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Insights on Legal Careers and Leadership from a Managing Partner’s Perspective

LEGALLY REVIEWED BY:
Callahan & Blaine
October 28, 2025

After three decades of practicing law and leading a litigation firm, the opportunity to speak with aspiring attorneys and future business leaders never loses its significance. Next week, I will address students at the University of Miami Herbert Business School in their Managing the Legal Factor course, discussing the realities of building a legal career, developing as a trial attorney, and transitioning into firm leadership. These conversations matter because the gap between what students imagine legal practice to be and what they actually experience can be jarring without proper guidance.

The students I will meet are primarily seniors, many of whom are applying to law school or planning careers in which they will work closely with attorneys in corporate or compliance roles. Their questions reflect the genuine concerns of people standing at a crossroads, weighing significant investments of time and money against uncertain career outcomes. These are the conversations I wish I had access to when making my own career decisions.

The Foundation of Interdisciplinary Education

My path to civil litigation began with degrees in philosophy, English, and history, followed by attendance at USC Law School. This was not a detour but a foundation. Philosophy taught me to identify logical fallacies and construct airtight arguments. English developed my ability to communicate complex ideas persuasively. History provided context for understanding how legal principles evolved.

When you stand before a jury, you are not reciting statutes. You are telling a story, making an argument, and appealing to reason. The liberal arts equipped me for this work in ways a narrower pre-law focus never could have. Critical thinking, clear writing, and understanding human nature matter more than memorizing case citations.

Making the Law School Decision

The decision to attend law school deserves careful analysis. Law school represents a significant three-year commitment and substantial tuition costs. Before committing, consider whether you genuinely enjoy rigorous analytical work. Legal practice involves reading dense documents, researching complex issues, and constructing detailed arguments. If you find this work tedious, law may not be the right fit for you.

I encourage students to gain exposure to actual legal work before committing. Work as a paralegal, intern at a law firm, or shadow attorneys. The reality of legal practice often differs from what you see on television. Many attorneys spend their days reviewing documents, drafting contracts, and negotiating settlements rather than delivering closing arguments to juries.

Developing Bold Litigation Strategy

Students often ask what I mean by “bold and decisive litigation strategy.” This approach means identifying what you need to win and pursuing it aggressively rather than responding to opposing counsel’s moves. It means taking cases to trial when settlement offers are inadequate, even when the trial involves uncertainty and expense.

Bold strategy requires confidence earned through preparation and experience. You must understand your case thoroughly, anticipate how judges and juries will react, and commit fully to your approach. The distinction between bold and reckless matters enormously. Bold means taking calculated risks based on thorough analysis. You earn the right to be bold through years of learning your craft.

The Value of Dual Perspective

Having litigated on both plaintiff and defense sides provides advantages that attorneys with experience on only one side cannot fully appreciate. As a plaintiff’s attorney, I can anticipate defense arguments before opposing counsel makes them. As a defense attorney, I recognize when plaintiffs have strong cases that should settle and when they have overvalued weak claims.

This dual perspective changes how you approach every case. Young attorneys often ask how to gain this experience. The answer is to remain open to opportunities on both sides early in your career. Spending several years on each side makes you significantly more effective.

Balancing Practice and Leadership

Managing partner responsibilities extend far beyond practicing law. I still handle significant cases and appear in court regularly, but these activities now compete with administrative duties, strategic planning, personnel management, and business development.

Leaders must make decisions that affect others’ careers and livelihoods. You hire and fire. You allocate work and compensation. You resolve conflicts between attorneys. Effective leadership requires skills different from those of effective lawyering. You must clearly communicate vision, build consensus when making decisive calls, and mentor young attorneys while holding them accountable.

The most important quality for legal leadership may be the ability to make difficult decisions and live with the consequences. Not every decision will be correct. Leaders who constantly second-guess themselves or avoid tough calls create dysfunction and uncertainty.

How Mid-Sized Firms Compete

Mid-sized firms occupy a competitive space between large international practices and boutique firms. We provide sophisticated legal services with more cost efficiency and personal attention than large firms. At Callahan & Blaine, PC, every attorney has at least 8 years of litigation experience, with most having 15 to 30 years. Our clients receive experienced counsel on every matter.

We have built our reputation through results, including the largest jury verdict in Orange County history at $934 million and the highest personal injury verdict in United States history at $50 million. These outcomes demonstrate that mid-sized firms can compete at the highest levels when they prioritize talent, preparation, and strategic thinking.

The Legal Function in Business

Business students who will work with attorneys need to understand how the legal function should support business operations. Law should inform decision-making proactively, not just respond to problems after they arise. Companies benefit when executives consult attorneys before making significant decisions, not after disputes emerge.

Common mistakes include inadequate contract review, insufficient documentation of business decisions, and failure to implement compliance programs. The regulatory environment, litigation risks, and reputational concerns have fundamentally changed how corporations must approach legal issues. This environment demands integrating legal considerations into business strategy from the beginning.

Life Beyond the Courtroom

Competitive golf has taught me valuable lessons about trial work, though I suspect my golf game has benefited more from litigation than the other way around. Both require mental discipline and the ability to recover from mistakes. You cannot let a bad hole ruin your round, just as you cannot let a difficult ruling destroy your case strategy. The difference is that in golf, nobody objects to your approach shot.

Raising six children has provided even more perspective on what truly matters. If you think managing a law firm is challenging, try negotiating dinner choices with six kids or mediating disputes over the television remote. Cases that once seemed overwhelmingly important now occupy their proper place in a full life. The attorneys who maintain long, successful careers typically have rich lives outside their practices. This balance prevents burnout and provides perspective that makes them better counselors to clients facing their own difficult decisions.

Advice for Future Leaders

Leadership positions go to those who consistently demonstrate competence and reliability over time. Junior attorneys who focus on doing excellent work, taking initiative, and solving problems develop reputations that lead to opportunities. Strong work habits matter more than raw talent. Show up prepared, meet deadlines, and deliver quality work.

Build your reputation deliberately through every case and interaction. Reputation develops from accumulated small decisions and actions others observe over years. This reputation becomes your most valuable professional asset. Whether you pursue law, business, or another field, success requires defining achievement beyond titles and compensation.

Contact Callahan & Blaine, PC

For over four decades, Callahan & Blaine, PC has represented clients in complex litigation across multiple practice areas. Our 29 attorneys bring deep experience to every matter, with our managing partner and leadership team collectively providing over 180 years of experience in complex litigation.

If you face legal challenges requiring experienced trial attorneys who understand both the technical and strategic aspects of litigation, contact our team to discuss how we may be able to help protect your interests.

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Legally reviewed by:
Callahan & Blaine
October 28, 2025

Callahan & Blaine, established in 1984, is a leading litigation firm with a legacy of delivering exceptional results for our clients. With over 700 years of combined trial experience and a proven track record of more than $1 billion in verdicts and settlements, our team of highly recognized attorneys specialize in handling complex and high-stakes civil cases with unparalleled efficiency and skill.

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