Your Business is growing fast: Are Your Leaders Up to the Task? We Build the System That Prepares Them—and Your Business—for the Next Level.
Strong leadership is the engine of growth. When your business accelerates, clarity, alignment, and capability become the difference between scaling with confidence—or slipping into chaos.
I’m Charlie Winn, l will help you design the leadership system your business needs to grow sustainably, empower your people, and free you to focus on what matters most.
As a Fast-Growing Businesses of 15-100 employees are you finding:
Your business has grown beyond the owner-centric stage, so you’re finding leadership challenges multiplying:
- You Can’t Do It All: More managers and leaders are needed—but they must be ready to lead and aligned to your vision, values, and purpose. Without this, growth stalls.
- Conflict and Misalignment has grown: Different communication styles and low self-awareness create drama, friction, and decisions that put people before the business.
- A lack of Structure to Collaborate and Execute is holding you back: Leaders need clear metrics, meeting rhythms, and alignment systems to keep pace with rapid growth. Without structure, teams silo, decisions slow, and opportunities are lost.
These are leadership system problems—and they’re exactly what we fix.
Start With the Leadership System Diagnostic:
A practical, insight-driven assessment showing exactly where your leadership system is supporting your growth—and where it’s holding you back.
For $690 + GST, you’ll receive:
- A tailored Leadership System Report detailing strengths, gaps, and priorities
- Session 1: Explore your biggest leadership challenges and identify priorities
- Session 2: Targeted coaching on one key leadership barrier
Walk away with clarity, focus, and the next steps to create a leadership system that scales as your business grows.
A Leadership System: for Rapid Growth Businesses
Fast-growing businesses need more than talented individuals—they need a leadership system that creates clarity, alignment, and capacity. Our Leadership System Diagnostic maps directly to the Orchard Coaching Framework, showing where your system is strong—and where it needs focus.
Lead Yourself
Growth • Balance • Awareness
Strong leaders start with self-awareness, resilience, and clarity. When leaders understand their impact, they make better decisions and lead others effectively.
Connected Leaders (TEAM)
Structure • Right Roles • Right People
Effective teams need clear structure, aligned roles, and strong collaboration. With shared metrics and accountability, leaders execute faster and avoid silos.
A Culture of Future Leaders
Development • Mindset • Alignment
Sustainable growth comes from developing the next generation of leaders. Align your team around vision and values to expand leadership capacity as your business grows.
Your Next Step: The Leadership System Diagnostic
Get clarity on leadership strengths, gaps, and priorities—plus two coaching sessions to tackle key challenges.
Create the leadership capacity your business needs to grow confidently.
Partner with Charlie & Orchard Coaching
Every business has its own unique challenges, and too often we’re stuck treating the symptoms rather than addressing the root causes holding us back. Not sure which program is right for you or your current and future leaders? Let’s start with a simple chat:
Initial Discussion: A 10-minute conversation or coffee to see if we’re a good fit and answer any questions. If needed, I’ll recommend the Leadership System Diagnostic.
Discovery Session: Start with the Leadership System Diagnostic to benchmark your business’ leadership maturity. We’ll debrief on the results and tackle a key challenge your organisation faces. The follow-up session will offer tailored recommendations to boost your leadership growth.
Programs: Group coaching focused on training your emerging leaders and enhancing their ability to coach others.
1-on-1 Coaching: Get personalised coaching with Charlie to overcome obstacles and develop the tools and mindset needed for sustainable leadership.
- Check mutual fit
- Answer questions
- Confirm where to start
- Assessment
- Debrief session
- Follow-up session ($690+GST)
- Leadership Circle Profiling
- Executive Coaching
- Future Leaders Program
- Leaders To Create Future Leaders™️ Program
Ready to take the next step?
LegacyBuilders: Leadership Retreat
Recharge | Rediscover | Re-inspire
What legacy will you leave behind? Who will benefit from your legacy? How are you leading now to achieve your legacy?
Answer these questions in the serenity of the Blue Mountains
Businesses I work with
Leaders to Create Future Leaders™️ Program
Imagine what your organisation could look like if you had more leaders stepping up?
What Charlie Winn’s clients say
Working one-on-one with Charlie has helped me reconnect with my purpose and sharpen my focus on what I do best. His coaching has been a catalyst for both personal and professional growth. To me his coaching style demonstrates a combination of empathy, strategic insight, and practical tools.
What sets Charlie apart is his ability to refocus attention on what drives success. His coaching style is both insightful and empowering, He helped me align my energy with the areas where I deliver the most impact.
I started working with Charlie when I was COO for an engineering consultancy. He was engaged to work with the CEO and myself to develop our Leadership strategies, and to assist our drive to unite our (relatively) junior workforce behind the company vision. Charlie also ran leadership workshops for the Executive Team in which he created a space that encouraged deep reflection, strategic thinking, and meaningful action. They are focused, driving teams toward clear outcomes and setting out frameworks for measurable progress."
Working with Charlie has been fantastic. He's empathetic, knowledgeable, and practical. His tailored approach ensures solutions are tailored to your unique situation.
I highly recommend Charlie as a Business and Leadership Coach. His personal connection combined with impressive coaching sets him apart. His coaching is a 'no-brainer' investment in both personal and business growth.”
That’s why we can all use someone in our corner. Charlie is the person I’ve chosen to help me bust through my own boundaries, real or imagined. He’s the perfect combination of coach and mentor.
He’s patient and compassionate yet has an unwavering focus on the larger goal or ambition. I have absolute trust in Charlie’s integrity and process and his clarity of thought and positivity is utterly infectious.
Charlie joined our advisory Committee or joined us as a mentor at this step, where we moved from being entrepreneurs and owners and had to step more into a managerial role to support the growth of our business.
And for me it’s always been a challenge to define that leadership role. Charlie is guiding us to find our own voice. It’s helped us be really confident.”
The change was engagement within the group coached increased plus improved working methods were initiated by management which have started the journey to create a unified organisation. Even though engagement improved the most fundamental shift in the organisation was the increased awareness of what is possible at the business or department level plus the triggering of discussions from angles which hadn’t occurred before which showed that people’s thinking had fundamentally transformed.
I couldn’t recommend Orchard Coaching any higher since we continue to engage, in fact we are increasing the work Orchard Coaching is doing at BOO. Do yourself a favor, accelerate the growth of your organisation by bringing Charlie and Orchard Coaching into your business – you will not regret it.
Get in Touch
Let’s have an initial no-obligation Discovery Call or chat to explore your
situation and needs. I’ll then explain how my Leadership Coaching can help you succeed.
I can’t wait to hear from you.
