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All About Us

What we do

Possibility Squared is all about human potential, dreaming big and taking action.

Even the most talented, driven people and organisation set themselves limits; imagine what would it be like if we didn’t do that? If we embraced our futures with a sense of curiosity and possibility?

We believe that everything is possible with the right approach. Our business is helping you find the approach that’s right for you.


unspecified qualities of a promising nature; potential.


multiplied by itself.

Why Choose Possibility Squared

Simon is a highly experienced automotive and financial services leader and executive coach with a passion for authentic, purpose driven leadership.  For over 30 years he has worked with leaders and teams to deliver extraordinary business and personal success.

As a fierce champion for your ambitions, his action oriented, deeply curious style will help you show up authentically, in line with your intrinsic values, to be fulfilled in all aspects of your life.

Simon’s particular interests lie in supporting leaders to achieve great success in-role, or in preparing them for their next role.  He blends extensive C-Suite experience, professional coaching, psychometric evaluation and qualitative 360 in a bespoke way with each client.

In a safe and courageous space, Simon helps his clients to explore their own perspectives as well as others, to determine a clear, purposeful and fulfilling future.

As well as coaching, Simon offers confidential, informed thinking-partnership to business leaders and management boards. Having led large teams in various Chief Officer roles, Simon understands the challenges of the board room and how to navigate them with integrity.  Simon provides these services alongside coaching as part of a blended leadership development offer or standalone following a coaching engagement.

Simon has consulted internally and externally on a wide range of topics including:

  • Customer, product and services strategy
  • Leadership behaviour and enablement
  • Psychological safety and colleague empowerment
  • Customer-aligned organisational design
  • Process simplification and digital transformation
  • New market entry and large-scale start-up

Sometimes it just takes a different perspective to completely transform.


  • Co-Active Training Institute, Certified Professional Co-Active Coach (CPCC)
  • International Coaching Federation, Full Member with ACC Status
  • Mastermind Institute, Neuroscience of Coaching
  • Be Talent, Psychometric evaluation and assessment tools including Winning Attitude, Blended 360, Resilience, Strengths and Decision Styles.


  • Leadership responsibility for over 25 years in the largest global automotive credit business
  • Executive Board of Management member in the roles of both Chief Commercial Officer and Chief Operating Officer
  • Extensive experience of Sales, Marketing, Planning and Customer Operations and of leading large-scale, regulated financial services functions holding FCA Senior Manager status
  • Significant track record of coaching and mentoring clients to senior roles, including promotion to Executive Board of Management and international positions
  • Direct responsibility for creating and leading significant business, culture and customer transformation activities.

About Simon

If you’ve ever written an ‘about me’ you’ll know where the delete key lives on the keyboard! What can I say that people will want to read? Will it be interesting and help my business? Can I be vulnerable and convincing at the same time?

The first thing to say is that I’ve been blessed with a great corporate career, holding board of management roles at the UKs leading captive automotive bank. But I didn’t start out that way, leaving school at 15 with very few qualifications and diving into work as a labourer. All I really cared about in those days was earning a few quid to have fun at the weekend.

So what changed?

Well, even then I was curious about possibility, but I noticed that not everyone shared that curiosity. So I started calling out the things that I saw could be improved, clumsily at first, but with more skill as I learned. I didn’t have a detailed plan for every step of my career, but I stayed curious, was open to possibility and took my chances as I went.

During all of this, I kept some secrets.

  • I’m an outsider. I never quite fit into the corporate template, which kept me away from groupthink but made me a lone voice sometimes.
  • I’m highly-tuned to risk. I can see what might go wrong and have an instinct for the most important things to focus on.
  • I’m lazy. So lazy that I see and pursue the shortest route to the best outcome. I’m always surprised by how hard we make things sometimes

In summary I could see things differently, know what’s important and get straight to the heart of putting it right.

This gave me great success at work, but it came at a price. I didn’t have the ‘foundations’ to be a leader, I’d done it a different way and sometimes I found it hard to cope. I had the technical tools, but not always the emotional ones. I was lucky, working with some great managers who helped invested in me to help me develop those capabilities. I had some great coaches, attended fantastic development programmes and even qualified professionally as a coach myself.

A great partner, two kids and two dogs played a huge part too!

And today? Well, Possibility Squared brings it all together and lets me do the work I was born to do. Use my curiosity, instinct and the lessons I’ve learned, to help other people see what’s possible for them.