A transformative guide to developing leaders who solve problems independently. Discover how to build accountability, foster critical thinking, and create organizations where people thrive through intentional coaching, strategic questioning, and genuine listening.
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Confidence was built every time I refused to let adversity write my story. Every time I chose to begin again, I became stronger than before.
Traci Leigh-Ane Skolaski · In Her Own Words
Her Story
About Traci
Traci L. Skolaski is a seasoned enterprise risk executive with more than two decades of experience building and leading comprehensive risk management programs across complex, multi-location organizations. Based in the Greater Milwaukee area, she currently serves as Senior Vice President of Risk Management at Hendricks Commercial Properties, where she oversees a broad portfolio encompassing insurance strategy, claims oversight, safety and loss control, regulatory compliance, cyber insurance, property tax appeals, and vendor risk governance. Her academic foundation is equally strong — she holds a Master of Science in Management and a Bachelor of Science in Business Administration, both from Cardinal Stritch University, where she earned a 4.0 GPA and received the Highest GPA in the Region Award. She further distinguished herself by being selected from a highly competitive group to attend the prestigious Lloyd's Academy in London, cementing her standing among the most credentialed professionals in her field. What sets Traci apart is the remarkable breadth of experience she brings to every role. Her career journey spans commercial real estate, hospitality, transportation, manufacturing, healthcare operations, emergency response, financial services, and legal administration — a diverse background that gives her a uniquely practical, enterprise-wide perspective on risk. That foundation has translated into measurable results throughout her career, including delivering over $1.8 million in realized savings at Hendricks Commercial Properties, reducing workers' compensation costs by $2.67 million in a single year at Milwaukee County Transit System, cutting actuarial reserves by $2 million at Tankstar USA, and supporting more than $1 million in insurance premium reductions. She has built and transformed risk functions from the ground up, bringing structure, accountability, and financial discipline to organizations that needed it most. Beyond her professional accomplishments, Traci is a committed leader, educator, and community advocate. She served for over seven years as an Adjunct Business Instructor at Madison Area Technical College, teaching courses in business law, human resources, project management, and labor relations to working adult learners. She has held board leadership roles — including president and vice president — with both the Jefferson City Area Chamber of Commerce and the Jefferson County Area Safety Network, and has volunteered as a church treasurer, reflecting her commitment to fiduciary responsibility and civic engagement. A frequent speaker at workers' compensation and OSHA seminars, she is recognized as a thoughtful voice in her industry. Her story is also one of personal resilience — she earned both her bachelor's and master's degrees while raising four children and working full time, a testament to the hard work, dedication, and honesty that define everything she does.
Her Interview
Ten minutes with Traci
01What do you attribute your success to?
I attribute my success to resilience, determination, and an unwavering belief that my circumstances would not define my future.
I grew up in a difficult environment marked by instability, abuse, and very little support. Despite frequent disruptions, including changing schools and starting over academically, I excelled in the classroom and graduated high school with a 4.25 GPA and 36 credits. As a young mother, I made sacrifices and chose a different path than the one I had envisioned, but I never stopped pursuing my education or my goals.
Throughout my life, I have faced significant personal and professional challenges, including abusive relationships, balancing full-time work while earning both my bachelor's and master's degrees with a 4.0 GPA, and a devastating car accident that abruptly ended a career I loved. The accident left me unable to work for nearly nine years, living with chronic pain and forcing me to rebuild nearly every aspect of my life.
What I learned during those years is that resilience is not about avoiding setbacks; it's about refusing to let them define you. When I was finally able to return to work, I started over, rebuilt my career, and ultimately returned to executive leadership. Those experiences gave me a deeper appreciation for people, empathy for challenges that may not be visible, and a perspective that has shaped my leadership style.
Today, I am passionate about transforming the role of risk management from a function that reacts to problems into a strategic partner that helps organizations succeed from the very beginning. Looking back, every challenge taught me something valuable. The difficult chapters strengthened my resolve, deepened my compassion, and ultimately led me to a life and a love I never imagined possible.
02What’s the best career advice you’ve ever received?
The best career advice I've ever received is to pause and listen. I'm naturally a strategic thinker and problem solver, and throughout my career I've often been able to see challenges, risks, and solutions several steps ahead. While that has been a tremendous asset, I've learned that leadership isn't just about seeing the path forward—it's about taking the time to understand the perspectives of the people walking that path with you.
I'll be honest—this is still something I actively work on. Sometimes my instinct is to jump straight to the solution. But some of my most important leadership lessons have come from slowing down, listening, and recognizing that great ideas can come from anyone in the room.
That lesson was reinforced for me when I read The Let Them Theory*. I wish I had read it 20 years ago. It taught me that not everything requires my energy, my response, or my attempt to change it. As a confident woman in leadership, I've been told I can be intimidating. Early in my career, I spent too much time worrying about how I was perceived. Today, I understand that I can't control other people's opinions—I can only control how I show up. So I focus on listening, leading with authenticity, treating people with respect, and letting go of what I can't control.*
The combination of those two lessons—pause and listen, and let them—has made me a stronger leader. One reminds me to stay curious and learn from others; the other reminds me not to carry the weight of everyone else's perceptions. Together, they've helped me lead with both confidence and humility.
03What advice would you give to young women entering your industry?
My advice to young women entering this industry is to embrace every opportunity with curiosity, humility, and confidence—even when the path ahead is unclear.
Many people believe successful careers follow a straight line. Mine certainly did not. Before finding my footing in risk management, I worked in healthcare, emergency dispatch, legal administration, commercial lending, and operations. At the time, those experiences seemed unrelated. Looking back, each one taught me skills that I rely on every day as a leader—critical thinking, empathy, communication, problem-solving, resilience, and the ability to remain calm under pressure.
Do not be afraid to take the unconventional path. Some of your greatest strengths will come from experiences that don't fit neatly on a résumé. Every challenge, setback, and career pivot teaches you something valuable if you're willing to learn from it.
Most importantly, do not allow anyone else to define your potential. There will be times when you are underestimated, doubted, or told that you don't fit the mold. Keep showing up. Keep learning. Keep doing the work. Confidence isn't about having all the answers; it's about trusting yourself to figure things out.
Your unique experiences, perspective, and voice are not obstacles to overcome—they are your competitive advantage.
04What are the biggest challenges or opportunities in your field right now?
One of the most persistent challenges in risk management is the perception that our role is simply to say "no." In reality, the most effective risk professionals are not roadblocks—they are problem solvers. When we are engaged early in the process, we can identify risks, develop creative solutions, and help organizations move forward with confidence. One of the greatest opportunities in our field is continuing to shift that narrative and demonstrate that risk management is a strategic business partner that enables growth rather than restricts it.
At the same time, our profession is navigating a rapidly evolving landscape driven by technology, cyber threats, and an increasingly litigious society. Artificial intelligence is perhaps the most significant opportunity and challenge we face today. I embrace AI because it has dramatically increased productivity, accelerated analysis, and allows professionals to focus more time on strategic decision-making. However, AI is a tool—not a substitute for expertise, judgment, or experience. Subject matter expertise remains essential to validating outputs, identifying blind spots, and making informed decisions.
The challenge is that the same technologies creating efficiencies are also creating new risks. Organizations must contend with increasingly sophisticated cyberattacks, fraud schemes, data privacy concerns, and the misuse of AI itself. As risk professionals, we have a responsibility to help organizations balance innovation with appropriate governance and controls.
Looking ahead, I believe the greatest opportunity for our profession is to move beyond being viewed solely as insurance buyers or compliance managers and become trusted advisors who help organizations navigate uncertainty. In a world where risks are evolving faster than ever, the ability to anticipate challenges, embrace innovation, and enable smart business decisions has never been more valuable.
05What values are most important to you in your work and personal life?
The values that guide both my professional and personal life are integrity, resilience, compassion, and continuous growth.
Integrity is the foundation of everything I do. I believe in doing the right thing, even when it is difficult, unpopular, or comes at a personal cost. Trust is earned through consistency, honesty, and accountability, and I strive to lead by example.
Resilience has been a defining theme throughout my life. I have faced significant personal and professional challenges, yet each obstacle reinforced my belief that adversity does not define us—how we respond to it does. Some of life's most difficult experiences have also become my greatest teachers.
Compassion is equally important to me. As a leader, I never want to forget that every person is carrying challenges we may not see. I believe people perform at their best when they feel respected, supported, and valued. The strongest leaders are those who can balance accountability with empathy.
Finally, I am committed to continuous growth. I am naturally curious and believe there is always something new to learn. Whether embracing emerging technologies like AI, learning from colleagues, or reflecting on my own experiences, I strive to keep evolving both professionally and personally.
These values influence not only how I lead, but also how I live. They have shaped my career, strengthened my relationships, and helped me navigate both success and adversity with gratitude and purpose.
Her Content Hub
Articles by Traci
Developing Thinkers, Not Followers
How to Develop Leaders Instead of Managing People Through Questions, Accountability, and Genuine Investment in Growth
If you walked into my office with a problem, the first question I’d probably ask isn’t, “What happened?”
It’s, “What have you tried?”
Some people are surprised by that question.
I’m not asking because I expect them to have solved the problem already. I’m asking because I believe one of the greatest responsibilities of a leader isn’t solving every problem—it’s developing people who can solve problems long after they no longer need you.
That’s the difference between managing people and developing leaders.
Over the years, through personal adversity, professional challenges, and leading teams across multiple organizations, I’ve developed a leadership philosophy that has shaped every team I’ve had the privilege to lead. It isn’t something I learned in a classroom. It has been shaped by experience, by failure, by success, and by watching people grow beyond what they believed was possible.
One lesson has remained constant throughout my career:
Leadership isn’t about having all the answers. It’s about developing people who can find them.
Early in my career, a manager shared a piece of advice that has stayed with me ever since:
“My job isn’t to have all the answers. That’s why I surround myself with talented people who can provide the ones I don’t. They make me look good.”
At the time, I thought he was simply talking about hiring talented people.
Years later, I realized he was talking about humility.
Great leaders don’t become successful because they know everything. They become successful because they create an environment where talented people contribute their expertise, challenge ideas, and make the team stronger.
I’ve taken that lesson one step further.
I don’t just want to surround myself with talented people.
I want to develop them into leaders.
I don’t want to be the smartest person in the room.
I want to build a room full of people who think.
Start With the “Why”
One of the biggest mistakes leaders make is assigning work without explaining the bigger picture.
People don’t just need to know what they’re doing.
They need to understand why it matters.
When people understand the strategy behind a decision, they begin making better decisions on their own. They stop checking boxes and start contributing to the organization’s success.
Understanding the “why” creates ownership.
Ownership creates accountability.
And accountability develops leaders.
Don’t Bring Me a Problem. Bring Me Your Thinking.
One of the questions I ask most often is simple:
“What have you tried?”
I encourage my team to work through challenges on their own first. Collaborate with peers. Do your research. Explore different approaches. Not every issue needs to come to me.
But when something does require escalation, I have one expectation:
Come prepared with at least two thoughtful options.
We may choose one.
We may combine both.
Or we may discover an entirely different path together.
That’s not the point.
The point is that you’ve taken ownership of the problem, analyzed the situation, and are prepared to have a strategic discussion instead of simply handing someone else a problem to solve.
If someone comes to me without ideas, I don’t solve it for them.
Instead, I ask them to schedule another meeting—later that day or within the next 24 hours—and come back prepared.
It would be much easier for me to simply provide the answer and move on.
But easy doesn’t build leaders.
It builds dependence.
Helping people learn to see the forest through the trees isn’t always easy. It requires patience. It requires coaching. Most importantly, it requires asking questions instead of immediately providing answers.
Over time, something remarkable happens.
The questions become better.
The conversations become more strategic.
Confidence grows.
Eventually, people stop looking for someone else to solve every problem because they’ve learned they are capable of solving many of them themselves.
That’s leadership.
When Leadership Starts Multiplying
I remember one employee who began noticing a pattern.
He realized I was usually thinking several steps ahead.
Instead of coming to meetings simply looking for answers, he changed the way he prepared.
Before every meeting, he researched the issue, gathered the facts, organized his questions, and thought through possible solutions. He scheduled time with me instead of stopping by unexpectedly because he wanted to make the best use of both our time.
Eventually, he shared that approach with the rest of the team.
He even told them:
“The best time to meet with her is toward the end of the day. She’ll still ask tough questions, but if you come prepared, you’ll leave with direction instead of just an answer.”
It wasn’t long before he was coaching others on how to prepare.
He wasn’t just changing his own approach.
He was influencing the culture of the team.
That’s when I realized leadership had moved beyond me.
It had become part of how the team thought.
My goal was never to make people think like me.
My goal was to teach them how to think.
Cross-Training Builds Stronger Organizations
Another principle I strongly believe in is cross-training.
Too many organizations rely on one person to hold critical knowledge.
That works—until it doesn’t.
Cross-training isn’t simply about preparing for vacations or turnover.
It’s about helping people understand how their work connects to everyone else’s.
When employees understand each other’s responsibilities, silos begin to disappear.
Collaboration improves.
Respect grows.
Organizations become stronger because knowledge is shared instead of protected.
The best teams don’t have one expert.
They have many.
Accountability Is Respect
Accountability has become a word people often associate with criticism.
I see it differently.
Accountability is one of the greatest forms of respect.
When we hold people accountable, we are telling them we believe they are capable of meeting higher expectations.
That doesn’t mean abandoning coaching.
It means setting clear expectations, providing the necessary resources, communicating openly, and then expecting ownership.
People often rise to the expectations we consistently reinforce.
Our responsibility as leaders isn’t to lower the bar.
It’s to help people reach it.
The Most Powerful Leadership Tool Is the Pause
The best leadership advice I’ve ever received was surprisingly simple:
Pause. Listen. And actually hear what the other person is saying.
As leaders—especially experienced leaders—we are often ten steps ahead.
While someone is explaining a problem, we’ve already identified possible solutions and started thinking about our next meeting.
I’ve had to learn that if I’m already preparing my response, I am no longer listening.
The pause matters.
It’s in those few extra seconds that we stop thinking about what we’re going to say and start understanding what someone else is really trying to tell us.
People may not always agree with your decision.
But they will almost always respect it if they know they were genuinely heard.
Sometimes the best leadership isn’t having the quickest answer.
Sometimes it’s asking one more question.
Sometimes it’s simply waiting.
Leadership Is About Leaving People Better Than You Found Them
Growing up, life taught me resilience long before I ever held a leadership title. An abusive childhood, an alcoholic father, and becoming independent at a young age shaped how I viewed responsibility, perseverance, and trust. Later in life, I faced other personal challenges that reinforced those lessons.
Those experiences taught me that everyone is carrying something we cannot see.
They taught me that confidence is built—not given.
They taught me that empathy and accountability are not opposites.
The best leaders practice both.
Throughout my career, I’ve had the privilege of leading teams, mentoring interns, coaching new professionals, and helping people discover strengths they didn’t always see in themselves.
Some of those interns are now leaders.
Some of the people I coached are now mentoring others.
Watching that happen has been one of the greatest rewards of my career.
The greatest compliment I’ve ever received hasn’t come from solving a difficult problem or leading a successful project.
It’s watching people I invested in become the leaders others now look to for guidance.
That’s when I realized the true measure of leadership isn’t what we accomplish ourselves.
It’s what continues because of the people we invested in.
I don’t want people to remember me because I always had the answers.
I hope they remember that I challenged them to think.
That I listened before I spoke.
That I expected more because I believed they were capable of more.
That I invested in their growth, even when it would have been easier to simply provide the answer.
Because if I’ve done my job well, they won’t need me forever.
They’ll become the leaders who ask someone else:
“What have you tried?”
To me, that’s the true legacy of leadership.
Not creating followers.
Creating leaders who create other leaders.
When circumstances force you to pivot, change your journey—not your destination.
Leadership Philosophy
- Explain the why before the what.
- Don’t bring me a problem. Bring me your thinking.
- Accountability is respect.
- Cross-train because resilient organizations share knowledge.
- Pause. Listen. Truly hear.
- Develop thinkers, not followers.
- When circumstances force you to pivot, change your journey—not your destination.
Traci L. Skolaski is a senior risk management executive with more than 20 years of experience leading enterprise risk, insurance, claims, safety, compliance, and operational resilience across complex organizations. She is passionate about developing leaders, building accountable teams, and creating resilient organizations where people—and businesses—can thrive.
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