April 21, 2026

What 23 Years of Criminal Defense Have Taught Me About High-Stakes Decision Making in the Boardroom

What 23 Years of Criminal Defense Have Taught Me About High-Stakes Decision Making in the Boardroom
Photo Courtesy: Edward Cohn

By: Edward F. Cohn, Esq. | Criminal Defense Attorney | Tucson, Arizona

Most business leaders will never stand inside a courtroom. But every single one of them will face moments that feel exactly like it, a moment when the pressure is immense, the stakes are real, the information is incomplete, and the decision cannot wait.

I have spent 23 years as a criminal defense attorney in Tucson, Arizona. I have stood between clients and felony charges, argued before juries, and worked through some of the most high-pressure situations a human being can experience. Over that time, I have come to understand something that nobody teaches in business school: the skills that win in a courtroom are the same skills that win in a boardroom. The contexts are different. The principles are identical.

Here is what two decades on the front lines of the legal system taught me about making decisions when everything is on the line.

1. Clarity Under Pressure Is a Skill, Not a Trait

When a client calls me at 2 a.m. after an arrest, the situation is always emotionally charged, the facts are always unclear, and the window to make smart decisions is always narrow. My job in that moment is not to react; it is to think clearly when clarity is the hardest thing to find.

Business leaders face the same dynamic constantly. A key employee quits the day before a major pitch. A supplier falls through the week before launch. A partner backs out of a deal mid-negotiation. The leaders who thrive are not the ones who never panic; they are the ones who have trained themselves to slow down and think when everything around them is moving fast.

The way I do it in the courtroom is simple: before I act, I ask myself what I know for certain, what I am assuming, and what I still need to find out. Those three questions take about thirty seconds, and they prevent ninety percent of costly mistakes.

2. The Facts Do Not Care About Your Feelings

In criminal defense, I cannot build a case on what I wish were true. I have to work with what I can prove. Early in my career, I learned that one of the most dangerous things an attorney can do is fall in love with a version of events that the evidence does not actually support. The courtroom will expose that immediately, and it will cost your client everything.

Entrepreneurs and executives make this mistake constantly. They fall in love with their product, their strategy, or their plan, and then they filter all incoming information through the lens of what they want to be true rather than what actually is. The market does not care about your feelings. Your competitors do not care about your narrative. The numbers are what they are.

The discipline of separating what you know from what you believe is one of the most valuable habits a decision-maker can build. I do it before every hearing. The best business leaders I have observed do it before every major move.

3. Silence Is Often Your Most Powerful Tool

One of the first things I tell every client is this: stop talking. Not because they are guilty. But in high-stakes situations, every word you say can and will be used to construct a narrative, and you rarely control how that narrative gets interpreted.

This translates directly to business. In negotiations, in difficult conversations with investors, in moments of conflict with partners or employees, the instinct to fill silence with words almost always backfires. The person who speaks first in a negotiation almost always concedes the most. The leader who over-explains a decision undermines confidence in it.

I earned a Certificate in Negotiation from Harvard Kennedy School because I wanted to understand the science behind what I was observing in courtrooms for years. The research confirms what experience taught me: strategic silence is not passivity. It is power. It creates pressure, forces the other side to commit, and gives you information you would never get if you kept talking.

4. Preparation Is the Only Thing That Performs Under Pressure

I have never won a case on instinct. Every favorable outcome I have achieved for a client was built on preparation, knowing the law, knowing the facts, knowing the opposing argument better than the person making it, and having a plan for every scenario before I walked into the room.

The myth of the “brilliant improviser” is appealing but dangerous. Yes, you have to be able to adapt in the moment. But adaptation without a foundation is just chaos. The reason experienced attorneys and experienced executives appear calm under pressure is not because they are fearless; it is because they have already thought through what they will do when things go wrong.

Before every significant hearing, I ask myself: What is the worst thing that can happen today, and what is my response if it does? That single question has saved my clients and me more times than I can count. The best business leaders I know run the same mental exercise before every major meeting, presentation, or negotiation.

5. You Cannot Win Alone, Know When to Call in the Right People

The most dangerous clients I have ever had are the ones who waited too long to call me. They thought they could handle it themselves. They thought the situation was not serious enough to warrant professional help. By the time they picked up the phone, options that had existed earlier had disappeared.

I see the same pattern in business constantly. Founders who try to handle legal, financial, or operational crises without the right expertise, not because they cannot afford help, but because they overestimate their own knowledge or underestimate the complexity of the situation. By the time they bring in the right people, the damage is already done.

Knowing the boundaries of your own expertise is not a weakness. It is one of the most important forms of strategic intelligence a leader can have. The best decision-makers I have encountered, in courtrooms and in business, are not the ones who know everything. They are the ones who know exactly who to call and when to call them.

The Courtroom and the Boardroom Are More Alike Than You Think

High-stakes decision-making is not a business concept or a legal concept. It is a human concept. Whether you are defending a client in front of a jury or defending a strategy in front of a board, the same fundamentals apply: think clearly under pressure, work with the facts as they are, know when to speak and when to stay silent, prepare for what you cannot predict, and build the right team around you.

Twenty-three years in criminal defense did not just make me a better attorney. It made me a sharper thinker, a more disciplined decision-maker, and a more effective advocate in every room I walk into.

Those skills are not exclusive to the legal profession. They are available to anyone willing to do the work.

Edward F. Cohn is a Tucson-based criminal defense attorney with over 23 years of experience representing clients in misdemeanor and felony cases, orders of protection, juvenile delinquency matters, and injunctions against harassment. He holds a J.D. from Western Michigan University Cooley Law School, an LL.M. from Boston University School of Law, and a Certificate in Negotiation from Harvard Kennedy School. He is recognized by the National Trial Lawyers Top 100 and holds a Martindale-Hubbell AV Preeminent rating, awarded consecutively from 2022 through 2026. Learn more at cohnjustice.com.

 

Disclaimer: This article is for informational purposes only and does not constitute legal advice, professional consultation, or an endorsement of any specific service. Readers should consult a qualified professional for guidance related to their individual circumstances.

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