Early Career Lessons: Enduring Experiences That Shaped Leaders

January 21, 2025

The path from entry-level roles to leadership positions is often paved with invaluable lessons learned along the way.

Our early career experiences, even those seemingly insignificant at the time, can profoundly shape our perspectives, values, and approaches to work.

To explore the transformative power of those early jobs and learnings, we asked a diverse group of leaders from our HR Spotlight community to reflect on their journeys and share the one lesson from their early career that continues to resonate with them today.

Their insights offer a glimpse into the foundational experiences that shaped them into the leaders they are today.

Read on!

William Hoggarth
CEO & Co-Founder, Chexperts Ltd

Trust Your Intuition and Enjoy the Journey

One of the most valuable lessons I learned early in my career is to trust my intuition and focus on doing work that I truly enjoy, even if it wasn’t part of the plan I initially envisioned for myself.

Fourteen years ago, fresh out of university, I joined a local company while searching for what I thought would be my “real” professional job. I quickly became immersed in the work and the niche industry, and I stopped looking for that so-called perfect role.

Fast-forward 10 years, and I became the youngest director in the company’s history at the age of 28.

That experience taught me that career paths don’t always follow a straight line, and that’s okay.

If you find joy and fulfillment in what you’re doing, lean into it.

Opportunities often emerge naturally when you’re fully invested in your work and pursuing something you’re passionate about.

Plans can change, but trusting yourself and enjoying the journey can lead you to incredible, unexpected destinations.

Peter Hunt
Director & Physiotherapist, The Alignment Studio

Listen Carefully and Treat Patients as Partners

Early in my career, while working in a busy sports physical therapy clinic, I learned the importance of listening carefully to patients and treating them as partners in their recovery.

One memorable case involved a semi professional rugby player recovering from a serious shoulder injury. He had been through multiple rounds of rehabilitation but felt frustrated and unheard by previous therapists.

Rather than focusing solely on the clinical presentation, I took the time to understand his goals and daily challenges, building a rapport that allowed him to fully articulate his concerns.

By combining this patient-centered approach with my knowledge of musculoskeletal anatomy and rehabilitation techniques, I was able to tailor a treatment plan that aligned with his specific needs.

The result was a quicker recovery, reduced risk of re-injury, and a player who not only returned to the field but felt more confident in his performance.

This experience taught me that technical expertise is only part of the equation. Strong communication and empathy are equally vital in achieving successful outcomes.

This lesson has carried through my 30 years in the profession and is embedded in the culture at The Alignment Studio.

By fostering a collaborative approach and empowering patients to take ownership of their health, we’ve helped countless clients, from athletes to desk workers, achieve long-term results that go beyond just pain relief.

It’s this balance of technical skill, active listening, and patient education that continues to define my practice and my philosophy.

Amaury Ponce
Business Owner, Ponce Tree Services

Pay Attention to Detail and Customer Needs

One of the most valuable lessons I learned early in my career came from working alongside my father when I was just starting out in the tree service industry.

I quickly realized the importance of paying close attention to detail and understanding the unique needs of each customer.

For example, I remember working on a tree pruning job for a client who was very particular about preserving the natural shape of their oak tree while ensuring the branches didn’t interfere with power lines.

My father taught me to slow down, assess the tree’s health, its growth pattern, and the client’s specific requests before making any cuts.

By combining technical skill with customer collaboration, we delivered results that exceeded expectations, and that customer referred us to three of their neighbors.

That experience instilled in me the value of thoughtful planning, precision, and great customer service, which remain the foundation of my business today.

As a certified arborist and TRAQ certified professional with over 20 years in the field, this early lesson has shaped the way I lead my team and interact with clients.

Whether we’re handling hazardous tree removals or providing routine maintenance, I always emphasize a customer-first approach, ensuring that their priorities guide every decision.

My qualifications and years of hands-on experience allow me to evaluate trees holistically, balancing safety, aesthetics, and the client’s vision.

That ability to merge expertise with personalized care is something I learned as a kid and carry with me to every project today.

Ronald Osborne
Founder, Ronald Osborne Business Coach

Solve Problems at Their Root Cause

Early in my career, while running my first telecommunications business, I learned the importance of solving problems at their root cause instead of just addressing the symptoms.

I recall a moment when one of our biggest clients was frustrated with recurring service disruptions. My team was working overtime to patch issues as they arose, but the complaints kept coming.

Instead of focusing on quick fixes, I decided to step back and deeply analyze the situation.

After days of reviewing systems and engaging directly with both clients and technicians, I discovered that the issue stemmed from outdated processes in how we maintained critical infrastructure.

By investing in streamlined protocols and retraining my team, we not only resolved the client’s concerns but also reduced our downtime across the board by over 30%.

That experience taught me that sustainable solutions come from identifying and addressing core inefficiencies.

This lesson has stayed with me throughout my career and is something I pass on to every business owner I coach.

Many businesses struggle with surface-level fixes, whether it’s in operations, staffing, or customer relations.

My MBA in finance helped me refine this problem-solving approach by teaching me how to break down complex systems and identify where the true bottlenecks lie.

Today, when I work with businesses in turnaround situations, one of the first things I do is look beyond the visible problems and uncover the hidden ones.

This principle has led to some of my most successful transformations, from increasing profitability in struggling companies to helping organizations scale more efficiently.

Solving problems at the root is a timeless strategy that every leader should master.

Daniel Oringel
Founder, Party With A Twist

Understand Every Role in a Team

One of the most powerful lessons I learned early in my career was the value of understanding every role in a team.

It wasn’t just about doing the job—it was about appreciating the challenges and opportunities each role brings.

Back in high school, I worked part-time at a bakery. It was fast-paced, with early mornings, long lines, and constant multitasking.

One day, I was asked to handle the cash register—something I hadn’t done before. It seemed simple at first, but as customers piled in and orders got complicated, I realized how much skill and focus it took to keep things running smoothly.

That experience stayed with me.

Fast forward to today, and I run my own business. That early lesson of stepping into another person’s shoes is something I still apply every day.

When I’m hiring for a role—whether it’s a balloon artist or an operations assistant—I spend time doing the job myself first. It helps me write better job descriptions, ask the right interview questions, and set clear expectations.

For example, when I was preparing to hire someone to manage inventory, I thought it was just about keeping stock levels up.

But after spending a month juggling inventory myself, I realized how much attention to detail it required—balancing supplies, tracking orders, and preparing for the unexpected. It made me appreciate the role on a deeper level, and it changed how I hired for the position.

The takeaway? Never underestimate the value of firsthand experience.

By rolling up your sleeves and stepping into someone else’s shoes, you gain empathy, insight, and a stronger connection to your team.

That lesson from my bakery days is something I’ll carry with me for the rest of my career.

Andrew Osborne
Owner, Ozzie Mowing & Gardening

Listen to Clients and Understand Their Vision

One of the most important lessons I learned early in my career was the value of listening to clients and truly understanding their vision before taking any action.

I remember working for a small landscaping company when I was just starting out, and we had a client who was very particular about their garden design. Instead of rushing into the project, I took the time to sit with them, listen carefully to their ideas, and ask detailed questions about the look and feel they wanted to achieve.

This approach not only built trust but also ensured the outcome exceeded their expectations. The experience taught me the power of communication and attention to detail, which I now prioritize in every project I take on at Ozzie Mowing and Gardening.

Over the years, as I’ve gained more knowledge and qualifications, including becoming a certified horticulturist, this lesson has only deepened in importance.

With over 700 projects under my belt, I’ve seen firsthand how tailored solutions that align with a client’s vision make all the difference.

For example, I once helped a client who wanted to transform their garden into a native oasis that attracted local wildlife. By listening to their specific goals and combining them with my expertise in plant selection and design, we created a thriving, sustainable space that brought their dream to life.

That early lesson on listening and understanding continues to guide me, ensuring every project is not just a job completed but a space my clients love.

Jamie Frew
CEO, Carepatron

Practice Active Listening for Better Solutions

Active listening.

In one of my first roles, I realized that truly understanding people’s concerns, ideas, or feedback often required more than just hearing their words but meant paying attention to the bigger context and the underlying needs they might not explicitly express.

At Carepatron, this lesson has been invaluable. Whether it’s engaging with customers or working with the team, I make a point to fully understand their challenges before jumping to solutions.

For example, when users provide feedback on a feature, we don’t just act on the surface request but dig deeper to understand the core problem they’re trying to solve. This approach has helped us design solutions that align more closely with their real-world needs.

Active listening has also taught me the value of patience and empathy in leadership.

It’s a skill that strengthens trust, improves collaboration, and leads to better decision-making. It may be a simple practice but it has made a lasting impact on how I approach both work and relationships.

Megan Dias
Career Services Coach, Parsity

Be Helpful and Find the Right Answers

A lesson I learned at a job early in my career was the importance of ACTUALLY being helpful.

Many times when asking for advice, guidance, or support, people might not know how to tangibly provide specific recommendations and the conversation begins circular without a clear and actionable next step.

What I’ve learned is if you do not know the “answer”, it’s best to say “I’m not sure but I will find out for you.”

This actually goes a long way because it shows the person is invested in problem solving to help you be successful.

Whenever I encounter anything I am not certain of, I always reassure the person that I will provide the answer after doing due diligence to determine how to best support.

Gary Edwards
Owner, Voceer

Embrace Mistakes as Learning Opportunities

One lesson I learned early in my career that has stuck with me is the importance of embracing mistakes as learning opportunities.

In my first job, I remember being terrified of making errors, thinking they would surely spell disaster. However, after a particularly challenging project where things didn’t go as planned, my mentor helped me see that each mistake was a chance to improve and refine my approach.

This mindset shift transformed the way I handle challenges.

Now, I actively learn from each misstep, using them to build resilience and enhance my problem-solving skills.

This approach has not only made me more effective in my work but also more open to taking on new and challenging projects.

Alex Morgan-Jones
Operations Manager, Optima Self Store

Communicate Clearly and Set Expectations

Early in my career, I learned the importance of clear communication and setting expectations.

While managing a small project, I assumed everyone was on the same page about deadlines and deliverables, which led to delays and confusion.

Since then, I’ve made it a priority to clearly outline goals, timelines, and responsibilities at the start of any project.

This lesson has been invaluable in fostering collaboration, avoiding misunderstandings, and ensuring smoother operations—something I apply every day in my current role.

The HR Spotlight team thanks these industry leaders for offering their expertise and experience and sharing their insights.

Do you wish to contribute to the next HR Spotlight article? Or is there an insight or idea you’d like to share with readers across the globe?

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