The Apprentice Mindset: Empathy in Leadership: Learning to Understand First

Date

Date

Date

July 28, 2025

July 28, 2025

July 28, 2025

Author

Author

Author

Gary Simpson

Gary Simpson

Gary Simpson

An AI Composite image of a leader engaging in discussion with a group of apprentices, listening intently to learn and build empathy
An AI Composite image of a leader engaging in discussion with a group of apprentices, listening intently to learn and build empathy
An AI Composite image of a leader engaging in discussion with a group of apprentices, listening intently to learn and build empathy

My career started as an apprentice, working across trades, responding to others’ planning and coordination, and doing our best to deliver the plan - solving problems on the job as we went.  I quickly learned that no matter how good a plan looked on paper, the real work happened through collaboration, communication, and the agility to adapt when things didn’t go to plan.  Those early lessons in humility and problem-solving have stayed with me throughout my career.

As my career progressed, I moved into design engineering.  My focus shifted to clarity: making technical information as accurate and easy to use as possible.  And with each new role, I saw and experienced how delivery could succeed - or not - depending on how well we understood what our customers needed, how they experienced our service, and how we could shape that experience through thoughtful process.

The real turning point came when I was seconded into a customer organisation.  As Future Landing Craft Manager, I worked side-by-side with civil servants, an industry ‘Rainbow Team’, and Royal Marines, tasked with procuring a new capability.  It was one of the more formative experiences in my career.  I saw up close the constraints, frustrations, and governance realities they navigated.  I gained a new respect for the world behind the requirements, and I’ve carried that empathy into every leadership role since.

Understanding Enables Leadership

One of the most important lessons I’ve learned is that every stakeholder - whether customer, colleague, or team member - is dealing with their own challenges within their context.  When we pause to see the world through their eyes, we often discover common ground.  We find co-designed solutions.  We lead better.

I’ve always sought a philosophy of delegation grounded in mutual trust and understanding, because without empathy, how can you know what support someone really needs?  How can you place decision-making at the right level if you don’t understand the day-to-day realities they face?

For me, empathy hasn’t been a soft skill, it’s been a strategic one.  It’s helped me lead with greater clarity, make better decisions, and build teams that feel seen and supported.

Leading with Understanding

Empathy doesn’t scale unless we choose to model it.  As Managing Director, I encouraged visible leadership - not just updates from the field, but time in the field.  Spending a day in the shoes of our front-line teams: observing, asking questions, understanding the friction points.

To achieve this, we ran productive utilisation studies.  Not just to ‘measure’, but to walk the shop floor.  Engaging.  Listening.  As a result, we learned what made work harder than it needed to be. We found opportunities to enable, unblock, and improve. Not by assuming, but by understanding.

I’ve also found that a powerful way to build deeper empathy is to find a reverse mentor.  Being mentored as a leader by someone who can speak truth to power and show you what dashboards and reports can’t.  It takes humility to listen well, but the reward is trust.

Seeing First, Then Leading

Leadership doesn’t begin with direction.  It begins with understanding.  With listening, and with noticing what others miss.

So much of what we call good leadership comes down to empathy in action: making it easier for people to do good work.  Seeing the friction they face and removing it.  Trusting them to get on with the job, because you’ve spent time understanding what that job really takes.

If you’re stepping into leadership, or looking to lead more effectively, I encourage you to start with presence, with proximity, and with questions.

What do you need to see more clearly, to lead more intentionally?

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Get in touch

I’m always excited to hear about your own experiences or collaborate on projects!

Get in touch

I’m always excited to hear about your own experiences or collaborate on projects!

Get in touch

I’m always excited to hear about your own experiences or collaborate on projects!

Built in Framer · ©2025 Gary Simpson ·

Built in Framer · ©2025 Gary Simpson ·

Built in Framer · ©2025 Gary Simpson ·