Hard-Won Wisdom: Early Career Lessons That Shaped Leaders' Paths
Think back to your first “real” job.
The lessons you learned—whether from a supportive mentor, a challenging project, or a memorable mistake—likely still resonate with you today.
These early experiences are more than just memories; they are the foundational principles that shape who we become as professionals.
With this in mind, we asked leaders from the HR Spotlight community:
What’s a lesson that you learned at a job early in your career that you still apply today?
From simple words of advice to career-altering learnings, their stories reveal the profound and lasting impact of our foundational years and offer invaluable guidance for anyone navigating their own journey.
Read on!
Robyn Davis Sekula
Vice President of Communications and Marketing, Presbyterian Foundation
Robyn Davis Sekula
In my mid-20s, I worked for someone who was fond of minimalistic notes, expecting us to do whatever it was he wanted that day by just a word or two in the note.
In one case, I didn’t know what he wanted, or when, so I ignored it because I didn’t want to look dumb and ask.
When it wasn’t complete by day’s end, he was not happy.
Once that note hit my desk, it was up to me to ask questions to ensure I knew what he wanted.
It’s not your fault the instructions weren’t clear – but it is your responsibility to make up for lack of clarity by asking clarifying questions.
Understanding the assignment is crucial.
Danny Ray
Founder, PinnacleQuote
Danny Ray
Early in my career, I worked in sales for a small insurance agency, and one lesson has stuck with me ever since, listening is more powerful than talking.
Above all, I learned that understanding a client’s needs is the foundation of building trust.
For example, instead of rushing to pitch a product, I focused on asking thoughtful questions and truly hearing the answers. In fact, this approach helped me not only close more sales but also build lasting relationships.
Furthermore, it taught me the value of patience and empathy, two traits that are essential in leadership.
Overall, this simple yet profound lesson has shaped how I connect with clients, lead teams, and grow my business today.
Listening isn’t just a skill; it’s a superpower.
Shane Skwarek
Founder & Chief Technologist, S-FX.com Small Business Solutions
Shane Skwarek
When I started my first job at the age of 14, my boss would often preach that “you never gyp a good worker.”
He’d often go out of his way to make sure that everyone was appreciated for their hard work, even if it was only giving you an extra $5.
At the time, it didn’t mean much – until I’d later start employing people myself.
When someone works hard for you, reward them in any way they can. Whether it’s monetarily, a gift card, or just a note of appreciation – people respond well when they know they’re valued.
More importantly, it’s a better investment to reward those who already work hard for you than it is to try and find someone to replace them.
Allison Jackson
Communication & Wellness Strategist, FractionX
Allison Jackson
My first job out of college was as a copywriter for a major insurance company. There were about 10 of us on the team.
As you might imagine, writing, proofreading, and editing was essential for the role.
We quickly learned the “Six Eyes Rule.” That meant in addition to your eyes, two other people needed to review your work for errors.
This rule has stuck with me for two decades — and has prevented many mistakes!
Genevieve Piturro
Founder, Genevieve Piturro
Genevieve Piturro
Early in my career in the TV syndication business in NYC, I worked for a very creative and bold man.
I was reserved and hard-working and never wanted to make a mistake.
We had an opportunity to market new TV movies, and I watched as his imagination fueled him with new promotional ideas. He wasn’t afraid to take a chance and I think he saw something in me that needed to wake up to that same attitude.
He took me aside one day and said, “Genevieve, I know you’re holding back – GO FOR IT!”
His words propelled me to dig deep for what I now call MOXIE. I picked up the phone and made a big ask. To my shock, the answer from the other side of the phone was, “I like it, YES let’s do it!”
And I have been best friends with my Moxie ever since!
Simon Royston
Founder and Managing Director, The Recruitment Lab
Simon Royston
My first Managing Director preached to me that one should ignore the client!
He argued that you should ignore the client, deliver on what was agreed and save a lot of procrastination and energy.
In today’s world in certain circumstances, it really can help.
Too often clients can be closely examining your methodologies and question your every move. Ultimately, the client came to you to solve a problem and that above all else is what matters.
That is not to say the client journey is unimportant.
One should always communicate and report progress or maybe seek further information in specific cases. Just be mindful that time is money, and you are paid to deliver on time and within budget.
Lisamarie Monaco
Co-Owner, InsuranceForBurial.com
Lisamarie Monaco
A lesson that I learned long ago and that is valuable to me still to this day is to approach a job by learning it from the back end forward.
I learned it is important to understand the behind the scenes processes, systems and workflows first so you gain a deeper understanding of how everything works and functions.
This allows you to have the tools you need independently in that role. And helps avoid relying on others to fill in any gaps or to even fix something when there is a bump in the road.
This lesson has served me well in my career and in everything I have done since implementing this in my life!
Michael Puck
Founder, Global Dog Art Gallery
Michael Puck
A lesson that I learned early in my career is to challenge everything.
After eight years in the German military, I moved into HR and transferred to the US. I had no experience with HR in the US, and when I learned how different the US healthcare system works from what I was accustomed to, I designed a model that would give employers more control over healthcare costs.
In the beginning, I was told many times that this model could never work. Even the Chief Medical Officer of our health insurance carrier told me not to waste my energy.
After considerable initial resistance (I even got laughed out of the boardroom by my peers on the leadership team), I got the green light to implement the program.
Right from the start the program engaged over 92% of the employees and even 70% of the spouses. As a result, the company did not receive any healthcare premium increases for five consecutive years, and we reduced the average number of health risks from 2.8 to 1.5. The underwriter calculated our net cost avoidance at over $7 million.
All of this only happened because I challenged the status quo. The skill of asking probing questions and challenging everything that doesn’t feel right or looks outdated has become the hallmark of my HR career.
Today, I am working for an HCM think tank where we take on the most pressing challenges today’s business and HR, in particular, face.
My professional focus these days is based on this early lesson in my career: Challenge Everything.
Karen Southall Watts
Early in my career I learned to prepare for inappropriate interview questions, because they will happen.
As a young woman I was often asked about pregnancy, potential pregnancy, and my children. Shockingly, these questions usually came from female interviewers and were often prefaced with remarks like, “I know I’m not supposed to ask this” or “Just between us women” as ways for interviewers to excuse their inappropriate and illegal behavior.
When the job market is tough, these types of questions increase, because employers know candidates are desperate and can be tricked or coerced into answering.
Later in my career as an educator and coach I advised clients and students to prepare for questions to pop up on age, religion, family issues, or national origin.
It’s important for candidates to know in advance how they will handle this—confront, deflect, or answer—and what these kinds of questions mean about an employer.
Craig Attiwill
Founder & CEO, Peloton Technologies
Craig Attiwill
A lesson I learned early in my career can be summed up in one quote: “Insanity is repeating the same mistakes and expecting different results.”
It’s not a quote from anyone in particular (I don’t think!), let alone anyone famous for their quotes. It’s just a life lesson from the collective.
It’s not just about learning quickly from your mistakes and moving on. It’s remembering that others have likely made these mistakes, and the result is not going to be any different for you.
One way to avoid the expensive learning process is to spend more time reading, researching and learning from peers – understand how others in your role or in your industry have tripped along the way, and then choose another path.
The HR Spotlight team thanks these industry leaders for offering their expertise and experience and sharing these 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?
Write to us at connect@HRSpotlight.com, and our team will help you share your insights.
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