A Conversation with Cass Wennlund On Navigating Law and Leadership

Cass Wennlund is a seasoned attorney and community leader based in New Lenox, Illinois, with over three decades of legal experience. As the founder of Wennlund & Associates, he has built a reputable law firm specializing in civil litigation, real estate, zoning, land use, and business law. Cass is known for his commitment to delivering high-quality legal services while maintaining a strong focus on community engagement and public service.

In addition to his legal work, Cass serves as the New Lenox Township Supervisor, where he advocates for vibrant economic development and transparent governance. His leadership is marked by a deep-rooted dedication to improving the well-being of his community through both legal expertise and civic involvement.

A firm believer in the power of education and mentorship, Cass Wennlund actively works to support and guide the next generation of legal professionals. Outside of his professional responsibilities, he enjoys spending time with his family, exploring the outdoors, and engaging in local initiatives aimed at community growth. Cass’s blend of legal acumen and civic leadership continues to make a meaningful impact in his hometown and beyond.

 What inspired you to pursue a career in law? 

Growing up in New Lenox, I always had a strong sense of responsibility to my community. I saw firsthand how local leaders could make a real difference in people’s lives. My father, who was deeply involved in community work, always emphasized justice and individual freedom. That influenced me to see the law not just as a profession but as a tool for ensuring individual freedom and helping communities thrive. That’s what inspired me to pursue a career in law—to be a voice for equal justice under the law, and to contribute to the betterment of society.

How has your background in community leadership shaped your approach to legal practice? 

Community leadership has made me much more attuned to the human side of the law. Legal issues don’t exist in a vacuum—they affect people’s lives in very real ways. Understanding community needs has shaped my practice to be more service-oriented. I’ve always strived to offer legal solutions that don’t just resolve disputes but also strengthen the community by ensuring access to justice.

What do you think is the biggest challenge facing the legal industry today? 

The biggest challenge today is staying relevant in a world that’s rapidly changing due to technology. AI, automation, and digital platforms are transforming how we practice law. While these tools offer great benefits in terms of efficiency and accuracy, they also present ethical challenges and concerns about job displacement. The legal industry must find a balance—embracing innovation while maintaining the integrity and personalized nature of legal representation. Adapting to these changes without losing the human element is critical.

Can you explain how technology has impacted your legal practice? 

Technology has been a game changer. From document management to legal research, everything has become faster and more efficient. Tools like AI contract review systems help us handle routine tasks, which frees up time to focus on more strategic work and client relationships. Technology has also improved accessibility. For example, clients can now view their case updates and communicate with us securely through online platforms. That level of transparency builds trust and allows us to provide better service.

How do you balance your time between running a law firm and serving as Township Supervisor? 

It’s definitely a juggling act! Time management and delegation are key. I’ve learned to trust my team at Wennlund & Associates to handle much of the day-to-day operations. Having a solid team allows me to focus on the bigger picture for both the firm and my responsibilities as township supervisor. I also set clear priorities—some weeks require more attention on legal matters, while others demand more focus on community leadership. Balancing both roles is challenging, but they complement each other well because both are about serving people.

What is one case that has had a lasting impact on you, and why? 

There was a property rights case early in my career where a family’s livelihood was at stake. The legal issue involved a zoning dispute that could have forced them to shut down their small business. We fought hard, and in the end, we won. That case reaffirmed for me why I went into law in the first place—it wasn’t just about winning in court, but about protecting people’s futures. The gratitude the family showed left a lasting impression and solidified my commitment to fight for justice, no matter how tough the battle.

How do you stay ahead of trends in both law and technology? 

Continuous learning is crucial. I attend legal tech conferences, subscribe to industry journals, and participate in webinars focused on emerging legal technologies. I’m also a firm believer in collaboration—talking to other legal professionals, tech experts, and community leaders helps me gain new perspectives. At the firm, we encourage an innovative mindset, where team members are always on the lookout for new tools or methods to improve how we work. Staying ahead isn’t just about adopting new technologies, but about fostering a culture of adaptability.

What advice would you give to young lawyers entering the profession today? 

Stay adaptable, stay ethical, and never forget the human element of law. The legal profession is changing rapidly, especially with the rise of technology, but the core of what we do—helping people—remains the same. Learn to use the tools that are available, but don’t lose sight of the importance of building relationships and providing compassionate counsel. Also, find ways to give back. Your role as a lawyer should always extend beyond the courtroom.

What’s your vision for the future of Wennlund & Associates? 

My vision is to continue growing in two key areas—community engagement and legal innovation. I want us to expand our reach while continuing to embrace technological advancements that make legal services more efficient. I also see the firm playing a larger role in educating the public about legal issues, whether through workshops, online resources, or community partnerships. Ultimately, I want Wennlund & Associates to be a firm that not only excels legally but also makes a meaningful impact on our clients’ lives.

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