Charlie Winn | Business Leadership Coach for Agency Owners

Helping professional services executives to build sustainable organisations
by inspiring and developing future leaders.

I’m Charlie Winn. I coach, mentor, and train you, your current and future leaders so you can create a sustainably growing organisation which doesn’t depend on you being at the centre of everything.

Professional services executives: what do you spend most of your time thinking about?

Are you struggling to find real ways to take your business to that next level?
Can your business not go a day without you being directly involved?
Do your people have the right values, thinking and skills to proactively grow your business?
Do your teams collaborate with a united vision? Or are they all disjointed?
Are the managers in your agency equipped to develop future leaders?
Are you in a critical transition point, and struggling to manage your employees?

You’re not alone. Most business owners feel the same way.

The difference is that you’re here looking for a solution.
That’s how I can help, as a trusted business Leadership Coach.

Hi, I'm Charlie.

I’m a Leadership Coach who works with agency owners and their leadership teams to help them establish the values, thought processes and skills necessary to become the agency they truly aspire to be.

As an expert in supporting owners to transform their businesses into purpose-driven organisations, I can help you turn value-based mindsets into a practical application that aligns your people with your vision and business goals to achieve profitable and sustainable results.

You’ve done an amazing job to get your business to this point.

However, if you now find yourself facing seemingly insurmountable obstacles that always get passed your way, my fresh perspective, coaching, mentoring and training can break through those frustrating barriers.

I’ll guide you to make the right decisions by using my structured and proven approach that will help you take your business to its true next level.

LegacyBuilders: Leadership Retreat

Join us in the Blue Mountains this August and rediscover your leadership style.

How can I help you?

Public Speaking Events

I can speak in front of audiences about what exceptional leadership looks like and how they can develop practical leadership skills for their own roles.

Offsite Workshop Facilitation

I host half-day workshops for groups of 8-30 business leaders to fine-tune their leadership skills and help improve collaboration within their organisation.

Leadership Launchpad

I help owners and executives become effective leaders with a proven 360-degree feedback & debrief process from people who influence their perception of leadership.

Executive Coaching

I take the time to understand your specific needs and refine your focus toward what’s important to build your leadership, confidence and skill development.

Leaders to Create Future Leaders™️ Program

Imagine what your organisation could look like if you had more leaders stepping up?

Businesses I work with

Is your organisation growing at a sustainable rate?

Businesses that don’t have control over their trajectory are underperforming and carry a high risk. On the other hand, sustainable growth means progressing at a rate that you, your team and your clients can maintain without causing so much pain that your agency starts to move backwards. Through business Leadership Coaching, I help you find this ideal balance to mitigate risk, reduce stress and promote your organisation’s profitability moving forward.

What Charlie Winn’s clients say

“He’s not a yes man, he doesn’t just nod and tell you how good you are. The challenges things and says well what about this, asks the right questions. In a nutshell I think that’s the biggest asset that Charlie brings to our business.”

Martin Wisata - Owner & Founder of Rocky Trail Entertainment & Destination

“Charlie's guidance has been instrumental in aligning my business with my long-term goals. His insights have transformed the way I approach challenges and leadership on the whole. Charlie's expertise when it comes to navigating leadership complexities has helped me develop effective communication and decision-making strategies. We've had great improvements in the clarity of our team's structure thanks to Charlie's work.

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.”

Mohamad Hannaway - CEO of The Frameshop

“Everyone has self-limiting beliefs, whether we know it or not.

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.

Poppy Stockell - Director, Producer & Writer of Sirius Pictures

“Martin & I met at University so we know each other really well and we work together really well. We have a very distinct set of skill sets that’s different but compliment each other. Charlie has been able to identify those differences and those connections points as well, so that we, not just on a professional level, but also on a personal level are now more aware of each other's strengths and where we can support each other better.

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.”

Juliana Wisata - Owner & Founder of Rocky Trail Entertainment & Destination

From the outset, Charlie spent the time to understand the business, its unique needs and various challenges which resulted in designing the engagement which seemed to perfectly fit the business’ current context. The customised design resulted in running a combination of management training sessions, team coaching and Executive coaching, the change was immediately recognised within the organisation.

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.

Gabriel Said - General Manager of BOO Studio

I highly recommend Charlie as a leadership coach. I recently completed the leadership circle profile and found the whole process really well organised and excellent value for money. Charlie helped me interpret the results and create actions around how I can become a more effective leader. He is a consummate professional and very experienced at asking the right questions.

Esther Colman - HR Dept Eastern Suburbs Sydney

As newly promoted General Manager, I was struggling to see myself more than the Production Manager I’d be promoted from. I was seeing my value in the business in only what I can "do" physically. Charlie could see the potential within me. After much patience from both Steve (owner) and Charlie, it finally clicked that my worth in the business was now much I do “in” the business but how I work “on” the business. Coming to this realisation changed everything. I was able to let go and allow my team to work freely which resulted in an increase in productivity. I was able to trust my team to work it out and come up with solutions on their own. With this new mindset, it is a much better place to work from - freer to think and open to new possibilities. This shift in mindset has influenced the financial growth of the business.

From Vich Bun, General Manager BOO Print

Benefits of Working With Orchard Coaching

Fulfil your dream vision for your business

Do you have a clear vision for your business? Is your leadership aligned with your vision and aware of how to get there? I can help.

Develop your key assets:
Your People

Is the leadership in your organisation as effective as it needs to be? Do you have the right people in the right positions? Let’s find out.

Improve your business performance and Profitability

Do you have a system that works to improve your business in perpetuity? I can help you establish a purpose- driven, sustainable agency.

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.

What are Charlie's Credentials?

Download the Credentials Deck for an overview of Charlie’s experience and how he will be able to help your business.

Helping professional services executives to build sustainable organisations
by inspiring and developing future leaders.

Professional services executives: what do you spend most of your time thinking about?

Hi, I'm Charlie.

LegacyBuilders: Leadership Retreat