confidence in difficult conversations;
- observable changes in leadership behaviour;
- a more successful transition into a new role; or
- reduced dependency on the executive across the organisation.
Not every outcome needs to be reduced to a number. However, both parties should be able to explain what they are working towards and how they will know whether the engagement is having an impact.
Coaching conversations may feel valuable in the moment, but the real measure is whether they lead to changes in thinking, behaviour, relationships or results.
Watch for dependency
The purpose of coaching should be to strengthen the executive’s capability, not create an ongoing dependency on the coach.
A strong coach should help the executive develop greater self-awareness, judgement and confidence over time. The executive should become better able to identify their own patterns, test their thinking and make decisions without needing the coach to validate every step.
Be cautious where the coach positions themselves as indispensable or where the engagement has no clear review point.
The goal should be greater leadership capacity—not permanent reliance.
Questions to ask a prospective leadership coach
Before appointing a coach, executives may find it useful to ask:
- What types of leadership challenges do you work with most effectively?
- How would you describe your coaching approach?
- What experience do you have working with leaders at my level?
- How do you balance support with challenge?
- How would you respond if you believed I was contributing to the problem?
- How do you consider organisational context and systems in your work?
- How will we agree on and assess progress?
- What professional and ethical framework guides your practice?
- Do you participate in coaching supervision or professional development?
- How will confidentiality work if my organisation is funding the engagement?
- When would you recommend another form of support instead of coaching?
- How do you ensure the engagement builds capability rather than dependency?
Final Tips
The right leadership coach should not simply make an executive feel heard.
They should help the executive think more clearly, see what they may be avoiding, understand the impact of their behaviour and make more deliberate leadership choices.
The relationship should involve trust, but also challenge. Reflection, but also action. Individual development, while remaining connected to the wider organisational system.
Ultimately, the right coach is not necessarily the person with the strongest profile, the most impressive title or the most comfortable style.
It is the person who can create the conditions for honest reflection, meaningful behavioural change and stronger leadership.
At Be Executive, we work closely with senior leaders, Boards and organisations across the community, health and purpose-led sectors. We understand that executive development is not separate from organisational performance – it is central to it.
If you are considering engaging a leadership or executive coach, Be Executive has worked alongside a number of experienced coaches, consultants and leadership practitioners across different sectors and levels of seniority.
We are happy to share referrals based on your individual needs, career stage and organisational context. Be Executive has no commercial affiliation with these providers and receives no referral fee; our recommendations are based solely on positive feedback, professional experience and trusted relationships.
