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Executive Coaching 

Leadership Compounds When It's Built From the  Inside Out

How I Work

The leaders I work with are not struggling. They are succeeding and beginning to sense that the leadership that got them here is reaching its limit. The business is scaling. The team is growing. The pressure is sustained. And somewhere in that, familiar patterns are starting to cost more than they used to.

This is the inflection point where executive coaching does its most important work.

I spent 20 years in leadership roles in marketing services before retraining as an executive coach. That experience shapes every conversation, not as a template for how to lead, but as a foundation for inquiry into what leadership is asking of you right now.

Every coaching engagement is built around what the leader in front of me needs, not a one-size-fits-all approach based on three multipliers that can help you compound your leadership:

 

  • Connected Awareness: Coaching helps you connect the beliefs and assumptions driving behaviour, making the implicit explicit. Connect what’s inside to how you lead, and everything that follows becomes a choice rather than a reaction. 

 

  • Choice Point: Coaching helps you develop the capacity to observe unhelpful thoughts and emotions as signals rather than instructions. That practice creates the choice point where, under pressure, intentionality replaces reactivity.

 

  • Consistent Practice: Coaching helps you turn a single choice into a consistent practice. Values-aligned actions practised daily compound into trust, culture, and leadership presence. A choice made consistently becomes identity.

Together, they produce change that compounds over time rather than fades after the next busy quarter. This is the methodology at the heart of the Compounding Leadership Coaching Programme I have developed through years of working with founders and leaders in fast-moving organisations.

 

The programme helps leaders identify their strengths and derailers and the impact they have on others, making the implicit beliefs and assumptions that push against behaviour change explicit, and leaving the leader with new mental models to consistently practise and apply in leading their team and organisation.

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Working Together

My executive coaching gives you space to slow down, think things through, and see situations more clearly.

I incorporate evidence-based assessments and structured feedback to support insight and focus. This can include tools such as Gallup StrengthsFinder, Hogan, and HBDI, as well as stakeholder interview feedback reports. These inputs provide an external perspective and help ground the work in others’ experiences of your leadership.

 

Coaching opportunities include:

 

Transition Points

Supporting career and role transitions — including founder-to-CEO, promotions, structural changes, or broader career decisions. The work clarifies direction, prepares you for important conversations, and builds practical plans for what’s next.

Leadership Impact

Helping you lead more intentionally as the business scales or your role and context change. This often involves strengthening leadership presence, improving how you delegate and develop others, building more effective relationships, and adopting a more flexible, situational approach to leading teams.

Personal Effectiveness

Building the inner capacity to lead well under pressure. This includes working with unhelpful thinking patterns, addressing self-defeating behaviours such as perfectionism or imposter syndrome, increasing tolerance for uncertainty, and sustaining performance and wellbeing over time.

Systemic Challenges

Clearer thinking and better decisions when the stakes are high. This includes developing new perspectives on business challenges, managing difficult stakeholders, leading organisational change, and strengthening judgment by surfacing and challenging assumptions.

What to Expect

My approach is practical and shaped around what will make the biggest difference for you. Most engagements follow a clear arc: clarity, insight, experimentation, and integration, reflecting years of working with founders and leaders in media, marketing, technology, and founder-led organisations.

 

Clarify goals and focus

Define what you want to change, what success looks like, and how progress will be measured — so attention stays on what truly matters.

See the wider system you’re leading

Look beyond individual behaviour to understand team dynamics, stakeholder relationships, and the broader organisational context shaping performance.

Notice patterns under pressure

Recognise the thinking and behavioural patterns that surface when the stakes are high — especially those that limit effectiveness or narrow choice.

Build on strengths while challenging negative compounding

Leverage what already works well while constructively challenging the habits and assumptions that no longer serve you.

Compound insights into action

Turn insight into small, precise changes in behaviour — practised consistently, with space for reflection and refinement — so change compounds rather than fades.

 

Throughout the work, I facilitate tripartite meetings with sponsors where relevant and incorporate assessments, stakeholder interviews, and feedback reports to ground the coaching in data and others’ experiences.

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Andrew Sherman Executive Coach logo pattern in background
  • LinkedIn
Jacquie Alley, Chief Operating Officer

"I have had the privilege of being involved in an Executive Coaching program with Andrew as he supported my transition to my current leadership role. His active listening, insights, encouragement and accountable process has been integral in my development and I stand much taller as a result. I would highly recommend Andrew as a role transition coach and thank him for being a strong supporter of mine."

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