Smart people overthink conversations

Hi there,

Smart people overthink things. That's not an insult, it's basically the deal you make in life when your brain works fast. You see angles other people miss, you overplan, your plans have plans. In most areas of life, that's an asset. But in giving presentations, speeches, and in important conversations, not so much…

Someone close to me is giving a best man speech soon. He's the kind of person who's good at most things he puts his mind to, which is exactly why this is hard. He keeps trying to get the speech perfect in his head before he writes a word of it. Running every version. Anticipating every reaction. It's not writer's block. It's the opposite. It's too much mind, not enough room to just say the things he knows so well in his heart.

I know this move well not from wedding speeches, but from giving closing arguments to a jury.

The Hidden Truth About Being Overprepared

As a trial lawyer, closing is the moment where you take weeks of testimony, contradictory witnesses, 179 exhibits, and make it all make sense in 15 or 20 minutes, to twelve people who did not go to law school.

Early on, I prepared for closing arguments like I was packing for every possible weather. Wool coat, swimsuit, hiking boots, umbrella, you know just in case… I’d cover every fact, every angle and every counterargument I might ever need. I walked into that courtroom carrying so much that I could barely lift it and when the moment came, I couldn't find a single thing.

What I eventually learned is that over-preparation and under-preparation feel almost identical from the inside. Both leave you standing there, stuck. The difference is one has too many notes and the other has none.

Lessons in communication

Here's what I’ve learned from reps in the courtroom where the stakes are high:

Presentations, speeches, and important conversations aren't scripts. It's a living thing. It breathes, it shifts, it goes somewhere you didn't plan for. Grip the plan too tight and you snap. Hold it loosely (a spine, not a script) and when the unexpected happens, you just look up, find your footing, and keep going.

Most people are never taught this, but when communication is literally your job and you’re paid to walk into a room and change someone’s mind, you figure it out fast.

Here's three things from a trial lawyer's playbook that nobody tells you works just as well outside the courtroom in every day life.

#1. Prime them

This is called priming and it's one of the most powerful moves in any conversation. Think of it like telling someone the weather before they get dressed. You're giving info for they what they need to show up right.

When you admit your thought is still forming, the pressure on you drops immediately and the other person stops waiting to evaluate and starts actually listening. They stop being a judge and become a collaborator. Nobody shuts down a 20% idea. Nobody brushes off someone who says they're nervous but need to talk. You've already set the tone of the conversation before it even starts.

#2. Pick your top 3 ideas

In a closing argument, the fastest way to lose a jury is to try to win on every point. It's like throwing all your darts at the board at one, while impressive, it literally hits nothing.

Pick the top three things you need to say, make those land clean, and everything else follows. As an overthinker, your brain tells you more detail means more persuasive. It doesn't. It means more noise and people tune out noise.

#3. Anchor your top ideas in 1 sentence

There's a difference between memorizing something and actually knowing it.

Memorizing is like reading directions off your phone, the second you lose wifi signal, you're lost.

Knowing it means you could explain the same idea to a five-year-old, then a teenager, then a boardroom of executives, then your friend over coffee at a ballgame and it lands every time, because it's yours.

One anchor sentence per idea is how you get there. Not a paragraph or a long script. One sentence that belongs to you so completely that no matter how sideways the conversation goes, you can always find your way back to it.

Final Thought

At the end of the day, conversations and big presentations will go sideways. That's not a failure of preparation. That's just what they do. They breathe. They surprise you.

Plus sometimes, the most memorable moments in any conversation are usually the ones nobody planned, the thing that just came out, the honest response, the laugh nobody saw coming.

So for your next big conversation, speech, or presentation, don’t overthink it. As an overthinker, overpreparer, you will make yourself overfull.

Prime them. Pick your three things. Find your one sentence for each. And then let the conversation be what it's going to be.

Less is more.

Catch you next week,

Shakila