Questions before we begin
Questions people often ask before we work together.
You do not need to know exactly what kind of support you need before getting in touch.
You may be thinking about coaching for yourself.
Exploring support for a senior leader.
Wondering whether a team needs facilitation or coaching.
Considering the Enneagram.
Or simply trying to work out what the right starting point might be.
This page answers some of the practical questions that tend to come up first. If yours is not here, ask me.
Executive Coaching
Questions about one-to-one coaching.
What is executive coaching?
Executive coaching is a confidential thinking partnership for leaders carrying responsibility, complexity or change. The work begins with what is actually happening in your leadership: a decision, relationship, team issue, transition, recurring pattern, or a sense that the way you have been leading no longer quite fits.
My role is not to tell you what to do. It is to create enough space, challenge and perspective for you to see what is happening more clearly, notice what may be shaping your response, and make more intentional choices about what happens next.
Who is executive coaching for?
I primarily work with CEOs, founders, directors and senior leaders, including people stepping into greater scope, responsibility or visibility.
Coaching can be useful when something is difficult, but it is not only for fixing problems. Many leaders begin coaching because something is going well and the next stage requires something different from them.
How long does coaching last?
Engagements vary depending on the person, context and purpose of the work. Some coaching supports a specific transition or challenge. Other relationships continue for longer where the work is broader or evolving.
We agree the shape of the engagement together after the initial conversation.
How often do sessions happen?
There is no single rhythm that suits every engagement. We agree a cadence that gives enough continuity for the work to build while leaving enough space for you to apply what emerges between sessions.
What happens in an executive coaching session?
We work with the real material of your leadership: a decision you need to make, a conversation you are avoiding, a relationship that has become difficult, a team dynamic, a transition, or something you can feel but have not yet named clearly.
Sometimes the work is strategic. Sometimes relational. Sometimes behavioural. Sometimes the most useful question is about identity. There is no fixed script.
Is executive coaching confidential?
Yes. The coaching conversation itself is confidential. Where an organisation is sponsoring the coaching, we contract clearly around purpose, confidentiality and any appropriate stakeholder involvement before the work begins.
Objectives or progress may sometimes be reviewed jointly, but there should be no ambiguity about what remains private.
What is the difference between coaching, mentoring, consulting and therapy?
Coaching helps you think, notice, choose and act more intentionally. Mentoring draws more explicitly on the mentor's own experience and advice. Consulting typically involves diagnosing a problem and recommending solutions. Therapy focuses primarily on psychological wellbeing, distress, healing and clinical or therapeutic concerns.
There can be overlap at the edges, but the purpose and contract are different.
Do you need experience in my industry to coach me?
Usually, no. I need enough understanding of your context to work intelligently with what is happening, but I am not there to become the technical expert in your role. Sometimes not being embedded in the same industry assumptions is useful.
What matters more is my ability to work with leadership, relationships, identity, judgement, systems and complexity.
How do I choose the right executive coach?
Credentials and experience matter. Fit matters too. You need someone you can think honestly with: someone you trust enough to challenge you, who can stay curious without becoming impressed by the role or intimidated by it.
The first conversation is partly about discovering whether that quality of working relationship exists.
Organisations & Coaching Sponsors
When an organisation is commissioning the work.
How does organisation-sponsored coaching begin?
We begin by clarifying the organisational context, why coaching is being considered and what useful change would look like. Where appropriate, the leader and sponsor may agree broad objectives together.
The individual coaching conversation itself remains confidential. A clear agreement at the beginning prevents confusion later.
How do you balance confidentiality with organisational objectives?
By contracting clearly from the start. The organisation should understand what the coaching is intended to support. The leader should understand what remains private.
Where progress or objectives are reviewed, that conversation is normally held transparently with the leader involved, rather than information being passed behind the scenes.
Can you coach several leaders in the same organisation?
Yes, where the relationships and confidentiality boundaries can be managed appropriately. Each coaching relationship remains distinct.
Where several leaders are being supported as part of a wider programme, we agree clearly how individual coaching connects to the wider organisational purpose.
Can executive coaching form part of a wider leadership programme?
Yes. Executive coaching can sit alongside wider leadership development, team work, facilitation or organisational programmes where that makes sense.
The coaching element is contracted clearly so that its purpose, confidentiality and relationship to the wider programme are understood from the beginning.
How is an engagement scoped and priced?
Every engagement is shaped by the context, number of people, format and depth of work required. After the initial conversation, I will recommend an appropriate shape for the work and provide clear fees before anything is agreed.
Can we have an initial conversation before committing?
Yes. Start with a 20-minute conversation. There is no agenda and no pitch. It is simply a chance to talk about what is happening, what you are considering, and whether I might be useful.
Teams & Facilitation
When the work is with the room.
How do I know whether my leadership team needs external facilitation?
External facilitation can be useful when the team cannot easily hold the conversation and manage the process at the same time. That may include an important decision, strategy work, conflict, a team reset, difficult conversations, significant change, competing perspectives, or a need for greater clarity or alignment.
An external facilitator holds the process so the team can focus on the work.
What is the difference between facilitation and team coaching?
Facilitation is usually focused on helping a group get somewhere important together. Team coaching focuses more deeply on how the team itself functions over time: its relationships, patterns, accountability, decision-making and collective behaviour.
Sometimes one facilitated conversation is enough. Sometimes it reveals deeper patterns that would benefit from team coaching.
Can you work with a leadership team experiencing conflict or low trust?
Yes. The starting point is understanding what is happening and whether there is enough willingness in the system to work with it. The aim is not to manufacture harmony.
Healthy teams need difference and challenge. The work is about helping the team use that difference more productively.
What happens before a team session?
I normally begin by speaking with the team leader and, where useful, other stakeholders or team members. We explore why now, what is happening, what has already been tried, what the team believes the issue is, what success would look like, and what stakeholders need from the team.
The purpose is not to arrive with a diagnosis. It is to enter the room with enough context to work intelligently.
Is a single workshop enough?
Sometimes. If there is a specific conversation, decision or piece of work to accomplish, one well-designed facilitated session may be exactly what is needed.
If the same relational or behavioural patterns repeatedly return, deeper team coaching or development may be more useful.
Can you facilitate senior, international or hybrid groups?
Yes. I work with leaders and teams internationally. Where format matters, we scope the practicalities case by case.
Enneagram for Leaders & Teams
A useful lens, when it is the right lens.
What is the Enneagram?
The Enneagram is a framework for understanding recurring patterns of attention, motivation and behaviour. Rather than simply describing personality traits, it can help people notice what they habitually pay attention to, what they tend to avoid, and how those patterns shape relationships, leadership and decision-making.
What is an iEQ9 assessment?
The iEQ9 is a professional Enneagram assessment designed to support individual, leadership and team development. You complete the assessment online and receive a detailed report exploring your likely Enneagram pattern and related themes.
The assessment is not the destination. It is the beginning of a conversation, explored together in a professional debrief.
Is the Enneagram different from other personality tools?
Some tools focus primarily on preferences or observable behaviour. The Enneagram pays particular attention to underlying motivation: what a person may be seeking, protecting or avoiding beneath the behaviour. It also considers how patterns may shift under pressure, when we feel secure, and as we develop.
Does the Enneagram put people into boxes?
It should do the opposite. Used well, the Enneagram gives people language for habitual patterns while making clear that those patterns are not the whole person. The purpose is greater awareness and choice, not a new identity label.
What if I do not agree with my assessment result?
The report is a starting point for exploration, not a verdict. Your experience matters. If something does not resonate, that becomes useful material for the conversation rather than something you have to accept.
Can the Enneagram be used with teams?
Yes. Where useful, it can help teams develop shared language for difference, attention, motivation and recurring relational patterns. It is one possible lens within team work, not a compulsory starting point.
Working With Robert
A few questions about how I work.
What is distinctive about Robert's approach?
My work combines executive coaching, Narrative Coaching, systemic awareness, facilitation, the Enneagram and more than 5,000 hours of coaching and facilitation. But the value is not in the list of methods.
I am interested in what is actually happening: the immediate challenge, the pattern underneath it, the role you are playing, what has become difficult to see from inside the situation, and what becomes possible when more of the picture comes into view.
I work with warmth, curiosity and challenge. The aim is not to perform expertise at you. It is to help create the conditions for useful thinking and meaningful action.
What experience does Robert have?
I am an ICF PCC accredited coach with more than 5,000 hours of coaching and facilitation experience. My background includes acting and physical theatre, executive coaching, leadership development, team work, facilitation, Narrative Coaching, systemic approaches, the Enneagram and embodiment.
What qualifications and professional approaches does Robert bring?
I bring together:
- ICF PCC
- Diploma in Transformational Coaching
- Narrative Coaching
- Systemic & analytic approaches
- iEQ9 Enneagram
- Physical Intelligence & embodiment
- Advanced coaching and supervision
Does Robert work independently?
Yes. Robert Stephenson Coaching is my independent coaching, team and facilitation practice. I work directly with leaders, teams and organisations across a range of contexts.
Do you work online and in person?
Yes. I work with leaders and teams internationally online, with selected in-person work by arrangement.
How do I start a conversation?
Book a 20-minute conversation. You do not need a polished brief. Tell me what is happening and what you are thinking about. From there, we can work out whether the next step makes sense.
Still have a question?
You do not need to have everything worked out before we speak.
If the question you have is not here, ask it. Or tell me what is happening and we can start there.