What 35 Years on Both Sides of the Courtroom Taught Me About Resolution

For most of my career, I was an advocate.

I prepared cases. I argued positions. I fought for outcomes.

That work taught me a great deal about litigation — mostly revolving around strategy, preparation, pressure and unpredictability.

But it wasn’t until I stepped out of the advocate’s role and into the mediator’s chair that I began to understand something I hadn’t fully appreciated before:

Winning and resolving are not the same thing.

As a litigator, the goal is to build the strongest possible version of your case and then press that advantage. That is exactly what good advocates do, and it matters enormously.

But in mediation, I’ve come to see that the lawyers and parties who achieve the best outcomes are not always the ones with the strongest arguments. The individuals that achieve the best outcomes in a trial are often the ones with the clearest understanding of risk.

There is a difference between knowing your case is strong and honestly evaluating what a jury might do with it.

After 35 years of watching the cases I have been involved in go to trial and then seeing those same cases produce results that surprised everyone in the room, taught me that uncertainty is always present. Those situations taught me that it doesn’t matter how well-prepared you are, how compelling your expert is, or how sympathetic your client may be. Trials involve human beings making decisions under imperfect conditions.

That reality doesn’t diminish the importance of strong advocacy. It simply means that the most effective lawyers I’ve observed — on both sides — are the ones who hold two things simultaneously: confidence in their case and an honest respect for what they cannot control.

Resolution, when it happens well, is not capitulation. It is clarity.

It is the product of parties who have done the hard work of evaluating not just what they believe but knowing what they can prove, how it will be received, and what the cost of being wrong might look like.

That is what 35 years taught me.

And it is what I bring to every mediation I conduct.

Contact me today at 407.493.0899 or visit my Appointments page to schedule your next mediation.