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☕ The Coffee Note That Shaped My Trial Philosophy

July 12, 2025/by Scott Key

Negotiation Lessons from Criminal Defense That Elevate Civil Practice

I couldn’t believe I’d made such a boneheaded move.

There I was—wedged into a slow-moving Starbucks line, about to be late for a meeting with a prosecutor. The mission? Negotiate a favorable outcome before my client’s case hit the grand jury.

So I improvised:
“Grabbing coffee. What’s your order?”

He responded. I showed up late—but with both drinks in hand.

While his contact was open on my phone, I typed his coffee preference into the notes. That tiny act became a bigger strategy: I started cataloging the details that make people feel seen—birthdays, kids’ names, anniversaries, favorite orders.

Turns out, the art of negotiation starts long before anyone mentions a statute.


1. Relationships Build Leverage—in Every Arena

In criminal defense, you quickly learn you’ll face the same adversaries repeatedly. That’s true in civil litigation too—especially in niche practices like land development.

Short-term victories lose value if they cost long-term trust. Whether you’re opposing counsel in a rezoning fight or working with local officials on a contested variance, relationships are your leverage.

I strive to be the kind of lawyer people respect and enjoy working with. Empathy isn’t fluff—it’s strategy.


2. Cases Are Made of People, Not Just Paper

Criminal work taught me to showcase the whole human behind the charges. Those life portfolios I compiled—white binders full of personal context—weren’t just courtroom props; they were bridges to understanding.

And I use the same storytelling in civil trial work.

In land use disputes, for instance, the story isn’t just zoning codes—it’s the livelihood of families, the impact on communities, the evolution of neighborhoods. Humanizing your client builds credibility—and influence.


3. Timing Is Tactic

The earlier you engage, the more control you have. Criminal cases taught me the importance of pre-indictment leverage—and that concept absolutely translates to civil litigation.

Before discovery kicks in, before tempers flare—early clarity can drive resolution. Whether I’m asserting qualified immunity under 42 USC § 1983 or drafting a Rule 37 letter, I aim to be the calm voice in the room… early and often.


4. Ego Is Expensive

In my early years, I fell into unnecessary rivalries with other young attorneys. And while some of those courtroom battles ended in my favor, I realized something better: a quiet dismissal beats a loud acquittal.

In civil practice, that lesson translates perfectly.

Firing off aggressive letters may impress the client copy list—but it rarely moves the needle in negotiations. Ego-driven posturing wastes time. I prefer clarity, courtesy, and precision. A smart lawyer knows when to speak softly and carry airtight documentation.


5. Negotiation Is a Long Game—So Play It Well

Sometimes you can settle. Sometimes you can’t. But civil or criminal, process matters.

You want opposing counsel to know you’re methodical, fair, and prepared to fight when needed. That kind of reputation isn’t built overnight—it’s earned through consistency, transparency, and respect.

And yes, sometimes, through a well-timed espresso.


📚 Sidebar: Resources to Deepen Your Trial Strategy

Curated tools for building relationships, refining negotiation, and winning cases with integrity

  • Negotiate to Win – ABA’s Practical Guide for Lawyers
    Constructive tips from legal pros on adapting negotiation styles and earning trust.
  • Legal Negotiation Skills 101 – Martindale-Avvo
    Breaks down emotional intelligence, strategy, and rapport-building essentials.
  • Five Golden Rules of Legal Negotiation – Expert Negotiator
    A compact blueprint for maximizing leverage in civil and criminal matters.
  • Strengthening Client Connections – National Law Review
    Strategies to build lasting client relationships and add everyday value.
  • Ten Rules to Improve Your Trial Wins – Plaintiff Trial Lawyer Tips
    From simplifying your case to appealing to juror self-interest, these tips align with meticulous courtroom storytelling.

Final Thought: Civility Wins Cases

Law isn’t just argument—it’s relationship management. I’ve found more success through kindness and quiet force than through theatrics.

As Twain put it:
“Never wrestle with a pig. You both get dirty, and the pig enjoys it.”

And as Proverbs says:
“A gentle answer turns away wrath.”

Whether defending a criminal case or challenging a land development petition, my aim is the same: prepare deeply, communicate respectfully, and negotiate like the long game matters—because it always does.

/wp-content/uploads/SK-Logo-Black-White.png 0 0 Scott Key /wp-content/uploads/SK-Logo-Black-White.png Scott Key2025-07-12 12:00:502025-07-12 12:04:03☕ The Coffee Note That Shaped My Trial Philosophy

Living a Fulfilling Life (as a Lawyer)

July 1, 2022/by admin
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Originalist Textualism 101 for Practitioners with Keith Blackwell

June 21, 2022/by admin
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What I’ve Read, Heard, And Am Pondering This Week: June 1

June 7, 2022/by admin
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Textualism As An Advocacy Tool

April 21, 2022/by admin
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What I’ve Read, Heard, And Am Pondering This Week: March 7

March 22, 2022/by admin
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https://scottkeylaw.com/wp-content/uploads/Scott-Key-March-7.jpg 720 1280 admin /wp-content/uploads/SK-Logo-Black-White.png admin2022-03-22 14:55:412024-10-09 11:15:40What I’ve Read, Heard, And Am Pondering This Week: March 7

Embracing the Legal Fundamentals with William Maselli

March 9, 2022/by admin
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https://scottkeylaw.com/wp-content/uploads/Criminal-defense-attorney-William-Maselli.jpg 720 1280 admin /wp-content/uploads/SK-Logo-Black-White.png admin2022-03-09 14:59:002024-10-09 11:15:48Embracing the Legal Fundamentals with William Maselli

Use the Tomato to Write More Words

November 7, 2019/by admin

The Pomodoro Technique has helped me to write briefs, prepare for trials, and stop procrastinating. It has also assisted me in getting more done over less time than it would ordinarily take. There’s a whole set of books and culture around it, but the method is easy to explain. Set a timer for twenty-five minutes. Work without allowing yourself any kind of interruption for that period of time. At the end of that block of time, you have earned a pomodoro (a tangible sign that you’ve completed a block of work). Take a five-minute break. Then reset the clock for another twenty-five minutes. Once you have four pomodoros, take a twenty-five minute break restart the entire process. On days when I don’t have court, my goal is to do eight to ten pomodoros. By the way, the technique was named by Francesco Cirillo, the guy who came up with I’d. Pomodoro is Italian for tomato, and apparently the timer he used was a kitchen timer shaped like a tomato. Hence, the Pomodoro technique. Here’s how the technique has helped.

* It forces you to go distraction-free for a period of time. A feature of The Pomodoro Technique is that you don’t get the pomodoro if you are interrupted by anything other than the task at hand during that period of time. You’re literally to reset the clock to twenty-five minutes. When you’re in a pomodoro, you’re ruthless and all out. Twenty-five distraction-free minutes is better than an hour of sort of doing work, while you check email, respond to texts, and take a peek at twitter. 

* The work compounds over time. The gathering of pomodoros allows you build momentum. By the time you stand up for your long break, you have done 100 minutes of work. And while your brain sees the four tomatoes you’ve earned, your brain also has accumulated the product of 100 hours of work. Another session of four, it’s eight pomodoros and 200 hours of work. Here is a sad commentary on what it was like for me before I employed this method. I would spend an entire day and and have little to show for my efforts aside from a bunch of outgoing email. Just doing four pomodoros was a huge increase in my daily output.

* A side benefit is that the time is tracked. If you keep a written log of your results, you can look back over time and see exactly what you worked on. Even if you write down what you did in a line or two, you can use this technique to built a work journal.

* It gets you working. It can be depressing and overwhelming to imagine the prospect of writing an entire brief, a paper, or preparing some big project. But you can easily wrap your head around the idea of doing twenty five minutes of work. There’s a sort of working inertia here. Your body at rest wants to stay at rest. And you’ll find, at the end of 25 minutes, if you’re on a roll, that a body in motion wants to stay in motion. So, you’ll sometimes not want to stop when the bell rings twenty-five minutes. And it’s easy to jump-start after a short break.

* You trick the brain. The brain can’t wrap itself around the idea of some big nebulous thing like “write the report,” or “get some work done.” Your brain can also have trouble with things like “complete a paragraph.” But “grab a tomato” is simple and tangible for the brain to see and accomplish

* You’re moving from goal-oriented thinking to systems thinking. Yes, you may be working toward the completion of a particular project. Yes, you may have a particular outcome in mind when you sit down to write. But the Pomodoro technique is a system. If you tell yourself that you will show up each day and complete 250 minutes (or whatever number you choose) of work, then you have committed to a particular set of behaviors — not to the achievement of a particular goal. Goals aren’t particularly helpful. At the beginning of every football season, every coach has the goal of winning a championship. But not every coach has a winning system. Many people set goals on December 31 for the new year. But almost nobody installs a system. The Pomodoro technique or any other process you might put into place provides a way to accomplish things, no matter what those things may be. It professionalizes a way of work. And while it’s not goal-oriented, goals have a prominent place. And you will find that somehow goals are achieved better when you do more than merely have them.

To anticipate a question, there is nothing magical about twenty-five minutes. You can experiment with the format all you like. You can completely overhaul it if you like. However, for me, this process has been a tangible and effective way to avoid procrastination, block out distractions, and move the ball down the field every single day that I do it. 

0 0 admin /wp-content/uploads/SK-Logo-Black-White.png admin2019-11-07 10:00:132019-11-07 10:00:13Use the Tomato to Write More Words

How and Where We Work

July 19, 2018/by admin

I almost never work in my office. The office is mainly a place to meet a client for the first time or a week or so before court. It is also the place where I retrieve mail that will be scanned into our system. My actual office is in my briefcase. I sprawl the contents of this office on tables in various courtroom law libraries or coffee shops throughout the state. Today is a prime example. I finished up a case this morning that required a court appearance. With the court appearance complete, I went to the closest coffee shop, where I called opposing counsel on a case tomorrow. But the real fun was in the written work I completed today. I work with an associate. She doesn’t even come to the office and works almost entirely remotely. We meet in person every week or two. But today I received an edited version of an amended motion for new trial that she reviewed for me. And I worked on editing an amended for new trial she prepared. We both work in the Apple universe, each with MacBooks and the big iPad pros. It’s a process that works great and one I’ll explain more in future blog posts.

0 0 admin /wp-content/uploads/SK-Logo-Black-White.png admin2018-07-19 16:26:272018-07-19 16:26:27How and Where We Work

New Podcast from GACDL

December 20, 2017/by admin

The Georgia Association of Criminal Defense Lawyers has a new podcast up. In episode 1, I interview criminal defense attorney and author Jason Sheffield about his new novel. But we get into some other topics such as attorney-client relationships, law practice management, and the good and bad of law school education in America. This was a fun interview. And I think you will enjoy it, too.

We have another episode recorded and in production

The podcast is available on iTunes and Soundcloud. Please go to iTunes and leave us a comment or a rating. And please reach out to me to suggest a guest for an upcoming show.

0 0 admin /wp-content/uploads/SK-Logo-Black-White.png admin2017-12-20 07:15:312017-12-20 07:15:31New Podcast from GACDL
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Related Resources

  • ☕ The Coffee Note That Shaped My Trial Philosophy
  • Living a Fulfilling Life (as a Lawyer)
  • Originalist Textualism 101 for Practitioners with Keith Blackwell
  • What I’ve Read, Heard, And Am Pondering This Week: June 1
  • Textualism As An Advocacy Tool
  • What I’ve Read, Heard, And Am Pondering This Week: March 7

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