Transformative leadership & culture

January 24, 2021

Stuart is an established performance psychologist who has worked with a broad spectrum of clients including Cirque du Soleil, Kings of Leon, Olympians, The Royal Ballet, and many others. Stuart is also the CEO of SkyPilots, a leadership development and training company, based out of Vancouver, with clients all around the world.

How did you first get started in your career?

I was a performer of various sorts — musician, athlete, even a radio DJ!  I realized how much the mental aspects of performance were common to all, and decided to study performance psychology.  Once qualified, I applied my performance coaching craft to a very wide variety of domains - from rock stars to surgeons, racing drivers to acrobats, olympic athletes to tech execs.

Why did you end up doing what you are doing?

I’ve always been interested in growing to be the best version of myself, and I have an inherent passion for helping others to do the same. Through experience working in different contexts and cultures, I realized that many people felt a gap between what they wanted to build in the world and what they actually spent their time on. I felt that way myself on many occasions, despite recognizing how much we need different leadership in the world.

When you think of leaders you admire, who is your biggest inspiration?

There are so many people who have inspired me, but one that springs to mind for many reasons is from my hometown — Terry Fox. The resilience and strength of character that man had was astonishing.  Bob Marley and Muhammed Ali being notable others for me.  I’ve always been drawn to those who transcend the identity of what initially made them known to us, who did something significant for the greater good — even despite the backlash they may endure.  Thankfully, there are many to choose from!

What type of leaders do you think the world needs right now?

The Dalai Lama said that real change will not come from decisions made by governments or the U.N.  I believe that to be true.  Transformative leaders serve a transcendent purpose -- looking beyond today's reality to creating a new future. To do this effectively, we must look inwards and manage our own hearts and minds, then action outwards from a balanced place within ourselves.

How do you apply that within the the work you do at SkyPilots?

I recognized that the best way for me to do my part in helping to bring the necessary action into the world was to provide a leadership program that helps people gain self-awareness and coaching skills through applied learning and action in the workplace.  This will ultimately benefit people through the expressed values of serving and empowering others, and development of skills in self-mastery, resilience, collaboration, being visionary, impactful and taking positive action.

What is the best part of your job? What is the biggest challenge?

The best part of my ‘job’ is witnessing my clients have those ‘aha!’ moments — insights into new areas of their growth, and revelations of the depths of their character.  The biggest challenge is ensuring they act on those insights and persevere through inevitable challenges to ensure these learning edges get integrated habitually over the short and long term, and applied where they make the most impact.  It's often a delicate tension between short term KPI's and maintaining a disciplined stance for the long term benefit of the greater good.

How has covid changed your work? What’s worse, and what’s better?

Covid-19 forced us to deliver everything remotely.  It’s much harder to ‘read the room’ when my clients are all boxed into a zoom window — that energy needs to be tended to so as to ensure the same collective experience.  However, tech has helpfully enabled powerful, vulnerable communication, which often leads to people having ‘breakthroughs’ or realizations in the moment.  What they adjust after these moments  — that’s what really matters!

How do you think we can improve diversity and inclusion in tech?

I think we have to be very conscious of the blindspots or assumptions we may make of the challenges visible minorities and women face day-to-day.  For example, there are notable and common differences between how men and women express their own competencies to others.  Often employees and leaders are under pressure to mirror how men are perceived to approach such matters (sometimes overconfident and may 'oversell' themselves).   Women are typically more honest about how they perceive their own abilities, and this often does not work in their favour.  I also think we need better understanding of some of the cultural differences that often come into play in leadership and teamwork.

How do you think corporate culture plays a part, and how can we develop that?

Notably, some cultures produce competitive individuals who can learn at a tremendous pace, but often struggle with collaboration or divergent thinking.  Some cultural norms allow for individuals to express a lot of creativity, but it can be difficult to coordinate their efforts or get things done quickly.  These are of course generalizations which are always problematic, but I think mentorship is key for female leaders and minorities, to ensure there is an increased awareness on all sides of these types of concerns, perceptions, and potential misunderstandings.  That being said, individual differences can give us the diversity of perspective we need, and we should harness our individual and collective strengths without ignoring that we all must continue to grow to remain competitive in an ever-changing and global market.

What advice would you give to someone who is starting their career?

Find mentors who are genuinely interested in your development.  Learn from the best team members you can work with.  Listen.  Be curious.  Focus on what you're passionate about and fully engage with it — the very pursuit of mastery will serve you with energy and resilience when the challenges come, and you will find an even deeper meaning and joy within that process over time.

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