Leadership can be isolating. Executive coaching provides leaders with the space to step away from the day-to-day, think more strategically and explore the challenges and opportunities they face.
Coaching isn’t about telling leaders how to lead. It’s about helping them think more clearly about how they want to lead. Through questioning, challenge and reflection, we help leaders explore their thinking, identify patterns that may be holding them back, consider different perspectives and turn insight into action.
The result is greater clarity, confidence and self-awareness, helping leaders make better decisions, navigate challenges and perform more effectively under pressure.
Coaching helps leaders understand how pressure affects their thinking, behaviour and decision-making. Developing greater self-awareness can help leaders respond rather than react, regulate emotion, communicate more effectively and make better decisions, supporting stronger leadership and more sustainable performance.
Typical coaching themes
I don’t see the coach’s role as providing the answers. My role is to create the space for leaders to step back, think differently, develop greater awareness and find their own way forward. That means listening carefully, asking questions that get beneath the immediate issue, challenging assumptions and established thinking, and helping leaders turn insight into action.
Where it adds value, I draw on leadership frameworks, behavioural psychology and practical neuroscience to help leaders understand what may be driving their behaviour, how they respond under pressure and how their behaviour can affect the people around them.
We may explore leadership identity, values and beliefs, strengths, emotional regulation, executive presence and behavioural flexibility. Established leadership frameworks can also provide useful ways to understand different approaches and consider how they can be used more intentionally in different situations.
The approach is tailored to the individual, their role and the challenges they are facing. There is no one-size-fits-all model of leadership, the aim is to help each leader develop an approach that is authentic, effective and sustainable.
Stage 1 — Stakeholder contracting
The initial contracting session brings together the coachee, organisational stakeholder and coach to agree the objectives, expectations, confidentiality and measures of success for the coaching programme.
Stage 2 — Chemistry & discovery
An initial one-to-one session to establish the coaching relationship, explore the coachee’s context in more depth and agree what they want to achieve through coaching.
Stage 3 — Executive & Leadership Coaching
Eight 90-minute one-to-one coaching sessions focused on the agreed objectives, while allowing space to address the challenges and opportunities that emerge along the way.
Stage 4 — Reviews
A mid-programme review and a final review to reflect on progress, learning and next steps. Where appropriate, stakeholder feedback can be incorporated while maintaining the confidentiality of the coaching relationship.
Before founding The Wingman Project, I spent more than three decades in the UK media industry, including over 20 years in senior leadership. I led large commercial teams, transformed commercial functions, supported private equity-backed businesses through growth and sale, managed complex agency and client relationships, led major pitch processes and navigated significant periods of growth and change.
I’ve experienced first-hand the pressure, responsibility, ambiguity and sometimes isolation that come with leadership. That experience matters, not because it means I have all the answers, but because I understand the environment in which leaders are trying to make decisions, manage people and perform under pressure.
I’m an ICF-trained Executive & Leadership Coach through the Barefoot Professional Coaching Programme, with additional professional training in solution focused hypnotherapy, behavioural change, NLP and using practical neuroscience.
My coaching brings together two perspectives: the lived experience of senior commercial leadership and the professional discipline of coaching. The result is a practical approach that understands both the realities of leadership and the individual behind the role.
How long does an executive coaching programme last?
The standard programme runs over approximately six months and includes stakeholder contracting, an initial chemistry and discovery session, followed by eight 90-minute coaching sessions. A midpoint review and final review provide opportunities to reflect on progress against the agreed objectives and consider next steps.
Do you coach women as well as men?
Yes. Executive coaching is available to both men and women. While The Wingman Project has specialist expertise in men's mental fitness, our executive coaching supports leaders of any gender.
How are objectives agreed with the organisation?
Objectives are agreed collaboratively during the initial stakeholder contracting session between the coachee, organisational stakeholder and coach. This creates clarity around what the coaching is intended to achieve while ensuring the coachee has ownership of their development.
Can the coaching programme be tailored?
Yes. While the standard programme provides a clear structure, the content and focus of the coaching are tailored to the individual, their role and the organisation’s objectives. The programme can also be adapted where there are specific organisational requirements.
What happens if coaching isn't the right fit?
The initial chemistry and discovery session provides an opportunity for the coach and coachee to establish whether there is a good working relationship and whether coaching is appropriate. If it becomes clear that a different form of support would be more suitable, this will be discussed openly with the individual and, where appropriate, the organisation.
Is coaching available online and in person?
Yes. Coaching can be delivered online or in person. In-person coaching is available at the organisation's offices or in the City of London, with other locations available by arrangement. The format can be agreed around the needs of the coachee and organisation.
How is progress measured?
Progress is reviewed against the objectives agreed at the start of the programme. Midpoint and final reviews provide structured opportunities to reflect on progress, learning and development, while individual coaching sessions continually explore what is challenging, what is changing and what the coachee is putting into practice.
How does confidentiality work?
Coaching is confidential. The content of coaching conversations remains between coach and coachee unless explicit permission is given to share information. Stakeholder reviews focus on progress against agreed objectives rather than the content of individual coaching conversations. Maintaining confidentiality is fundamental to creating the trust required for meaningful development.
Can solution focused hypnotherapy be included?
Yes. Where appropriate and agreed with the individual, solution focused hypnotherapy can complement executive coaching, particularly in areas such as confidence, emotional regulation, resilience and performance under pressure. It is never assumed to be part of the coaching programme and would always be discussed and agreed separately.
Book an introductory conversation with Chris on chris@thewingmanproject.co.uk